2-羟基苯乙酸甲酯 | 22446-37-3

• 物质功能分类: 化学农药原药 - 杀菌剂 - 唑类杀菌剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-羟基苯乙酸甲酯
• 中文别名: 苯乙酸,2-羟基-,甲酯；(2-羟基苯基)-乙酸甲酯
• 英文名称: methyl (2-hydroxyphenyl)acetate
• 英文别名: methyl 2-(2-hydroxyphenyl)acetate；(2-hydroxy-phenyl)-acetic acid methyl ester；methyl o-hydroxyphenylacetate
• CAS: 22446-37-3
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: BVBSGGBDFJUSIH-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124℃
• 沸点：
  115-120℃ (0.3 Torr)
• 密度：
  1.181±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、甲醇（少许）
• 保留指数：
  1370.6

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2942000000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: (2-Hydroxy-phenyl)-acetic acid methyl ester
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: (2-Hydroxy-phenyl)-acetic acid methyl ester
CAS number: 22446-37-3

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H10O3
Molecular weight: 166.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质： 本品为白色粉状结晶，熔点70～72℃，难溶于水，但能溶于苯、甲苯和丙酮。

用途： 2-羟基苯乙酸甲酯是杀菌剂嘧菌酯的中间体。

生产方法： 其制备方法是将2-羟基苯乙酸加入含有氯化亚砜的甲醇溶液中，在室温下搅拌3小时，然后过滤。反应液在减压下浓缩后得到的残渣溶于乙醚，用碳酸氢钠溶液洗涤，并用水洗。随后，通过蒸馏乙醚溶液获得残留物，并使用乙醚/石油醚进行重结晶以得到最终产品。

反应信息

• 作为反应物：
  描述：

  2-羟基苯乙酸甲酯 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 三乙胺 、 copper(l) chloride 、 sodium nitrite 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 2.5h， 生成 芬氯酸
  参考文献：
  名称：

  具有抗炎活性的取代的（2-苯氧基苯基）乙酸。1。

  摘要：

  描述了一系列取代的（2-苯氧基苯基）乙酸的合成和抗炎活性。在佐剂关节炎试验中的初步筛选显示苯氧基环中的卤素取代大大增强了活性。用最小致溃疡剂量（MUD）衡量的致溃疡潜力在几乎所有测试的酸中均很低。[2-（2,4-二氯苯氧基）苯基]乙酸具有最有利的效价和低毒性，包括致溃疡性，该化合物现已用于治疗。

  DOI：

  10.1021/jm00364a004
• 作为产物：
  描述：

  苯乙酸甲酯 在 [RhCl2(p-cymene)]2 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以52%的产率得到2-羟基苯乙酸甲酯
  参考文献：
  名称：

  弱配位对钌（II / IV）催化的远端CH加氧的见解。

  摘要：

  芳基乙酰胺和烷基苯基乙酰基酯的CH羟基化反应是通过使用通用钌（II / IV）催化挑战远端弱O-配位而实现的。钌（II）催化的芳基乙酰胺的CH氧化通过CH活化，钌（II / IV）的氧化和还原性消除进行，从而提供了经济地获取有价值的酚的方法。所述p -cymene -钌（II / IV）歧管，通过详细的实验和DFT计算性研究确定。

  DOI：

  10.1002/chem.202003062
• 作为试剂：
  描述：

  1-(bromomethyl)-4-phenethylbenzene 、 2-羟基苯乙酸甲酯 在 2-羟基苯乙酸甲酯 作用下， 以90的产率得到methyl 2-(2-((4-phenethylbenzyl)oxy)phenyl)acetate
  参考文献：
  名称：

  J. Med. Chem. 2013, 56, 8948-8952

  摘要：

  DOI：

文献信息

• [EN] NOVEL CARBOXAMIDE DERIVATIVES AS HIV INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS CARBOXAMIDES COMME INHIBITEURS DU VIH
  申请人：HETERO RESEARCH FOUNDATION

  公开号：WO2011061590A1

  公开（公告）日：2011-05-26

  The present invention relates to carboxamide derivatives of Formula (I), where B1, B2, X, L, n, R, R1, R2, Z1, Z2, Rx and Ry are as defined in the claims, as compounds and compositions for inhibiting Human Immunodeficiency Virus (HIV) and process for making the compounds.

  本发明涉及公式（I）的羧酰胺衍生物，其中B1、B2、X、L、n、R、R1、R2、Z1、Z2、Rx和Ry如权利要求中所定义的那样，作为抑制人类免疫缺陷病毒（HIV）的化合物和组合物，以及制备这些化合物的方法。
• Redox‐Neutral Coupling between Two C(sp ³ )−H Bonds Enabled by 1,4‐Palladium Shift for the Synthesis of Fused Heterocycles
  作者：Ronan Rocaboy、Ioannis Anastasiou、Olivier Baudoin

  DOI：10.1002/anie.201908460

  日期：2019.10.7

  secondary C-H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C-H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp3 )-C(sp3 ) bonds.

