甲基丙烯酸异丁酯 | 97-86-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甲基丙烯酸异丁酯
• 中文别名: 2-甲基丙基-2-甲基-2-丙烯酸酯,异丁烯酸异丁酯；异丁烯酸异丁酯；2-甲基丙基-2-甲基-2-丙烯酸酯；酸异丁酯；IBMA
• 英文名称: Isobutyl methacrylate
• 英文别名: 2-methylpropyl 2-methylprop-2-enoate
• CAS: 97-86-9
• 化学式: C₈H₁₄O₂
• mdl: MFCD00008931
• 分子量: 142.198
• InChiKey: RUMACXVDVNRZJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  -37 °C
• 沸点：
  155 °C (lit.)
• 密度：
  0.886 g/mL at 25 °C (lit.)
• 蒸气密度：
  3.82 (vs air)
• 闪点：
  107 °F
• LogP：
  2.95 at 20℃
• 物理描述：
  Isobutyl methacrylate is a colorless liquid with a flash point of 120°F. When heated to high temperatures it may release acrid smoke and fumes. If it is subjected to heat for prolonged periods or becomes contaminated, it is subject to polymerization. If the polymerization takes place inside a container, the container may violently rupture. The vapors are heavier than air. It may be irritating to skin and eyes and produce a narcotic effect. It is used in making acrylic resins.
• 颜色/状态：
  Liquid
• 溶解度：
  In water, 1300 mg/L at 25 °C
• 蒸汽压力：
  3.63 mm Hg at 25 °C
• 亨利常数：
  Henry's Law constant = 5.2X10-4 atm-cu m/mole at 25 °C (est)
• 自燃温度：
  390 °C
• 分解：
  When heated to decomposition it emits acrid smoke and fumes.
• 聚合：
  Exposure to heat, light, peroxide activators, catalysts or storage without air contact may result in exothermic polymerization. If the permissible storage period or storage temperature is noticeably exceeded, exothermic polymerization may occur.
• 气味阈值：
  0.016 - 0.069 ppm
• 折光率：
  Index of refraction: 1.4199 at 20 °C/D
• 保留指数：
  925 ;928 ;923 ;928 ;928 ;926 ;926 ;929.4 ;928
• 稳定性/保质期：

  1. 甲基丙烯酸异丁酯的毒性基本与甲基丙烯酸甲酯相同，防护要求也一致。参见甲基丙烯酸甲酯。

  2. 稳定性：稳定

  3. 禁配物：强氧化剂、强酸、强碱

  4. 应避免接触的条件：受热、光照、紫外线以及与空气接触

  5. 聚合危害：可能发生聚合

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

甲基丙烯酸甲酯和其他短链烷基-甲基丙烯酸酯首先在多个组织中通过非特异性的羧酸酯酶水解为甲基丙烯酸和结构上相应的醇。/短链烷基-甲基丙烯酸酯/

Methyl methacrylate and other short chain alkyl-methacrylate esters are initially hydrolyzed by non-specific carboxylesterases to methacrylic acid and the structurally corresponding alcohol in several tissues. /Short chain alkyl-methacrylate esters/

来源:Hazardous Substances Data Bank (HSDB)

代谢

甲基丙烯酸酯可以在体外与谷胱甘肽（GSH）结合，尽管它们表现出较低的活性，因为双键处添加亲核试剂受到α-甲基侧链的阻碍...因此，酯水解被认为是烷基-甲基丙烯酸酯的主要代谢途径，而GSH结合在其代谢中仅发挥次要作用，可能只有在达到非常高的组织浓度时才会发生。/短链烷基-甲基丙烯酸酯/

Methacrylate esters can conjugate with glutathione (GSH) in vitro, although they show a low reactivity, since the addition of a nucleophile at the double bond is hindered by the alpha-methyl side-group ... Hence, ester hydrolysis is considered to be the major metabolic pathway for alkyl-methacrylate esters, with GSH conjugation only playing a minor role in their metabolism, and then possibly only when very high tissue concentrations are achieved. /Short chain alkyl-methacrylate esters/

来源:Hazardous Substances Data Bank (HSDB)

代谢

IBMA，像MMA一样，应该被身体的羧酸酯酶迅速代谢。IBMA的水解产生甲基丙烯酸和异丁醇，它们通过生理途径进一步代谢，其中甲基丙烯酰辅酶A是缬氨酸途径的生理底物。

IBMA, like MMA, is supposed to be rapidly metabolized by body carboxylesterases. Hydrolysis of IBMA yields methacrylic acid and iso-butanol which are further metabolized by physiological pathways, methacroyl CoA being a physiological substrate of the valine pathway.

