4-(氯甲基)-2-甲基-1,3-噻唑 | 39238-07-8

• 物质功能分类: 香精与香料 - 合成香料 - 内酯和含氧杂环化合物
• 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-甲基-1,3-噻唑
• 中文别名: 4-氯甲基-2-甲基噻唑.盐酸盐；4-氯甲基-2-甲基噻唑
• 英文名称: 4-(chloromethyl)-2-methyl-1,3-thiazole
• 英文别名: 4-Chloromethyl-2-methylthiazole
• CAS: 39238-07-8
• 化学式: C₅H₆ClNS
• mdl: MFCD00067725
• 分子量: 147.628
• InChiKey: AQBBZYVPKBIILN-UHFFFAOYSA-N

物化性质

• 熔点：
  160-165°C (dec.)
• 沸点：
  217℃
• 密度：
  1.271
• 闪点：
  85℃
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  8
• 危险品标志：
  Xi
• 危险类别码：
  R34
• 危险品运输编号：
  3261
• 海关编码：
  2934100090
• 包装等级：
  III
• 危险类别：
  8
• 安全说明：
  S23,S26,S27,S36/37/39,S45
• 危险性防范说明：
  P501,P273,P272,P260,P270,P202,P201,P264,P280,P391,P308+P313,P361+P364,P303+P361+P353,P333+P313,P301+P330+P331,P301+P312+P330,P304+P340+P310,P305+P351+P338+P310,P405
• 危险性描述：
  H311,H302,H314,H317,H341,H411
• 储存条件：
  密封、阴凉、干燥处保存。

SDS

Name:	4-Chloromethyl-2-Methylthiazole Hydrochloride Material Safety Data Sheet
Synonym:	None Known
CAS:	39238-07-8

Section 1 - Chemical Product MSDS Name:4-Chloromethyl-2-Methylthiazole Hydrochloride Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
39238-07-8	4-Chloromethyl-2-Methylthiazole Hydroc	ca. 100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Lachrymator (substance which increases the flow of tears).
Potential Health Effects
Eye:
Produces irritation, characterized by a burning sensation, redness, tearing, inflammation, and possible corneal injury. Lachrymator (substance which increases the flow of tears). May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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. Do NOT allow victim to rub eyes or keep eyes closed.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4C/39F.)

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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# 39238-07-8: 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:
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: 166 - 168 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: C5H6ClNS.HCl
Molecular Weight: 184.09

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, hydrogen cyanide, sulfur dioxide, carbon monoxide, oxides of nitrogen, carbon dioxide, sulfuric acid, nitric acid.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 39238-07-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Chloromethyl-2-Methylthiazole Hydrochloride - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 39238-07-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 39238-07-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 39238-07-8 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

制备方法与用途

简介

4-(氯甲基)-2-甲基-1,3-噻唑是一种烷基化的噻唑类衍生物，在高温下容易发生分解反应。它常用于有机合成，作为基础原料引入目标有机分子结构中的噻唑单元，并广泛应用于噻唑类HIV蛋白酶抑制剂的合成。

制备

在一个干燥的1升反应器中，将1,3-二氯丙-2-酮（12.7克）和硫代乙酰胺（7.5克）溶解在干燥的乙醇（70毫升）中，并在氩气环境下加热至回流。搅拌反应5.5小时后，冷却至室温并将反应混合物减压浓缩。得到的深色结晶残留物溶于水（250 mL）中，然后缓慢加入固体NaHCO3以使体系pH值约为8。使用乙醚（Et2O，4 x 100毫升）萃取混合物，并将合并的有机溶液在无水MgSO4上进行干燥处理。过滤去除干燥剂后，将所得滤液减压浓缩，在真空下通过减压蒸馏（压力为0.05托）提纯残留物以得到目标产物分子4-(氯甲基)-2-甲基-1,3-噻唑。

反应信息

• 作为反应物：
  描述：

  4-(氯甲基)-2-甲基-1,3-噻唑 在 吡啶 、 正丁基锂 、 草酰氯 、 硝基甲烷 、 丁硫醇 、 dimethyl sulfide borane 、 (1R)-(+)-pinene 、 2,4,6-三氯苯甲酰氯 、 ammonium chloride 、 氟化氢吡啶 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 二异丙胺 、 间氯过氧苯甲酸 、 magnesium bromide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 59.33h， 生成 埃博霉素B
  参考文献：
  名称：

