4-氯甲基-2-(2-噻吩基)-1,3-噻唑 | 54679-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-氯甲基-2-(2-噻吩基)-1,3-噻唑
• 英文名称: 4-(chloromethyl)-2-(2-thienyl)-1,3-thiazole
• 英文别名: 4-(chloromethyl)-2-(thiophen-2-yl)-1,3-thiazole；Chlormethyl-4-(thienyl-2)-2-thiazol；4-chloromethyl-2-thiophen-2-yl-thiazole；4-chloromethyl-2-(2-thienyl)thiazole；4-chloromethyl-2-(thien-2-yl)thiazole；4-(chloromethyl)-2-thiophen-2-yl-1,3-thiazole
• CAS: 54679-16-2
• 化学式: C₈H₆ClNS₂
• mdl: MFCD01571296
• 分子量: 215.727
• InChiKey: CGJJBHKYGNSTDK-UHFFFAOYSA-N

物化性质

• 熔点：
  52 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险类别码：
  R34
• 海关编码：
  2934999090
• 安全说明：
  S26,S36/37/39,S45
• 危险品标志：
  C

SDS

Name:	4-(Chloromethyl)-2-(2-thienyl)-1 3-thiazole 97% Material Safety Data Sheet
Synonym:
CAS:	54679-16-2

Section 1 - Chemical Product MSDS Name:4-(Chloromethyl)-2-(2-thienyl)-1 3-thiazole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
54679-16-2	4-(Chloromethyl)-2-(2-thienyl)-1,3-thi	97%	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. 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.
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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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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. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives 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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 54679-16-2: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 51 - 53 deg C
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: C8H6ClNS2
Molecular Weight: 216

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 54679-16-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(Chloromethyl)-2-(2-thienyl)-1,3-thiazole - 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: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

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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# 54679-16-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 54679-16-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 54679-16-2 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：

  4-氯甲基-2-(2-噻吩基)-1,3-噻唑 在 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.68h， 生成 4-{[(1,3-benzothiazol-2-yl)sulfonyl]fluoromethyl}-2-(2-thienyl)-1,3-thiazole
  参考文献：
  名称：

  氟化苯并噻唑基砜的高产率合成：氟-朱里亚烯化反应的通用合成子。

  摘要：

  [反应：见正文]报道了用于合成氟烯烃的一般的高产率串联亲电氟化反应和改性的朱莉娅烯化反应。通过去质子氟化反应合成了一系列基于α-氟1,3-苯并噻唑-2-基砜的合成子。对于高产率氟化而言，至关重要的是非均相反应条件，因为在均相条件下仅回收了起始砜。将如此获得的α-氟1，3-苯并噻唑-2-基砜与各种醛和酮进行缩合反应，以提供高产率的区域特异性氟化烯烃。

  DOI：

  10.1021/ol060002+
• 作为产物：
  描述：

  4-chloromethyl-2-thiophen-2-yl-4,5-dihydro-thiazol-4-ol 在 氯化亚砜 作用下， 反应 0.5h， 生成 4-氯甲基-2-(2-噻吩基)-1,3-噻唑
  参考文献：
  名称：

  4-氯甲基噻唑的改良合成

  摘要：

  据报道由硫代酰胺和1，3-二氯丙酮进行的2-取代的4-氯甲基噻唑的两次反应合成。第一步，在非质子溶剂中在碳​​酸氢盐存在下，进行环化成2-取代的4-氯甲基-4-羟基噻唑啉。该中间体脱水成2-取代的4-氯甲基噻唑是通过与亚硫酰氯，硫酰氯，磷酰氯，三氯化磷或五氯化磷反应而完成的。硫代酰胺上的取代基，例如氨基，烷基或芳基，显示不影响反应的成功。作为趋势，烷基硫代酰胺比芳基硫代酰胺的4-氯甲基噻唑产率更高。使用该方法制备的4-氯甲基噻唑的产率与使用酸催化方法获得的产率相当。

  DOI：

  10.1002/jhet.5570230253

文献信息

• [EN] ARYLOXY AND ARYLALKYLENEOXY SUBSTITUTED IMIDAZOQUINOLINES<br/>[FR] IMIDAZOQUINOLINES SUBSTITUEES PAR ARYLOXY ET ARYLALKYLENEOXY
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2005020999A1

  公开（公告）日：2005-03-10

  Imidazoquinoline compounds with an aryloxy or arylalkyleneoxy or hydroxy substituent at the 6, 7, 8, or 9-position, pharmaceutical compositions containing the compounds, intermediates, and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.

