(S)-(-)-1-(2-溴苯基)乙胺 | 140632-12-8

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-(-)-1-(2-溴苯基)乙胺
• 英文名称: (S)-1-(2-bromophenyl)ethylamine
• 英文别名: (S)-1-(2-Bromophenyl)ethanamine；(1S)-1-(2-bromophenyl)ethanamine
• CAS: 140632-12-8
• 化学式: C₈H₁₀BrN
• mdl: MFCD06761911
• 分子量: 200.078
• InChiKey: DSAXBVQQKYZELF-LURJTMIESA-N

物化性质

• 熔点：
  143-146℃
• 沸点：
  249℃
• 密度：
  1.400
• 闪点：
  104℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-1-(2-Bromophenyl)ethanamine
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: (S)-1-(2-Bromophenyl)ethanamine
CAS number: 140632-12-8

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H10BrN
Molecular weight: 200.1

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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, nitrogen oxides, 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：

  (S)-(-)-1-(2-溴苯基)乙胺 在 氢氧化钾 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正庚烷 、 二氯甲烷 、 乙基苯 为溶剂， 反应 2.5h， 生成 2-((S)-1-(2-bromophenyl)ethylamino)-5-isopropyl-5-methylthiazol-4(5H)-one
  参考文献：
  名称：

  2-(S)-Phenethylaminothiazolones as Potent, Orally Efficacious Inhibitors of 11β-Hydroxysteriod Dehydrogenase Type 1

  摘要：

  11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) is the enzyme that converts cortisone to cortisol. A growing body of evidence suggests that selective inhibition of 11 beta-HSD1 could potentially treat metabolic syndrome as well as type 2 diabetes. Through modification of our initial lead 1, we have discovered trifluoromethyl thiazolone 17. This compound had a K-i of 22 nM, possessed low in vivo clearance, and showed a 91% inhibition of adipose 11 beta-HSD1 enzymatic activity in a mouse ex vivo pharmacodynamic model.

  DOI：

  10.1021/jm061214f
• 作为产物：
  描述：

  (E)-1-(2-bromophenyl)ethanone O-benzyloxime 在 硼烷四氢呋喃络合物 、 C₁₉H₂₃BNO₃^(1-)*H⁽¹⁺⁾ 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以97%的产率得到
  参考文献：
  名称：

  通过螺硼酸盐催化还原纯 (E)-和 (Z)-O-苄基肟非外消旋伯胺的不对称合成：在拟钙剂合成中的应用

  摘要：

  使用衍生自稳定的螺硼酸酯，通过硼烷介导的单一异构体 ( E )- 和 ( Z ) -O-苄基肟醚的还原，合成了高对映体纯的 (1-芳基)-和 (1-萘基)-1-乙胺( S )-二苯基缬氨醇和乙二醇作为手性催化剂。伯 ( R )-芳基乙胺是通过使用 15% 的催化剂将纯 ( Z )-乙酮肟醚还原至 99% ee来制备的。描述了使用对映纯(1-萘-1-基)乙胺作为手性前体合成新的和已知的拟钙剂类似物的两种方便且容易的方法。

  DOI：

  10.1021/jo400371x

文献信息

• Transaminases Applied to the Synthesis of High Added-Value Enantiopure Amines
  作者：Caroline E. Paul、María Rodríguez-Mata、Eduardo Busto、Iván Lavandera、Vicente Gotor-Fernández、Vicente Gotor、Susana García-Cerrada、Javier Mendiola、Óscar de Frutos、Iván Collado

  DOI：10.1021/op4003104

  日期：2014.6.20

  stereoselective amination of (hetero)aromatic ketones using transaminases have been studied, such as temperature, pH, substrate concentration, cosolvent, and source and percentage of amino donor, to further optimize the production of enantiopure amines using both (S)- and (R)-selective biocatalysts from commercial suppliers. Interesting enantiopure amino building blocks have been obtained, overcoming some limitations