  上表素B和D的总合成

  摘要：

  描述了收敛的全合成的埃坡霉素B（2）和D（4）。关键步骤是通过Normant偶联在C12-C13上建立所需的（Z）-立体化学，Wadsworth-Emmons甲基酮28与膦酸酯8的烯键化，醛5与醛酸与酮酸衍生物的烯酸酯的非对映选择性醛醇缩合以形成C6-C7键，酸52的选择性脱保护和大内酯化。

  DOI：

  10.1021/jo048742o
• 作为产物：
  描述：

  4-氯甲基-2-甲基噻唑盐酸盐 在 potassium carbonate 作用下， 以 乙醚 、 水 为溶剂， 反应 0.25h， 以99.5%的产率得到4-(氯甲基)-2-甲基-1,3-噻唑
  参考文献：
  名称：

  TETRA-SUBSTITUTED NDGA DERIVATIVES VIA ETHER BONDS AND CARBAMATE BONDS AND THEIR SYNTHESIS AND PHARMACEUTICAL USE

  摘要：

  本文披露了包括各种末端基团的北二羟基愈创木酸衍生物化合物，这些基团通过一个侧链与相应的羟基残基O基团通过醚键或氨甲酸酯键结合在一起，以及制备它们的方法、使用它们的方法以及包括它们的用于治疗疾病和疾病的工具包，特别是由病毒感染引起或与之相关的疾病，如HIV感染、HPV感染或HSV感染，炎症性疾病，如各种类型的关节炎和炎症性肠病，代谢性疾病，如糖尿病，血管性疾病，如高血压和黄斑变性，或增生性疾病，如各种类型的癌症。

  公开号：

  US20130303531A1
• 作为试剂：
  描述：

  4-(氯甲基)-2-甲基-1,3-噻唑 、 在 4-(氯甲基)-2-甲基-1,3-噻唑 作用下， 生成
  参考文献：
  名称：

  Bioorg. Med. Chem. Lett. 2006, 16, 1788-1794

  摘要：

  DOI：

文献信息

• Combination of FBPase inhibitors and insulin sensitizers for the treatment of diabetes
  申请人：Metabasis Therapeutics, Inc.

  公开号：US06756360B1

  公开（公告）日：2004-06-29

  Pharmaceutical compositions containing an FBPase inhibitor and an insulin sensitizer are provided as well as methods for treating diabetes and diseases responding to increased glycemic control, an improvement in insulin sensitivity, a reduction in insulin levels, or an enhancement of insulin secretion.

  提供含有FBPase抑制剂和胰岛素增敏剂的药物组合物，以及治疗糖尿病和对增加糖代谢控制、改善胰岛素敏感性、降低胰岛素水平或增强胰岛素分泌有响应的疾病的方法。
• [EN] 1H-PYRAZOLO[4,3-B]PYRIDINES AS PDE1 INHIBITORS<br/>[FR] 1H-PYRAZOLO [4,3-B] PYRIDINES EN TANT QU'INHIBITEURS DE PDE1
  申请人：H LUNDBECK AS

  公开号：WO2018007249A1

  公开（公告）日：2018-01-11

  The present invention provides 1H-pyrazolo[4,3-b]pyridin-7-amines of formula (I) as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.

  本发明提供了式(I)的1H-吡唑并[4,3-b]吡啶-7-胺作为PDE1抑制剂，并将其用作药物，特别用于治疗神经退行性疾病和精神疾病。
• MACROCYCLES AS PDE1 INHIBITORS
  申请人：H. Lundbeck A/S

  公开号：US20190185489A1

  公开（公告）日：2019-06-20

  The present invention provides macrocycles of formula (I) as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.

  本发明提供了式(I)的大环化合物作为PDE1抑制剂，并将其用作药物，特别用于治疗神经退行性疾病和精神疾病。
• 1H-PYRAZOLO[4,3-B]PYRIDINES AS PDE1 INHIBITORS
  申请人：H. Lundbeck A/S

  公开号：US20190194189A1

  公开（公告）日：2019-06-27

  The present invention provides 1H-pyrazolo[4,3-b]pyridines of formula (I) as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.

  本发明提供了式(I)的1H-吡唑并[4,3-b]吡啶类化合物作为PDE1抑制剂，并将其用作药物，特别用于治疗神经退行性疾病和精神疾病。
• Compounds and methods
  申请人：Marino P. Joseph

  公开号：US20050222212A1

  公开（公告）日：2005-10-06

  Compounds of this invention are non-peptide, reversible inhibitors of bacterial methionine aminopeptidases, useful in treating bacterial infections.

  该发明的化合物是非肽类、可逆的细菌蛋氨酸氨肽酶抑制剂，可用于治疗细菌感染。