3-甲氧基苯酚 | 150-19-6

• 物质功能分类: 化学试剂 - 有机试剂 - 醚类
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-甲氧基苯酚
• 中文别名: 间甲氧基酚；间羟基苯甲醚；3-甲氧基酚；间甲氧基苯酚；间苯二酚单甲醚；3-羟基苯甲醚
• 英文名称: 3-Methoxyphenol
• 英文别名: O-methylresorcine；m-methoxyphenol
• CAS: 150-19-6
• 化学式: C₇H₈O₂
• mdl: MFCD00002267
• 分子量: 124.139
• InChiKey: ASHGTJPOSUFTGB-UHFFFAOYSA-N

物化性质

• 熔点：
  -17 °C
• 沸点：
  113-115 °C/5 mmHg (lit.)
• 密度：
  1.131 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）
• LogP：
  1.340
• 蒸汽压力：
  0.02 mmHg
• 亨利常数：
  5.80e-08 atm-m3/mole
• 保留指数：
  1211;1206.9;1211;1211
• 稳定性/保质期：
  1. 常温常压下稳定。 2. 存在于香料烟烟叶和烟气中。 3. 天然存在于芸香油、芹菜子油、烟叶油、橙叶蒸馏液和海狸香中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

毒理性

• 毒性数据

大鼠LC50 = 11,500毫克/立方米/4小时

LC50 (rat) = 11,500 mg/m3/4hr

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

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  29095090
• 危险品运输编号：
  UN 2810 6.1/PG 3
• 危险类别：
  6.1
• RTECS号：
  SL7524000
• 包装等级：
  III
• 危险标志：
  GHS05,GHS06
• 危险性描述：
  H302 + H332,H311,H315,H318
• 危险性防范说明：
  P280,P305 + P351 + P338,P312
• 储存条件：
  请将密封存储在干燥阴凉的地方。

SDS

Name:	3-Methoxyphenol 97% Material Safety Data Sheet
Synonym:	m-Hydroxyanisol
CAS:	150-19-6

Section 1 - Chemical Product MSDS Name:3-Methoxyphenol 97% Material Safety Data Sheet
Synonym:m-Hydroxyanisol

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
150-19-6	3-METHOXYPHENOL	97%	205-754-6

Hazard Symbols: XN
Risk Phrases: 20/21/22 36

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes.
Potential Health Effects
Eye:
Causes severe eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin. May cause skin discoloration.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation.
Chronic:
Chronic exposure may cause visual disturbances.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. Get medical aid if cough or other symptoms appear.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Water or foam may cause frothing. Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use only in a well-ventilated area.
Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 150-19-6: Russia: 0.5 mg/m3 TWA Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear pink red
Odor: Odor of caramel and phenol
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 243 - 246 deg C @ 760.00mm Hg
Freezing/Melting Point: -17 deg C
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble in water
Specific Gravity/Density: 1.1310g/cm3
Molecular Formula: C7H8O2
Molecular Weight: 124.14

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Bases - acid chlorides - acid anhydrides - oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 150-19-6: SL7524000 LD50/LC50:
CAS# 150-19-6: Draize test, rabbit, eye: 5% Severe; Draize test, rabbit, eye: 100%; Draize test, rabbit, skin: 100%; Inhalation, mouse: LC50 = 11500 mg/m3/4H; Inhalation, rat: LC50 = 11500 mg/m3/4H; Oral, mouse: LD50 = 312 mg/kg; Oral, mouse: LD50 = 312 mg/kg; Oral, rat: LD50 = 597 mg/kg; Oral, rat: LD50 = 597 mg/kg; Skin, rat: LD50 = 682 mg/kg.
Carcinogenicity:
3-METHOXYPHENOL - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36 Irritating to eyes.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 150-19-6: No information available.
Canada
CAS# 150-19-6 is listed on Canada's NDSL List.
CAS# 150-19-6 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 150-19-6 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

3-甲氧基苯酚又称为间甲氧基苯酚，是间苯二酚的单甲醚，是一种关键的医药化工原料。它广泛应用于塑料抗氧化防老剂、杀菌剂以及感光材料等多个领域。

制备 催化剂制备：

1. 将1摩尔十六烷基三甲基溴化铵加入到0.1摩尔/升氢氧化钠水溶液中，搅拌混合溶解。缓慢加入1摩尔正硅酸乙酯继续搅拌。

2. 溶胶在100℃下进行水热晶化三天。产物经过滤、洗涤，并在60℃烘箱中干燥过夜。

3. 在500℃下焙烧6小时，得到纯硅MCM-41分子筛。

4. 取300克的MCM-41分子筛加入到0.1摩尔/升氯化锌溶液中。确保氯化锌与MCM-41的质量比为1:20，并添加少量有机分散剂。

5. 快速搅拌升温，进行回流水解。然后缓慢滴加饱和碳酸氢铵溶液至溶液呈中性，停止加热并自然冷却静置一段时间。

6. 过滤洗涤后低温烘干，固体物在硫酸铵溶液中浸渍，除去溶液，并在烘箱中烘干。随后在马弗炉中于600℃下焙烧7小时，得到S2O82-/Al-MCM-41催化剂。

3-甲氧基苯酚制备：

在反应精馏塔的反应段装载上述步骤(1)制备的S2O82-/Al-MCM-41催化剂。该反应精馏塔包括反应段、提馏段和精馏段，其中反应段的理论塔板数为10块；提馏段为12块，而精馏段的理论塔板数为25块。

