2,6-氯甲酰吡啶 | 3739-94-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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: 2,6-氯甲酰吡啶
• 中文别名: 2,6-吡啶二羰酰氯；2,6-吡啶二甲酰氯
• 英文名称: 2,6-Pyridinedicarbonyl dichloride
• 英文别名: pyridine-2,6-dicarbonyl dichloride；2,6-pyridinedicarbonyl chloride；2,6-pyridinedicarboxylic acid chloride；2,6-pyridinedicarboxyl chloride；pyridine-2,6-dicarbonyl chloride
• CAS: 3739-94-4
• 化学式: C₇H₃Cl₂NO₂
• mdl: MFCD00006289
• 分子量: 204.012
• InChiKey: GWHOGODUVLQCEB-UHFFFAOYSA-N

物化性质

• 熔点：
  56-58 °C (lit.)
• 沸点：
  284 °C (lit.)
• 密度：
  1.4521 (rough estimate)
• 闪点：
  284°C
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S24/25,S26,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  3
• 海关编码：
  2933399090
• 危险品运输编号：
  UN 3261 8/PG 2
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H314
• 储存条件：
  请将产品存放在避光、通风且干燥的地方，并密封保存。

SDS

Name:	2 6-Pyridinedicarboxylic Acid Chloride 97% Material Safety Data Sheet
Synonym:	2,6-Pyridinedicarbonyl Dichloride
CAS:	3739-94-4

Section 1 - Chemical Product MSDS Name:2 6-Pyridinedicarboxylic Acid Chloride 97% Material Safety Data Sheet
Synonym:2,6-Pyridinedicarbonyl Dichloride

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3739-94-4	2,6-Pyridinedicarboxylic Acid Chloride	97%	223-125-4

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.Corrosive.Lachrymator (substance which increases the flow of tears).
Potential Health Effects
Eye:
Causes eye burns. 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 and corneal damage.
Skin:
Causes skin burns. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
Causes gastrointestinal tract burns. May cause perforation of the digestive tract. May cause cardiac disturbances. May cause central nervous system effects. May cause systemic effects.
Inhalation:
Causes chemical burns to the respiratory tract. Aspiration may lead to pulmonary edema. May cause cardiac abnormalities. May cause systemic effects. Central nervous system effects, which appear to predominate in acute cases are characterized by abnormal fatigue, memory difficulties and dizziness.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Destroy contaminated shoes.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

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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. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.
Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Do NOT get water inside containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use dry chemical, carbon dioxide, alcohol-resistant foam, or water spray.

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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. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Use only in a well-ventilated area. Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Do not ingest or inhale. Do not allow contact with water. Discard contaminated shoes. Keep from contact with moist air and steam.
Storage:
Keep container closed when not in use. Corrosives area. Store protected from moisture.

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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# 3739-94-4: 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: brown
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 284 deg C @ 760.00mmHg
Freezing/Melting Point: 56.00 - 58.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H3Cl2NO2
Molecular Weight: 204.01

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, moisture, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Moisture, oxidizing agents, strong bases.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3739-94-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,6-Pyridinedicarboxylic Acid Chloride - 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, N.O.S.*
Hazard Class: 8
UN Number: 1759
Packing Group: II
IMO
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing Group: II
RID/ADR
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing group: II

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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 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 3739-94-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3739-94-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3739-94-4 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

2,6-吡啶二羰酰氯

2,6-吡啶二羰酰氯是一种有机中间体和医药中间体，主要用于实验室研发过程及化工医药研发中的酰化反应。它可以通过两种方法制备：

方法一

将5.00克（30毫米摩尔）的2,6-吡啶二甲酸溶解在二氯甲烷中，于0℃下滴加11.43克（90毫米摩尔）草酰氯。滴加完成后，升温至25℃，搅拌反应生成2,6-吡啶二甲酰氯，产率为95%。

方法二

将2,6-吡啶二甲酸溶解在二氯甲烷中，加入一定量的二氯亚砜，在70℃下回流反应，使吡啶-2,6-二羧酸的两个羧基酰氯化。随后除去产生的杂质，即可制得2,6-吡啶二羰酰氯。

反应信息

• 作为反应物：
  描述：

  2,6-氯甲酰吡啶 在 sodium hydrogensulfide 、 盐酸 作用下， 以 水 为溶剂， 反应 2.83h， 以49.9%的产率得到2,6-吡啶二硫代羧S-酸
  参考文献：
  名称：

