cis-3-氯丙烯酸 | 1609-93-4

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酸
• 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: cis-3-氯丙烯酸
• 中文别名: 顺-3-氯代丙烯酸；顺-3-氯丙烯酸；顺-3-氯代丙烯酸, 98+%
• 英文名称: 3-chloroacrylic acid
• 英文别名: cis-3-Chloroacrylic acid；(Z)-3-chloroprop-2-enoic acid
• CAS: 1609-93-4
• 化学式: C₃H₃ClO₂
• 分子量: 106.509
• InChiKey: MHMUCYJKZUZMNJ-UPHRSURJSA-N

物化性质

• 熔点：
  61-62 °C(lit.)
• 沸点：
  118.27°C (rough estimate)
• 密度：
  1.2288 (rough estimate)
• 溶解度：
  可溶于氯仿（轻微）、甲醇（非常轻微）
• 稳定性/保质期：
  常温常压下稳定，避免与氧化物、碱和热直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S24/25,S26
• 危险类别码：
  R34
• WGK Germany：
  3
• 海关编码：
  2916190090
• 危险品运输编号：
  UN 3261 8/PG 2
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P301+P330+P331,P280,P305+P351+P338,P310
• 危险性描述：
  H314
• 储存条件：
  密封冷藏

SDS

Name:	Cis-3-Chloroacrylic Acid 98% Material Safety Data Sheet
Synonym:	None known
CAS:	1609-93-4

Section 1 - Chemical Product MSDS Name:Cis-3-Chloroacrylic Acid 98% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1609-93-4	Cis-3-Chloroacrylic Acid	98	216-545-4

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Corrosive.
Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns. May cause perforation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May cause systemic effects.
Inhalation:
May cause severe irritation of the respiratory tract with sore throat, coughing, shortness of breath and delayed lung edema. Causes chemical burns to the respiratory tract. The toxicological properties of this substance have not been fully investigated.
Aspiration may lead to pulmonary edema. May cause systemic effects.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Destroy contaminated shoes.
Ingestion:
Do not induce vomiting. 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 immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Use extinguishing media appropriate to the surrounding fire. Substance is noncombustible.
Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
Extinguishing Media:
Do NOT get water inside containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use dry chemical, carbon dioxide, alcohol-resistant foam, or water spray.
Cool containers with flooding quantities of water until well after fire is out.

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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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Do not breathe dust, vapor, mist, or gas. Keep container tightly closed. Avoid ingestion and inhalation. Discard contaminated shoes.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Corrosives area.

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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# 1609-93-4: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white
Odor: acrid odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 61.00 - 62.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C3H3ClO2
Molecular Weight: 106.51

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1609-93-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Cis-3-Chloroacrylic Acid - Not listed by ACGIH, IARC, or NTP.

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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
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: II
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: II
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1609-93-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1609-93-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1609-93-4 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

反应信息

• 作为反应物：
  描述：

  cis-3-氯丙烯酸 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 240.0h， 以96.5%的产率得到3,3-dichloropropionic acid
  参考文献：
  名称：

  Glutathione Transferase Zeta-Catalyzed Biotransformation of Dichloroacetic Acid and Other α-Haloacids

  摘要：

  Dichloroacetic acid (DCA) is a common drinking-water contaminant, is hepatocarcinogenic in rats and mice, and is a therapeutic agent used clinically in the management of lactic acidosis. Recent studies show that glutathione transferase Zeta (GSTZ) catalyzes the oxygenation of DCA to glyoxylic acid [Tong et al. (1998) Biochem. J. 331, 371-374]. In the present studies, the substrate selectivity of GSTZ, the kinetics of DCA metabolism, and the fate of DCA and glutathione were investigated. The results showed that GSTZ catalyzed the oxygenation of bromochloro-, bromofluoro-, chlorofluoro-, dibromo-, and dichloroacetic acid, but not difluoroacetic acid, to glyoxylic acid. GSTZ also catalyzed the biotransformation of fluoroacetic acid to S-(carboxymethyl)glutathione, and of(R, S)-2-bromopropionic acid, (R)-, (S)-, and (R,S)-2-chloropropionic acid, and (R,S)-2-iodopropionic acid, but not (R,S)-2-fluoropropionic acid, to S-(alpha-methylcarboxymethyl)glutathione; and of 2,2-dichloropropionic acid to pyruvate. No biotransformation of 3,3-dichloropropionic acid was detected, and no GSTZ-catalyzed fluoride release from ethyl fluoroacetate and fluoroacetamide was observed. The relative rates of DCA biotransformation by hepatic cytosol were mouse > rat > human. Immunoblotting showed the presence of GSTZ in mouse, rat, and human liver cytosol. C-13 NMR spectroscopic studies showed that [2-C-13]glyoxylic acid was the only observable, stable metabolite of [2-13C]DCA. Also, glutathione was required, but was neither consumed nor oxidized to glutathione disulfide, during the oxygenation of DCA to glyoxylic acid. These results are consistent, with a reaction mechanism that involves displacement of chloride from DCA by glutathione to afford S-(alpha-chlorocarboxymethyl)glutathione, which may undergo hydrolysis to give the hemithioacetal S-(alpha-hydroxycarboxymethyl)glutathione. Elimination of glutathione from the hemithioacetal would give glyoxylic acid.

