(R)-(-)-仲丁胺 | 13250-12-9

• 物质功能分类: 有机原料 - 氨基化合物 - 无环单胺、多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (R)-(-)-仲丁胺
• 中文别名: (R)-(-)-2-氨基丁烷；(R)-(-)-2-丁胺
• 英文名称: (R)-sec-butylamine
• 英文别名: (R)-butan-2-amine；(R)-(-)-2-Aminobutane；(2R)-butan-2-amine
• CAS: 13250-12-9
• 化学式: C₄H₁₁N
• 分子量: 73.138
• InChiKey: BHRZNVHARXXAHW-SCSAIBSYSA-N

物化性质

• 熔点：
  -105°C
• 比旋光度：
  -7.5 º (c=neat 19 ºC)
• 沸点：
  63 °C(lit.)
• 密度：
  0.72 g/mL at 25 °C(lit.)
• 闪点：
  -19°C
• 稳定性/保质期：
  常温常压下稳定，避免与氧化物、酸、空气和二氧化碳接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  3
• 危险品标志：
  F,C,N
• 安全说明：
  S16,S26,S28,S36/37/39,S45,S61,S9
• 危险类别码：
  R20/22,R50,R11,R35
• WGK Germany：
  3
• 海关编码：
  2921199090
• 包装等级：
  II
• 危险类别：
  3
• 危险品运输编号：
  UN 2733
• 储存条件：
  常温密闭保存，阴凉、通风、干燥处存放。

SDS

Name:	(R)-(-)-2-Aminobutane 98% Material Safety Data Sheet
Synonym:	(R)-Sec-Butylamine
CAS:	13250-12-9

Section 1 - Chemical Product MSDS Name:(R)-(-)-2-Aminobutane 98% Material Safety Data Sheet
Synonym:(R)-Sec-Butylamine

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13250-12-9	(R)-(-)-2-Aminobutane	98	236-232-6

Hazard Symbols: F C N
Risk Phrases: 11 20/22 35 50

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Harmful by inhalation and if swallowed. Causes severe burns. Very toxic to aquatic organisms.Corrosive.Dangerous for the environment.
Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. May cause cyanosis of the extremities. 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. May cause gastrointestinal irritation with nausea, vomiting and diarrhea. Causes gastrointestinal tract burns. May cause perforation of the digestive tract. Ingestion of large amounts may cause CNS depression. May cause systemic effects.
Inhalation:
Causes chemical burns to the respiratory tract. Aspiration may lead to pulmonary edema. Vapors may cause dizziness or suffocation. May cause systemic effects. May cause burning sensation in the chest.
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:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. 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:

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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. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Will burn if involved in a fire. Use water spray to keep fire-exposed containers cool. Water may be ineffective. Material is lighter than water and a fire may be spread by the use of water. Containers may explode in the heat of a fire.
Flammable liquid and vapor. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. For large fires, use water spray, fog, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Water may be ineffective. Do NOT use straight streams of water.

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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. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation. A vapor suppressing foam may be used to reduce vapors.

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Section 7 - HANDLING and STORAGE
Handling:
Use only in a well-ventilated area. Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Discard contaminated shoes. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.
Flammables-area.

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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 general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 13250-12-9: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: amine-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 57 - 60 deg C @ 760.00mm Hg
Freezing/Melting Point: -104 deg C
Autoignition Temperature: Not available.
Flash Point: -19 deg C ( -2.20 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: in water: > 10 mg/l
Specific Gravity/Density: .7240g/cm3
Molecular Formula: C4H11N
Molecular Weight: 73.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Acids, acid chlorides, acid anhydrides, carbon dioxide, strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13250-12-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-(-)-2-Aminobutane - 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: AMINES, FLAMMABLE, CORROSIVE, N.O.S.*
Hazard Class: 3 (8)
UN Number: 2733
Packing Group: II
IMO
Shipping Name: AMINES, FLAMMABLE, CORROSIVE, N.O.S.
Hazard Class: 3.1
UN Number: 2733
Packing Group: II
RID/ADR
Shipping Name: AMINES, FLAMMABLE, CORROSIVE, N.O.S.
Hazard Class: 3
UN Number: 2733
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F C N
Risk Phrases:
R 11 Highly flammable.
R 20/22 Harmful by inhalation and if swallowed.
R 35 Causes severe burns.
R 50 Very toxic to aquatic organisms.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 33 Take precautionary measures against static
discharges.
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# 13250-12-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13250-12-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13250-12-9 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：

