(S)-3-氨基-3-苯基丙醇 | 82769-76-4

• 物质功能分类: 化学试剂 - 有机试剂 - 芳烃
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (S)-3-氨基-3-苯基丙醇
• 中文别名: S-3-氨基-3-苯丙醇；(S)-β-苯丙氨醇
• 英文名称: (S)-3-amino-3-phenylpropanol
• 英文别名: (S)-3-amino-3-phenylpropan-1-ol；(S)-3-amino-3-phenyl-1-propanol；(S)-1-phenyl-3-hydroxypropylamine；(3S)-3-amino-3-phenylpropan-1-ol
• CAS: 82769-76-4
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: SEQXIQNPMQTBGN-VIFPVBQESA-N

物化性质

• 熔点：
  68-69 °C
• 沸点：
  273.23°C (rough estimate)
• 密度：
  1.0406 (rough estimate)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

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
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	(S)-3-Amino-3-Phenylpropan-1-ol 95% (98% E.E.) Material Safety Data Sheet
Synonym:	None Known
CAS:	82769-76-4

Section 1 - Chemical Product MSDS Name:(S)-3-Amino-3-Phenylpropan-1-ol 95% (98% E.E.) Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
82769-76-4	(S)-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.Corrosive.
Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns. May cause perforation of the digestive tract. May cause systemic effects.
Inhalation:
Causes chemical burns to the respiratory tract. Aspiration may lead to pulmonary edema. May cause systemic effects.
Chronic:
Effects may be delayed.

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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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation. Place under an inert atmosphere.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale. Handle under an inert atmosphere. Store protected from air.
Use only in a chemical fume hood. Discard contaminated shoes.
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# 82769-76-4: 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: Liquid
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:
Incompatible materials, exposure to air.
Incompatibilities with Other Materials:
Oxidizing agents.
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# 82769-76-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-3-Amino-3-Phenylpropan-1-ol - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

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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: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 82769-76-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 82769-76-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 82769-76-4 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

用途：达泊西汀盐酸盐中间体

反应信息

• 作为反应物：
  描述：

  (S)-3-氨基-3-苯基丙醇 在 吡啶 、 三氧化硫吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.17h， 生成 (S)-3-氧代-1-苯基丙基氨基甲酸叔丁酯
  参考文献：
  名称：

  双环胍TBD的手性类似物：合成，结构和布朗斯台德碱催化。

  摘要：

  从（S）-β-苯丙氨酸开始，可通过脂肪酶催化的动力学拆分轻松获得，通过还原胺化组装手性三胺，最后环化形成标题化合物10。在苯甲酸胍盐的晶体中有六个成员环10的分子中的构象接近于具有在伪轴向位置上的苯基取代基的包膜。未质子化的胍10催化蒽酮和马来酰亚胺的Diels-Alder反应（25-30％ee）。它也促进了一些环加合物的逆醛醇反应作为强布朗斯台德碱，并且具有对映异构体的动力学拆分。在三种情况下，逆醛醇产品（48-83％ee）可以重结晶至高对映体纯度（> / = 95％ee）。几种化合物的绝对构型由异常X射线衍射和化学相关性支持。

  DOI：

  10.3762/bjoc.12.176
• 作为产物：
  描述：

  (S)-1-苯基-3-丁烯-1-醇 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正庚烷 、 重水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 64.0h， 生成 (S)-3-氨基-3-苯基丙醇
  参考文献：
  名称：

  基于芳香醛的对映选择性烯丙基化合成氟布芬代谢物和达泊西汀

  摘要：

  芳醛对映选择性烯丙基化得到手性高烯丙醇被用作氟布芬代谢物和达泊西汀合成的关键步骤。在前一种情况下，高烯丙醇部分 (99% ee) 转化为五元内酯环，光学纯度保持良好，目标化合物氟布芬代谢物以 95% ee 获得。在后一种情况下，高烯丙醇部分 (97% ee) 经过几个步骤转化为 3-氨基丙醇部分。在合成过程中，观察到光学纯度逐渐降低，目标化合物达泊西汀以 85% ee 获得。

  DOI：

  10.1002/ejoc.201301899
• 作为试剂：
  描述：

  4,4-二氟环己烷羰酰氯 、 (S)-3-氨基-3-苯基丙醇 在 (S)-3-氨基-3-苯基丙醇 作用下， 以89的产率得到4,4-二氟-N-((1S)-3-羟基-1-苯基丙基)环己烷甲酰胺
  参考文献：
  名称：