  DOI：

  10.1021/tx980144f
• 作为产物：
  描述：

  丙炔酸 在 copper(l) chloride 盐酸 作用下， 反应 10.0h， 以78%的产率得到cis-3-氯丙烯酸
  参考文献：
  名称：

  光学纯环氧聚炔的一般途径：拒食性天然产物的不对称合成

  摘要：

  描述了使用光学纯的（2R，3S）-5-溴-2,3-环氧-4-戊炔-1-醇1a作为关键中间体的通用的不对称方法。从该中间体以6个步骤进行了2种环氧聚炔天然产物的合成，总收率为42％。

  DOI：

  10.1016/s0040-4020(01)82372-3

文献信息

• [EN] FGFR4 INHIBITORS<br/>[FR] INHIBITEURS DE FGFR4
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2016164754A1

  公开（公告）日：2016-10-13

  We provide FGFR inhibitors, their salts, methods of manufacture, and methods of use.

  我们提供FGFR抑制剂，它们的盐，制造方法和使用方法。
• [EN] PYRIMIDINE FGFR4 INHIBITORS<br/>[FR] INHIBITEURS DE FGFR4 PYRIMIDINE
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2015057938A1

  公开（公告）日：2015-04-23

  Provided herein are compounds of Formula I useful as FGFR4 inhibitors, as well as methods of use of the same.

  本文提供了作为FGFR4抑制剂有用的I式化合物，以及其使用方法。
• HYDROCHLORINATION OF 2,3-ACETYLENIC ACIDS WITH THIONYL CHLORIDE IN DIMETHYLFORMAMIDE
  作者：Neudo A. Urdaneta、Julio C. Herrera、José Salazar、Simón E. López

  DOI：10.1081/scc-120012990

  日期：2002.1

  ABSTRACT The reaction of 2,3-acetylenic acids (1a–d) with thionyl chloride in DMF under mild conditions gave E,Z-3-chloro-2-alkenoic acids (2a–d) or esters (3a–d) depending on treating the reaction mixture with either water or alcohols.

  摘要 在温和条件下，2,3-炔酸（1a-d）与亚硫酰氯在 DMF 中的反应得到 E,Z-3-氯-2-链烯酸（2a-d）或酯（3a-d），具体取决于用水或醇处理反应混合物。
• [EN] FUSED PYRIMIDINE COMPOUNDS, COMPOSITIONS AND MEDICINAL APPLICATIONS THEREOF<br/>[FR] COMPOSÉS DE PYRIMIDINE FUSIONNÉS, COMPOSITIONS ET APPLICATIONS MÉDICALES ASSOCIÉES
  申请人：JUBILANT BIOSYS LTD

  公开号：WO2021062327A1

  公开（公告）日：2021-04-01

  The present disclosure relates to a class of fused pyrimidine compounds of Formula I, their stereoisomers, tautomers, pharmaceutically acceptable salts, polymorphs, solvates, and hydrates thereof. The present disclosure also relates to a process of preparation of these fused pyrimidine compounds, and to pharmaceutical compositions containing them.

  本公开涉及一类式I的融合嘧啶化合物，它们的立体异构体、互变异构体、药用可接受盐、多型体、溶剂合物和水合物。本公开还涉及制备这些融合嘧啶化合物的方法，以及含有它们的药物组合物。
• Irreversible inhibitors of tyrosine kinases
  申请人：Warner-Lambert Company

  公开号：US06344459B1

  公开（公告）日：2002-02-05

  The present invention provides compounds that are irreversible inhibitors of tyrosine kinases. Also provided is a method of treating cancer, restenosis, atherosclerosis, endometriosis, and psoriasis and a pharmaceutical composition that comprises a compound that is an irreversible inhibitor of tyrosine kinases.

  本发明提供了一种不可逆抑制酪氨酸激酶的化合物。还提供了一种治疗癌症、再狭窄、动脉粥样硬化、子宫内膜异位症和牛皮癣的方法，以及包含一种不可逆抑制酪氨酸激酶的化合物的药物组合物。

表征谱图