2-氯-5-氯甲基噻唑 | 105827-91-6

• 物质功能分类: 化学农药原药 - 杀虫剂中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-氯-5-氯甲基噻唑
• 中文别名: 利托那韦中间体一；2-氯-5-(氯甲基L)噻唑；2-氯-5-(氯甲基)噻唑；2-氯-5-氯甲基-1,3-噻唑
• 英文名称: 2-chloro-5-chloromethylthiazole
• 英文别名: 2-chloro-5-(chloromethyl)-1,3-thiazole
• CAS: 105827-91-6
• 化学式: C₄H₃Cl₂NS
• mdl: MFCD01073549
• 分子量: 168.047
• InChiKey: VRMUIVKEHJSADG-UHFFFAOYSA-N

物化性质

• 熔点：
  31
• 沸点：
  268.6±32.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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
• 安全说明：
  S26,S37
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2934100090
• 危险品运输编号：
  UN2922 - class 8 - PG 2 - EHS - acidic - Corrosive liquids, toxic, n.o.s., HI： all
• 包装等级：
  Ⅱ
• 危险类别：
  8
• 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：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Chloro-5-chloromethylthiazole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Chloro-5-chloromethylthiazole
CAS number: 105827-91-6

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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.

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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: C4H3Cl2NS
Molecular weight: 168.0

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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, hydrogen chloride, 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

制备方法与用途

简介

2-氯-5-氯甲基噻唑（简称CCMT）是一种淡黄色结晶或淡黄色液体，含量≥98%，熔点为29-31℃。它是合成噻虫嗪、噻虫啉和氯噻啉等第二代新烟碱类杀虫剂的重要中间体。这类杀虫剂与第一代新烟碱类杀虫剂相比，具有用量更低、杀虫谱更广、安全性更高的优点，不仅能防治地上和地下害虫，还能用于茎叶、土壤和种子处理。

合成方法

以3-氯丙烯为原料：将氯气（或能产生氯气的化合物如磺酰氯）与1-异硫氰酸基-2-丙烯的氯仿溶液同时注入到回流的氯仿中反应。该反应需要过量的氯气，副产物较多，粗品纯度仅为41.1%，简单蒸馏后的纯度也仅提高至47.8%，收率为50.4%。1-异硫氰酸基-2-丙烯可通过3-氯丙烯与硫氰酸钠反应后重排制备。

化学性质 本品为无色液体，熔点30℃，沸点108～110℃/2.4kPa，在室温下呈针状结晶，不溶于水，可溶解在二氯甲烷、氯仿和四氯化碳等溶剂中。

用途 2-氯-5-氯甲基噻唑是杀虫剂噻虫嗪和噻虫胺的中间体。它用作农药和医药中间体，并用于合成噻虫嗪、噻虫胺和医药利托那韦。当前，噻虫嗪作为新一代烟碱类杀虫剂，备受关注，具有广阔的市场前景；而利托那韦作为一种抗人免疫缺陷病毒（HIV）药物，在没有特效药的情况下也至关重要。

生产方法 其制备方法是在反应瓶中加入2-氯丙烯基异硫氰酸酯和溶剂氯仿，然后滴加氯化硫酰，并保持内温30℃。滴加完成后在室温下继续反应2.5小时，此时内温升至36℃。反应结束后，蒸馏除去溶剂和剩余的氯化硫酰，残渣溶于二氯甲烷中，用NaHCO₃溶液和水分别洗涤、干燥后，减压蒸去溶剂得产品。

反应信息

• 作为反应物：
  描述：

  2-氯-5-氯甲基噻唑 在 氢气 、 镍 作用下， 以 甲醇 、 水 为溶剂， 67.5 ℃ 、1.2 Pa 条件下， 反应 33.0h， 以62.8%的产率得到5-氯甲基噻唑
  参考文献：
  名称：

  一种利托那韦中间体5-羟甲基噻唑的合成方法

  摘要：

  本发明公开了一种利托那韦中间体5‑羟甲基噻唑的合成方法，将2‑氯‑5‑氯甲基噻唑200g、缚酸剂240g、甲醇600g、雷尼镍催化剂120g、水加入氢化釜中，氮气置换三次，氢气置换3次，加压至1.0‑1.4PA，升温至67.5℃，保温32‑38h；取样2‑氯‑5‑氯甲基噻唑≤0.3%，反应完毕，泄压，过滤，回收雷尼镍，减压脱干有机层拉干1小时，用EA洗涤，合并，减压回收有机层，精馏得到5‑氯甲基噻唑。其工艺步骤简单，生产周期短、收率高、工艺三废量低，能有效兼顾工业生产的成本、安全，适合工业化大生产。

  公开号：

  CN111548321A
• 作为产物：
  描述：

  天然芥菜籽油 在 N-氯代丁二酰亚胺 、 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到2-氯-5-氯甲基噻唑
  参考文献：
  名称：

  Method for producing 2-chloro-5-chloromethyl-1,3-thiazole

  摘要：

  一种制备2-氯-5-氯甲基-1,3-噻唑的方法，其中式CH2=CH—CH2-NCS的烯丙基异硫氰酸酯在-40°C至+30°C的温度下，在反应条件下为惰性的溶剂中，与每摩尔烯丙基异硫氰酸酯1至2摩尔的氯化剂反应；向所得反应混合物中，在0°C至所用溶剂的沸点的反应温度下，加入每摩尔烯丙基异硫氰酸酯1至5摩尔的氧化剂，然后从反应混合物中分离出2-氯-5-氯甲基-1,3-噻唑，并可选择通过结晶转化为高纯度的2-氯-5-氯甲基-1,3-噻唑。

  公开号：

  US20030153767A1

文献信息

• PREPARATION METHOD AND USE OF COMPOUNDS HAVING HIGH INSECTICIDAL ACTIVITIES
  申请人：Li Zhong

  公开号：US20090111847A1

  公开（公告）日：2009-04-30

  The present invention discloses a kind of nitromethylene derivatives as well as their preparation method and their uses. The insecticidal activity tests show that the nitromethylene derivatives of the present invention not only show high insecticidal activities against insects with piercing-sucking type or scratching type mouthparts, such as aphid, leafhopper, plant hopper, thrips and white fly and their resistant strains, but also show high insecticidal activities against Lissorhoptrus oryzophilus , carmine spider mite, and they can also be used to prevent sanitary pest, and white ant.

