(Z)-3-bromoacrylic acid | 1609-92-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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
• 英文名称: (Z)-3-bromoacrylic acid
• 英文别名: (Z)-3-bromoprop-2-enoic acid
• CAS: 1609-92-3
• 化学式: C₃H₃BrO₂
• 分子量: 150.96
• InChiKey: POAWTYXNXPEWCO-UPHRSURJSA-N

物化性质

• 熔点：
  113.5-114.5 °C
• 沸点：
  222.4±13.0 °C(Predicted)
• 密度：
  1.899±0.06 g/cm3(Predicted)

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

• 海关编码：
  2916190090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (Z)-3-Bromoacrylic acid
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: (Z)-3-Bromoacrylic acid
CAS number: 1609-92-3

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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.

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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.

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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.

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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, refrigerated.
Storage:

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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.

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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: C3H3BrO2
Molecular weight: 151.0

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

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (Z)-3-bromoacrylic acid 在 氯化亚砜 作用下， 生成 (Z)-3-bromo-propenoyl chloride
  参考文献：
  名称：

  1-乙烯基-4-甲基-2,6,7-三氧杂双环[2.2.2]辛烷：不饱和均烯酸酯阴离子当量

  摘要：

  （E）-1-（2-氯乙烯基）-或（E）-1-（2-溴乙烯基）-4-甲基-2,6,7-三恶双环[2.2.2]辛烷与叔丁基锂的金属化一种不饱和的均烯酸酯阴离子当量，其拦截卤代烷，醛，酮和内酯，得到β-烷基化或β-酰化原酸酯，进而提供β-取代的丙烯酸酯。

  DOI：

  10.1016/s0040-4039(00)96117-3
• 作为产物：
  描述：

  3,3-二溴丙酸 在 potassium carbonate 作用下， 生成 (Z)-3-bromoacrylic acid
  参考文献：
  名称：

  Thomas-Mamert, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1894, vol. 118, p. 652

  摘要：

  DOI：

文献信息

• Asymmetric total synthesis of cryptoconcatone I
  作者：Ranjan Kumar Acharyya、Pratik Pal、Shrestha Chatterjee、Samik Nanda

  DOI：10.1039/c9ob00399a

  日期：——

  Asymmetric total synthesis of the naturally occurring cryptoconcatone I, which possesses a γ-Z-butenolide framework, is described here for the first time. Asymmetric propargylation, E-selective cross metathesis, and regioselective reductive epoxide ring opening were employed to access the enantiopure terminal alkyne. Late stage bimetallic cascade cyclization of the alkyne with (Z)-3-bromoacrylic acid

  本文首次描述了具有γ- Z-丁烯内酯骨架的天然存在的隐康酮C的不对称全合成。使用不对称的炔丙基化，E选择性交叉复分解和区域选择性还原性环氧开环来访问对映纯末端炔烃。炔烃与（Z）-3-溴丙烯酸的晚期双金属级联环化以有效方式提供了天然产物。
• POLYFLUORINATED COMPOUNDS ACTING AS BRUTON TYROSINE KINASE INHIBITORS
  申请人：He Wei

  公开号：US20160200730A1

  公开（公告）日：2016-07-14

  Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.

  本文描述了一种新型的多氟取代吡唑嘧啶化合物或其盐。这些化合物是布鲁顿酪氨酸激酶（BTK）抑制剂。这些化合物可能具有更好的BTK抑制选择性和药代动力学特性。本文披露了这些化合物的合成方法。本文还披露了多氟取代苯甲酮和取代苯氧基苯的新型合成方法。还披露了包括上述BTK抑制剂的药物组合物。本发明还涉及包含上述化合物作为活性成分的药物配方。本发明还包括通过给予BTK抑制剂及其配方来治疗和抑制自身免疫疾病、过敏性疾病、炎症性疾病和癌症的治疗方法。
• Total Synthesis of Polyene Natural Product Dihydroxerulin by Mild Organocatalyzed Dehydrogenation of Alcohols
  作者：Hexin Xie、Shilei Zhang、Hao Li、Xinshuai Zhang、Sihan Zhao、Zian Xu、Xixi Song、Xinhong Yu、Wei Wang

  DOI：10.1002/chem.201103325

  日期：2012.2.20

  Polyene synthesis: An efficient approach to the total synthesis of polyene natural product dihydroxrulin (1) is described. A novel, mild, direct organocatalytic IBX‐mediated dehydrogenation process of simple alcohols to enals has been developed, which serves as a key step in the synthesis (see scheme).

  多烯合成：描述了一种多烯天然产物二氢木鲁林（1）的全合成的有效方法。已经开发了一种新颖的，温和的，直接的由有机醇IBX介导的简单醇脱氢制氢成烯醛的方法，这是合成中的关键步骤（参见方案）。
• Synthesis of Phthalides and 3,4-Dihydroisocoumarins Using the Palladium-Catalyzed Intramolecular Benzannulation Strategy
  作者：Taishi Kawasaki、Shinichi Saito、Yoshinori Yamamoto

  DOI：10.1021/jo016336o

  日期：2002.4.1

  A novel method for the synthesis of phthalides and 3,4-dihydroisocoumarins via the palladium-catalyzed intramolecular benzannulation of bis-enyne and enyne-diyne systems is described. Various kinds of substituted phthalides 9 and 17 and 3,4-dihydroisocoumarins 19 were synthesized from 8, 16, and 18, respectively, in moderate to excellent yields. The benzannulation reaction proceeded chemoselectively

  描述了一种新的方法，可通过钯催化双烯炔和烯炔-二炔系统的分子内苯环合成苯二甲酸酯和3,4-二氢异香豆素。分别由8、16和18合成了各种取代的邻苯二甲酸酯9和17以及3,4-二氢异香豆素19，产率中等至优异。苯环化反应进行化学选择，得到相应的稠环化合物A，而没有形成区域异构体产物B（eq 6）。此外，该方法学被应用于生物活性的3-正丁基邻苯二甲酸酯23的合成。
• Efficient and diastereoselective synthesis of (+)-Goniobutenolide A via palladium-catalyzed ene-yne cross coupling-lactonization cascade
  作者：Martin Kotora、Ei-ichi Negishi

  DOI：10.1016/s0040-4039(96)01972-7

  日期：1996.12

  (+)-Goniobutenolide A was synthesized in six steps in 21.4% overall yield from (R)-mandelic acid via Pd-catalyzed ene-yne cross coupling-lactonization cascade with essentially complete control of the exocyclic alkene geometry. Copyright (C) 1996 Elsevier Science Ltd

  (+)-Goniobutenolide A通过钯催化的烯炔交叉偶联-内酯化级联反应，从(R)-苯甘氨酸出发，在六个步骤中以21.4%的总产率合成。该反应对exo-环烯烃的几何结构控制近乎完全。版权 © 1996 Elsevier Science Ltd

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