  在这个研究中，披露了在6、7、8或9位具有芳基氧基、芳基烷氧基或羟基取代基的咪唑喹啉化合物，包含这些化合物的药物组合物、中间体以及这些化合物作为免疫调节剂的使用方法，用于调节动物体内细胞因子生物合成，以及用于治疗包括病毒性和肿瘤性疾病在内的疾病。
• Chemical Compounds
  申请人：Turnbull Philip Stewart

  公开号：US20090170907A1

  公开（公告）日：2009-07-02

  This invention relates to non-steroidal compounds that are modulators of androgen, glucocorticoid, mineralocorticoid, and progesterone receptors, and also to the methods for the making and use of such compounds.

  这项发明涉及非甾体化合物，它们是雄激素、糖皮质激素、矿质皮质激素和孕激素受体的调节剂，以及这些化合物的制备和使用方法。
• Heterocyclic compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06211215B1

  公开（公告）日：2001-04-03

  Heterocyclic compounds represented by the general formula (I) wherein R stands for an optionally substituted aromatic heterocyclic group; X stands for oxygen atom, an optionally oxidated sulfur atom, —C(═O)— or —CH(OH)—; Y stands for CH or N; m denotes an integer of 0 to 10: n denotes an integer of 1 to 5: cyclic group  stands for an optionally substituted aromatic azole group; and ring A is optionally further substituted, or salts thereof. The compound (I) possesses action of inhibiting tyrosine kinase and useful as antitumor agents.

  通式（I）代表的杂环化合物，其中R代表一个可选择取代的芳香杂环基团；X代表氧原子，一个可选择氧化的硫原子，—C(═O)—或—CH(OH)—；Y代表CH或N；m表示0到10的整数；n表示1到5的整数；环状基团代表一个可选择取代的芳香唑基团；环A可以是可选择进一步取代的，或其盐。化合物（I）具有抑制酪氨酸激酶的作用，并可用作抗肿瘤剂。
• [EN] INDAZOLE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS D'INDAZOLE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013024011A1

  公开（公告）日：2013-02-21

  A compound of formula I: stereoisomers or a pharmaceutically acceptable salt thereof, wherein X, X1, X2, X3, R1, R2, R3, R4, R5 and R6 are described herein, compositions including the compounds and methods of making and using the compounds for the treatment of diseases.

  公式I的化合物：其立体异构体或其药学上可接受的盐，其中X、X1、X2、X3、R1、R2、R3、R4、R5和R6如本文所述，包括该化合物的组合物以及用于治疗疾病的制备和使用该化合物的方法。
• Structure–Activity Relationships of Novel Thiazole-Based Modafinil Analogues Acting at Monoamine Transporters
  作者：Predrag Kalaba、Marija Ilić、Nilima Y. Aher、Vladimir Dragačević、Marcus Wieder、Martin Zehl、Judith Wackerlig、Stanislav Beyl、Simone B. Sartori、Karl Ebner、Alexander Roller、Natalie Lukic、Tetyana Beryozkina、Eduardo Rene Perez Gonzalez、Philip Neill、Jawad Akbar Khan、Vasiliy Bakulev、Johann Jakob Leban、Steffen Hering、Christian Pifl、Nicolas Singewald、Jana Lubec、Ernst Urban、Harald H. Sitte、Thierry Langer、Gert Lubec

  DOI：10.1021/acs.jmedchem.9b01938

  日期：2020.1.9

  of a series of compounds based on these scaffolds, which resulted in several new selective DAT inhibitors and gave valuable insights into the structure-activity relationships. Introduction of the second chiral center and subsequent chiral separations provided all four stereoisomers, whereby the S-configuration on both generally exerted the highest activity and selectivity on DAT. The representative

  非典型的多巴胺再摄取抑制剂（例如莫达非尼）用于治疗睡眠障碍，并被研究为可卡因成瘾和认知增强的潜在疗法。我们不断努力寻找对多巴胺转运蛋白（DAT）具有更高抑制活性和选择性的莫达非尼类似物，先前已导致了有希望的含噻唑衍生物CE-103，CE-111，CE-123和CE-125。在这里，我们描述了基于这些支架的一系列化合物的合成和活性，从而产生了几种新型的选择性DAT抑制剂，并提供了对结构-活性关系的宝贵见解。第二个手性中心的引入和随后的手性分离提供了所有四种立体异构体，因此，S构型在DAT上通常都表现出最高的活性和选择性。通过计算机，体外和体内研究进一步表征了该系列的代表性化合物，这些研究证明了该化合物类别的安全性和功效。