2-氯代丙烯酸甲酯 | 80-63-7

• 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: 2-氯代丙烯酸甲酯
• 中文别名: Α-氯丙烯酸甲酯；2-氯丙烯酸甲酯；alpha-氯丙烯酸甲酯；甲基氯代丙酸酯
• 英文名称: methyl 2-chloroacrylate
• 英文别名: methyl α-chloroacrylate；methyl 2-chloroprop-2-enoate；methyl 2-chloropropenoate；2-chloroacrylic acid methyl ester
• CAS: 80-63-7
• 化学式: C₄H₅ClO₂
• mdl: MFCD00051368
• 分子量: 120.535
• InChiKey: AWJZTPWDQYFQPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  -37 °C
• 沸点：
  52 °C (50 mmHg)
• 密度：
  1.189
• 闪点：
  33 °C
• 物理描述：
  Methyl 2-chloroacrylate is a colorless liquid. Used to make acrylic high polymer with properties closely resembling those of polymethylmethacrylate. Monomer for specialty polymers (e.g., aircraft glazing). (EPA, 1998)
• 颜色/状态：
  COLORLESS LIQUID
• 溶解度：
  less than 1 mg/mL at 72° F (NTP, 1992)
• 分解：
  When heated to decomposition it emits toxic fumes of /hydrogen chloride/.
• 聚合：
  METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/
• 折光率：
  Index of refraction: 1.4420 @ 20 °C/D
• 保留指数：
  748;766;766;748;766
• 稳定性/保质期：

  遇热分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。 Lacrimator (Lachrymator) - 刺激眼睛并引起流泪的物质。 Toxic Pneumonitis - 由于吸入金属烟雾或有毒气体和蒸气引起的肺部炎症。

Dermatotoxin - Skin burns. Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears. Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

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

毒理性

• 毒性数据

大鼠LC50 = 500毫克/立方米/2小时

LC50 (rat) = 500 mg/m3/2h

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

毒理性

• 人类毒性摘录

这是一种呼吸毒剂，吸入其蒸汽可能导致肺水肿。即使在非常低的浓度（5-10 ppm）下，这种单体蒸汽对眼睛也有很强的刺激性。

IT IS ... A RESPIRATORY POISON, & BREATHING ITS VAPORS CAN CAUSE PULMONARY EDEMA. EVEN AT VERY LOW CONCN (5-10 PPM) THE VAPORS OF THIS MONOMER HAVE VERY IRRITATING ACTION ON EYES.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

将一个CH3基团...替换为一个氯原子会显著增加其刺激性特性。

REPLACEMENT OF A CH3 GROUP ... BY A CHLORINE ATOM CONSIDERABLY INCREASES THE IRRITANT PROPERTIES.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

甲基-α-氯丙烯酸酯是一种强烈的发疱剂；皮肤上微量接触就会引起大水泡。

Methyl-alpha-chloroacrylate is a strong vesicant; a trace on the skin causes large blisters.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  T+
• 安全说明：
  S16,S26,S36/37/39,S38,S45
• 危险类别码：
  R26,R34,R10,R24/25
• 海关编码：
  29161995
• 危险品运输编号：
  UN 2927
• 包装等级：
  II
• 危险类别：
  6.1(a)
• 储存条件：
  密封贮藏，存放在阴凉干燥处，并远离火源。

SDS

Name:	Methyl Alpha-Chloroacrylate 99% (GC) Material Safety Data Sheet
Synonym:	2-Chloroacrylic Acid, Methyl Ester; Methyl-Alpha-Chloroacrylate; Methyl-2-Chloroacrylate; Methyl 2-Chloro-2-Propenoate
CAS:	80-63-7

Section 1 - Chemical Product MSDS Name:Methyl Alpha-Chloroacrylate 99% (GC) Material Safety Data Sheet
Synonym:2-Chloroacrylic Acid, Methyl Ester; Methyl-Alpha-Chloroacrylate; Methyl-2-Chloroacrylate; Methyl 2-Chloro-2-Propenoate

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
80-63-7	Methyl-2-Chloroacrylate	99	201-298-7

Hazard Symbols: C
Risk Phrases: 10 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Flammable. Causes burns.Corrosive.Lachrymator (substance which increases the flow of tears).
Potential Health Effects
Eye:
Causes eye burns. Lachrymator (substance which increases the flow of tears). May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. This material is a vesicant, that is, it will induce blistering. May cause cyanosis of the extremities. 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. May cause gastrointestinal irritation with nausea, vomiting and diarrhea. Causes gastrointestinal tract burns. May cause perforation of the digestive tract. Ingestion of large amounts may cause CNS depression. May cause systemic effects.
Inhalation:
May be fatal if inhaled. Causes chemical burns to the respiratory tract. Aspiration may lead to pulmonary edema. Vapors may cause dizziness or suffocation. May cause systemic effects. May cause burning sensation in the chest.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid immediately. 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. 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. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Will burn if involved in a fire. Use water spray to keep fire-exposed containers cool. Containers may explode in the heat of a fire. Flammable liquid and vapor. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. For large fires, use water spray, fog, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Water may be ineffective. Do NOT use straight streams of water.