  (R)-(-)-仲丁胺 生成
  参考文献：
  名称：

  KLEIN, MICHAEL;WINGEN, UTE;BUSS, VOLKER, J. AMER. CHEM. SOC., 109,(1987) N 21, 6488-6492

  摘要：

  DOI：
• 作为产物：
  描述：

  仲丁胺 在 磷酸吡哆醛 、 ω-transaminase from Thermomicrobium roseum 、 piruvate 作用下， 以 aq. buffer 为溶剂， 反应 12.0h， 以25.2%的产率得到(R)-(-)-仲丁胺
  参考文献：
  名称：

  新型高温稳定ω-转氨酶的鉴定及其在高温下手性胺的酶促合成中的应用†

  摘要：

  从A新的热稳定ω转氨酶Thermomicrobium玫瑰色其显示广泛的底物特异性和高对映选择性鉴定，表达和生化表征。通过在高温下进行不对称合成和动力学拆分，证明了这种酶去除挥发性抑制副产物的优势。

  DOI：

  10.1039/c6ra15110h
• 作为试剂：
  描述：

  (2-溴-1,3-苯并噻唑-6-基)乙腈 、 (R)-(-)-仲丁胺 、 ethyl acetate n-hexane 在 (R)-(-)-仲丁胺 、 1,4-二氧六环 、 乙酸乙酯 、 碳酸氢钠 、 Brine 、 magnesium sulfate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 以The title compound (1.35 g, 70% yield) was isolated as a light orange oil by ISCO (40% AcOEt/hexane)的产率得到(R)-2-(2-(sec-butylamino)benzo[d]thiazol-6-yl)acetonitrile
  参考文献：
  名称：

  Benzothiazole and azabenzothiazole compounds useful as kinase inhibitors

  摘要：

  公式（I）的化合物，其对映异构体，顺反异构体或其药学上可接受的盐，其中A如此描述。公开了公式（II）的化合物，其对映异构体，顺反异构体或其药学上可接受的盐，其中G，X和Y中的每个都独立地是CH或N，在每次出现时，其中至少一个G，X或Y是N，而另外两个G，X或Y是CH; B，R1，R2，R3，R4，R5，R8，R9和Z如此描述。还公开了含有公式（I）和公式（II）化合物的药物组合物，以及治疗与p38激酶活性相关的疾病的方法。

  公开号：

  US07473784B2

文献信息

• Separate Sets of Mutations Enhance Activity and Substrate Scope of Amine Dehydrogenase
  作者：Robert D. Franklin、Conner J. Mount、Bettina R. Bommarius、Andreas S. Bommarius

  DOI：10.1002/cctc.201902364

  日期：2020.5.7

  average of 2.5‐fold higher activity toward aliphatic ketones and an 8.0 °C increase in melting temperature. L‐AmDH‐TV did not show significant changes in relative activity for different substrates. In contrast, L39A, L39G, A112G, and T133G in varied combinations added to L‐AmDH‐TV changed the shape of the substrate binding pocket. L‐AmDH‐TV was not active on ketones larger than 2‐hexanone. L39A and L39G

  将突变引入衍生自嗜热脂肪芽孢杆菌的亮氨酸胺脱氢酶（L‐AmDH）亮氨酸脱氢酶（LeuDH）的目的是提高活性和扩大底物接受度。包括D32A，F101S和C290V在内的三重变体（L‐AmDH‐TV）对脂族酮的活性平均提高了2.5倍，熔融温度提高了8.0°C。L‐AmDH‐TV在不同底物的相对活性方面未显示出显着变化。相反，添加到L‐AmDH‐TV中的L39A，L39G，A112G和T133G的各种组合改变了底物结合袋的形状。L-AmDH-TV在大于2-己酮的酮上不起作用。L39A和L39G可以激活高达2-癸酮的直链酮，并与A112G结合起来可以活化更长的支链酮，包括5-甲基-2-辛酮。
• Structural Requirements for Binding of Anandamide-Type Compounds to the Brain Cannabinoid Receptor
  作者：Tzviel Sheskin、Lumir Hanuš、Joram Slager、Zvi Vogel、Raphael Mechoulam

