2-氨基-3-腈基-4,5,6,7--四氢苯并[B]噻吩 | 4651-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-氨基-3-腈基-4,5,6,7--四氢苯并[B]噻吩
• 中文别名: 2-氨基-4,5,6,7-四氢苯并[b]噻吩-3-腈；2-氨基-3-腈基-4,5,6,7--四氢苯并噻吩；2-氨基-4,5,6,7-四氢-1-苯并噻吩-3-甲腈
• 英文名称: 3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene
• 英文别名: 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene；2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile；2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile；2‐amino‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐3‐carbonitrile
• CAS: 4651-91-6
• 化学式: C₉H₁₀N₂S
• mdl: MFCD00128278
• 分子量: 178.258
• InChiKey: ADHVMGAFAKSNOM-UHFFFAOYSA-N

物化性质

• 熔点：
  151-153°C
• 沸点：
  398.1±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R20/21/22,R36/37/38
• 危险品运输编号：
  3439
• 海关编码：
  2934999090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  应将产品存放在室温环境中，避免光照，并保存在惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile
CAS number: 4651-91-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H10N2S
Molecular weight: 178.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氨基-3-腈基-4,5,6,7--四氢苯并[B]噻吩 在 盐酸 、 溶剂黄146 、 三乙胺 、 苯基硫脲 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 11.5h， 生成 5,6,7,8-四氢[1]七并噻吩[2,3-d]嘧啶-4(3h)-硫酮
  参考文献：
  名称：

  噻吩并[2,3-d]嘧啶衍生物作为EGFR / HER2双重抑制剂和细胞凋亡诱导剂的设计，合成和抗癌评估。

  摘要：

  许多激酶的失调与癌症的发展直接相关，酪氨酸激酶家族是当前癌症治疗方案中最重要的靶标之一。在这项研究中，我们设计并合成了一系列噻吩并[2,3-d]嘧啶衍生物，作为EGFR和HER2酪氨酸激酶抑制剂。在体外评估所有合成的化合物对EGFRWT的抑制活性。并测试了对EGFRWT表现出有希望的IC50值的最具活性的化合物对突变EGFRT790M和HER2激酶的抑制活性。此外，测试了这些化合物对四种癌细胞系（HepG2，HCT-116，MCF-7和A431）的抗肿瘤活性。化合物13g，13h和13k对所检查的细胞系表现出最高活性，IC50值为7.592±0。相当于厄洛替尼的32至16.006±0.58 µM（IC50为4.99±0.09至13.914±0.36 µM）。此外，选择了最有效的抗肿瘤药（13k）进行进一步研究，以确定其对MCF-7细胞系中细胞周期进程和细胞凋亡的影响。结果表明，该化合物阻滞了细胞周期的G2

  DOI：

  10.1016/j.bioorg.2019.102944
• 作为产物：
  描述：

  环己酮 在 三乙烯二胺 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 水 为溶剂， 反应 7.12h， 生成 2-氨基-3-腈基-4,5,6,7--四氢苯并[B]噻吩
  参考文献：
  名称：

  DABCO水溶液，一种用于快速有机催化Knoevenagel缩合和Gewald反应的有效介质

  摘要：

  在水和1,4-二氮杂双环[2.2.2]辛烷的存在下，几种醛和环状酮与丙二腈和氰基乙酸乙酯进行有效的Knoevenagel缩合反应，从而在相当短的时间内产生各自的ab-不饱和体系。结果，容易获得高收率的结合产物。产物可以逐步地或原位地进行Gewald反应，以在4--7小时内有效地产生它们各自的2-氨基噻吩。

  DOI：

  10.3906/kim-1309-38

文献信息

• A facile synthesis of some novel fused [1,2,4]triazolo[3,4-b][1,3,4]thiadiazol derivatives
  作者：Kerru Nagaraju、Yalagala Kotaiah、Chinnam Sampath、Nallapaneni Harikrishna、Chunduri Venkata Rao

  DOI：10.1080/17415993.2012.734306

  日期：2013.6.1

  A series of novel 3-[6-(4-substituted phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-ylmethyl]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one derivatives (7a–7h) have been synthesized from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (1) through a multi-step reaction sequence. The key intermediate (6) on condensation with various substituted aromatic carboxylic acids in

