S-(-)-N,N-二甲基-3-羟基-3-(2-噻吩)丙胺 | 132335-44-5

• 物质功能分类: 有机原料 - 氨基化合物 - 含氧基氨基化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: S-(-)-N,N-二甲基-3-羟基-3-(2-噻吩)丙胺
• 中文别名: (S)-3-(二甲氨基)-1-(2-噻吩基)-1-丙醇；6(S)-(-)-N,N-二甲基-3-羟基-3-(2-噻吩)丙胺；(S)-(-)-3-(二甲氨基)-1-(2-噻吩基)-1-丙醇；(S)-(-)-N,N-二甲基-3-羟基-2-噻吩基丙胺；(s)-(-)-N,N-二甲基-3-羟基-2-噻吩基丙胺；(s)-(-)N，N-二甲基-3-羟基3-(2-硫代)丙胺；S(-)-N，N-二甲基-3-羟基-3-(2-噻吩基)-1-丙胺；S-(-)N,N-二甲基-3-羟基-3-(2-噻吩基)丙胺；(s)-(-)-N,N-二甲基-3-羟基-(2-噻吩)丙胺；(S)-(-)N,N-二甲基-3-羟基-3-(2-噻吩基)丙胺；S-1-萘基-1-乙醇
• 英文名称: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol
• 英文别名: (S)-3-(dimethylamino)-1-(thiophen-2-yl)propan-1-ol；(S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine；(1S)-3-(dimethylamino)-1-thiophen-2-ylpropan-1-ol
• CAS: 132335-44-5
• 化学式: C₉H₁₅NOS
• mdl: MFCD07782107
• 分子量: 185.29
• InChiKey: XWCNSHMHUZCRLN-QMMMGPOBSA-N

物化性质

• 熔点：
  78-80°C
• 沸点：
  290°C
• 密度：
  1.111
• 闪点：
  129°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2942000000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20°C freezer

SDS

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Section I.Chemical Product and Company Identification
Chemical Name (S)-3-(Dimethylamino)-1-(2-thienyl)-1-propanol
Portland OR
Synonym 2-Thiophenemethanol, α-[2-(dimethylamino)ethyl]-, (αS)-
(CA INDEX NAME)
(S)-2-[3-(Dimethylamino)-1-hydroxy-1-propyl]thiophene
Chemical Formula C9H15NOS
132335-44-5
CAS Number

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
(S)-3-(Dimethylamino)-1-(2-thienyl)-1-propanol 132335-44-5 Min. 98.0 (GC, Not available. Not available.
T)

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Section III. Hazards Identification
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
Acute Health Effects
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
CARCINOGENIC EFFECTS : Not available.
Chronic Health Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
Eye Contact
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
Inhalation If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
Not available.
Auto-Ignition
Flammability May be combustible at high temperature.
Flammable Limits Not available.
Flash Points Not available.
Combustion Products These products are toxic carbon oxides (CO, CO2), nitrogen oxides (NO, NO2), sulfur oxides (SOx).
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
(S)-3-(Dimethylamino)-1-(2-thienyl)-1-propanol

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Section VI. Accidental Release Measures
Spill Cleanup Irritating material.
Use a shovel to put the material into a convenient waste disposal container. Consult federal, state, and/or local authorities for
Instructions
assistance on disposal.

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Section VII. Handling and Storage
Handling and Storage IRRITANT. Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in a
dry, cool place. Avoid excessive heat and light. Do not breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents, acids.

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Section VIII. Exposure Controls/Personal Protection
Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended
Engineering Controls
exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants
below the exposure limit.
Splash goggles. Lab coat. Dust respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
Personal Protection
specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Solid. (Crystal, powder. White - almost Solubility
Physical state @ 20°C Soluble in methanol.
white.)
Not available.
Specific Gravity
Molecular Weight 185.29 Partition Coefficient Not available.
Boiling Point Not available. Not applicable.
Vapor Pressure
Melting Point 77 to 81°C (170.6 to 177.8°F) Vapor Density Not available.
Not available. Not available.
Refractive Index Volatility
Critical Temperature Not available. Odor Not available.
Not available. Not available.
Viscosity Taste

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Section X. Stability and Reactivity Data

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Stability
Conditions of Instability Avoid excessive heat and light.
Incompatibilities Reactive with oxidizing agents, strong acids.