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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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation. A vapor suppressing foam may be used to reduce vapors.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Do not get on skin or in eyes. Do not ingest or inhale.
Use with adequate ventilation. Discard contaminated shoes. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use.
Refrigerator/flammables.

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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 general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 80-63-7: 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 minimize contact with skin.
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: Liquid
Color: colorless
Odor: chlorine-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 52 deg C @ 50.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 33 deg C ( 91.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C4H5ClO2
Molecular Weight: 120.54

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: May occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 80-63-7: AS6380000 LD50/LC50:
CAS# 80-63-7: Draize test, rabbit, skin: 500 mg Severe; Inhalation, mouse: LC50 = 500 mg/m3/2H; Inhalation, rabbit: LC50 = 500 mg/m3/2H; Inhalation, rat: LC50 = 500 mg/m3/2H; Oral, rat: LD50 = 68 mg/kg; Skin, rabbit: LD50 = 270 mg/kg.
Carcinogenicity:
Methyl-2-Chloroacrylate - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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: FLAMMABLE LIQUID, CORROSIVE, N.O.S*
Hazard Class: 3 (8)
UN Number: 2924
Packing Group: III
IMO
Shipping Name: FLAMMABLE LIQUID, CORROSIVE, N.O.S.
Hazard Class: 3.3 (8)
UN Number: 2924
Packing Group: III
RID/ADR
Shipping Name: FLAMMABLE LIQUID, CORROSIVE, N.O.S.
Hazard Class: 3
UN Number: 2924
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 10 Flammable.
R 34 Causes burns.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 25 Avoid contact with eyes.
S 28 After contact with skin, wash immediately
with...
S 33 Take precautionary measures against static
discharges.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 80-63-7: No information available.
Canada
CAS# 80-63-7 is listed on Canada's NDSL List.
CAS# 80-63-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 80-63-7 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：

  2-氯代丙烯酸甲酯 在 溴 作用下， 以 四氯化碳 为溶剂， 生成 methyl 2,3-dibromo-2-chloropropanoate
  参考文献：
  名称：

  不饱和酯的卤代反应-II：将Cl 2，BrCl和Br 2加到一氯丙酸的甲基酯上

  摘要：

  在离子和自由基条件下，将氯，溴化氯和溴加到2-氯丙酸甲酯1，顺式3-氯丙酸甲酯2和反式-3-氯丙酸甲酯3中，得到区域异构体混合物。两个反式-和CIS观察卤素物质的-addition，溴优先增加了非卤化碳原子。

  DOI：

  10.1016/s0040-4020(01)91588-1
• 作为产物：
  描述：

  三氯乙烯 在 basic copper carbonate powder 、 硫酸 作用下， 生成 2-氯代丙烯酸甲酯
  参考文献：
  名称：

  Manufacture of esters

  摘要：

  公开号：

  US02379104A1
• 作为试剂：
  描述：

  N-甲氧基苯甲酰胺 在 silver hexafluoroantimonate 、 2-氯代丙烯酸甲酯 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 重水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以30%的产率得到N-methoxy-2-deuteriobenzamide
  参考文献：
  名称：

  铑 (III) 催化 (4 + 2) 环化合成异喹诺酮、1,2-苯并噻嗪和萘并[1',2':4,5]咪唑并[1,2-a]吡啶衍生物

  摘要：

  在这项研究中，我们报告了一种新颖且有效的合成方法，通过Rh(III) 催化的 (4 + 2) 苯甲酰胺与未报道的偶联试剂 2-氯丙烯酸甲酯的环化来构建异喹诺酮支架。因此，其他有价值的1,2-苯并噻嗪和萘并[1',2':4,5]咪唑并[1,2- a ]吡啶衍生物也通过类似的合成方案获得。因此，我们开发的方法以高产率和反应多功能性为特色。

  DOI：

  10.1021/acs.joc.2c01376

文献信息

• Chiral Calcium Complexes as Brønsted Base Catalysts for Asymmetric Addition of α-Amino Acid Derivatives to α,β-Unsaturated Carbonyl Compounds
  作者：Susumu Saito、Tetsu Tsubogo、Shū Kobayashi

  DOI：10.1021/ja0709730

  日期：2007.5.1

  promote the catalytic asymmetric 1,4-addition reactions and [3+2] cycloaddition reactions of α-amino acid derivatives with α,β-unsaturated carbonyl compounds have been developed. The reactions proceeded smoothly in the presence of 5−10 mol % of the chiral calcium catalyst to afford the desired adducts in high yields with high diastereo- and enantioselectivities. A wide range of α,β-unsaturated esters and

