乙二醇甲醚 | 109-86-4

• 物质功能分类: 有机原料 - 醚类化合物及其衍生物 - 醚、醚醇
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙二醇甲醚
• 中文别名: 羟乙基·甲基醚；乙二醇独甲醚；甲氧基乙醇；乙二醇单甲醚；乙二醇一甲醚；2-甲氧基乙醇；甲基溶纤剂；EM；羟乙基甲醚
• 英文名称: 2-methoxy-ethanol
• 英文别名: ethylene glycol monomethyl ether；2-methoxyethan-1-ol；ethylene glycol methyl ether；2-methoxyethane-1-ol；methoxyethanol；2-Methoxyethanol
• CAS: 109-86-4
• 化学式: C₃H₈O₂
• mdl: MFCD00002867
• 分子量: 76.0953
• InChiKey: XNWFRZJHXBZDAG-UHFFFAOYSA-N

物化性质

• 熔点：
  -85 °C
• 沸点：
  124-125 °C(lit.)
• 密度：
  0.965 g/mL at 25 °C(lit.)
• 蒸气密度：
  2.62 (vs air)
• 闪点：
  115 °F
• 溶解度：
  Very soluble in acetone, dimethylsulfoxide, and 95% ethanol (quoted, Keith and Walters, 1992). Miscible with N,N-dimethylformamide, ether, and glycerol (Windholz et al., 1983).
• 最大波长(λmax)：
  λ: 213 nm Amax: 1.00λ: 240 nm Amax: 0.20λ: 260 nm Amax: 0.05λ: 300-400 nm Amax: 0.01
• 介电常数：
  15.8（20℃）
• 暴露限值：
  TLV-TWA skin 5 ppm (15.5 mg/m3) (ACGIH), 25 ppm (77.5 mg/m3) (OSHA).
• LogP：
  -0.77 at 20℃
• 物理描述：
  Ethylene glycol monomethyl ether appears as a clear colorless liquid. Flash point of 110°F. Less dense than water. Vapors are heavier than air.
• 颜色/状态：
  Colorless liquid
• 气味：
  Mild agreeable odor
• 味道：
  Bitter
• 蒸汽密度：
  2.62 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  9.5 mm Hg at 25 °C
• 亨利常数：
  Henry's Law constant = 3.3X10-7 atm-cu m/mol at 25 °C
• 大气OH速率常数：
  1.25e-11 cm3/molecule*sec
• 稳定性/保质期：
  1. 具有醇和醚的化学性质，可与邻苯二甲酸、蓖麻酸、油酸等生成酯。 2. 稳定性 [25]：稳定。 3. 禁配物 [26]：酰基氯、酸酐、强氧化剂。 4. 避免接触的条件 [27]：空气、光照。 5. 聚合危害 [28]：不聚合。
• 自燃温度：
  285 °C
• 分解：
  Thermal decomposition 204 - 232 °C
• 腐蚀性：
  Methyl cellosolve will attack some forms of plastics, rubber, and coatings.
• 燃烧热：
  -5250 cal/g
• 汽化热：
  45.17 kJ/mol at 25 °C; 37.54 kJ/mol at 124.1 °C
• 表面张力：
  30.84 mN/m at 25 °C
• 电离电位：
  9.60 eV
• 气味阈值：
  Odor Threshold Low: 0.09 [mmHg]; Odor Threshold High: 61.0 [mmHg]; Detection odor threshold from AIHA (mean = 2.4 ppm)
• 折光率：
  Index of refraction: 1.4024 at 20 °C/D
• 解离常数：
  14.8 (at 25 °C)
• 相对蒸发率：
  0.5 (n-Butyl acetate = 1)
• 保留指数：
  629 ;629 ;617 ;630 ;626 ;623 ;612.3 ;611.8 ;618 ;616 ;617 ;616 ;617 ;616

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  5
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

2-甲氧基乙醇（2-ME）的代谢转化产生两种主要代谢物：甲氧基乙酸（MAA）和2-甲氧基乙酰甘氨酸。代谢成二氧化碳代表了一个次要的、少量的途径。在大鼠血浆中，2-ME转化为MAA的速度很快，半衰期为0.6小时，但MAA的排泄速度很慢，在大鼠中的半衰期约为20小时，在人体中为77小时。

The metabolic transformation of /2-methoxyethanol/ (2-ME) gives two primary metabolites: /methoxyacetic acid/ (MAA) and 2-methoxyacetyl glycine. Metabolism to carbon dioxide represents a secondary, minor route. The conversion in plasma of 2-ME to MAA is rapid, with a half-life of 0.6 hr in rats, but the excretion of MAA is slow, with a half-life of about 20 hr in the rat and 77 hr in man.