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Section XI. Toxicological Information
RTECS Number Not available.
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Not available.
Toxicity Data
CARCINOGENIC EFFECTS : Not available.
Chronic Toxic Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the eye
Acute Toxic Effects
is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.

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Section XII. Ecological Information
Ecotoxicity Not available.
Environmental Fate Not available.
Continued on Next Page
(S)-3-(Dimethylamino)-1-(2-thienyl)-1-propanol

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Section XIII. Disposal Considerations
Waste Disposal Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
DOT Classification Not a DOT controlled material (United States).
PIN Number Not applicable.
Proper Shipping Name Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not available.
(Canada)
EINECS Number (EEC) 603-565-7
EEC Risk Statements R36/37/38- Irritating to eyes, respiratory system and skin.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

S-(-)-N,N-二甲基-3-羟基-3-(2-噻吩)丙胺是盐酸度洛西汀的重要中间体，适用于医药研发和实验室研究。

反应信息

• 作为反应物：
  描述：

  S-(-)-N,N-二甲基-3-羟基-3-(2-噻吩)丙胺 在 盐酸 、 甲酸 、 sodium hydride 、 三乙胺 、 锌 、 氯甲酸-2,2,2-三氯乙酯 作用下， 反应 48.92h， 生成 度洛西汀
  参考文献：
  名称：

  LY248686的不对称合成和绝对立体化学

  摘要：

  用[（2 R，3 S -（+）-4--二甲基氨基-1,2-二苯基-3-甲基-2] 2：1络合物还原3-（二烷基氨基）-1-芳基-1-丙烷-丁醇]（8）和氢化铝锂（LAH）在高ee（80-88％）中提供了相应的1,3-氨基醇，开发了该方法并将其用于合成LY248686（1），这是一种强力抑制剂血清素（5HT）和去甲肾上腺素（NE）的摄取，通过单晶X射线分析已确定了绝对构型。

  DOI：

  10.1016/s0040-4039(00)97251-4
• 作为产物：
  描述：

  3-二甲基氨基-1-(2-噻吩基)-1-丙酮 在 RuCl₂(1,1'-bis(diphenyphosphino)ferrocene)[(1S,1'S)-6,6'-dibromo-1,1'-biisoindoline] 、 potassium tert-butylate 、 氢气 作用下， 以 丙醇 为溶剂， 20.0 ℃ 、5.07 MPa 条件下， 反应 30.0h， 生成 S-(-)-N,N-二甲基-3-羟基-3-(2-噻吩)丙胺
  参考文献：
  名称：

  含刚性手性二胺和非手性二膦的钌催化剂用于芳族酮的高对映选择性加氢

  摘要：

  一个手性元素就足够了：一种含有刚性手性二胺（BIDN）和可商购的廉价非手性膦（DPPF）的新型钌催化剂对于酮的对映选择性氢化非常有效（请参阅方案）。获得了高反应活性（S / C高达100000）和出色的对映选择性（高达99％  ee）。

  DOI：

  10.1002/chem.201100820
• 作为试剂：
  描述：

  1-氟萘 在 草酸 作用下， 以 异丁酰胺 、 水 、 S-(-)-N,N-二甲基-3-羟基-3-(2-噻吩)丙胺 、 乙酸乙酯 、 mineral oil 为溶剂， 以80%的产率得到(S)-(+)-N,N-二甲基-3-(1-萘氧基)-3-(2-噻吩基)丙胺草酸盐
  参考文献：
  名称：

  Gastro-resistant pharmaceutical oral compositions comprising duloxetine or its pharmaceutically acceptable derivatives

  摘要：

  本发明涉及一种药物组合物，包括一个活性核心，其中包括度洛西汀或其药学上可接受的衍生物，一个分离层，其中包括一种水溶性碱性物质，以及一个胃肠抗性涂层，其中包括一种甲基丙烯酸共聚物选择的胃肠抗性聚合物，以及可选的覆盖层。

  公开号：

  EP2133072A1

文献信息

• Oxalic Diamides and <i>tert</i>-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction
  作者：Zhixiang Chen、Yongwen Jiang、Li Zhang、Yinlong Guo、Dawei Ma

