2-氯-5-氯甲基吡啶 | 70258-18-3

• 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 - 吡啶及其衍生物
• 中文名称: 2-氯-5-氯甲基吡啶
• 中文别名: 2,5-二氯甲基吡啶；二氯五氯甲基吡啶；2-氯-5-(氯甲基)吡啶
• 英文名称: 2-chloro-5-(chloromethyl)pyridine
• 英文别名: 4-chloro-3-picolyl chloride
• CAS: 70258-18-3
• 化学式: C₆H₅Cl₂N
• mdl: MFCD00125366
• 分子量: 162.018
• InChiKey: SKCNYHLTRZIINA-UHFFFAOYSA-N

物化性质

• 熔点：
  37-42 °C(lit.)
• 沸点：
  267.08°C (rough estimate)
• 密度：
  1.4411 (rough estimate)
• 闪点：
  >230 °F
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：
  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  LACHRYMATOR, CORROSIVE
• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S25,S26,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  3
• 海关编码：
  2933399010
• 危险品运输编号：
  UN 3261 8/PG 2
• 包装等级：
  II
• 危险标志：
  GHS05,GHS07
• 危险性描述：
  H302,H314
• 危险性防范说明：
  P280,P305 + P351 + P338,P310
• 危险类别：
  8
• 储存条件：
  存放在密封容器中，并置于阴凉、干燥处。存储地点需上锁，钥匙应由技术人员及其助手妥善保管。同时，存储地点应远离氧化剂。

SDS

Name:	2-Chloro-5-chloromethylpyridine tech. 90% Material Safety Data Sheet
Synonym:
CAS:	70258-18-3

Section 1 - Chemical Product MSDS Name:2-Chloro-5-chloromethylpyridine tech. 90% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
70258-18-3	2-Chloro-5-chloromethylpyridine	90	unlisted

Hazard Symbols: C
Risk Phrases: 34

---

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:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

---

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. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Do not get in eyes, on skin, or on clothing. Do not breathe dust. Use only with adequate ventilation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

---

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# 70258-18-3: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 37-42 deg C
Autoignition Temperature: Not available.
Flash Point: > 230 deg F (> 110.00 deg C)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H5Cl2N
Molecular Weight: 161.9477

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
High temperatures, dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, acid chlorides, acid anhydrides.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 70258-18-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Chloro-5-chloromethylpyridine - 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:

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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 25 Avoid contact with eyes.
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# 70258-18-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 70258-18-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 70258-18-3 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

2-氯-5-氯甲基吡啶 简介

2-氯-5-氯甲基吡啶（简称CCMP）是一种重要的医药中间体和合成吡啶类农药原药如吡虫啉、啶虫脒、氟啶胺等的重要中间体。

合成

将2-氯吡啶基-4-亚甲基二乙基膦酸酯溶解在CH2Cl2（20 mL）和过量的亚硫酰氯（5-10 mL）中。溶液回流1小时后，冷却至室温，并在真空中除去挥发物。用饱和NaHCO3中和残留物，再用CH2Cl2（3 x 40 mL）提取残留物。合并有机物并用MgSO4干燥。过滤有机物，浓缩至约3-5 mL后通过二氧化硅塞纯化产物（用CH2Cl2洗脱）。最后，在真空中除去挥发物得到2-氯-5-氯甲基吡啶。

合成路线


化学性质

2-氯-5-氯甲基吡啶纯品为无色结晶，熔点35～36℃，沸点88～90℃/400pa。工业品多为橘红色液体或黏稠状，具有刺激性气味，并溶于多种有机溶剂中，弱碱性且能溶于有机酸。

用途

2-氯-5-氯甲基吡啶主要用作农药吡虫啉和啶虫脒的中间体。同时，它也是生产农用化学品吡虫啉、啶虫咪以及医药品的重要中间体。

生产方法

目前工业上多采用2-氯-5-甲基吡啶为原料进行合成。具体操作是将2-氯-5-甲基吡啶和溶剂加到反应釜中，加入催化剂后，在回流条件下通入氯气进行反应。反应结束后，先常压脱溶，再转入蒸馏釜中真空脱去前馏分，从釜底得到2-氯-5-氯甲基吡啶。

此外，还有以烟酸为原料、3-甲基吡啶为原料或2-氯-5-三氯甲基吡啶为原料等多种不同的合成路线。而美国瑞利公司(Reilly Industries Inc.)开发的路线则直接以环戊二烯和丙醛为起始原料，通过环合生成2-氯-5-氯甲基吡啶，产品纯度高达95%以上且不含异构体2-氯-3-氯甲基吡啶。

反应信息

• 作为反应物：
  描述：

  2-氯-5-氯甲基吡啶 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 8.0h， 生成 1H-咪唑-2-胺,1-[(6-氯-3-吡啶基)甲基]-4,5-二氢-
  参考文献：
  名称：

  一种高收率合成吡虫啉的方法

  摘要：

  本发明提供了一种高收率合成吡虫啉的方法，以2‑氯‑5‑氯甲基吡啶、乙二胺和卤化氰为原料，经胺化、环化、硝化等步骤合成吡虫啉。该方法生产过程安全性高、产品纯度好、收率高，易于实现工业化。