  本发明公开了一种亚硝基甲烯衍生物，以及它们的制备方法和用途。杀虫活性测试表明，本发明的亚硝基甲烯衍生物不仅对具有刺吸型或擦伤型口器的昆虫（如蚜虫、叶蝉、植食蝗、蓟马和烟粉虱及其抗性品系）表现出高杀虫活性，而且对水稻纵卷叶象、胭脂蜘蛛螨等也表现出高杀虫活性，它们还可用于预防卫生害虫和白蚁。
• [EN] PIPERIDINE OR PIPERAZINE LINKED IMIDAZOLE AND TRIAZOLE DERIVATIVES AND METHODS OF USE THEREOF FOR IMPROVING THE PHARMACOKINETICS OF A DRUG<br/>[FR] DÉRIVÉS D'IMIDAZOLE ET DE TRIAZOLE LIÉS À LA PIPÉRIDINE OU LA PIPÉRAZINE ET LEURS PROCÉDÉS D'UTILISATION POUR AMÉLIORER LA PHARMACOCINÉTIQUE D'UN MÉDICAMENT
  申请人：MERCK SHARP & DOHME

  公开号：WO2015070367A1

  公开（公告）日：2015-05-21

  The piperidine or piperazine linked imidazole and triazole derivatives, compositions comprising said compounds, alone or in combination with other drugs, and methods of using the compounds for improving the pharmacokinetics of a drug are provided. The compounds of the invention are useful in human and veterinary medicine for inhibiting CYP3A4 and for improving the pharmacokinetics of a therapeutic compound that is metabolized by CYP3A4.

  提供了与哌啶或哌嗪连接的咪唑和三唑衍生物，包括所述化合物的组合物，单独或与其他药物结合使用的方法，以及用于改善药物的药代动力学的化合物的方法。该发明的化合物在人类和兽医学中用于抑制CYP3A4并改善由CYP3A4代谢的治疗化合物的药代动力学。
• BISARYL-BONDED ARYLTRIAZOLONES AND USE THEREOF
  申请人：Furstner Chantal

  公开号：US20130190330A1

  公开（公告）日：2013-07-25

  The present application relates to novel bisaryl-linked 5-aryl-1,2,4-triazolone derivatives, to processes for preparing them, to their use alone or in combinations for the treatment and/or prevention of diseases and also to their use for the production of medicaments for the treatment and/or prevention of diseases, more particularly for the treatment and/or prevention of cardiovascular disorders.

  本申请涉及新型的双芳基连接的5-芳基-1,2,4-三唑啉酮衍生物，涉及制备它们的方法，涉及它们单独或组合用于治疗和/或预防疾病，以及涉及它们用于生产用于治疗和/或预防疾病的药物，尤其是用于治疗和/或预防心血管疾病的药物。
• [EN] AZOLOPYRIMIDINE FOR THE TREATMENT OF CANCER-RELATED DISORDERS<br/>[FR] AZOLOPYRIMIDINE POUR LE TRAITEMENT DE TROUBLES LIÉS AU CANCER
  申请人：ARCUS BIOSCIENCES INC

  公开号：WO2018136700A1

  公开（公告）日：2018-07-26

  Compound that is an inhibitor of at least one of the A2A and A2B adenosine receptors, and compositions containing the compound and methods for synthesizing the compound, are described herein. The use of such compound and compositions for the treatment of a diverse array of diseases, disorders, and conditions, including cancer- and immune-related disorders that are mediated, at least in part, by the adenosine A2A receptor and/or the adenosine A2B receptor.

  本文描述了一种至少抑制A2A和A2B腺苷受体中至少一种的化合物，以及含有该化合物的组合物和合成该化合物的方法。利用这种化合物和组合物治疗各种疾病、紊乱和病况，包括至少部分由腺苷A2A受体和/或腺苷A2B受体介导的癌症和免疫相关紊乱。
• Synthesis and insecticidal activities of novel neonicotinoid analogs bearing an amide moiety
  作者：Jian Wu、Song Yang、Bao-An Song、Pinaki S. Bhadury、De-Yu Hu、Song Zeng、Hua-Peng Xie

  DOI：10.1002/jhet.663

  日期：2011.7

  A series of novel neonicotinoid analogs containing an amide moiety were synthesized, characterized, and subsequently evaluated for their insecticidal activity. According to the preliminary bioassay, the compounds 6c, 6e, 6f, 6j, 6n, and 6r exhibited > 50% activity against Nilaparvata lugens at 100 mg/L. Amongst the active compounds, 6f and 6r revealed insecticidal activities similar to that displayed

  合成，表征了一系列新颖的含有酰胺部分的新烟碱类似物，并随后对其杀虫活性进行了评估。根据初步的生物测定，化合物6c，6e，6f，6j，6n和6r在100 mg / L的浓度下对褐飞虱具有> 50％的活性。在活性化合物中，6f和6r的杀虫活性与标准丁苯丙酸所显示的相似。J.杂环化​​学。（2011）