  通过从三取代的芳基溴化物进行的1,4-Pd转移，可以使两个C（sp3）-H键形成一个C（sp3）-C（sp3）键进行分子内偶联。与大多数C（sp3）-C（sp3）交叉脱氢偶联相反，该反应在氧化还原中性条件下进行，其中C-Br键充当内部氧化剂。此外，它允许两个中等酸性的伯或仲CH键之间的偶联，其在一侧与氧或氮原子相邻，而在另一侧为苄基或与羰基相邻。从易于获得的邻溴苯酚和苯胺前体中获得了各种有价值的稠合杂环。第二个CH键裂解成功地被羰基插入取代，以生成其他类型的C（sp3）-C（sp3）键。
• Design and Synthesis of a Series of <scp>l</scp>-<i>trans</i>-4-Substituted Prolines as Selective Antagonists for the Ionotropic Glutamate Receptors Including Functional and X-ray Crystallographic Studies of New Subtype Selective Kainic Acid Receptor Subtype 1 (GluK1) Antagonist (2<i>S</i>,4<i>R</i>)-4-(2-Carboxyphenoxy)pyrrolidine-2-carboxylic Acid
  作者：Niels Krogsgaard-Larsen、Claudia G. Delgar、Karina Koch、Patricia M. G. E. Brown、Charlotte Møller、Liwei Han、Tri H. V. Huynh、Stinne W. Hansen、Birgitte Nielsen、Derek Bowie、Darryl S. Pickering、Jette Sandholm Kastrup、Karla Frydenvang、Lennart Bunch

  DOI：10.1021/acs.jmedchem.6b01516

  日期：2017.1.12

  receptor antagonists are valuable tool compounds for studies of neurological pathways in the central nervous system. On the basis of rational ligand design, a new class of selective antagonists, represented by (2S,4R)-4-(2-carboxyphenoxy)pyrrolidine-2-carboxylic acid (1b), for cloned homomeric kainic acid receptors subtype 1 (GluK1) was attained (Ki = 4 μM). In a functional assay, 1b displayed full antagonist

  离子型谷氨酸受体拮抗剂是用于研究中枢神经系统中神经通路的有价值的工具化合物。在合理的配体设计的基础上，针对（1 S）克隆的同型海藻酸受体亚型1的新型选择性拮抗剂，以（2 S，4 R）-4-（2-羧基苯氧基）吡咯烷-2-羧酸（1b）为代表达到（GluK1）（K i = 4μM）。在功能测定中，1b表现出完全的拮抗剂活性，IC 50 = 6±2μM。当结合在GluK1的配体结合结构域中时，获得1b的晶体结构。与具有谷氨酸的结构相比，可以看到13–14°的畴开放，与1b是拮抗剂。构效关系研究表明，连接吡咯烷环和苯环的束缚原子（C，O或S）的化学性质在受体选择性谱中起关键作用，并且苯环上的取代基被很好地容纳由GluK1受体。
• Green Esterification of Carboxylic Acids Promoted by <i>tert</i> ‐Butyl Nitrite
  作者：Yonggao Zheng、Yanwei Zhao、Suyan Tao、Xingxing Li、Xionglve Cheng、Gangzhong Jiang、Xiaobing Wan

  DOI：10.1002/ejoc.202100326

  日期：2021.5.14

  TBN‐catalyzed green esterification of carboxylic acids has been developed, which features a broad range of substrates and excellent functional groups tolerance. The mechanistic study confirmed that the nitrous acid formed in situ in the system is the actual catalyst for this transformation.

  已经开发了TBN催化的羧酸绿色酯化反应，它具有多种底物和出色的官能团耐受性。机理研究证实，在系统中原位形成的亚硝酸是该转化的实际催化剂。
• Aryl thiopyrano[2,3,4-C,D]indoles as inhibitors of leukotriene
  申请人：Merck Frosst Canada, Inc.

  公开号：US05314900A1

  公开（公告）日：1994-05-24

  Compounds having the formula I: ##STR1## are inhibitors of 5-lipoxygenase and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, psoriasis, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有I式化合物的化合物：##STR1##是5-脂氧合酶的抑制剂和白细胞三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还有助于治疗心绞痛、脑血管痉挛、肾小球肾炎、肝炎、内毒素血症、银屑病、葡萄膜炎和异体移植排斥，并预防动脉粥样硬化斑块的形成。

表征谱图