1-甲基-2-硫基-1H-咪唑-5-羧酸甲酯 | 68892-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-甲基-2-硫基-1H-咪唑-5-羧酸甲酯
• 中文别名: 2-疏基-1-甲基-1H-咪唑-5-甲酸甲酯；1-甲基-2-巯基O-1H-咪唑-5-羧酸甲酯
• 英文名称: methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate
• 英文别名: 1-methyl-5-carbomethoxy-2-thio-imidazole；methyl 3-methyl-2-sulfanylidene-1H-imidazole-4-carboxylate
• CAS: 68892-07-9
• 化学式: C₆H₈N₂O₂S
• mdl: MFCD00206762
• 分子量: 172.208
• InChiKey: MXRBCICJILKUCS-UHFFFAOYSA-N

物化性质

• 熔点：
  188 °C
• 沸点：
  240.6±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S24/25
• 海关编码：
  2933290090

SDS

Name:	Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	68892-07-9

Section 1 - Chemical Product MSDS Name:Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
68892-07-9	Methyl 2-mercapto-1-methyl-1H-imidazol	97%	272-595-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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 water spray, dry chemical, carbon dioxide, or chemical foam.

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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:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 68892-07-9: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 189 - 191 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: C6H8N2O2S
Molecular Weight: 172.2

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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:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 68892-07-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 2-mercapto-1-methyl-1H-imidazole-5-carboxylate - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 68892-07-9: No information available.
Canada
CAS# 68892-07-9 is listed on Canada's NDSL List.
CAS# 68892-07-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 68892-07-9 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-甲基-2-硫基-1H-咪唑-5-羧酸甲酯 在 水 、 sodium hydroxide 作用下， 反应 0.5h， 以363 g的产率得到2,3-二氢-3-甲基-2-硫氧代-1H-咪唑-4-羧酸
  参考文献：
  名称：

  SUBSTITUTED 2-THIOIMIDAZOLYLCARBOXAMIDES AS PESTICIDES

  摘要：

  本发明涉及一般式（I）中的化合物，其中Q、V、T、W、X、Y、n和A具有描述中给出的含义，以及用于其制备和用于控制动物害虫的方法。

  公开号：

  US20180007900A1
• 作为产物：
  描述：

  sodium thiocyanide 、 N-甲酰基-N-甲基甘氨酸甲酯 在 甲酸乙酯 作用下， 生成 1-甲基-2-硫基-1H-咪唑-5-羧酸甲酯
  参考文献：
  名称：

  甲巯咪唑的可扩展工艺

  摘要：

  观察到咪唑羧酸盐的碱水解是可扩展合成抗甲状腺药物甲巯咪唑的有效途径。3-甲基-2-硫代-2,3-二氢-1H-咪唑-1-甲酸乙酯 ( 12 ) 是 1-甲基-1H-咪唑 ( 4 ) 与氯甲酸乙酯 ( 11 ) 反应中的关键中间体) 和硫磺。化合物12在碱存在下分两步水解得到甲巯咪唑( 1 )，总收率为78％。该过程通过质量源于设计 (QbD) 概念进行了研究，并观察到其稳健性。

  DOI：

  10.1021/acs.oprd.2c00185

文献信息

• Convenient Synthesis of Methyl 1-Methyl-2,4-dibromo-5-imidazolecarboxylate
  作者：John F. O'Connell、Jonathan Parquette、William E. Yelle、Wilhelm Wang、Henry Rapoport

  DOI：10.1055/s-1988-27702

  日期：——

  Three syntheses of methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8) are presented. One proceeds from sarcosine via ring closure, bromination, and desulfurization. The second uses N-methylimidazole, polybromination, and selective halogen-metal interchange. The third and most efficient and preparatively useful route begins with diaminomaleonitrile (13). Ring closure with triethyl orthoformate followed by methylation and hydrolysis affords 1-methyl-4,5-imidazoledicarboxylic acid (16). Regioselective decarboxylation followed by esterification yields methyl 1-methyl-5-imidazolecarboxylate (18). Subsequent dibromination gives the completely substituted imidazole 8. The primary purification in this sequence is fractional sublimation of 18 after the esterification step. An overall yield of 26% is achieved from diaminomaleonitrile (13) to methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8), which is a key intermediate for the synthesis of tricyclic imidazo cooked food mutagens.

