(R)-3-氨基-3-苯基丙醇 | 170564-98-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 氨基醇类衍生物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (R)-3-氨基-3-苯基丙醇
• 中文别名: 3-氨基-3-苯基-丙醇；R-3-氨基-3-苯丙醇；(R)-3-氨基-3-苯丙醇
• 英文名称: (R)-3-amino-3-phenylpropan-1-ol
• 英文别名: (R)-3-amino-3-phenyl-1-propanol；(3R)-3-amino-3-phenylpropan-1-ol
• CAS: 170564-98-4
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: SEQXIQNPMQTBGN-SECBINFHSA-N

物化性质

• 熔点：
  77°C(lit.)
• 沸点：
  273.23°C (rough estimate)
• 密度：
  1.0406 (rough estimate)
• 溶解度：
  二氯甲烷（微溶）、DMSO（微溶）、甲醇（微溶、加热）
• 稳定性/保质期：

  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2922199090
• 危险品运输编号：
  UN 3259 8/PG III
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Name:	(R)-3-Amino-3-phenylpropan-1-ol 95% (98% e.e.) Material Safety Data Sheet
Synonym:	None
CAS:	170564-98-4

Section 1 - Chemical Product MSDS Name:(R)-3-Amino-3-phenylpropan-1-ol 95% (98% e.e.) Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
170564-98-4	(R)-3-Amino-3-phenylpropan-1-ol	95	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Air sensitive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns. Amines have been known to cause skin irritation and sensitization.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Destroy contaminated shoes.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Discard contaminated shoes. Do not breathe dust.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area. Do not expose to air. Store under an inert atmosphere.

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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# 170564-98-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Solid
Color: Not available.
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: C9H13NO
Molecular Weight: 151.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions. Air sensitive.
Conditions to Avoid:
Dust generation, exposure to air.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 170564-98-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-3-Amino-3-phenylpropan-1-ol - 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
Shipping Name: CORROSIVE LIQUID, BASIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3267
Packing Group: III
IMO
Shipping Name: CORROSIVE LIQUID, BASIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3267
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE LIQUID, BASIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3267
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 170564-98-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 170564-98-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 170564-98-4 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

制备方法与用途

制备方法

医药中间体。

用途简介

暂无相关信息。

反应信息

• 作为反应物：
  描述：

  (R)-3-氨基-3-苯基丙醇 在 N-羟基-7-氮杂苯并三氮唑 、 lithium hydroxide monohydrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 tert-butyl (3R,5S)-3-(cyclopropyl((1-(3-methoxypropyl)-1H-indol-3-yl)methyl)carbamoyl)-5-(((R)-3-hydroxy-1-phenylpropyl)carbamoyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Structure-Based Design of Substituted Piperidines as a New Class of Highly Efficacious Oral Direct Renin Inhibitors

  摘要：

  A cis-configured 3,5-disubstituted piperidine direct renin inhibitor, (syn,rac)-1, was discovered as a high-throughput screening hit from a target-family tailored library. Optimization of both the prime and the nonprime site residues flanking the central piperidine transition-state surrogate resulted in analogues with improved potency and pharmacokinetic (PK) properties, culminating in the identification of the 4-hydroxy-3,5-substituted piperidine 31. This compound showed high in vitro potency toward human renin with excellent off-target selectivity, 60% oral bioavailability in rat, and dose-dependent blood pressure lowering effects in the double-transgenic rat model.

  DOI：

  10.1021/ml500137b
• 作为产物：
  描述：

  3-氨基-3-苯基-1-丙醇 在 sodium hydroxide 、 phosphate buffer 、 penicillin G acylase immobilized on epoxy-resin 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 (R)-3-氨基-3-苯基丙醇
  参考文献：
  名称：

  Preparation of enantiomerically pure (R)- and (S)-3-amino-3-phenyl-1-propanol via resolution with immobilized penicillin G acylase

  摘要：

  Ethyl 2,4-dioxo-4-phenylbutyrate, obtained by condensation of acetophenone with diethyl oxalate, was converted to 3-oxo-3-phenyl-1-propanol in 90% yield by reaction with baker's yeast. Reductive amination with sodium cyanoborohydride in the presence of ammonium acetate gave the racemic 3-amino-3-phenyl-1-propanol in 65% yield. Enzymatic resolution of the corresponding N-phenylacetyl derivative with penicillin G acylase, immobilized on an epoxy resin gave (S)-amide and (R)-amino alcohol in high enantiomeric purity (ee > 99%) and > 45% yields for each enantiomer. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.022