来源:Hazardous Substances Data Bank (HSDB)

代谢

代谢在2-甲氧基乙醇（ME）诱导的睾丸毒性中的作用已经在Sprague-Dawley大鼠中进行了研究。在给一组动物注射了[(14)C]ME（250 mg/kg，ip）后，有证据表明睾丸损伤，表现为精原细胞群体的耗竭。在处理后的48小时内，尿液中检测到的放射性活性占剂量的55%。通过高效液相色谱和同位素稀释分析，主要的尿代谢物被鉴定为甲氧基乙酸（MAA）和甲氧基乙酰甘氨酸（分别占尿液中放射性活性的50至60%和18至25%）。血浆分析显示ME迅速转化为MAA（ME消失的t1/2 = 0.6 +/- 0.03小时），并且放射性活性逐渐清除（t1/2 = 19.7 +/- 2.3小时）。在[(14)C]ME给药前1小时用吡唑（400 mg/kg，ip）预处理动物，可以完全防止ME的睾丸毒性。在48小时内，从吡唑预处理组的尿液中检测到的放射性活性（18%）显著低于仅ME组。主要的放射性峰与ME共同色谱（占尿液总放射性活性的30至36%）。MAA和甲氧基乙酰甘氨酸不是主要的代谢物。血浆分析显示ME转化为MAA的转化几乎完全被抑制（ME消失的t1/2 = 42.6 +/- 5.6小时，放射性活性的清除t1/2 = 51.0 +/- 7.8小时）。结果表明，代谢激活是2-甲氧基乙醇对男性生殖系统产生毒性的必要条件。

The role of metabolism in 2-methoxyethanol (ME)-induced testicular toxicity has been investigated with Sprague-Dawley rats. Following administration of [(14)C]ME (250 mg/kg, ip) to a group of animals, there was evidence of testicular damage, identified as depletion of the spermatocyte population. Radioactivity detected in urine over 48 hr after treatment accounted for 55% of the dose. The major urinary metabolites were identified by HPLC and isotope dilution analysis, as methoxyacetic acid (MAA) and methoxyacetylglycine (accounting for 50 to 60% and 18 to 25%, respectively, of urinary radioactivity). Analysis of plasma revealed a rapid conversion of ME to MAA (t1/2 for disappearance of ME = 0.6 +/- 0.03 hr) and gradual clearance of radioactivity (t1/2 = 19.7 +/- 2.3 hr). Pretreatment of animals with pyrazole (400 mg/kg, ip) 1 hr prior to [(14)C]ME dosing gave complete protection against the testicular toxicity of ME. Radioactivity detected in the urine from the pyrazole-pretreated groups over 48 hr (18%) was significantly lower than in the ME-only group. The major radioactive peak co-chromatographed with ME (30 to 36% of the total urinary radioactivity). MAA and methoxyacetylglycine were not major metabolites. Analysis of plasma revealed almost complete inhibition of the conversion of ME to MAA (t1/2 for disappearance of ME = 42.6 +/- 5.6 hr, clearance of radioactivity t1/2 = 51.0 +/- 7.8 hr). The results demonstrate that metabolic activation is required for 2-methoxyethanol to exert toxicity to the male reproductive system.

来源:Hazardous Substances Data Bank (HSDB)

代谢

邻苯二甲酸二甲氧基乙酯（DMEP）的次级代谢物甲氧基乙酸（MAA），而不是其对应的二酯或其初级代谢物甲氧基乙基邻苯二甲酸盐和甲氧基乙醇（ME），干扰了培养中器官形成期大鼠胚胎的正常生长和发育。这些体内观察结果表明，DMEP在体内的致畸性是由于二酯经酶切断裂生成ME，随后在母体环境中将ME氧化为MAA。 /邻苯二甲酸二甲氧基乙酯的代谢物/

The secondary metabolite of dimethoxyethyl phthalate (DMEP) methoxyacetic acid (MAA), but not the diester or its primary metabolites monomethoxyethyl phthalate and methoxyethyanol (ME) interfered with normal growth and development of organogenesis phase rat embryos in culture. These in vivo observations suggested that the teratogenicity of DMEP in vivo was due to enzymic cleavage of the diester to ME, followed by oxidation of the latter to MAA in the maternal compartment. /Metabolites of dimethoxyethyl phthalate/

