2-[2-(苯硫基)苯基]乙酸 | 1527-17-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 2-[2-(苯硫基)苯基]乙酸
• 中文别名: 2-[2-(苯基硫代)苯基]乙酸
• 英文名称: 2-[2-(phenylsulfanyl)phenyl]acetic acid
• 英文别名: 2-(2-(phenylthio)phenyl)acetic acid；2-(Phenylthio)benzolessigsaeure；BTB15078；[2-(phenylthio)phenyl]acetic acid；phenylthiobenzeneacetic acid；<2-(Phenylthio)-phenyl>-essigsaeure；2-[2-(Phenylthio)Phenyl]Acetic Acid；2-(2-phenylsulfanylphenyl)acetic acid
• CAS: 1527-17-9
• 化学式: C₁₄H₁₂O₂S
• mdl: MFCD01312192
• 分子量: 244.314
• InChiKey: JMIYLNQBNSEKAO-UHFFFAOYSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  205 °C(Press: 1.2 Torr)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Name:	2-[2-(phenylthio)phenyl]acetic acid 97% Material Safety Data Sheet
Synonym:
CAS:	1527-17-9

Section 1 - Chemical Product MSDS Name:2-[2-(phenylthio)phenyl]acetic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1527-17-9	2-[2-(Phenylthio)phenyl]acetic acid	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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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:
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:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1527-17-9: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 116 - 120 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C14H12O2S
Molecular Weight: 244

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1527-17-9: AJ3262000 LD50/LC50:
Not available.
Carcinogenicity:
2-[2-(Phenylthio)phenyl]acetic acid - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 1527-17-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1527-17-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1527-17-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

2-[(苯硫基)苯基]乙酸是一种羧酸类衍生物，可作为医药中间体使用。

反应信息

• 作为反应物：
  描述：

  2-[2-(苯硫基)苯基]乙酸 在 polyphosphoric acid 作用下， 反应 4.0h， 以92%的产率得到二苯并[B,F]硫杂卓-10(11H)-酮
  参考文献：
  名称：

  烷基腈与芳基亚砜的氧化还原中性 α-芳基化：快速亲电重排

  摘要：

  通过简单地将 Tf2O 和 DABCO 引入腈和芳基亚砜的混合物中，已经开发了一种简便的腈的 α-芳基化。转化由两个连续步骤组成：（i）Tf2O 引发的亲电组装和（ii）DABCO 触发的重排。每个步骤都可以通过改变温度和/或碱来独立调整。这种可调节性允许该方法适应广泛的基材。这种新协议的显着特点包括显着的效率（20 分钟，-30 °C）、独特的区域选择性和高功能组兼容性，这在传统方法中可能是具有挑战性的问题。核磁共振研究不仅确定了一种独特的、高度不稳定的锍亚胺配合物，而且还证明了温度在这一关键中间体的形成和操作中的重要性。进一步的 DFT 计算表明，亲电组装，然后去除 HOTf（通过碱），最后 [3,3]-σ 重排是反应的三个关键阶段。此处还展示了产品的多功能可转化性和该反应的易扩展性。

  DOI：

  10.1021/jacs.7b00969
• 作为产物：
  描述：

  2-(2-碘苯基)乙酸甲酯 在 copper(l) iodide 、 新铜试剂 、 potassium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 10.0h， 生成 2-[2-(苯硫基)苯基]乙酸
  参考文献：
  名称：

  Synthesis of targeted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines as potential lead molecules with promising anti-breast cancer activity

  摘要：

  A targeted library of substituted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines (prototypes I, II and III), and structurally analogous to tamoxifen have been synthesized as a new class of anti-breast cancer agents. All the prototype molecules exhibited potential antiproliferative activity against ER + ve and ER-ye breast cancer cell lines. Dibenzo[b,f]thiepine prototypes were found to be more active. Of all the compound tested, 14b exhibited potent in-vitro antiproliferative activity at 133 mu M and 5 mu M concentration in MCF-7 and MDA-MB-231 cell lines and was devoid of any cytotoxicity in normal HEK cells even at 50 mu M. Cell cycle analysis showed that the compound 14b inhibited cell proliferation due to G0/G1 arrest in MCF-7 cells. Annexin-V FITC and PI staining experiments confirmed that the cell inhibition was primarily due to apoptosis and not by necrosis, which was also supported by LDH release assay experiment. Molecular docking studies showed better binding interaction of the new dibenzo[b,f]thiepine analogue 14b with the estrogen receptor (ER) as compared to 4-hydroxy-tamoxifen and this enhanced binding might be responsible for its estrogen antagonistic activity that induces cell cycle arrest, apoptosis and inhibition of breast cancer cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.035

文献信息

• Ramoplanin derivatives possessing antibacterial activity
  申请人：Raju G. Bore

  公开号：US20060211603A1

  公开（公告）日：2006-09-21

  Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.

