(S)-3-溴-alpha-甲基苄醇 | 134615-22-8

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 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)-3-溴-alpha-甲基苄醇
• 中文别名: (S)-1-(3-溴苯基)乙醇；(S)-3-溴-ALPHA-甲基苄醇；(S)-3-溴-α-甲基苄醇
• 英文名称: (S)-1-(3-bromophenyl)ethan-1-ol
• 英文别名: (S)-1-(3-bromophenyl)ethanol；1-(3-bromophenyl)ethanol；1-(3-bromophenyl)ethan-1-ol；(1S)-1-(3-bromophenyl)ethanol
• CAS: 134615-22-8
• 化学式: C₈H₉BrO
• mdl: MFCD06201859
• 分子量: 201.063
• InChiKey: ULMJQMDYAOJNCC-LURJTMIESA-N

物化性质

• 沸点：
  264℃
• 密度：
  1.470
• 闪点：
  114℃
• 稳定性/保质期：
  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36,S37,S39
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	(S)-3-Bromo-alpha-methylbenzyl alcohol 95% (98% e.e.) Material Safety Data Sheet
Synonym:	(S)-1-(3-Bromophenyl)ethano
CAS:	134615-22-8

Section 1 - Chemical Product MSDS Name:(S)-3-Bromo-alpha-methylbenzyl alcohol 95% (98% e.e.) Material Safety Data Sheet
Synonym:(S)-1-(3-Bromophenyl)ethano

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
134615-22-8	(S)-3-Bromo-alpha-methylbenzyl alcohol	95%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 134615-22-8: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Clear liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H9BrO
Molecular Weight: 201.06

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 134615-22-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-3-Bromo-alpha-methylbenzyl alcohol - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 134615-22-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 134615-22-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 134615-22-8 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：

  (S)-3-溴-alpha-甲基苄醇 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 15-冠醚-5 、 盐酸羟胺 、 氨 、 sodium hydride 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.09h， 生成 (S)-1-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]ethyl alcohol-O-tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Preparation of novel 3H-trifluoromethyldiazirine-based photoactivatable potassium channel antagonists

  摘要：

  The preparation of a series of photoactivatable precursors for use in photoaffinity labelling of potassium channels is described. 3H-Diazirine functionalities were incorporated into the previously described potassium channel antagonists 1-3. The ability to perform enantioselective reductions and Wittig reactions in the presence of 3H-diazirines was central to this work. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.007
• 作为产物：
  描述：

  3'-溴苯乙炔 在 三氟甲磺酸 、 RuCl[(S,S)-FsDPEN](p-cymene) 、 水 、 sodium formate 作用下， 以 2,2,2-三氟乙醇 、 水 为溶剂， 反应 36.0h， 生成 (S)-3-溴-alpha-甲基苄醇
  参考文献：
  名称：

  CF3SO3H/钌串联催化从炔烃一锅法合成手性醇†

  摘要：

  描述了通过在 CF 3 CH 2 OH水溶液中结合 CF 3 SO 3 H 和氟化手性二胺 Ru( II )配合物，从现成的炔烃通过串联催化的实用一锅法合成手性醇。非常有趣的是，氟化催化剂和溶剂的组合对反应性和对映选择性表现出积极的氟效应。在简单温和的条件下，以高收率和优异的立体选择性获得了一系列具有广泛官能团耐受性的手性醇。

  DOI：

  10.1039/c8ra02224k

文献信息

• Discovery of Dipeptide-Derived Catalysts for the Enantioselective Addition of Dimethylzinc to Aldehydes
  作者：Seock Yong Kang、Yong Sun Park

  DOI：10.1002/ejoc.201200063

  日期：2012.3

  new class of modular chiral catalysts derived from various amino acid-L-Pro dipeptides was prepared, and the catalysts were tested for their ability to catalyze the enantioselective addition of dimethylzinc to aromatic aldehydes. Dipeptides derived from L-Asp-L-Pro were identified as effective catalysts for the addition at room temperature with up to 97:3 er and 95 % yield.