将间苯二酚与甲醇进料至反应精馏塔内进行醚化反应。控制反应温度在80～82℃之间，进料位置位于反应精馏塔填料的上端。反应后从塔釜连续采出合成的3-甲氧基苯酚产品。检测结果显示，间苯二酚转化率为98.1%，3-甲氧基苯酚的选择性为95.3%，且采出产品的HPLC纯度超过95%。

化学性质

无色透明到淡黄色液体，沸点244℃。

用途

是一种重要的有机合成中间体。

反应信息

• 作为反应物：
  描述：

  3-甲氧基苯酚 在 硫酸 sodium tetrahydroborate 作用下， 生成 4-(hydroxymethyl)-7-methoxycoumarin
  参考文献：
  名称：

  带有不同类型键的荧光氨基酸缀合物的光解研究

  摘要：

  3-氧代-3 H-苯并吡喃衍生物的合成和光化学反应，这些酯通过酯，酸酐，氨基甲酸酯和碳酸酯键与代表性的I-氨基酸相连，位于主链的氨基和羧酸基团或侧链的羟基上，进行了。在不同的照射波长（254、300和350 nm）下研究了所得共轭物对光解的稳定性，其中酸酐和酯键在所研究的条件下最敏感。

  DOI：

  10.1016/j.tet.2006.11.082
• 作为产物：
  描述：

  间苯二甲醚 在 copper(I) oxide 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以83%的产率得到3-甲氧基苯酚
  参考文献：
  名称：

  Cu 2 O催化芳烷基醚的高效脱烷基

  摘要：

  已经描述了在廉价且易于重复使用的Cu 2 O催化下使芳基烷基醚脱烷基的有效方案。以高收率获得苯酚产物，并且对一系列官能团的耐受性良好。溶剂的选择对催化至关重要，事实证明，CH 3 OH是最佳选择。机理研究表明，该反应可能通过单电子转移（SET）过程进行。

  DOI：

  10.1016/j.tet.2018.03.070
• 作为试剂：
  描述：

  sodium ethanolate 、 四氯苯醌 在 3-甲氧基苯酚 作用下， 生成 2,3,5,6-tetraethoxycyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Briggs,L.H. et al., Australian Journal of Chemistry, 1976, vol. 29, p. 179 - 190

  摘要：

  DOI：

文献信息

• BENZOTHIOPHENE INHIBITORS OF RHO KINASE
  申请人：Kahraman Mehmet

  公开号：US20080021026A1

  公开（公告）日：2008-01-24

  The present invention relates to compounds and methods which may be useful as inhibitors of Rho kinase for the treatment or prevention of disease.

  本发明涉及化合物和方法，这些化合物和方法可能作为Rho激酶的抑制剂在治疗或预防疾病方面有用。
• Phenyl 4-(2-oxopyrrolidin-1-yl)benzenesulfonates and phenyl 4-(2-oxopyrrolidin-1-yl)benzenesulfonamides as new antimicrotubule agents targeting the colchicine-binding site
  作者：Mathieu Gagné-Boulet、Chahrazed Bouzriba、Atziri Corin Chavez Alvarez、Sébastien Fortin

  DOI：10.1016/j.ejmech.2020.113136

  日期：2021.3

  agents designated as N-phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB–SOs) and phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamides (PIB–SAs). Our previous structure-activity relationship studies (SAR) focused on the aromatic ring B of PIB-SOs and PIB-SAs leaving the impact of the phenylimidazolidin-2-one moiety (ring A) on the binding to the colchicine-binding site (C-BS) poorly studied. Therefore