文献信息

• [EN] BENZOLACTAM COMPOUNDS AS PROTEIN KINASE INHIBITORS<br/>[FR] COMPOSÉS BENZOLACTAMES UTILISÉS EN TANT QU'INHIBITEURS DE PROTÉINE KINASE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2017068412A1

  公开（公告）日：2017-04-27

  The invention provides a compound of formula (0): or a pharmaceutically acceptable salt, N-oxide or tautomer thereof. The compounds are inhibitors of ERK 1/2 kinases and will be useful in the treatment of ERKl/2-mediated conditions. The compounds are therefore useful in therapy, in particular in the treatment of cancer.

  该发明提供了一个化合物，其化学式为(0)：或其药学上可接受的盐、N-氧化物或互变异构体。这些化合物是ERK 1/2激酶的抑制剂，并将在治疗ERKl/2介导的疾病中发挥作用。因此，这些化合物在治疗中特别是在癌症治疗中是有用的。
• Chiral Arylated Amines via C−N Coupling of Chiral Amines with Aryl Bromides Promoted by Light
  作者：Geyang Song、Liu Yang、Jing‐Sheng Li、Wei‐Jun Tang、Wei Zhang、Rui Cao、Chao Wang、Jianliang Xiao、Dong Xue

  DOI：10.1002/anie.202108587

  日期：2021.9.20

  molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing

  Buchwald-Hartwig CN 偶联反应已在有机合成中得到广泛应用。在过去二十年左右的时间里，已经引入了许多改进的催化剂，现在可以很容易地使用各种胺和芳基亲电试剂。然而，缺乏可用于偶联各种手性胺和芳基卤而不会侵蚀过量对映体 ( ee) 的方案）。本文报道了一种基于光驱动的分子 Ni 催化的方法，该方法能够使旋光胺、氨基醇和氨基酸酯与芳基溴进行立体保留 CN 偶联，无需任何外部光敏剂。该方法对多种偶联伙伴有效，包括那些带有对碱和亲核试剂敏感的官能团的偶联伙伴，从而为获取合成重要的手性N-芳基胺、氨基醇和氨基酸酯提供了可行的替代方案。92 个例子证明了它的可行性，ee高达 99% 。
• [EN] 6-AMINO-QUINOLINE-3-CARBONITRILS AS COT MODULATORS<br/>[FR] 6-AMINO-QUINOLINE-3-CARBONITRILES UTILISÉS COMME MODULATEURS DE LA KINASE COT
  申请人：GILEAD SCIENCES INC

  公开号：WO2017007694A1

  公开（公告）日：2017-01-12

  The present disclosure relates generally to modulators of Cot (cancer Osaka thyroid) and methods of use and manufacture thereof.

  本公开涉及一般与Cot（癌症大阪甲状腺）的调节剂以及其使用和制造方法。
• [EN] COT MODULATORS AND METHODS OF USE THEREOF<br/>[FR] MODULATEURS DE COT ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：GILEAD SCIENCES INC

  公开号：WO2017007689A1

  公开（公告）日：2017-01-12

  The present disclosure relates generally to modulators of Cot (cancer Osaka thyroid) and methods of use and manufacture thereof.

  本公开涉及通常与Cot（大阪甲状腺癌）调节剂及其使用和制造方法。
• PYRIDO PYRIMIDINES
  申请人：Anderson Kevin

  公开号：US20120184542A1

  公开（公告）日：2012-07-19

  Compounds of formula and pharmaceutically acceptable salts thereof are described, as well as the pharmaceutical compositions containing said compounds and their pharmaceutically acceptable salts, and the use of said compounds and pharmaceutical compositions for the treatment, control or amelioration of proliferative diseases, including cancer, Down syndrome or early onset Alzheimer's disease.

  具有该公式的化合物以及它们的药用可接受盐被描述，以及包含所述化合物及其药用可接受盐的药物组合物，以及所述化合物和药物组合物用于治疗、控制或改善增生性疾病，包括癌症、唐氏综合症或早发性阿尔茨海默病的使用。