来源:Hazardous Substances Data Bank (HSDB)

代谢

当人类志愿者吸入5 ppm的EGME（甲基乙二醇单甲醚）4小时后，吸入的EGME中有76%被保留，吸收的剂量中有85%以2-甲氧基乙酸的形式出现在尿液中。来源于EGME分解的2-甲氧基乙酸的半衰期在人类中为66至89小时。

When human volunteers inhaled 5 ppm EGME for 4 hours, 76% of the inspired /ethylene glycol monomethyl ether/ (EGME) was retained and 85% of the absorbed dose appeared in the urine as 2-methoxyacetic acid. The human elimination half-time for the 2-methoxyacetic acid arising from the catabolism of EGME was 66 to 89 hours.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：2-甲氧基乙醇（2-ME）是一种无色液体，具有醚类气味。它用作纤维素醋酸酯、天然和合成树脂、某些醇溶性染料的溶剂；在指甲油、快干漆和搪瓷以及木纹染色剂中也有应用。它还可用作喷气燃料防冰剂。人类暴露和毒性：该物质对眼睛和呼吸道有轻微刺激性，可能对中枢神经系统、血液、骨髓、肾脏和肝脏产生影响。高水平的暴露可能导致昏迷。该液体脱脂皮肤。曾报告了两例男性（分别为41岁和23岁）因摄入100毫升2-ME引起的非致命性中毒案例。除了激动和混乱之外，主要临床特征是恶心、发绀、过度换气、轻微心动过速和代谢性酸中毒。其中一名患者出现了中度肾衰竭的迹象。没有发现肝脏损伤的证据，两名患者在4周内康复。慢性蒸汽中毒导致中毒性脑病和骨髓抑制的证据，但没有溶血。观察到肺、肾和肝的变化。研究发现，子宫内接触2-ME的个体表现出特征性的畸形特征、无法解释的精神迟缓和持续的细胞遗传学损伤。子宫内接触2-ME可能导致端粒染色体重排和端粒长度缩短。对接触2-ME和2-乙氧基乙醇的工人的流行病学研究显示，对男性生殖系统有不良影响的证据，表现为精子数量减少的频率增加。动物毒性研究：在豚鼠中，每天皮下注射0.5或1.0毫升/公斤，连续5天，导致虚脱、呼吸困难并死亡。对急性处理2-ME的动物进行临床检查和尸检，发现无尿、尿液中的钙化管型、膀胱粘膜刺激、胃肠道出血、肺水肿以及肝脏和睾丸损伤。在小鼠中，口服2-ME 1-2周或其代谢物甲氧基乙酸2周，产生了胸腺萎缩，并选择性地消耗了未成熟的胸腺细胞。雄性大鼠在给予200毫克/公斤2-ME后，在第4周的生育能力下降，并在此后的研究中保持低水平。一项研究报告称，在大鼠接触2-ME后，其后肢部分丧失运动功能。这种后肢瘫痪与在暴露第二周注意到的小胶质细胞毒性相一致。小鼠和大鼠在吸入2-ME后观察到胚胎毒性，兔子在暴露后出现畸形。在母鼠经灌胃处理2-ME后，其后代出现了行为和神经化学改变。该研究还发现，母鼠处理2-ME的剂量依赖性增加心血管畸形和异常心电图（EKG）胎儿的发病率。最常见的EKG异常是QRS波延长。在CD-1小鼠胚胎中，研究了2-ME细胞毒性与数字发育畸形的关系，这些胚胎在妊娠第11天接受了剂量。2-ME扩大了前轴生理性细胞坏死的区域，并在处理24小时后改变了肢体芽的形状。在给予250和350毫克2-ME/公斤后，前轴组织和前数字软骨细胞凝聚减少或缺失。在CHO细胞中，当研究染色体畸变（在6830微克/毫升或更高）和姐妹染色单体交换（3170微克/毫升或更高）时，在非常高的2-ME浓度下报告了阳性诱变结果。然而，体内染色体畸变和微核的研究结果为阴性。生态毒性研究：2-ME在104毫克/升时抑制绿藻的生长，在100毫克/升时抑制蓝藻（蓝绿藻）的生长。