  公开号：

  CN110746397B
• 作为产物：
  描述：

  3-甲基吡啶 在 氯 作用下， 反应 0.25h， 以51%的产率得到2-氯-5-氯甲基吡啶
  参考文献：
  名称：

  一种2-氯-5-氯甲基吡啶的合成方法

  摘要：

  本发明公开了一种2‑氯‑5‑氯甲基吡啶的合成方法，3‑甲基吡啶经汽化后，以氮气作为载气，与氯气混合后通入装有负载型氯化钯催化剂的管式反应器中，进行氯化反应得到2‑氯‑5‑氯甲基吡啶。本发明以3‑甲基吡啶和氯气为原料，选用负载型氯化钯催化剂，一步反应得到2‑氯‑5‑氯甲基吡啶，不仅可以加快反应速率，同时有助于提高目的产物选择性，2‑氯‑5‑氯甲基吡啶的摩尔收率达到50％左右。且反应产生三废少，反应所用贵金属钯易于回收，综合成本更低。

  公开号：

  CN107628989B
• 作为试剂：
  描述：

  ethyl 4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate 、 4-碘苄基溴 在 2-氯-5-氯甲基吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 1-[(4-iodophenyl)methyl]-4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate
  参考文献：
  名称：

  [EN] HETEROCYCLIC FUSED CINNOLINE M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS
  [FR] MODULATEURS ALLOSTÉRIQUES POSITIFS D'UN RÉCEPTEUR M1 DE CINNOLINE FUSIONNÉE HÉTÉROCYCLIQUE

  摘要：

  本发明涉及式(I)的杂环融合喹啉化合物，这些化合物是M1受体阳性变构调节剂，并且在治疗M1受体参与的疾病，如阿尔茨海默病、精神分裂症、疼痛或睡眠障碍方面有用。该发明还涉及包含这些化合物的药物组合物，以及在治疗M1受体介导的疾病中使用这些化合物和组合物。

  公开号：

  WO2010123716A1

文献信息

• SUBSTITUTED ARYL AND HETEROARYL CARBOXYLIC ACID HYDRAZIDES OR SALTS THEREOF AND USE THEREOF TO INCREASE STRESS TOLERANCE IN PLANTS
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20180206495A1

  公开（公告）日：2018-07-26

  Substituted aryl- and heteroarylcarbonyl hydrazides The invention relates to substituted aryl- and heteroarylcarbonyl hydrazides of the general formula (I) or salts thereof where the radicals of the formula (I) are each as defined in the description for enhancing stress tolerance in plants to abiotic stress, and for enhancing plant growth and/or for increasing plant yield.

  该发明涉及通式（I）的取代芳基和杂芳基羰基肼或其盐，其中通式（I）的基团如描述中所定义，用于增强植物对非生物胁迫的耐受性，促进植物生长和/或增加植物产量。
• Thieno-pyrimidine compounds having fungicidal activity
  申请人：Brewster Kirkland William

  公开号：US20070093498A1

  公开（公告）日：2007-04-26

  The present invention relates to thieno[2,3-d]-pyrimidine compounds having fungicidal activity.

  本发明涉及具有杀真菌活性的噻吩[2,3-d]-嘧啶化合物。
• [EN] BRUTON'S TYROSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA TYROSINE KINASE DE BRUTON
  申请人：PFIZER

  公开号：WO2014068527A1

  公开（公告）日：2014-05-08

  Disclosed herein are compounds that form covalent bonds with Bruton's tyrosine kinase (BTK). Methods for the preparation of the compounds are disclosed. Also disclosed are pharmaceutical compositions that include the compounds. Methods of using the BTK inhibitors are disclosed, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, and inflammatory diseases or conditions. (Formula I)

  本文披露了一种与Bruton's酪氨酸激酶（BTK）形成共价键的化合物。公开了制备这些化合物的方法。还披露了包括这些化合物的药物组合物。公开了使用BTK抑制剂的方法，单独或与其他治疗剂联合治疗自身免疫疾病或症状、异源免疫疾病或症状、癌症，包括淋巴瘤，以及炎症性疾病或症状的方法。 (化学式I)
• CYCLOPROPYLAMINES AS LSD1 INHIBITORS
  申请人：Incyte Corporation

  公开号：US20150225379A1

  公开（公告）日：2015-08-13

  The present invention is directed to cyclopropylamine derivatives which are LSD1 inhibitors useful in the treatment of diseases such as cancer.

  本发明涉及环丙胺衍生物，这些衍生物是LSD1抑制剂，可用于治疗癌症等疾病。
• [EN] SUBSTITUTED HETEROCYCLIC AZA DERIVATIVES<br/>[FR] DÉRIVÉS AZA HÉTÉROCYCLIQUES SUBSTITUÉS
  申请人：GRUENENTHAL GMBH

  公开号：WO2013013817A1

  公开（公告）日：2013-01-31

  The invention relates to heterocyclic aza derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  这项发明涉及杂环氮杂基衍生物作为辣椒素受体配体，含有这些化合物的药物组合物，以及这些化合物用于治疗和/或预防疼痛以及其他疾病和/或紊乱。

表征谱图