2-溴双环[2.2.1]-2-庚烯 | 694-90-6

• 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: 2-溴双环[2.2.1]-2-庚烯
• 英文名称: 2-bromobicyclo[2.2.1]hept-2-ene
• 英文别名: 2-bromonorbornene；2-bromo-norborn-2-ene；2-Brom-norborn-2-en
• CAS: 694-90-6
• 化学式: C₇H₉Br
• 分子量: 173.052
• InChiKey: YFZLLLGFQCVYCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903890090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromobicyclo[2.2.1]hept-2-ene
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: 2-Bromobicyclo[2.2.1]hept-2-ene
CAS number: 694-90-6

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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.
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: C7H9Br
Molecular weight: 173.1

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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：

  2-溴双环[2.2.1]-2-庚烯 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.25h， 生成 (1R,4S,4aR,7R,12aS,E)-13,13-dimethyl-2,3,4,4a,6,7,8,9,12,12a-decahydro-1,4:7,10-dimethanobenzo[10]annulen-5(1H)-one
  参考文献：
  名称：

  Paquette, Leo A.; DeRussy, Donald T.; Vandenheste, Thierry, Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5562 - 5573

  摘要：

  DOI：
• 作为产物：
  描述：

  降冰片烯 在 正丁基锂 、 potassium tert-butylate 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以33%的产率得到2-溴双环[2.2.1]-2-庚烯
  参考文献：
  名称：

  钯催化双环烯烃的加氢苯基化

  摘要：

  研究了钯催化双环烯烃的加氢苯基化反应。发现这些反应是完全化学和立体选择性的，仅以中等至良好的收率在双环烯烃的较少取代的双键上仅给出外显子产物。对于不对称的双环烯烃，在双环烯烃上具有各种取代基的区域选择性为52:48至100：0。

  DOI：

  10.1016/s0040-4020(02)01277-2

文献信息

• 5-Aryltetrazoles from Direct C–H Arylation with Aryl Bromides
  作者：Yuan Zhang、Jack Chang Hung Lee、Matthew R. Reese、Brian P. Boscoe、John M. Humphrey、Christopher J. Helal

  DOI：10.1021/acs.joc.0c00085

  日期：2020.4.17

  A mild, direct C–H arylation of 1-substituted tetrazoles to 5-aryltetrazoles is developed using a Pd/Cu cocatalytic system with readily available aryl bromides. The methodology avoids late-stage usage of azides and tolerates a wide range of functionalities.

  使用Pd / Cu共催化体系和易于获得的芳基溴化物，可以将1-取代的四唑温和地直接进行CH芳基化为5-芳基四唑。该方法避免了叠氮化物的后期使用，并具有广泛的功能性。
• Relevance of oxyanion stereochemistry to chirality transfer in anionic oxy-Cope rearrangements
  作者：Leo A. Paquette、George D. Maynard

  DOI：10.1021/ja00039a011

  日期：1992.6

  undergo anionic oxy-Cope rearrangement under the exclusice control of oxyanion orientation with a 58-64% preference for equatorial oxygen. Six semicyclic dienols have also been synthesized where the preferred oxyanion-driven sigmatropic rearrangement pathway is obligatorily pitted against π-facial biases offered by 4-tert-butylcyclohexenyl, norbornenyl, and camphenyl rings. These rearrangements therefore

  几何和光学纯 (3R,5E)- 和 (3R,5Z)-1,5-heptadien-3-ols 在氧阴离子取向的排他控制下经历阴离子氧-Cope 重排，对赤道氧的偏好为 58-64%。还合成了六种半环二烯醇，其中优选的氧阴离子驱动的 sigmatropic 重排途径必须与 4-叔丁基环己烯基、降冰片烯基和凸轮苯基环提供的 π 面偏差相抗衡。因此，这些重排为控制手性转移水平和方向的那些因素提供了特别严格的测试。数据显示氧阴离子不喜欢参与 1,3-二轴关系
• Deoxygenation of aldehydes and ketones; a new general reaction of dibromocarbene and dibromocarbonyl ylides
  作者：Zhenwei Huan、John A. Landgrebe、Kimberly Peterson

  DOI：10.1016/s0040-4039(00)88035-1

  日期：1983.1

  The treatment of a variety of aldehydes and ketones with phenyl)tribromomethyl)mercury results in the production of carbon monoxide from the deoxygenation of the carbonyl group by dibromocarbene.

  用苯基（三溴甲基）汞处理各种醛和酮会导致羰基被二溴卡宾脱氧而生成一氧化碳。
• An efficient protocol for the synthesis of brominated norbornene, norbornadiene,and benzonorbornadiene
  作者：Selçuk EŞSİZ

  DOI：10.3906/kim-1809-11

  日期：——

  An efficient protocol for the synthesis of 2-bromonorbornene, 2-bromonorbornadiene, 2-bromobenzonorbornadiene, 2,3-dibromonorbornene, 2,3-dibromonorbornadiene, and 2,3-dibromobenzonorbornadiene in good yields has been developed. 1,2-Dibromotetrachloroethane is used as the brominating agent for these reactions. The results are discussed in comparison with alternative methods in the literature.

  已经开发了以高收率合成2-溴降冰片烯，2-溴降冰片二烯，2-溴苯并降冰片二烯，2，3-二溴降冰片烯，2，3-二溴降冰片二烯和2，3-二溴苯并降冰片二烯和2，3-二溴苯并降冰片二烯的有效方案。1,2-二溴四氯乙烷用作这些反应的溴化剂。与文献中的替代方法相比，对结果进行了讨论。
• Synthesis of some trimethyltinnorbornanols
  作者：Dennis D. Davis、Harry T. Johnson

  DOI：10.1016/s0022-328x(00)88514-9

  日期：1975.2

  syn-7-trimethyltin-endo-2-norbornanol, and anti-7-trimethyltin- endo-2-norbornanol. The syn-trimethyltin group is found to have little steric interference towards exo attack at the C-2 and C-3 positions of the norbornyl skeleton in both hydroboration and metal hydride reduction.

  报道了四种三甲基锡降冰片醇的立体有择合成。这些包括syn -7-三甲基锡-exo -2-降冰片醇，抗-7-trimethyltin- exo -2-降冰片醇，syn -7-三甲基锡-内酯-2-降冰片醇和抗-7-三甲基锡-内酯-2-降冰片醇。发现在硼氢化和金属氢化物还原中，顺-三甲基锡基团对降冰片基骨架的C-2和C-3位的外切进攻几乎没有空间干扰。