来源:Hazardous Substances Data Bank (HSDB)

代谢

丙烯酸酯和甲基丙烯酸酯主要通过迈克尔加成反应或谷胱甘肽-S-转移酶与谷胱甘肽结合而解毒。它们还可能通过羧酸酯酶发生水解。较低分子量的酯类被迅速代谢和排出，因此，不太可能引起累积毒性。

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

催泪剂（Lacrimator或Lachrymator）- 一种刺激眼睛并引起流泪的物质。

Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 毒性数据

LCLo（大鼠）= 200,000 毫克/立方米/4小时

LCLo (rat) = 200,000 mg/m3/4h

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 解毒与急救

立即急救：确保已经进行了充分去污。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、气囊面罩装置或口袋面罩，按训练进行操作。根据需要执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。/酯类及相关化合物/

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Esters and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道（如需要，使用口咽或鼻咽气道）。必要时进行抽吸。观察呼吸不足的迹象，必要时辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。提供低刺激环境。监测休克并视必要进行治疗……预见癫痫发作并视必要进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能够吞咽，有强烈的呕吐反射，并且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。通过快速复温治疗冻伤……。/酯类及相关化合物/

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Provide a low-stimulus environment. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Treat frostbite by rapid rewarming ... . /Esters and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊阀面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……监测心率和必要时治疗心律失常……开始静脉输注D5W/SRP：“保持开放”，最低流速/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸钠林格氏液（LR）。对于伴有低血容量迹象的低血压，谨慎给予液体。如果病人在正常液体容量下出现低血压，考虑使用血管加压药。注意液体过载的迹象……使用丙美卡因盐酸协助眼部冲洗……/酯类及相关化合物/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  Xi,N
• 安全说明：
  S24,S37,S61
• 危险类别码：
  R10,R36/37/38,R50,R43
• WGK Germany：
  1
• 海关编码：
  2916140000
• 危险品运输编号：
  UN 2283 3/PG 3
• 危险类别：
  3
• RTECS号：
  OZ4900000
• 包装等级：
  III
• 危险标志：
  GHS02,GHS07,GHS09
• 危险性描述：
  H226,H315,H317,H319,H335,H400
• 危险性防范说明：
  P261,P273,P280,P305 + P351 + P338
• 储存条件：
  储存注意事项： - 通常商品含有阻聚剂。 - 应存放在阴凉、通风的库房中，库温不宜超过37℃。 - 远离火种和热源。 - 包装需密封，避免与空气接触。 - 应与其他化学品分开存放，尤其是氧化剂、酸类和碱类，切忌混储。 - 不宜大量储存或长期保存。 - 使用防爆型照明和通风设施，并禁止使用能产生火花的机械设备和工具。 - 储存区应配备泄漏应急处理设备和合适的收容材料。

SDS

第一部分：化学品名称

制备方法与用途

化学性质
无色液体，易溶于醇和醚，而不溶于水。

用途
甲基丙烯酸异丁酯用作有机合成单体，广泛应用于树脂、塑料、涂料、印刷油墨、胶粘剂、润滑油添加剂、牙科材料、纤维处理剂及纸张涂饰剂等的生产。

此外，它还适用于树脂和涂料的合成以及粘结剂的制备。

生产方法
甲基丙烯酸异丁酯通过甲基丙烯酸与异丁醇在硫酸催化下进行酯化反应生成，然后经过精馏得到成品。另一种方法则是以丙酮氰醇为原料制得甲基丙烯酸。

反应信息

• 作为反应物：
  描述：

  甲基丙烯酸异丁酯 在 titanium(III) chloride 、 硫酸 、 双氧水 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Smith, Peter; Robertson, Jill Suzanne, Canadian Journal of Chemistry, 1988, vol. 66, p. 1153 - 1158

  摘要：

  DOI：
• 作为产物：
  描述：

  α-isobutoxy-isobutyric acid isobutyl ester 生成 甲基丙烯酸异丁酯
  参考文献：
  名称：

  Weizmann; Sulzbacher; Bergmann, Journal of the American Chemical Society, 1948, vol. 70, p. 1157