IDENTIFICATION AND USE: 2-Methoxyethanol (2-ME) is a colorless liquid with ether-like odor. It is used as a solvent for cellulose acetate, natural and synthetic resins, some alcohol-soluble dyes; in nail polishes, quick-drying varnishes and enamels, and wood stains. It is also used as a as a jet fuel de-icer. HUMAN EXPOSURE AND TOXICITY: The substance is mildly irritating to the eyes and respiratory tract and may cause effects on the central nervous system, blood, bone marrow, kidneys and liver. Exposure at high levels could cause unconsciousness. The liquid defats the skin. Two non-fatal cases of poisoning by consuming 100 mL 2-ME in men aged 41 and 23 were reported. In addition to agitation and confusion, the predominant clinical features were nausea, cyanosis, hyperventilation, slight tachycardia, and metabolic acidosis. In one patient there were suggestions of moderate kidney failure. No evidence of liver damage was found and both patients recovered within 4 weeks. Chronic poisonings from vapors lead to toxic encephalopathy and evidence of bone marrow depression without hemolysis. Lung, kidney and liver changes have been observed. It was found that individuals exposed in utero to 2-ME showed characteristic dysmorphic features, unexplained mental retardation, and persistent cytogenetic damage. Exposure to 2-ME in utero could result in terminal chromosome rearrangements and shortening of telomere length. Epidemiological studies of workers exposed to 2-ME and 2-ethoxyethanol have shown some evidence of adverse effect on the male reproductive system, with an increased frequency of reduced sperm counts. ANIMAL TOXICITY STUDIES: In guinea pigs, 5 daily sc injections of either 0.5 or 1.0 mL/kg caused prostration, labored breathing, and death. Clinical exam and autopsy of the animals acutely treated with 2-ME revealed anuria, calcified casts in urine, irritation of bladder mucosa, hemorrhage in GI tract, lung edema, and liver and testicular injury. In mice, oral administration of 2-ME for 1-2 wks, or its metabolite methoxyacetic acid for 2 wks, produced thymic atrophy, and a selective depletion of immature thymocytes. The fertility of male rats treated with 200 mg/kg 2-ME declined at week 4 and remained low for the rest of the study. One study reported a partial loss of motor function in the hindlimbs of rats after exposure to 2-ME. This hindlimb paralysis coincided with the glial cell toxicity noted during the second week of exposure. Fetotoxicity in mice and rats and malformations in rabbits were observed following exposure by inhalation to 2-ME. Behavioral and neurochemical alterations were seen in the offspring of rats exposed to 78 mg 2-ME/cu m. The research also found a dose-dependent increase in incidence of fetuses with cardiovascular malformations and abnormal electrocardiograms (EKG) from mothers treated with 2-ME by gavage. The most prevalent EKG abnormality was a prolonged QRS wave. The role of 2-ME cytotoxicity in digital maldevelopment in CD-1 mouse embryos was examined following dosage on gestation day 11. The area of preaxial physiological cell necrosis was enlarged by 2-ME, and the shape of the limb buds was altered 24 hr after treatment. Preaxial tissue and the predigital chondrocyte condensations were reduced or missing following 250 and 350 mg 2-ME/ kg. There were reports of positive mutagenicity results at very high 2-ME concentrations in CHO cells when investigated for chromosome aberration (at 6830 ug/mL or more) and sister chromatid exchange (3170 ug/mL or more). However, in vivo studies for chromosome aberrations and micronuclei were negative. ECOTOXICITY STUDIES: Growth inhibition of green algae by 2-ME was noted at 104 mg/L and of cyanobacteria (blue-green algae) at 100 mg/L.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

这种物质可以通过吸入、皮肤接触和摄入被身体吸收。

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 暴露途径

吸入，皮肤吸收，吞食，皮肤和/或眼睛接触

inhalation, skin absorption, ingestion, skin and/or eye contact

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 症状

眼睛、鼻子、喉咙刺激；头痛、嗜睡、乏力（虚弱、疲劳）；共济失调、震颤；贫血苍白。在动物中：生殖、致畸效应。

irritation eyes, nose, throat; headache, drowsiness, lassitude (weakness, exhaustion); ataxia, tremor; anemic pallor; In Animals: reproductive, teratogenic effects

来源:The National Institute for Occupational Safety and Health (NIOSH)

吸收、分配和排泄

在大鼠注射1.0毫克/千克的2-甲氧基乙醇后，30分钟内在尿液中检测到该物质，注射后总共持续7小时，血液中最后一次见到该物质后3小时。

The material /2-methoxyethanol/ was detected in rat urine 30 min after an ip administration of 1.0 mg/kg and remained present for a total of 7 hr after the injection, 3 hr after it was last seen in the blood.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

