1-溴环庚烯 | 18317-64-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 1-溴环庚烯
• 英文名称: 1-bromocycloheptene
• 英文别名: 1-bromocyclohept-1-ene；1-bromo-cycloheptene；1-Brom-cyclohepten
• CAS: 18317-64-1
• 化学式: C₇H₁₁Br
• mdl: MFCD09878419
• 分子量: 175.068
• InChiKey: VYAZDEWSYBZNPG-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C(Solv: water (7732-18-5))
• 沸点：
  81-82°C/2mm
• 密度：
  1.3345 g/cm3(Temp: 23 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2903890090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Bromocyclohept-1-ene
Synonyms: 1-Bromo-1-cycloheptene

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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: 1-Bromocyclohept-1-ene
CAS number: 18317-64-1

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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, under −20◦C.
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: C7H11Br
Molecular weight: 175.1

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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：

  1-溴环庚烯 生成 1-iodocycloheptene
  参考文献：
  名称：

  Neumann,H.; Seebach,D., Chemische Berichte, 1978, vol. 111, p. 2785 - 2812

  摘要：

  DOI：
• 作为产物：
  描述：

  环庚酮 在 亚磷酸三苯酯 、 溴 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以59%的产率得到1-溴环庚烯
  参考文献：
  名称：

  铜催化的（环）烯基/芳基溴化物和二级氧化膦的 C-P 交叉偶联与原位卤素交换

  摘要：

  已经开发了用于（环）烯基/芳基溴化物和二级氧化膦之间的铜催化卤素交换/CP 交叉偶联的协议。碘化钠的添加通过促进有机溴化物与相应碘化物的原位卤素交换来增加交叉偶联的产率。

  DOI：

  10.1002/ejoc.202100456

文献信息

• The<i>in situ</i>-Generated Nickel(0)-catalyzed Homo-coupling of Alkenyl Halides with Zinc Powder. A Specific Outcome in Stereochemistry
  作者：Kentaro Takagi、Harutaka Mimura、Saburo Inokawa

  DOI：10.1246/bcsj.57.3517

  日期：1984.12

  The catalytic activity of nickel(0) generated in situ from nickel(II) salt was examined in a dehalogenative coupling of alkenyl halides with zinc powder. The reaction of alkenyl bromides took place provided that potassium iodide was present to assist the reduction of nickel(II) with zinc powder, and also to convert the alkenyl bromides to the corresponding alkenyl iodides. A speculative view concerning

  在烯基卤化物与锌粉的脱卤偶联中检测了从镍 (II) 盐原位生成的镍 (0) 的催化活性。烯基溴化物的反应发生，前提是存在碘化钾以帮助用锌粉还原镍 (II)，并将烯基溴化物转化为相应的烯基碘化物。为了解释观察到的独特立体化学，提出了关于歧化步骤的推测性观点。
• Formation of Enehydrazine Intermediates through Coupling of Phenylhydrazines with Vinyl Halides: Entry into the Fischer Indole Synthesis
  作者：Fuxu Zhan、Guangxin Liang

  DOI：10.1002/anie.201207173

  日期：2013.1.21

  Cut to the chase: Direct formation of an enehydrazine, an intermediate in the classic Fischer indole synthesis, solves the regioselectivity problem associated with indolization. This approach not only achieves selective synthesis of indoles through proper selection of the vinyl halide, but also leads to quick construction of desoxyeseroline and esermethole, as well as the key structural motif in the

  追逐目标：直接形成烯肼（Fischer吲哚经典合成中的中间体）可解决与吲哚化有关的区域选择性问题。这种方法不仅通过卤乙烯的适当选择实现吲哚的选择性合成，而且导致快速施工desoxyeseroline和esermethole的，以及在关键结构基序Akuammiline生物碱vincorine。
• Cyanation of 1-Halocycloalkenes Catalyzed by Tetracyanocobaltate(I). Convenient Synthesis of 1-Cyanocycloalkenes
  作者：Takuzo Funabiki、Hirohito Kishi、Yoshihiro Sato、Satohiro Yoshida

  DOI：10.1246/bcsj.56.649

  日期：1983.2

  1-Cyanocycloalkenes (1-cyanocyclopentene, -hexene, -heptene, and -octene) were readily synthesized by catalytic cyanation of the corresponding 1-halocycloalkenes with tetracyanocobaltate(I). Reactivities of methyl-substituted 1-chlorocyclohexenes were lower than that of 1-chlorocyclohexene, and 1-chloro-2-methylcyclohexene scarecely reacted. Hydrogenation and isomerization of 1-cyanocycloalkenes were

  1-氰基环烯烃（1-氰基环戊烯、-己烯、-庚烯和-辛烯）很容易通过相应的 1-卤代环烯烃与四氰基钴酸盐 (I) 的催化氰化反应合成。甲基取代的1-氯环己烯的反应活性低于1-氯环己烯，且1-氯-2-甲基环己烯反应缓慢。仅用 1-氰基环庚烯和 1-氰基-6-甲基环己烯分别观察到 1-氰基环烯烃的氢化和异构化。
• Diastereo‐ and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes
  作者：Jing Li、Alexander Preinfalk、Nuno Maulide

  DOI：10.1002/anie.201900801

  日期：2019.4.23

  A flexible redox-neutral coupling of aldehydes and alkenes enables rapid access to stereotriads starting from a single stereocenter with perfect levels of enantio- and diastereoselectivity under mild conditions. The versatility of the method is highlighted by the installation of heteroatoms along the tether, which enables a route to structurally diverse building blocks. The formal synthesis of (+)-neopeltolide

  醛和烯烃的灵活的氧化还原-中性偶合使得在温和条件下可以从单一的立体中心快速进入立体三单元组，同时具有理想水平的对映体和非对映体选择性。该方法的多功能性是通过在系链上安装杂原子而突出显示的，这使一条通往结构多样的构建基块的途径成为可能。（+）-neopeltolide的正式合成进一步证明了这种方法的合成效用。
• Synthesis of<i>α</i>,<i>β</i>-Unsaturated Carboxylic Acids by Nickel(II)-Catalyzed Electrochemical Carboxylation of Vinyl Bromides
  作者：Hisato Kamekawa、Hiroki Kudoh、Hisanori Senboku、Masao Tokuda

  DOI：10.1246/cl.1997.917

  日期：1997.9

  Electrochemical carboxylation of alkyl-substituted vinyl bromides (1a-1g) in the presence of 20 mol% of NiBr2•bpy under an atmospheric pressure of carbon dioxide with a platinum cathode and a magnesium anode gave the corresponding α,β-unsaturated carboxylic acids (2a-2g) in yields of 53-82%.

  在20摩尔%的NiBr2•bpy存在下，烷基取代的乙烯基溴化物（1a-1g）在大气二氧化碳压力下，通过铂阴极和镁阳极进行电化学羧化反应，以53-82%的产率得到了相应的α，β-不饱和羧酸（2a-2g）。