  研究了使用转氨酶影响（杂）芳族酮的立体选择性胺化的关键参数，例如温度，pH，底物浓度，助溶剂以及氨基供体的来源和百分比，以进一步优化同时使用这两种方法生产对映体纯胺的方法（S） -和（R）选择性生物催化剂来自商业供应商。已经获得了有趣的对映纯氨基结构单元，克服了传统化学合成方法的某些局限性。扩大代表性方法的规模，提供对映体纯形式的卤代和杂芳族胺，分离产率高。
• Biocatalytic transamination with near-stoichiometric inexpensive amine donors mediated by bifunctional mono- and di-amine transaminases
  作者：James L. Galman、Iustina Slabu、Nicholas J. Weise、Cesar Iglesias、Fabio Parmeggiani、Richard C. Lloyd、Nicholas J. Turner

  DOI：10.1039/c6gc02102f

  日期：——

  Bifunctional transaminases enable a strategy for the production of chiral amines using small excesses of diamine donors.

  双功能转氨酶使得利用少量过量的二胺供体生产手性胺的策略成为可能。
• Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine
  作者：Ying Xie、Hongjie Pan、Xiao Xiao、Songlei Li、Yian Shi

  DOI：10.1039/c2ob26782a

  日期：——

  An asymmetric biomimetic transamination of aromatic ketones to optically active amines with o-HOPhCH2NH2 as amine source catalyzed by hydroquinine-derived chiral base is described. Up to 85% ee was obtained.

  描述了由氢醌衍生的手性碱催化的邻-HOPhCH 2 NH 2作为胺源的芳香族酮的不对称仿生氨基转移成旋光胺。获得了高达85％的ee。
• Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases
  作者：Lía Martínez-Montero、Vicente Gotor、Vicente Gotor-Fernández、Iván Lavandera

  DOI：10.1039/c6gc01981a

  日期：——

  A one-pot/two-step chemoenzymatic sequential methodology has been developed for the selective amination of secondary alcohols by combining the laccase from Trametes versicolor/TEMPO catalytic system with the stereoselective action of transaminases.

  已开发出一种一锅法/两步法的化学酶串联方法，通过将来自Trametes versicolor的漆酶/TEMPO催化系统与转氨酶的立体选择性作用相结合，实现了对次级醇的选择性胺化。
• Discovery of pyrido[2,3-d]pyrimidine-based inhibitors of HCV NS5A
  作者：David A. DeGoey、David A. Betebenner、David J. Grampovnik、Dachun Liu、John K. Pratt、Michael D. Tufano、Wenping He、Preethi Krishnan、Tami J. Pilot-Matias、Kennan C. Marsh、Akhteruzzaman Molla、Dale J. Kempf、Clarence J. Maring

  DOI：10.1016/j.bmcl.2013.04.009

  日期：2013.6

  Efforts to improve the genotype 1a potency and pharmacokinetics of earlier naphthyridine-based HCV NS5A inhibitors resulted in the discovery of a novel series of pyrido[2,3-d]pyrimidine compounds, which displayed potent inhibition of HCV genotypes 1a and 1b in the replicon assay. SAR in this system revealed that the introduction of amides bearing an additional ‘E’ ring provided compounds with improved

  努力提高早期基于萘啶的 HCV NS5A 抑制剂的基因型1a效力和药代动力学导致发现了一系列新的吡啶并[2,3- d ]嘧啶化合物，它们在复制子中显示出对 HCV 基因型 1a 和 1b 的有效抑制作用化验。该系统中的 SAR 表明，引入带有额外“E”环的酰胺为化合物提供了改进的效力和药代动力学。在酰胺部分引入手性中心导致观察到复制子效力的立体化学依赖性，并为连接可用于提高系列溶解度的官能团提供位点。化合物21被选择用于在感染HCV的黑猩猩中给药。对病毒载量大幅下降的观察为化合物系列在体内抑制 HCV 复制提供了积极的概念证明。