雄性Fischer 344大鼠单次口服大约1或8.7毫摩尔/千克的(14)C-乙二醇单甲基醚。大约50到60%的给药(14)C通过尿液排出，约12%在48小时内以(14)CO2的形式消除。

Male Fischer 344 rats were given a single oral dose of approx 1 or 8.7 mmol/kg of (14)C-ethylene glycol monomethyl ether. Approx 50 to 60% of the admin (14)C was excreted in urine, and about 12% was eliminated as (14)CO2 within 48 hr.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

乙二醇单甲醚（EGME）的吸收和其主要代谢物甲酸甲酯（MAA）的尿液排泄在七名男性志愿者静息状态下实验性接触EGME时进行了研究。接触浓度设定为16 mg/m³，这是目前的阈限值。在4小时的接触期间，高保留率（0.76）保持不变。结合恒定的肺通气量和固定的接触浓度，这导致吸收速率随时间没有显著变化。吸入的EGME总量相当于0.25 mg/kg的剂量。在接触开始后直至120小时内，尿液中有MAA检出。平均消除半衰期为77.1小时。通过外推计算出的MAA排泄总量平均为吸入EGME的85.5%。...

The uptake of /ethylene glycol monomethyl ether/ (EGME) and the urinary excretion of its major metabolite /methoxyacetic acid/ (MAA) was studied in seven male volunteers during experimental exposure to EGME at rest. The exposure concentration was set at 16 mg/cu m, the present Threshold Limit Value. A high retention (0.76) remained unchanged during the 4-hr exposure period. In combination with a constant pulmonary ventilation and a fixed exposure concentration this resulted in an uptake rate that showed no significant variation in time. The total amount of EGME inhaled corresponded to a dose of only 0.25 mg/kg. During and up to 120 hr after the start of the exposure, MAA was detected in the urine. The elimination half-life was on average 77.1 hr. The total amount of MAA excreted was calculated by extrapolation and averaged 85.5% of the inhaled EGME. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当前研究评估了（14）C标记的2ME的代谢以及孕鼠和大鼠胎儿组织中甲氧基乙酸的分布，这些大鼠在怀孕期间要么暴露于10毫赫兹的射频辐射，要么处于假手术条件。此外，对血浆和胎儿蛋白的加合物的形成进行了检测，作为观察到的2ME/RF致畸性的可能生物标志物。大鼠在妊娠第13天通过灌胃给予（乙醇-1,2-(14)C）-2ME（150毫克/千克，161微居里/大鼠平均），然后立即在射频辐射下将体温升高至42°C/30分钟。同时，假手术和射频大鼠在3、6、24或48小时后被处死，以收集母血、尿液、胎儿和胚胎液。组织要么被消化以确定放射性，要么用三氯乙酸（TCA）脱蛋白并用高效液相色谱（HPLC）分析以量化2ME代谢物。结果显示，在测试的组织中，2ME和七种代谢物存在，主要代谢物MA在6小时达到峰值。MA，一种近端致畸物，在给药后48小时可在母血清、尿液、胎儿和胚胎液中检测到。RF动物的总（14）C清除率在24-48小时期间显著降低（p>0.05），但血清、胎儿和胚胎液的MA值对于假手术和射频大鼠是相似的。此外，假手术或射频大鼠的尿液或组织的2ME代谢物轮廓没有差异，因此排除了射频辐射对MA产生的影响作为解释报告的RF/2ME协同作用的可能原因。随后，通过分析共价结合的放射性来评估血清和胎儿蛋白结合的加合物。血清蛋白结合在3小时和6小时时，假手术大鼠显著高于射频大鼠，假手术大鼠在6小时时最高（519 +/- 95微克/克蛋白），而射频血清值在24小时时最高（266 +/- 79微克/克蛋白）。胎儿蛋白结合在6小时时假手术大鼠显著高于射频大鼠，但在24小时时两组的结合最高（假手术=229 +/- 71微克/克，射频=185 +/- 48微克/克）。认为2ME后蛋白加合物的形成与甲氧基乙醛的水平有关，甲氧基乙醛是形成MA的一种反应中间体。