  [EN] TROPANE DERIVATIVES USEFUL IN THERAPY
  [FR] DERIVES DU TROPANE UTILES EN THERAPIE

  摘要：

  本发明提供式(I)的化合物：其中R1为C3-6环烷基，可选地被一个或多个氟原子取代，或C1-6烷基，可选地被一个或多个氟原子取代，或C3-6环烷基甲基，可选地被一个或多个氟原子取代；R2为苯基，可选地被一个或多个氟原子取代，以及其药学上可接受的盐和溶剂，以及制备该化合物所用的中间体，包含该化合物的组合物和用途的制备过程。

  公开号：

  WO2001090106A2

文献信息

• Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins
  作者：Jakob F. Schneider、Markus B. Lauber、Vanessa Muhr、Domenic Kratzer、Jan Paradies

  DOI：10.1039/c1ob05059a

  日期：——

  focuses on readily accessible thiourea hydrogen bond catalysts derived from amino acids, whose steric and electronic features are modulated by their degree of substitution at the carbinol carbon center. These catalysts were applied in the asymmetric transfer hydrogenation of nitroolefins furnishing the chiral products in up to 99% yield and 86% enantiomeric excess. The proposed catalyst's mode of action

  本文着重于易于访问的内容 硫脲衍生自氨基酸的氢键催化剂，其位阻和电子特征受其在甲醇碳中心的取代度的调节。这些催化剂被用于硝基烯烃的不对称转移氢化，从而以高达99％的收率和86％的对映体过量提供手性产物。所提出的催化剂的作用方式得到机理研究的支持。
• 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。
• Palladium‐Catalyzed Regioselective and Stereospecific Ring‐Opening Suzuki‐Miyaura Arylative Cross‐Coupling of 2‐Arylazetidines with Arylboronic Acids
  作者：Youhei Takeda、Kazuya Toyoda、W. M. C. Sameera、Norimitsu Tohnai、Satoshi Minakata

  DOI：10.1002/adsc.202100195

  日期：2021.6.8

  We have developed a palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki–Miyaura arylative cross-coupling of N-tosyl-2-arylazetidines to give enantioenriched 3,3-diarylpropylamines. This reaction represents an example of transition-metal-catalyzed ring-opening cross-coupling using azetidines as a non-classical alkyl electrophile. Density functional theory rationalized the mechanism

  我们开发了一种钯催化的区域选择性和对映特异性开环 Suzuki-Miyaura 芳基化交叉偶联的N-甲苯磺酰基-2-芳基氮杂环丁烷，得到对映体富集的 3,3-二芳基丙胺。该反应代表了使用氮杂环丁烷作为非经典烷基亲电子试剂的过渡金属催化开环交叉偶联的一个例子。密度泛函理论使完整催化循环的机制合理化，包括决定选择性的氮杂环丁烷开环、与水反应、决定速率的金属转移和还原消除。通过多组分人工力诱导反应（MC-AFIR）方法系统地确定了选择性决定开环步骤的过渡态，以解释反应的区域选择性。
• [EN] AMINOPYRIMIDINE DERIVATIVES FOR USE AS MODULATORS OF KINASE ACTIVITY<br/>[FR] DÉRIVÉS AMINOPYRIMIDINES À UTILISER EN TANT QUE MODULATEURS D'ACTIVITÉ KINASE
  申请人：MERCK PATENT GMBH

  公开号：WO2013040044A1

  公开（公告）日：2013-03-21

  The invention provides novel heterocyclic amine compounds accord¬ ing to Formula (I) and their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.

  这项发明提供了根据式（I）制备的新型杂环胺化合物，以及它们的制备和用于治疗高增殖性疾病，如癌症。
• Heterocyclic inhibitors of ERK2 and uses thereof
  申请人：——

  公开号：US20030092714A1

  公开（公告）日：2003-05-15

  Described herein are compounds that are useful as protein kinase inhibitors having the formula: 1 wherein Z 1 and Z 2 are each independently nitrogen or CH and Ring A, T m R 1 , QR 2 , U n R 3 , and Sp are as described in the specification. The compounds are especially useful as inhibitors of ERK2 and for treating diseases in mammals that are alleviated by a protein kinase inhibitor, particularly diseases such as cancer, inflammatory disorders, restenosis, diabetes, and cardiovascular disease.

  本文描述了一些化合物，这些化合物可用作蛋白激酶抑制剂，其化学式如下： 1 其中Z 1 和Z 2 分别独立地为氮或CH，环A，T m R 1 ，QR 2 ，U n R 3 和Sp如规范中所述。这些化合物特别适用于ERK2的抑制剂，并用于治疗通过蛋白激酶抑制剂缓解的哺乳动物疾病，特别是癌症、炎症性疾病、再狭窄、糖尿病和心血管疾病等疾病。