  制备了一类新的模块化手性催化剂，这些催化剂来源于各种氨基酸-L-Pro 二肽，并测试了催化剂催化二甲基锌对芳香醛的对映选择性加成的能力。源自 L-Asp-L-Pro 的二肽被确定为在室温下添加的有效催化剂，效率高达 97:3，产率为 95%。
• Dynamic Kinetic Resolution of Alcohols by Enantioselective Silylation Enabled by Two Orthogonal Transition‐Metal Catalysts
  作者：Jan Seliger、Martin Oestreich

  DOI：10.1002/anie.202010484

  日期：2021.1.4

  A nonenzymatic dynamic kinetic resolution of acyclic and cyclic benzylic alcohols is reported. The approach merges rapid transition‐metal‐catalyzed alcohol racemization and enantioselective Cu‐H‐catalyzed dehydrogenative Si‐O coupling of alcohols and hydrosilanes. The catalytic processes are orthogonal, and the racemization catalyst does not promote any background reactions such as the racemization

  报道了无环和环状苯甲醇的非酶动态动力学拆分。该方法融合了快速过渡金属催化的醇外消旋化和对映选择性 Cu-H 催化的醇和氢硅烷的脱氢 Si-O 偶联。催化过程是正交的，并且外消旋催化剂不会促进任何背景反应，例如甲硅烷基醚的外消旋及其非选择性形成。常用的钌半夹心配合物并不合适，但双功能钌钳形配合物完美地实现了这一目的。由此，可以高产率和良好的对映选择水平实现外消旋醇混合物的对映选择性硅烷化。
• Copper-Catalyzed Asymmetric Hydrogenation of Aryl and Heteroaryl Ketones
  作者：Scott W. Krabbe、Mark A. Hatcher、Roy K. Bowman、Mark B. Mitchell、Michael S. McClure、Jeffrey S. Johnson

  DOI：10.1021/ol4021223

  日期：2013.9.6

  High throughput screening enabled the development of a Cu-based catalyst system for the asymmetric hydrogenation of prochiral aryl and heteroaryl ketones that operates at H2 pressures as low as 5 bar. A ligand combination of (R,S)-N-Me-3,5-xylyl-BoPhoz and tris(3,5-xylyl)phosphine provided benzylic alcohols in good yields and enantioselectivities. The electronic and steric characteristics of the ancillary

  高通量筛选使得能够开发用于在低至5 bar的H 2压力下进行的前手性芳基和杂芳基酮的不对称氢化的Cu基催化剂体系。（R，S）-N -Me-3，5-二甲苯基-BoPhoz和三（3，5-二甲苯基）膦的配体组合以良好的收率和对映选择性提供了苄醇。辅助三芳基膦的电子和空间特性对于确定反应性和选择性均很重要。
• Novel access to N,N′-diaryl-trans-1,2-diaminocyclohexane ligands. A cheap and easy way to prepare ligand for asymmetric transfer hydrogenation
  作者：Bilal El-Asaad、Boris Guicheret、Estelle Métay、Iyad Karamé、Marc Lemaire

  DOI：10.1016/j.molcata.2015.10.030

  日期：2016.1

  is performed under air or in the presence of an hydrogen trap. The interest of the synthesized ligands were evaluated in the reduction of aromatic ketones. The alcohols were efficiently and selectively obtained with an iridium complex and a mixture of formic acid and sodium formate.

  由1,2-二氨基环己烷和环己酮衍生物通过非均相钯催化制备N，N'-二芳基-反式-1,2-二氨基环己烷配体。在一个步骤中，在空气中或在氢阱存在下进行烷基化，然后进行芳构化。在减少芳族酮的过程中评估了合成配体的兴趣。用铱络合物以及甲酸和甲酸钠的混合物有效和选择性地获得了醇。
• Asymmetric transfer hydrogenation of ketones by N,N-containing quinazoline-based ruthenium(II) complexes
  作者：Cigdem Kucukturkmen、Ahmet Agac、Aysel Eren、Idris Karakaya、Mehmet Aslantas、Omer Celik、Sabri Ulukanli、Semistan Karabuga

  DOI：10.1016/j.catcom.2015.11.013

  日期：2016.1

  Coordination with RuCl2(PPh3)dppb gave ruthenium(II) N-heterocyclic complexes 4b–d. The structure of complex 4b was fully illuminated by X-ray crystallography. The steric environment of these chiral ruthenium complexes 4b–d was evaluated in asymmetric transfer hydrogenation (ATH) of prochiral ketones in the presence of NaOiPr by using 2-propanol as the hydrogen source and solvent. The resultant catalytic

  从光学纯的氨基酸开始合成了一组新的基于喹唑啉的手性配体。与RuCl 2（PPh 3）dppb配位得到钌（II）N-杂环配合物4b–d。配合物4b的结构通过X射线晶体学被完全照亮。通过使用2-丙醇作为氢源和溶剂，在NaO i Pr存在的情况下，在手性酮的不对称转移氢化（ATH）中评估了这些手性钌配合物4b-d的空间环境。所得的催化体系可以实现非常好的对映选择性（高达91％）和高产率（高达99％）。