(S)-1-(1H-苯并咪唑-2-基)-3-甲基丁胺 | 59592-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (S)-1-(1H-苯并咪唑-2-基)-3-甲基丁胺
• 中文别名: （S）-（-）-2-（α-（异丁基）甲胺）-1H-苯并咪唑；(S )-(-)- 2 - (A -(I -丁基)甲胺)-1H -苯并咪唑
• 英文名称: 2-(1-amino-3-methyl)butyl-benzimidazole
• 英文别名: 1-(1H-bezo[d]imidazole-2-yl)-3-methylbutan-1-amine；(1S)-1-(1H-Benzimidazol-2-yl)-3-methylbutan-1-amine
• CAS: 59592-31-3
• 化学式: C₁₂H₁₇N₃
• mdl: MFCD10558903
• 分子量: 203.287
• InChiKey: NZXOCEISVOCBCD-VIFPVBQESA-N

物化性质

• 熔点：
  109-112°C
• 比旋光度：
  -0.9° (c 1.0 CHCl3)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

SDS

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Section 1: Product Identification
Chemical Name: (S)-(-)-2-(alpha-(i-butyl)methanamine)-1H-benzimidazole, min. 98% (S)-i-Bu-BIMAH
CAS Registry Number: 59592-31-3
Formula: C12H17N3
EINECS Number: none
Chemical Family: organic amine
Synonym: (S)-i-Bu-BIMAH

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 59592-31-3 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation, eyes
Eye Contact: Dust causes moderate irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No information available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: none
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Store in a tightly sealed container under an inert atmosphere of nitrogen or argon. Keep in a cool, dry,
Handling and Storage:
well-ventilated place.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white to off-white solid
Molecular Weight: 203.28
Melting Point: 109-112 °
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: prolonged exposure to air
Incompatibility: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, nitrogen oxides, and organic fumes

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Not regulated under SARA 313
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (S)-1-(1H-苯并咪唑-2-基)-3-甲基丁胺 生成 tert-butyl N-[5-[[(1S)-1-(1H-benzimidazol-2-yl)-3-methylbutyl]amino]-1-cyclohexyl-3-hydroxy-5-oxopentan-2-yl]carbamate
  参考文献：
  名称：

  RADDATZ, PETER;HOLZEMANN, GUNTER;SCHMITGES, CLAUS J.;MINCK, KLAUS OTTO

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 溶剂黄146 为溶剂， 反应 0.33h， 生成 (S)-1-(1H-苯并咪唑-2-基)-3-甲基丁胺
  参考文献：
  名称：

  Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere

  摘要：

  A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP-7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00283-1

文献信息

• A Novel Dual Organocatalyst for the Asymmetric Pinder Reaction and a Mechanistic Proposal Consistent with the Isoinversion Effect Thereof
  作者：Fotini Moschona、Athena Vagena、Veroniki P. Vidali、Gerasimos Rassias

  DOI：10.3390/molecules26216398

  日期：——

  and enantioselectivity. To the best of our knowledge, there has been only one attempt prior to this work towards the development of a catalytic enantioselective Pinder reaction. In our approach, we designed, synthesized, and tested dual chiral organocatalysts by combining BIMAH amines, (2-(α-(alkyl)methanamine)-1H-benzimidazoles, and a Lewis acid motif, such as squaramides, ureas and thioureas. The

  一般而言，Pinder 反应涉及可烯醇化酸酐和醛之间的反应，该反应首先通过 Knoevenagel 反应进行，然后进行闭环过程，生成具有至少两个手性中心的内酯。这些支架经常存在于天然产物和合成生物活性分子中，因此引起了有机合成和药物化学的浓厚兴趣，特别是在控制非对映选择性和对映选择性方面。据我们所知，在这项工作之前，只有一次尝试开发催化对映选择性 Pinder 反应。在我们的方法中，我们通过结合 BIMAH 胺、(2-(α-(烷基)甲胺)-1H-苯并咪唑和路易斯酸基序，如方酰胺、脲和硫脲，设计、合成和测试了双手性有机催化剂。最佳催化剂是带有双(3,5-三氟甲基)硫脲的异丙基BIMAH衍生物，它可以从各种芳香醛中得到Pinder产物，其非对映异构体比例>98:2，对映选择性高达92 ee%。有趣的是，这种对映选择性催化过程在较高浓度下增加，并表现出同向转化效应，即相对于温度的倒“U”形依赖性
• Insight into the corrosion mitigation performance of three novel benzimidazole derivatives of amino acids for carbon steel (X56) in 1 M HCl solution
  作者：Qahtan A. Yousif、Zainb Fadel、Ahmed M. Abuelela、Eid H. Alosaimi、Saad Melhi、Mahmoud A. Bedair

  DOI：10.1039/d3ra01837g

  日期：——

  Three organic molecules having benzimidazole were synthesized and used for protection of carbon steel (X56) from corrosion in 1.00 M HCl. They showed a maximum protective efficiency range between 95% and 98% indicating high corrosion inhibition.

  合成了三种含有苯并咪唑的有机分子，用于保护碳钢（X56）免受 1.00 M HCl 的腐蚀。它们的最大保护效率介于 95% 和 98% 之间，表明它们具有很强的腐蚀抑制能力。
• Rida; Soliman; Badawy, Pharmazie, 1986, vol. 41, # 8, p. 563 - 565
  作者：Rida、Soliman、Badawy

  DOI：——

  日期：——
• RADDATZ, PETER;HOLZEMANN, GUNTER;SCHMITGES, CLAUS J.;MINCK, KLAUS OTTO
  作者：RADDATZ, PETER、HOLZEMANN, GUNTER、SCHMITGES, CLAUS J.、MINCK, KLAUS OTTO

  DOI：——

  日期：——
• Aminosäurederivate
  申请人：MERCK PATENT GmbH

  公开号：EP0222283B1

  公开（公告）日：1992-12-30