  摘要：

  DOI：

文献信息

• [EN] BENZAMIDE OR BENZAMINE COMPOUNDS USEFUL AS ANTICANCER AGENTS FOR THE TREATMENT OF HUMAN CANCERS<br/>[FR] COMPOSÉS BENZAMIDE OU BENZAMINE À UTILISER EN TANT QU'ANTICANCÉREUX POUR LE TRAITEMENT DE CANCERS HUMAINS
  申请人：UNIV TEXAS

  公开号：WO2017007634A1

  公开（公告）日：2017-01-12

  The described invention provides small molecule anti-cancer compounds for treating tumors that respond to cholesterol biosynthesis inhibition. The compounds selectively inhibit the cholesterol biosynthetic pathway in tumor-derived cancer cells, but do not affect normally dividing cells.

  所描述的发明提供了用于治疗对胆固醇生物合成抑制作出反应的肿瘤的小分子抗癌化合物。这些化合物选择性地抑制肿瘤来源的癌细胞中的胆固醇生物合成途径，但不影响正常分裂的细胞。
• Additives and products including oligoesters
  申请人：——

  公开号：US20030199593A1

  公开（公告）日：2003-10-23

  The present invention relates to oligoesters and their use or the creation of additives. Oligoester containing additives and/or oligoesters themselves may be used for formulating pharmaceutical preparations, cosmetics or personal care products such as shampoos and conditioners. These oligoesters are particularly useful for the creation of multi-purpose additives that can impart conditioning, long substantivity and/or UV protection. Individual oligoesters and oligoester mixtures are described.

  本发明涉及寡酯及其用途或添加剂的制备。含有寡酯的添加剂和/或寡酯本身可用于配制药物制剂、化妆品或个人护理产品，如洗发水和护发素。这些寡酯对于制备能够赋予调理、长效性和/或紫外线保护的多功能添加剂特别有用。描述了单独的寡酯和寡酯混合物。
• [EN] A DENTAL COMPOSITION<br/>[FR] COMPOSITION DENTAIRE
  申请人：STICK TECH OY

  公开号：WO2020035321A1

  公开（公告）日：2020-02-20

  A dental composition comprising10-50 wt-% of a methacrylate-based first matrix component, a polymerisation system and as a second matrix component 1-50 wt-% of a compound having a general formula (I).

  一种牙科组合物，包括10-50重量％的甲基丙烯酸酯基第一基体组分，一个聚合体系，以及作为第二基体组分的具有一般式(I)的化合物，其含量为1-50重量％。
• Enol ethers
  申请人：Eastman Chemical Company

  公开号：US10889536B1

  公开（公告）日：2021-01-12

  Disclosed are enol ethers compounds. The enol ethers exhibit low volatile organic content and are useful in a variety of chemical applications. The enol ethers can be used in applications as diluents, wetting agents, coalescing aids, paint additives and as intermediates in chemical processes. The enol ethers also have particular utility as film-hardening additives in coating formulations.

  披露了烯醇醚化合物。这些烯醇醚具有低挥发性有机成分，并且在各种化学应用中很有用。这些烯醇醚可以用作稀释剂、润湿剂、凝聚助剂、涂料添加剂以及化学过程中的中间体。这些烯醇醚在涂料配方中还具有特殊的用途，可作为硬化膜添加剂。
• AMPHOTERICIN B DERIVATIVES WITH IMPROVED THERAPEUTIC INDEX
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20160215012A1

  公开（公告）日：2016-07-28

  Provided are certain derivatives of amphotericin B (AmB) characterized by reduced toxicity and retained anti-fungal activity. Certain of the derivatives are C16 urea derivatives of AmB. Certain of the derivatives are C3, C5, C8, C9, C11, C13, or C15 deoxy derivatives of AmB. Certain of the derivatives include C3′ or C4′ modifications of the mycosamine appendage of AmB. Also provided are methods of making AmB derivatives of the invention, pharmaceutical compositions comprising AmB derivatives of the invention, and methods of use of AmB derivatives of the invention.

  提供了一些特定的两性霉素B（AmB）衍生物，其具有降低毒性和保留抗真菌活性的特点。其中一些衍生物是AmB的C16脲衍生物。其中一些衍生物是AmB的C3、C5、C8、C9、C11、C13或C15去氧衍生物。其中一些衍生物包括对AmB的甲氨葡萄糖胺附属物的C3′或C4′修饰。还提供了制备该发明的AmB衍生物的方法，包括该发明的AmB衍生物的药物组合物，以及该发明的AmB衍生物的使用方法。

表征谱图