(R)-(-)-2-氯-1-苯乙醇 | 56751-12-3

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 醇的卤化、磺化、硝化或亚硝化衍生物
• 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: (R)-(-)-2-氯-1-苯乙醇
• 中文别名: (R)-(-)-α-(氯甲基)苯甲醇；(R)-2-氯-1-苯乙醇；(R)-(-)-A-(氯甲基)苯甲醇
• 英文名称: (R)-2-chloro-1-phenylethanol
• 英文别名: 2-chloro-1-phenylethanol；(R)-2-chloro-1-phenylethan-1-ol；(1R)-2-chloro-1-phenylethanol
• CAS: 56751-12-3
• 化学式: C₈H₉ClO
• 分子量: 156.612
• InChiKey: XWCQSILTDPAWDP-QMMMGPOBSA-N

物化性质

• 比旋光度：
  -48.2 º (C=2.8% IN CYCLOHEXANE)
• 沸点：
  110°C 6mm
• 密度：
  1.185 g/mL at 25 °C (lit.)
• 闪点：
  >230 °F
• 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)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  2
• 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

• 安全说明：
  S23,S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  2810
• 海关编码：
  2906299090
• 包装等级：
  III
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  存放于2-8°C的阴凉干燥处

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: (R)-(−)-2-Chloro-1-phenylethanol
Product name
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 56751-12-3
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C8H9ClO
Molecular Weight : 156,61 g/mol
CAS-No. : 56751-12-3
No components need to be disclosed according to the applicable regulations.

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SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Hydrogen chloride gas
Carbon oxides, Hydrogen chloride gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Normal measures for preventive fire protection.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK
(EU EN 14387) respirator cartridges. Use respirators and components tested and approved under
appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: clear, viscous, liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point 113 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 1,185 g/mL at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-氯-1-苯乙醇 在 [Ir(η5-C5Me5)(C6H4-2-CH2NHCH3)(NCCH3)](PF6) 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 0.08h， 生成 (±)-2-氯-1-苯基乙醇
  参考文献：
  名称：

  通过使用阳离子半三明治钌和铱化合物对手性胺和醇进行快速消旋

  摘要：

  脂肪酶催化的醇和胺类拆分仅产生所需对映体纯产品的50％。但是，添加消旋化催化剂会导致100％的动态动力学拆分（DKR）收率。需要快速且与酶促反应条件相容的新型外消旋化催化剂。我们表明，阳离子半三明治钌和iridacycle络合物在手性醇和胺的外消旋中具有很高的活性和效率。在用碱活化后，这些络合物能够选择性消旋醇，而未活化的络合物则是胺消旋的选择性催化剂。我们已将消旋环应用于外消旋β-氯醇的DKR中，以在双相系统中以高收率和高ee产生手性环氧化物（ee =对映体过量）。

  DOI：

  10.1002/chem.200902103
• 作为产物：
  描述：

  alpha-氯乙酰苯 在 葡萄糖 作用下， 反应 72.0h， 以99%的产率得到(R)-(-)-2-氯-1-苯乙醇
  参考文献：
  名称：

  安大略念珠菌透化全细胞有效合成 (R)-2-Chloro-1-(3-chlorophenyl) 乙醇

  摘要：

  摘要 ( R )-2-氯-1-(3-氯苯基)乙醇是合成3-肾上腺素受体(3-AR)激动剂的关键医药中间体。研究了安大略念珠菌静息细胞催化 2-氯-1-(3-氯苯基)乙酮不对称还原为 (R)-2-氯-1-(3-氯苯基)乙醇。在底物浓度为 10 g/L 时，微生物细胞在最佳反应条件下表现出优异的催化活性，产物 ee 为 99.9%，产率为 99.0%。十六烷基三甲基溴化铵预处理后，透化的安大略念珠菌细胞的活性提高了 2 倍以上，并且在显着缩短的 24 小时反应时间内可以在 99.9% 的 ee 和 97.5% 的产率下生产产物，底物浓度为 30克/升。

  DOI：

  10.1016/s1872-2067(11)60363-x

文献信息

• New chiral phosphinamide catalysts for highly enantioselective reduction of ketones
  作者：Mark P. Gamble、John R. Studley、Martin Wills

  DOI：10.1016/0040-4039(96)00404-2

  日期：1996.4

  A novel class of recoverable and highly stable phosphinamide catalysts for the asymmetric reduction of ketones by borane is described. Enantiomeric excesses of up to 92% have been obtained using 10 mol% of the optimum catalyst.