  我们最近设计并制备了新的有效抗微管剂家族，命名为N4-（2-氧代咪唑啉-1-基）苯磺酸苯酯（PIB-SOs）和4-（2-氧代咪唑啉-1-基）苯磺酰胺（PIB-SAs）。我们之前的结构活性关系研究（SAR）专注于PIB-SO和PIB-SA的芳香环B，而苯基咪唑啉二-2-酮部分（环A）对秋水仙碱结合位点的结合（C -BS）学习得不好。因此，本研究的目的是评估由吡咯烷-2-酮部分取代咪唑烷-2--2-酮（IMZ）的效果。为此，设计，制备了15种新的4-（2-氧杂吡咯烷-1-基）苯磺酸苯基酯（PYB-SO）和15种苯基4-（2-氧杂吡咯烷-1-基）苯磺酸酰胺（PYB-SA）衍生物，化学表征和生物学评估。PYB-SO和PYB-SA在低纳摩尔至低微摩尔范围内显示抗增殖活性（0。在人HT-1080，HT-29，M21和MCF7癌细胞系上分别为0087–8.6μM和0.056–21μM）。而且，它们阻断了G2
• Design and synthesis of novel, potent and selective hypoxanthine analogs as adenosine A 1 receptor antagonists and their biological evaluation
  作者：Summon Koul、Vidya Ramdas、Dinesh A. Barawkar、Yogesh B. Waman、Neela Prasad、Santosh Kumar Madadi、Yogesh D. Shejul、Rajesh Bonagiri、Sujay Basu、Suraj Menon、Srinivasa B. Reddy、Sandhya Chaturvedi、Srinivas Rao Chennamaneni、Gaurav Bedse、Rhishikesh Thakare、Jayasagar Gundu、Sumit Chaudhary、Siddhartha De、Ashwinkumar V. Meru、Venkata Palle、Anita Chugh、Kasim A. Mookhtiar

  DOI：10.1016/j.bmc.2017.02.029

  日期：2017.3

  Multipronged approach was used to synthesize a library of diverse C-8 cyclopentyl hypoxanthine analogs from a common intermediate III. Several potent and selective compounds were identified and evaluated for pharmacokinetic (PK) properties in Wistar rats. One of the compounds 14 with acceptable PK parameters was selected for testing in in vivo primary acute diuresis model. The compound demonstrated

  多管齐下的方法用于从常见的中间体III合成各种C-8环戊基次黄嘌呤类似物的文库。鉴定了几种有效的和选择性的化合物，并评估了Wistar大鼠的药代动力学（PK）特性。选择具有可接受的PK参数的化合物14之一用于体内原发性急性利尿模型的测试。该化合物在该模型中显示出明显的利尿活性。
• Design and Synthesis of Sn-Porphyrin Based Molecular Gates
  作者：Aurélie Guenet、Ernest Graf、Nathalie Kyritsakas、Mir Wais Hosseini

  DOI：10.1021/ic902265e

  日期：2010.2.15

  The design, synthesis, and structural characterization, both in solution by 1H NMR and in the solid state by X-ray diffraction on single crystals, of a series of molecular gates based on Sn-porphyrin derivatives are presented. The molecular system is based on a porphyrin core bearing at the meso positions either phenyl or pyridyl groups as a stator, octahedral Sn(IV) cation located at the center of

  提出了一系列基于锡卟啉衍生物的分子门的设计，合成和结构表征，无论是通过1 H NMR在溶液中还是在固体中通过X射线衍射在单晶上。分子系统是基于在卟啉芯轴承内消旋位置任一苯基或吡啶基作为定子，八面体的Sn（IV）阳离子位于卟啉作为铰链的中心，和不同的手柄至Sn-连接到卟啉O轴向键。还报道了在不同酸存在下复合物的稳定性。
• Synthesis of near-infrared fluorescent rhodamines <i>via</i> an S_NAr^H reaction and their biological applications
  作者：Qing Wang、Kun Huang、Songtao Cai、Chang Liu、Xiaojie Jiao、Song He、Liancheng Zhao、Xianshun Zeng

  DOI：10.1039/c8ob01701h

  日期：——

  the preparation of a wide variety of π-extended near-infrared fluorescent rhodamine dyes. Using this strategy, seven rectilinearly π-extended rhodamines (RE1–RE7) that had fluorescence emission wavelengths in the near-infrared region were synthesized. RE1, RE3, and RE4 were lysosome targetable and showed good photostabilities. In addition, using dye RE1 as a precursor, we constructed a novel NIR fluorescent

  由于减少了来自生物样品的干扰吸收和荧光，减少了散射并提高了组织穿透深度，近红外（NIR）染料在生物医学中引起了人们的极大兴趣。在这种情况下，我们报告了使用芳香族氢的独特分子内亲核取代（S N Ar H）策略合成直线π延伸的若丹明染料的方法。该策略利用了预先组织的芳族氨基氮与x吨离子中电子不足的碳之间的S N Ar H反应。S N Ar H本文提出的反应可在没有过渡金属催化剂的温和条件下进行，并且有望实现多种π扩展的近红外荧光若丹明染料的制备。使用这种策略，合成了在近红外区域具有荧光发射波长的七个直线π扩展的若丹明（RE1-RE7）。RE1，RE3和RE4可溶酶体靶向，并显示出良好的光稳定性。此外，我们以染料RE1为前体，构建了一种新型的NIR荧光开启探针（RE1-Cu），可用于检测Cu 2+ 在活细胞中的含量，证明了我们近红外功能荧光染料的价值。

表征谱图