  一系列新型3-[6-(4-取代苯基)-[1,2,4]三唑并[3,4-b][1,3,4]噻二唑-3-基甲基]-5,6,7 ,8-四氢[1]苯并噻吩并[2,3-d]嘧啶-4(3H)-one衍生物(7a-7h)由2-氨基-4,5,6,7-四氢苯并[b]噻吩合成-3-腈 (1) 通过多步反应序列。关键中间体 (6) 在磷酰氯存在下与各种取代的芳族羧酸缩合得到一系列标题化合物 (7a-7h)。所有新合成化合物的结构均基于其 IR、1H-NMR、13C-NMR 和液相色谱质谱数据。
• Synthesis, Antibacterial Activity, and Docking Studies of 1,2,3-triazole-tagged Thieno[2,3-<i>d</i> ]pyrimidinone Derivatives
  作者：M. Aruna Kumari、S. Triloknadh、N. Harikrishna、M. Vijjulatha、C. Venkata Rao

  DOI：10.1002/jhet.2995

  日期：2017.11

  Novel (1‐(substituted phenyl)‐1H‐1,2,3‐triazol‐4‐yl)methyl‐2‐(4‐oxo‐5,6,7,8‐tetrahydrobenzo[1,2]thieno[2,3‐d]pyrimidin‐3(4H)‐yl)acetate derivatives were synthesized. All the compounds showed significant antibacterial activity against Gram‐negative (Escherichia coli and Klebsiella pneumonia) and Gram‐positive (Bacillus subtilis and Bacillus cereus) bacteria. Particularly, (1‐(3‐nitrophenyl)‐1H‐1,2,

  新型（1-（取代苯基）-1 H -1,2,3-三唑-4-基）甲基-2-（4-氧代-5,6,7,8-四氢苯并[1,2]噻吩并[2合成了，3 - d ]嘧啶-3（4 H）-基）乙酸酯衍生物。所有化合物对革兰氏阴性菌（大肠杆菌和肺炎克雷伯菌）和革兰氏阳性菌（枯草芽孢杆菌和蜡状芽孢杆菌）均显示出显着的抗菌活性。特别是，（1-（3-硝基苯基）-1 H -1,2,3-三唑-4-基）甲基-2-（4-氧代-5,6,7,8-四氢苯并[1，2]噻吩发现[2,3 - d ]嘧啶-3（4 H）-基）乙酸酯对大肠杆菌最有效，MIC 25μg/ ml的肺炎克雷伯菌和枯草芽孢杆菌。分子对接也在枯草芽孢杆菌的嘌呤核糖开关和大肠杆菌的硫胺素焦磷酸核糖开关上进行。
• Facile Synthesis and Anticancer Activity of Novel 4-Aminothieno[2,3-d]pyrimidines and Triazolothienopyrimidines
  作者：Fatma S. M. Abu El-Azm、Amira T. Ali、Mohamed H. Hekal

  DOI：10.1080/00304948.2019.1666635

  日期：2019.11.2

  biological activities. They are known to display multiple therapeutic properties, such as anti-inflammatory, antimicrobial, antiproliferative, antidiabetic and analgesic activities. They are structural analogs of biogenic purines and can be considered as potential nucleic acid antimetabolites. Consequently, preparation of thienopyrimidine derivatives with interesting biological activities has attracted

  噻吩并嘧啶在许多生物活动中起着重要作用。众所周知，它们具有多种治疗特性，例如抗炎、抗菌、抗增殖、抗糖尿病和镇痛活性。它们是生物嘌呤的结构类似物，可被视为潜在的核酸抗代谢物。因此，具有令人感兴趣的生物活性的噻吩并嘧啶衍生物的制备引起了特别关注，并且已经开发了多种用于合成噻吩并嘧啶的方法。合成 4-氨基噻吩并[2,3-d]嘧啶的最常用方法包括在乙醇-水混合物中通过氢氧化钠对 2-(苯甲酰硫脲基)噻吩-3-腈进行热闭环，然后加入卤代烷。为了继续我们对合成生物活性杂环化合物的兴趣，我们设计了一种简单易行的关键反应物 2 合成方法。 四氢苯并 [b] 噻吩衍生物 A 与氯乙酰氯反应，通过改进的程序提供相应的 N-氯乙酰氨基衍生物 1 Sauter 等人。（方案1）。在回流的乙醇中用硫氰酸铵处理化合物 1，得到化合物 2 而不是 2-亚氨基-4-氧噻唑烷衍生物 3（方案 1）。在产品的红外光谱中，NH2
• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。
• [EN] COMPOUNDS FOR TREATING VIRAL INFECTIONS<br/>[FR] COMPOSÉS POUR TRAITER DES INFECTIONS VIRALES
  申请人：PASTEUR INSTITUT KOREA

  公开号：WO2015158908A1

  公开（公告）日：2015-10-22

  The present invention relates to small molecule compounds and their use in the treatment of diseases, in particular viral diseases, in particular hepatitis C virus (HCV).

  本发明涉及小分子化合物及其在治疗疾病中的应用，特别是病毒性疾病，尤其是丙型肝炎病毒（HCV）。