  介绍了三种合成甲基1-甲基-2,4-二溴-5-咪唑甲酸酯(8)的方法。第一种方法是通过肌氨酸的环化、溴化和脱硫步骤进行。第二种方法使用N-甲基咪唑、多溴化和选择性卤素-金属互换。第三种方法最为高效且实用，始于二氨基富马腈(13)。通过三乙基原甲酸酯进行环化，随后甲基化和水解得到1-甲基-4,5-咪唑二羧酸(16)。区域选择性脱羧后再酯化得到甲基1-甲基-5-咪唑甲酸酯(18)。后续的双溴化得到完全取代的咪唑8。在此序列中主要的纯化步骤是酯化步骤后的分馏升华。从二氨基富马腈(13)到甲基1-甲基-2,4-二溴-5-咪唑甲酸酯(8)的总收率为26%，后者是合成三环咪唑熟食诱变剂的关键中间体。
• [EN] NON-SYSTEMIC TGR5 AGONISTS<br/>[FR] AGONISTES DE TGR5 NON SYSTÉMIQUES
  申请人：ARDELYX INC

  公开号：WO2013096771A1

  公开（公告）日：2013-06-27

  Compounds of structure (I), or a stereoisomer, tautomer, pharmaceutically acceptable salt or prodrug thereof, wherein R1, R2, R3, R4, R8, R9, R10, R11, R12, A1, A2, X, Y and Z are as defined herein. Uses of such compounds as TGR5 antagonists and for treatment of various indications, including Type II diabetes meletus are also provided.

  结构(I)的化合物，或其立体异构体、互变异构体、药学上可接受的盐或前药，其中R1、R2、R3、R4、R8、R9、R10、R11、R12、A1、A2、X、Y和Z如本文所定义。提供了这些化合物作为TGR5拮抗剂的用途，以及用于治疗各种适应症，包括II型糖尿病。
• Design of Gut-Restricted Thiazolidine Agonists of G Protein-Coupled Bile Acid Receptor 1 (GPBAR1, TGR5)
  作者：Tao Chen、Nicholas William Reich、Noah Bell、Patricia D. Finn、David Rodriguez、Jill Kohler、Kenji Kozuka、Limin He、Andrew G. Spencer、Dominique Charmot、Marc Navre、Christopher W. Carreras、Samantha Koo-McCoy、Jocelyn Tabora、Jeremy S. Caldwell、Jeffrey W. Jacobs、Jason Gustaf Lewis

  DOI：10.1021/acs.jmedchem.8b00308

  日期：2018.9.13

  Bile acid signaling and metabolism in the gastrointestinal tract have wide-ranging influences on systemic disease. G protein-coupled bile acid receptor 1 (GPBAR1, TGR5) is one of the major effectors in bile acid sensing, with demonstrated influence on metabolic, inflammatory, and proliferative processes. The pharmacologic utility of TGR5 agonists has been limited by systemic target-related effects

  胃肠道中的胆汁酸信号和新陈代谢对全身性疾病具有广泛的影响。G蛋白偶联的胆汁酸受体1（GPBAR1，TGR5）是胆汁酸感测的主要效应器之一，已证明对代谢，炎症和增殖过程有影响。TGR5激动剂的药理作用受到全身靶标相关作用的限制，例如过多的胆囊填充和阻塞胆囊排空。但是，受肠道限制的TGR5激动剂有可能避免这些副作用，因此被开发成安全性可接受的药物。我们描述了一系列肠道受限的TGR5激动剂的发现和优化，这些激动剂在小鼠中引发了有效的反应，而胆囊相关的影响也最小。该系列包括12（TGR5 EC 50：人，143 nM；小鼠，1.2 nM），一种具有最小系统可用性的化合物，可能对2型糖尿病，非酒精性脂肪性肝炎或炎性肠病患者具有治疗价值。
• [EN] HINDERED DISULFIDE DRUG CONJUGATES<br/>[FR] CONJUGUÉS MÉDICAMENTEUX À PONT DISULFURE ENCOMBRÉ
  申请人：GENENTECH INC

  公开号：WO2017064675A1

  公开（公告）日：2017-04-20

  The invention relates generally to disulfide drug conjugates wherein a linker comprising a sulfur-bearing carbon atom substituted with at least one hydrocarbyl or substituted hydrocarbyl is conjugated by a disulfide bond to a cysteine sulfur atom of a targeting carrier, and wherein the linker is further conjugated to a drug moiety. The invention further relates to activated linker-drug conjugates suitable for conjugation to a targeting carrier by a disulfide bond. The invention further relates to methods for preparing hindered disulfide drug conjugates.

  该发明一般涉及二硫键药物偶联物，其中含有至少一个被至少一个碳氢化合物或取代碳氢化合物所取代的含硫碳原子的连接剂通过二硫键与靶向载体的半胱氨酸硫原子偶联，并且连接剂进一步与药物部分偶联。该发明进一步涉及适合通过二硫键与靶向载体偶联的活化连接剂-药物偶联物。该发明还进一步涉及制备受阻二硫键药物偶联物的方法。
• Imidazolylthioalkenoic acids and -alkenols and leukotriene antagonistic
  申请人：Smithkline Beckman Corporation

  公开号：US04769386A1

  公开（公告）日：1988-09-06

  The imidazolylthio substituted alkanoic acids represented by the formula (I) or (IA) as defined herein have been found to be leukotriene antagonists and useful in the treatment of diseases in which leukotrienes are a factor, such as asthma.

  以下公式（I）或（IA）所代表的咪唑硫取代的烷酸已被发现为白三烯拮抗剂，并可用于治疗白三烯是因素的疾病，如哮喘。