  DOI：10.1021/jm960752x

  日期：1997.2.1

  inactive or less active than comparable compounds in the n-6 series. Alkylation or dialkylation of the alpha carbon adjacent to the carbonyl group retains the level of binding in the case of anandamide (compounds 48, 49); however, alpha-monomethylation or alpha,alpha-dimethylation of N-propyl derivatives (50-53) potentiates binding and leads to the most active compounds seen in the present work (Ki values

  为了建立与脑大麻素受体（CB1）结合的结构要求，我们合成了许多脂肪酸酰胺，乙醇酰胺和一些相关的简单衍生物，并确定了它们的Ki值。还检查了一些α-甲基或α，α-二甲基花生四烯酰基烷基酰胺。在20：4，n-6系列中，未取代的酰胺是惰性的；N-单烷基化，至少直至分支的戊基，导致显着的结合。N，N-二烷基化，在一个烷基上具有或不具有羟基化，导致活性的消除。在ω碳原子上的N-单烷基的羟基化保持活性。在20x，n-6序列中，x必须为3或4；否则，x为3。只有两个双键的存在会导致失活。在n-3系列中 报告的有限数据表明，衍生的乙醇酰胺比n-6系列中的同类化合物无活性或活性较低。对于邻氨基苯甲酰胺（化合物48、49），与羰基相邻的α碳的烷基化或二烷基化保持结合水平。但是，N-丙基衍生物（50-53）的α-单甲基化或α，α-二甲基化可增强结合并导致本研究中活性最高的化合物（Ki值为6.9 +/- 0.7至8
• CHEMICAL COMPOUNDS
  申请人：Deng Jianghe

  公开号：US20090143372A1

  公开（公告）日：2009-06-04

  The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  这项发明涉及新型吲哚羧酰胺衍生物。具体而言，该发明涉及符合以下式I的化合物： 其中R1、R2、R3、U和V如下定义，并且其药学上可接受的盐。该发明的化合物是IKK2的抑制剂，可用于治疗与不当IKK2（也称为IKKβ）活性相关的疾病，如类风湿性关节炎、哮喘和慢性阻塞性肺病（COPD）。因此，该发明进一步涉及包含该发明化合物的药物组合物。该发明还进一步涉及使用该发明化合物或包含该发明化合物的药物组合物抑制IKK2活性和治疗相关疾病的方法。
• Asymmetric Synthesis of Optically Pure Pharmacologically Relevant Amines Employing ω-Transaminases
  作者：Dominik Koszelewski、Iván Lavandera、Dorina Clay、David Rozzell、Wolfgang Kroutil

  DOI：10.1002/adsc.200800496

  日期：——

  ω-transaminases were tested for the synthesis of enantiomerically pure amines from the corresponding ketones employing D- or L-alanine as amino donor and lactate dehydrogenase to remove the side-product pyruvate to shift the unfavourable reaction equilibrium to the product side. Both enantiomers, (R)- and (S)-amines, could be prepared with up to 99% ee and >99% conversions within 24 h at 50 mM substrate concentration

  测试了各种ω-转氨酶，以D-或L-丙氨酸为氨基供体和乳酸脱氢酶从相应的酮合成对映体纯的胺，以除去副产物丙酮酸，从而将不利的反应平衡转移至产物侧。（R）-和（S）-胺这两种对映异构体均可以在50 mM底物浓度下于24小时内以高达99％ee和> 99％的转化率制备。胺化反应的活性和立体选择性取决于所用的ω-转氨酶和底物。此外，助溶剂显着影响转氨酶的立体选择性和活性。通过使用ATA-117获得（R对映体和ATA-113或ATA-103，以15％v v -1 DMSO进入（S）对映体。
• 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% 。

表征谱图