...The current study evaluated the metabolism of (14)C-labeled 2ME and the distribution of methoxyacetic acid (MA) in maternal and fetal tissues of pregnant Sprague-Dawley rats either exposed to RF radiation at 10 mHz or sham conditions. Additionally, adduct formation for both plasma and fetal protein was tested as a possible biomarker for the observed 2ME/RF teratogenicity. Rats were administered (ethanol-1,2-(14)C)-2ME (150 mg/kg, 161 uCi/rat average) by gavage on day 13 of gestation immediately before RF radiation body temperature elevation to 42 °C/30 min. Concurrent sham and RF rats were sacrificed at 3, 6, 24 or 48 hr for harvest of maternal blood, urine, fetuses and embryonic fluid. Tissues were either digested for determination of radioactivity or deproteinized with /Trichloroacetic Acid/ (TCA) and analyzed by HPLC for quantification of 2ME metabolites. Results show the presence of 2ME and seven metabolites, with the major metabolite, MA, peaking at 6 hr in the tissues tested. MA, the proximal teratogen, was detectable in maternal serum, urine, fetus and embryonic fluid 48 hr after dosing. Clearance of total body (14)C was significantly reduced for the RF animals (p>0.05) for the 24-48 hr period, but MA values for serum, fetus and embryonic fluid were similar for both sham and RF rats. Additionally, no difference was noted for 2ME metabolite profiles in urine or tissue for sham or RF rats thus eliminating an effect of RF radiation on MA production as a possible explanation for the reported RF/2ME synergism. Subsequently, serum and fetus protein-bound adducts were evaluated by analysis of covalently bound radioactivity. Serum protein binding was significantly higher for sham than RF rats at 3- and 6-hr -- highest for sham rats at 6 hr (519 +/- 95 ug as parent 2ME/g of protein) whereas RF serum values were highest at 24 hr (266 +/- 79 ug/g protein). Fetal protein binding was significantly higher for sham rats at 6 hr, but binding was highest for both groups at 24 hr (sham = 229 +/- 71 ug/g, RF = 185 +/- 48 ug/g). Formation of protein adducts after 2ME is thought to be related to levels of methoxyacetaldehyde, a reactive intermediate in the formation of MA.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 职业暴露等级：
  C
• 职业暴露限值：
  TWA: 0.1 ppm (0.3 mg/m3) [skin]
• TSCA：
  Yes
• 危险等级：
  3
• 立即威胁生命和健康浓度：
  200 ppm
• 危险品标志：
  T
• 安全说明：
  S16,S23,S26,S36/37,S45,S53
• 危险类别码：
  R60,R20/21/22,R10,R61
• WGK Germany：
  3
• 海关编码：
  2942000000
• 危险品运输编号：
  UN 1188 3/PG 3
• 危险类别：
  3
• RTECS号：
  ZC0110000
• 包装等级：
  III
• 危险标志：
  GHS02,GHS07,GHS08
• 危险性描述：
  H226,H302 + H312 + H332,H360FD,H370,H373
• 危险性防范说明：
  P201,P210,P260,P302 + P352 + P312,P304 + P340 + P312,P308 + P311
• 储存条件：
  储存注意事项： - 储存于阴凉、通风良好的库房中。 - 远离火源和热源，库温不宜超过37℃。 - 包装要求密封，避免与空气接触。 - 应与其他化学品分开存放，尤其是氧化剂等，并确保不混储。 - 使用防爆型照明和通风设施。 - 禁止使用可能产生火花的机械设备和工具。 - 储区应配备泄漏应急处理设备及合适的收容材料。

SDS

第一部分：化学品名称

制备方法与用途

乙二醇单甲醚（MOE）简介

乙二醇单甲醚（简称MOE），又称为乙二醇甲醚，是一种无色透明液体。它能与水、醇、醋酸、丙酮以及DMF混溶。作为一种重要的溶剂，广泛用于各种油脂类、醋酸纤维素、硝酸纤维素、醇溶性染料和合成树脂的溶解。

应用

MOE常被用作珐琅和清漆的快速干燥溶剂，涂层稀释剂，在染料工业中作为渗透剂和匀染剂。此外，它还用于印刷油墨及密封剂的制造，并作为增塑剂使用。近年来，随着在制药行业、航空喷气燃料防冰剂、刹车油稀释剂等领域的需求增加，其用量逐年提升。

MOE可通过环氧乙烷与甲醇反应制备而成。

制备

CN201110440309.9提供了一种工艺简单且产品质量稳定的色谱级有机溶剂——乙二醇单甲醚的制备方法。具体步骤如下：

1. 将原料乙二醇单甲醚以30mL-100mL/min的速度通过装有吸附剂的吸附柱进行吸附。
2. 吸附后，将流出液加入重量比为0.1%的2,4-二硝基苯肼搅拌1h～2h。随后，再经过装有干燥剂的干燥柱处理，确保含水量控制在≤0.05%。
3. 干燥后的乙二醇单甲醚打入精馏釜进行精馏。加入量为乙二醇单甲醚重量比的0.1%-0.3%氢化钙，在底温度180～300℃、液体温度130℃～150℃、顶温124℃下，控制回流比10∶2～8。精馏后通过微孔滤膜过滤，获得色谱级乙二醇单甲醚。