  描述了用于硼烷不对称还原酮的一类新型可回收且高度稳定的次膦酰胺催化剂。使用10摩尔％的最佳催化剂，可获得高达92％的对映体过量。
• Enantioselective reduction of ketones by borane catalysed by oxazaphospholidine oxides
  作者：Olivier Chiodi、Frédéric Fotiadu、Maud Sylvestre、Gérard Buono

  DOI：10.1016/0040-4039(95)02078-0

  日期：1996.1

  New enantioselective catalysts for the asymmetric reduction of ketones by borane are described. Easily prepared by oxidation of chiral oxazaphospholidines, these compounds increase sensitively the reduction rate of numerous ketones and induce ee's up to 94% in the case of the 2-chloroacetophenone.

  描述了用于硼烷不对称还原酮的新型对映选择性催化剂。通过手性氧杂氮杂膦酸的氧化可轻松制备，这些化合物灵敏地提高了许多酮的还原率，在2-氯苯乙酮的情况下，诱导的ee最高可达94％。
• Chiral N-heterocyclic carbene iridium catalyst for the enantioselective hydrosilane reduction of ketones
  作者：Yoshiki Manabe、Kanako Shinohara、Hanako Nakamura、Hiro Teramoto、Satoshi Sakaguchi

  DOI：10.1016/j.molcata.2016.05.020

  日期：2016.9

  NHC–Ag complex derived from N -(1-naphthalenylmethyl)-substituted benzimidazolium salt L12 , affording the corresponding alcohol in 92% yield and with 92% ee. Moreover, the evaluation of an Ir catalyst precursor showed that cationic [Ir(cod) 2 ]BF 4 complex could be used. Furthermore, the introduction of a chiral hydroxyamide side arm into the benzimidazolium salt was critical for the successful design of

  摘要 已开发了在室温下原位生成的 N-杂环卡宾 (NHC) Ir 配合物催化 (EtO) 2 MeSiH 对酮的对映选择性还原。在不对称氢化硅烷化反应中合成并筛选了一系列苯并咪唑盐。结果，[IrCl(cod)] 2 和 N-(1-萘基甲基)-取代的苯并咪唑盐 L12 衍生的 NHC-Ag 络合物的组合催化体系有效地还原苯丙酮，以 92% 的收率得到相应的醇，并且具有 92% 的 ee。此外，对Ir催化剂前体的评估表明可以使用阳离子[Ir(cod) 2 ]BF 4 络合物。此外，在苯并咪唑盐中引入手性羟基酰胺侧臂对于 NHC 配体的成功设计至关重要。
• Enantiocomplementary C-H Bond Hydroxylation Combining Photo-Catalysis and Whole-Cell Biocatalysis in a One-Pot Cascade Process
  作者：Yongzhen Peng、Danyang Li、Jiajie Fan、Weihua Xu、Jian Xu、Huilei Yu、Xianfu Lin、Qi Wu

  DOI：10.1002/ejoc.201901682

  日期：2020.2.21

  An alternative one‐pot cascade protocol combining photo‐catalysis and whole‐cell biocatalysis for the production of enantiocomplementary alcohols was developed.

  开发了将光催化和全细胞生物催化相结合的另一种单锅级联方案，用于生产对映体互补醇。
• Ketone-Alcohol Hydrogen-Transfer Equilibria: Is the Biooxidation of Halohydrins Blocked?
  作者：Fabricio R. Bisogno、Eduardo García-Urdiales、Haydee Valdés、Iván Lavandera、Wolfgang Kroutil、Dimas Suárez、Vicente Gotor

  DOI：10.1002/chem.201001233

  日期：——

  (HT) fashion, stoichiometric amounts of α‐halo carbonyl compounds have been employed as hydrogen acceptors. The reason that these substrates lead to quasi‐quantitative conversions has been tacitly attributed to both thermodynamic and kinetic effects. To provide a clear rationale for this behavior, we investigate herein the redox equilibrium of a selected series of ketones and 2‐propanol by undertaking

  为确保醇氧化的准不可逆性以及氢转移（HT）方式使酮还原，已使用化学计量的α-卤代羰基化合物作为氢受体。这些底物导致准定量转化的原因被默认归因于热力学和动力学效应。为了提供这种行为的明确理由，我们在这里通过结合实验和理论方法的研究来研究所选系列的酮和2-丙醇的氧化还原平衡。首先，研究了短乳杆菌（LBADH）的（R）特异性醇脱氢酶在这些底物上的活性。苯乙酮/（R的对接酶活性位点中的）-1-苯乙醇和α-氯苯乙酮/（S）-2-氯-1-苯乙醇证实似乎没有结构上的卤代醇缺乏反应性的原因。相应的铝催化Meerwein-Ponndorf-Verley-Oppenauer（MPVO）反应提供的转化率与LBADH得到的转化率相似，从而证实了这一假设，表明所观察到的反应性与所用催化剂无关。虽然酶促还原反应的初始速率和IRν（CO）值与普遍认为吸电子基团增加了羰基的亲电性的普遍看法相反，但计算得出的ΔG这些系列