  DOI：10.1021/jacs.8b12142

  日期：2019.2.27

  A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic

  已经开发了一种用于制备烷基芳基醚的稳健实用的方案，该方案依赖于使用两种类型的配体来促进 Cu 催化的（杂）芳基卤化物的烷氧基化。反应范围非常适用于各种偶联伙伴，尤其是具有挑战性的仲醇和（杂）芳基氯。在与芳基氯化物和溴化物偶联的情况下，两个草酸二酰胺作为强大的配体。叔丁醇首先被证明是铜催化偶联反应的配体，导致芳基碘化物在室温下完成烷氧基化。此外，许多碳水化合物衍生物适用于该偶联反应，以 29-98% 的产率提供相应的碳水化合物-芳基醚。
• 중간체로서 광학 활성 3-아미노-1-프로판올 유도체의 제조방법 및 상기 중간체를 이용한 (S)-둘록세틴의 제조방법
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR20150043955A

  公开（公告）日：2015-04-23

  본 발명에 따른 높은 광학 활성을 가지는 3-아미노-1-프로판올 유도체의 제조방법 및 이를 이용한 거울상 이성질체적으로 순수한 둘록세틴의 제조방법은 광학 활성을 가지는 3-아미노-1-프로판올 유도체를 종래의 어떤 방법보다도 더 높은 수율과 광학적 순도(ee)로 수득할 수 있으며, 이를 중간체로 이용함으로써 거울상 이성질체적으로 순수하며 높은 광학적 순도(ee)로 둘록세틴을 제조할 수 있다.

  根据本发明，具有高光学活性的3-氨基-1-丙醇衍生物的制备方法以及利用该方法制备高光学纯度的镜像立体异构体的方法，通过利用具有高光学活性的3-氨基-1-丙醇衍生物，可以比传统方法获得更高的产率和光学纯度（ee），并且可以利用其作为中间体制备出具有镜像立体异构体纯度和高光学纯度（ee）的二乙酰胺。
• Lutidine‐Based Chiral Pincer Manganese Catalysts for Enantioselective Hydrogenation of Ketones
  作者：Linli Zhang、Yitian Tang、Zhaobin Han、Kuiling Ding

  DOI：10.1002/anie.201814751

  日期：2019.4

  activities (up to 9800 TON; TON=turnover number), broad substrate scope (81 examples), good functional‐group tolerance, and excellent enantioselectivities (85–98 % ee) in the hydrogenation of various ketones. These aspects are rare in earth‐abundant metal catalyzed hydrogenations. The utility of the protocol have been demonstrated in the asymmetric synthesis of a variety of key intermediates for chiral drugs

  已经开发了一系列含有基于核苷的手性钳式配体的Mn I配合物，这些配合物具有模块化和可调的结构。该配合物在各种酮的氢化反应中显示出前所未有的高活性（高达9800 TON； TON =周转数），广泛的底物范围（81个实例），良好的官能团耐受性和出色的对映选择性（85-98％ee）。这些方面在稀土金属催化的氢化反应中很少见。该协议的实用性已在手性药物的多种关键中间体的不对称合成中得到证明。初步的机理研究表明，底物与催化剂相互作用的外层模式可能主导了催化作用。
• 手性氨基-吡啶-膦三齿配体、锰络合物、其制备方法和应用
  申请人：中国科学院上海有机化学研究所

  公开号：CN111320651B

  公开（公告）日：2023-01-17

  本发明公开了一种手性氨基‑吡啶‑膦三齿配体、锰络合物、其制备方法和应用。本发明手性氨基‑吡啶‑膦三齿配体如式II所示，该手性氨基‑吡啶‑膦三齿配体的锰络合物可用于高效、高对映选择性地催化氢化酮类化合物制备手性醇类化合物。本发明的手性氨基‑吡啶‑膦三齿配体和锰络合物合成工艺简单，稳定性好，催化活性高，反应条件温和。
• 一种含芳胺NH的三齿氮膦配体、制备方法及其应用
  申请人：洛阳师范学院

  公开号：CN113024615A

  公开（公告）日：2021-06-25

  本发明公开了一种含芳胺NH的三齿氮膦配体、制备方法及其应用，属于有机合成技术领域。本发明的三齿氮膦配体是目前第一例既含喹啉胺结构又含手性二茂铁的三齿氮膦配体，该类型配体的贵金属配合物在不对称氢化反应中表现出好的选择性和极高的催化活性，同时该配体的廉价金属配合物在不对称氢化反应中也能表现出好的选择性和催化活性，且无论从电子效应还是空间结构上都非常容易修饰，因此，该配体具有巨大的潜在应用价值。该配体与过渡金属络合物形成的催化剂能够用于催化多种反应，且可以用于多种药物的合成，具有重要的工业应用价值。