化学性质

MOE是一种无色透明的液体，具有轻微的芳香气味，能与水、醇类混溶，并能溶解于多种有机溶剂中。

性质

• 类别：易燃液体
• 毒性分级：中毒
  • 急性毒性：
    • 大鼠口服LD50:2370毫克/公斤
    • 小鼠口服LD50:2560毫克/公斤
• 刺激数据：
  • 皮肤-兔子463毫克/24小时轻度
  • 眼睛-兔子500毫克/24小时轻度
• 爆炸物危险特性：与空气混合可爆
• 可燃性危险特性：遇明火、高温或氧化剂较易燃，燃烧时产生刺激烟雾
• 储运特性：
  • 库房通风、低温干燥
  • 需与氧化剂分开存放

灭火剂

使用干粉、干砂、二氧化碳、泡沫及1211灭火剂进行灭火。

职业标准

• TWA：16毫克/立方米
• STEL：120毫克/立方米

反应信息

• 作为反应物：
  描述：

  乙二醇甲醚 在 potassium hydroxide 、 N-甲基-N-亚硝基对甲苯磺酰胺 作用下， 以 乙醚 、 水 为溶剂， 生成 重氮甲烷
  参考文献：
  名称：

  在氧化钙作为除酸剂的条件下，需要最少的重氮甲烷的改进的Arndt-Estert合成法

  摘要：

  描述了一种通过改进的Arndt-Eistert合成方法获得α-重氮酮的实用方法。该方法允许在氧化钙存在下使用化学计算量的重氮甲烷有效地转化酰卤，而不会伴随乙烯酮或卤代酮的形成。将获得的α'-溴化-α-二氮酮用作合适的底物，用于合成有趣的α-芳基氨基-α'-卤代甲基酮。

  DOI：

  10.1021/jo101105g
• 作为产物：
  描述：

  2-(2-methoxy-ethoxy)-tetrahydro-pyran 在 甲醇 作用下， 反应 0.5h， 以97%的产率得到乙二醇甲醚
  参考文献：
  名称：

  Synthesis of sulfonic acid functionalized carbon catalyst from glycerol pitch and its application for tetrahydropyranyl protection/deprotection of alcohols and phenols

  摘要：

  A novel carbon catalyst with -SO3H, -OH and -COOH functional groups was prepared from glycerol pitch by in situ partial carbonization and sulfonation with sulfuric acid. The activity of the catalyst was investigated through tetrahydropyranylation and dehydropyranylation of a wide variety of alcohols and phenols at room temperature by changing the solvent medium from dichloromethane to methanol. Excellent yields, short reaction times, easy and quick isolation of the products and reusability of the catalyst are the main attractions of this method. The novel carbon catalyst holds great potential in the green chemical processes. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.05.025
• 作为试剂：
  描述：

  7-氟-4-喹唑啉酮 在 吡啶 、 copper(l) iodide 、 1,10-菲罗啉 、 potassium [¹⁸F]fluoride 、 乙二醇甲醚 、 二苯基膦叠氮化物 、 potassium trifluoromethansulfonate 、 copper(II) bis(trifluoromethanesulfonate) 、 potassium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.33h， 生成 1-[4-((7-(dimethylamino)quinazolin-4-yl)oxy)-phenyl]-3-(4-[ ¹⁸F]fluorophenyl)urea
  参考文献：
  名称：

  评估用于检测肺部炎症的集落刺激因子 1 受体的正电子发射断层扫描示踪剂

  摘要：

  集落刺激因子 1 受体 (CSF1R) 是一种 III 型受体酪氨酸激酶，对于免疫细胞的激活、存活、增殖和分化至关重要。炎症期间其在巨噬细胞中的表达显着增加，在调节炎症消退和终止中发挥着至关重要的作用。因此，CSF1R 已成为炎症性疾病治疗干预和成像的关键靶点。在此，我们开发了一种放射性示踪剂，1-[4-((7-(二甲基氨基)喹唑啉-4-基)氧基)苯基]-3-(4-[ 18 F]氟苯基)脲([ 18 F] 17 ) ，用于 CSF1R 的体内正电子发射断层扫描 (PET) 成像。化合物17对 CSF1R 表现出与众所周知的 CSF1R 抑制剂 PLX647 相当的抑制效力。通过芳基三甲基锡前体的放射氟化成功地进行了[ 18 F] 17的放射合成，合成结束时收率约为12%，纯度保持在98%以上。体内稳定性和生物分布研究表明，[ 18 F] 17在注射后 30 分钟仍保持 >90% 完整，甚至在注射后