  开发了一种基于钙络合物的新型催化剂体系，可促进 α-氨基酸衍生物与 α,β-不饱和羰基化合物的催化不对称 1,4-加成反应和 [3+2] 环加成反应。在 5-10 mol% 的手性钙催化剂存在下，反应顺利进行，以高产率提供所需的加合物，并具有高非对映选择性和对映选择性。适用范围广泛的 α,β-不饱和酯和酰胺，其他甘氨酸甚至 dl-丙氨酸衍生物与几种 α,β-不饱和羰基化合物反应，以高产率提供相应的取代吡咯烷衍生物，并具有优异的非对映选择性和对映选择性. 在与 dl-丙氨酸衍生物的反应中，季不对称碳被有效地构建。
• Preparation of α-Haloacrylate Derivatives via Dimethyl Sulfoxide-Mediated Selective Dehydrohalogenation
  作者：Wei Li、Jianchang Li、Zhao-Kui Wan、Junjun Wu、Walter Massefski

  DOI：10.1021/ol7021142

  日期：2007.10.1

  selective dehydrohalogenation to form alpha-haloacrylate analogues. A variety of alpha-halo Michael acceptors were prepared in dimethyl sulfoxide under mild, base-free conditions, including the preparation of alpha-bromoacrolein and alpha-chloro- and bromoacrylonitriles. Synthesis of these molecules has been reported in the literature to be difficult. Among all the existing dehydrohalogenation procedures

  二甲基亚砜使α，β-二卤代丙酸酯衍生物进行有效的选择性脱卤化氢反应，形成α-卤代丙烯酸酯类似物。在温和，无碱的条件下，在二甲基亚砜中制备了多种α-卤代迈克尔受体，包括α-溴丙烯醛和α-氯丙烯腈和溴丙烯腈的制备。这些分子的合成在文献中已经报道是困难的。在所有现有的脱卤化氢程序中，该协议是最简便，实用和对环境无害的过程。
• [EN] HETEROAROMATIC DERIVATIVES AS NIK INHIBITORS<br/>[FR] DÉRIVÉS HÉTÉROAROMATIQUES EN TANT QU'INHIBITEURS DE NIK
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2018002217A1

  公开（公告）日：2018-01-04

  The present invention relates to pharmaceutical agents useful for therapy and/or prophylaxis in a mammal, and in particular to inhibitors of NF-κB-inducing kinase (NIK - also known as MAP3K14) useful for treating diseases such as cancer, inflammatory disorders, metabolic disorders and autoimmune disorders. The invention is also directed to pharmaceutical compositions comprising such compounds, and to the use of such compounds or pharmaceutical compositions for the prevention or treatment of diseases such as cancer, inflammatory disorders, metabolic disorders including obesity and diabetes, and autoimmune disorders.

  本发明涉及对哺乳动物疗法和/或预防有用的药物，特别是对NF-κB诱导激酶（NIK - 也称为MAP3K14）的抑制剂，用于治疗癌症、炎症性疾病、代谢性疾病和自身免疫性疾病。该发明还涉及包含这些化合物的药物组合物，以及利用这些化合物或药物组合物预防或治疗癌症、炎症性疾病、包括肥胖和糖尿病在内的代谢性疾病以及自身免疫性疾病。
• N-1H-tetrazol-5-yl-2-thiophene carboxamides,
  申请人：Warner-Lambert Company

  公开号：US04748183A1

  公开（公告）日：1988-05-31

  The present invention is for compounds having the formula of N-1H-tetrazol-5-yl-2-thiophenecarboxamides, N-1H-tetrazol-5-yl-2-pyrrolecarboxamides, N-1H-tetrazol-5-yl-2-furancarboxamides or analogs of each of the carboxamides. The compounds are useful for the treatment of allergic or inflammatory conditions or diseases. Thus, pharmaceutical compositions and methods of use are also the invention. Processes of preparation for the compounds are also the invention.

  本发明涉及具有N-1H-四唑-5-基-2-噻吩羧酰胺、N-1H-四唑-5-基-2-吡咯羧酰胺、N-1H-四唑-5-基-2-呋喃羧酰胺或每种羧酰胺的类似物的化合物。这些化合物可用于治疗过敏或炎症性疾病。因此，药物组合物和使用方法也属于本发明。制备这些化合物的方法也是本发明的一部分。
• Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling
  作者：Christopher C. Nawrat、Christopher R. Jamison、Yuriy Slutskyy、David W. C. MacMillan、Larry E. Overman

  DOI：10.1021/jacs.5b07678

  日期：2015.9.9

  Alkyl oxalates are new bench-stable alcohol-activating groups for radical generation under visible light photoredox conditions. Using these precursors, the first net redox-neutral coupling of tertiary and secondary alcohols with electron-deficient alkenes is achieved.

  草酸烷基酯是新型的实验室稳定的醇活化基团，用于在可见光光氧化还原条件下产生自由基。使用这些前体，实现了叔醇和仲醇与缺电子烯烃的首次净氧化还原中性偶联。

表征谱图