  新型拉莫普兰衍生物已被披露。这些拉莫普兰衍生物表现出抗菌活性。由于本发明的化合物对革兰氏阳性细菌表现出强效活性，它们是有用的抗微生物药剂。该化合物的合成方法和使用方法也已被披露。
• [EN] SPIRO COMPOUNDS USEFUL AS ANTAGONISTS OF THE H1 RECEPTOR<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXO GROUP LTD

  公开号：WO2009016085A1

  公开（公告）日：2009-02-05

  The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, for treating diseases and conditions of the central nervous system (CNS), in particular sleep disorders.

  该发明提供了化合物的公式(I)或其药学上可接受的盐，用于治疗中枢神经系统（CNS）疾病和症状，特别是睡眠障碍。
• A Cu-Catalysed Radical Cross-Dehydrogenative Coupling Approach to Acridanes and Related Heterocycles
  作者：Timothy E. Hurst、Richard J. K. Taylor

  DOI：10.1002/ejoc.201601336

  日期：2017.1.3

  The synthesis of acridanes and related compounds through a Cu‐catalysed radical cross‐dehydrogenative coupling of simple 2‐[2‐(arylamino)aryl]malonates is reported. This method can be further streamlined to a one‐pot protocol involving the in situ fomation of the 2‐[2‐(arylamino)aryl]malonate by α‐arylation of diethyl malonate with 2‐bromodiarylamines under Pd catalysis, followed by Cu‐catalysed cyclisation

  据报道，通过简单的 2-[2-(芳基氨基)芳基]丙二酸酯的铜催化自由基交叉脱氢偶联合成吖啶类和相关化合物。该方法可以进一步简化为一锅法，涉及通过丙二酸二乙酯与 2-溴二芳基胺在 Pd 催化下进行 α-芳基化，然后在 Cu 催化下原位形成 2-[2-(芳基氨基)芳基]丙二酸酯环化。
• Spiro Compounds Useful as Antagonists of the H1 Receptor
  申请人：Botta Maurizio

  公开号：US20100311734A1

  公开（公告）日：2010-12-09

  The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, for treating diseases and conditions of the central nervous system (CNS), in particular sleep disorders.

  该发明提供了化合物I式或其药学上可接受的盐，用于治疗中枢神经系统（CNS）的疾病和症状，特别是睡眠障碍。
• Overcoming chloroquine resistance in malaria: Design, synthesis and structure–activity relationships of novel chemoreversal agents
  作者：Aicha Boudhar、Xiao Wei Ng、Chiew Yee Loh、Wan Ni Chia、Zhi Ming Tan、Francois Nosten、Brian W. Dymock、Kevin S.W. Tan

  DOI：10.1016/j.ejmech.2016.04.058

  日期：2016.8

  Malaria remains a significant infectious disease with even artemisinin-based therapies now facing resistance in the field. Development of new therapies is urgently needed, either by finding new compounds with unique modes of action, or by reversing resistance towards known drugs with 'chemosensitizers' or 'chemoreversal' agents (CRA). Concerning the latter, we have focused on the resistance mechanisms developed against chloroquine (CQ). We have synthesized a series of compounds related to previously identified CRAs, and found promising novel compounds. These compounds show encouraging results in a coumarin labeled chloroquine uptake assay, exhibiting a dose response in resensitising parasites to the antimalarial effects of chloroquine. Selected compounds show consistent potency across a panel of chloroquine and artemisinin sensitive and resistant parasites, and a wide therapeutic window. This data supports further study of CRAs in the treatment of malaria and, ultimately, their use in chloroquine-based combination therapies. (C) 2016 Elsevier Masson SAS. All rights reserved.