  DOI：

  10.1021/acs.molpharmaceut.4c00337

文献信息

• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。
• [EN] THIOPHENE DERIVATIVES FOR THE TREATMENT OF DISORDERS CAUSED BY IGE<br/>[FR] DÉRIVÉS DE THIOPHÈNE POUR LE TRAITEMENT DE TROUBLES PROVOQUÉS PAR IGE
  申请人：UCB BIOPHARMA SRL

  公开号：WO2019243550A1

  公开（公告）日：2019-12-26

  Thiophene derivatives of formula (I) and a pharmaceutically acceptable salt thereof are provided. These compounds have utility for the treatment or prevention of disorders caused by IgE, such as allergy, type 1 hypersensitivity or familiar sinus inflammation.

  提供了公式（I）的噻吩衍生物及其药用可接受的盐。这些化合物对于治疗或预防由IgE引起的疾病具有用途，如过敏、1型超敏反应或家族性鼻窦炎。
• [EN] AURORA KINASE MODULATORS AND METHOD OF USE<br/>[FR] MODULATEURS D'AURORA KINASE ET PROCÉDÉ D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2009117157A1

  公开（公告）日：2009-09-24

  The present invention relates to chemical compounds having a general formula (I) wherein A1-5 and 7-8, D', L1, L2, R1, R3, R6-8, n and o are defined herein, and synthetic intermediates, which are capable of modulating the activity of Aurora kinase proteins and, thereby, influencing various disease states and conditions related to the activities of Aurora kinases. For example, the compounds are capable of influencing the process of cell cycle and cell proliferation to treat cancer and cancer-related diseases. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of Aurora kinase.

  本发明涉及具有一般式(I)的化合物，其中在此定义了A1-5和7-8，D'，L1，L2，R1，R3，R6-8，n和o，以及合成中间体，这些化合物能够调节枢纽激酶蛋白的活性，从而影响与枢纽激酶活动相关的各种疾病状态和病况。例如，这些化合物能够影响细胞周期和细胞增殖过程，以治疗癌症和与癌症相关的疾病。该发明还包括包括这些化合物的药物组合物，以及治疗与枢纽激酶活性相关的疾病状态的方法。
• Lewis Acid-Catalyzed Deprotection of <i>p</i>-Methoxybenzyl Ether
  作者：Abderrahim Bouzide、Gilles Sauvé

  DOI：10.1055/s-1997-990

  日期：1997.10

  The p-methoxybenzyl protecting group was readily removed from alcohols and phenols using catalytic amounts of AlCl3 or SnCl2•2H2O in the presence of EtSH at room temperature. Under these mild conditions other protecting groups such as methyl and benzyl ethers, p-nitrobenzoyl esters, TBDPS ethers and isopropylidene acetal were unchanged.

  使用催化量的AlCl3或SnCl2•2H2O，在室温下并伴有乙硫醇（EtSH）的条件下，p-甲氧基苄基保护基能轻易地从醇和酚中去除。在这些温和的条件下，其他保护基团如甲基醚和苄基醚、对硝基苯甲酸酯、TBDPS醚和异丙叉缩酮保持不变。
• SUBSTITUTED PYRROLOPYRIMIDINE COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH
  申请人：Signal Pharmaceutical LLC

  公开号：US20140200206A1

  公开（公告）日：2014-07-17

  Provided herein are Pyrrolopyrimidine Compounds having the following structure: wherein R 1 , R 2 , R 3 , and L are as defined herein, compositions comprising an effective amount of a Pyrrolopyrimidine Compound, and methods for treating or preventing breast cancer, more particularly triple negative breast cancer, comprising administering an effective amount of such Pyrrolopyrimidine Compounds to a subject in need thereof.

  本文提供具有以下结构的吡咯吡嘧啶化合物： 其中R1、R2、R3和L如本文所定义，包含有效量吡咯吡嘧啶化合物的组合物，以及治疗或预防乳腺癌，更具体地是三阴性乳腺癌的方法，包括向需要的受试者施用有效量的这种吡咯吡嘧啶化合物。

表征谱图