  吡啶2,6-二硫代羧酸及其金属配合物：新德里Metalloβ-内酰胺酶-1的新抑制剂。

  摘要：

  关键字： NDM-1抑制剂；海洋来源的链霉菌；耐碳青霉烯的肠杆菌科; 金属螯合剂

  DOI：

  10.3390/md18060295
• 作为产物：
  描述：

  2,6-二甲基吡啶 在 potassium permanganate 、 氯化亚砜 作用下， 生成 2,6-氯甲酰吡啶
  参考文献：
  名称：

  螯合双（亚氨基）吡啶钴配合物：Li+阳离子活化生成乙烯聚合催化剂的合成、还原和证据

  摘要：

  用FeCl 2 或CoCl 2 处理双(亚氨基苄基)吡啶螯合席夫碱配体8 (ligPh) 产生相应的(ligPh) MCl 2 配合物9 (Fe)和10 (Co)。10与甲基锂或“丁二烯-镁”的反应导致还原得到相应的(ligPh)Co(I)Cl产物11。类似地，双(芳基亚氨基乙基)吡啶配体(ligMe)与CoCl2反应得到(ligMe) )CoCl2 (12)。通过用“丁二烯-镁”处理来还原成(ligMe)CoCl (13)。配合物 13 在甲苯中与 Li[B(C6F5)4] 反应，然后用吡啶处理，得到 [(ligMe)Co+-吡啶] (15)。Co(II) 络合物 10 或 12 与约 3 摩尔当量的甲基锂分别得到钴 (I) 配合物 16 和 17。用Li[B(C6F5)4]处理(ligMe)CoCH3(17)得到低活性的乙烯聚合催化剂。同样，在用化学计量量的 Li[B(C6F5)4 处理后，复合物

  DOI：

  10.1021/ja052129k

文献信息

• Iron-Doped Single-Walled Carbon Nanotubes as New Heterogeneous and Highly Efficient Catalyst for Acylation of Alcohols, Phenols, Carboxylic Acids and Amines under Solvent-Free Conditions
  作者：Hashem Sharghi、Mahboubeh Jokar、Mohammad Mahdi Doroodmand

  DOI：10.1002/adsc.201000365

  日期：2011.2.11

  single-walled carbon nanotubes (Fe/SWCNTs) represent an efficient and new heterogeneous reusable catalyst for the acylation of a variety of alcohols, phenols, carboxylic acids and amines with acid chlorides or acid anhydrides under solvent-free conditions. The reactions of various primary, secondary, tertiary, and benzylic alcohols, diols, phenols, as well as aromatic and aliphatic amines give acylated

  掺杂铁的单壁碳纳米管（Fe / SWCNT）代表了一种高效且新型的多相可重复使用的催化剂，用于在无溶剂条件下将各种醇，酚，羧酸和胺与酰氯或酸酐酰化。各种伯，仲，叔和苯甲醇，二醇，苯酚以及芳族和脂族胺的反应均以极好的收率得到了酰化的加合物。
• METHOD FOR THE CATALYTIC REDUCTION OF ACID CHLORIDES AND IMIDOYL CHLORIDES
  申请人：Nikonov Georgii

  公开号：US20140228579A1

  公开（公告）日：2014-08-14

  The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pr i 3 P)Ru(NCMe) 2 ] + [PF 6 ] − .

  本申请涉及用于催化还原酸氯化物和/或亚胺酰氯化物的方法。该方法包括在催化剂的存在下，将酸氯化物或亚胺酰氯化物与硅烷还原剂反应，所述催化剂例如为[Cp(Pr i 3 P)Ru(NCMe) 2 ] + [PF 6 ] − 。
• Rhodium(III)-Catalyzed Oxidative Olefination of Picolinamides: Convenient Synthesis of 3-Alkenylpicolinamides
  作者：Jun Zhou、Bo Li、Zhen-Chao Qian、Bing-Feng Shi

  DOI：10.1002/adsc.201300895

  日期：2014.3.24

  A rhodium(III)‐catalyzed selective olefination of picolinamide derivatives has been developed. The reaction shows high regioselectivity, low catalyst loading (0.5 mol%), high yield and good functional group tolerance, providing a convenient strategy for the synthesis of 3‐alkenylpicolinamides.

  已开发了铑（III）催化的吡啶甲酰胺衍生物的选择性烯烃化反应。该反应显示出高区域选择性，低催化剂负载量（0.5 mol％），高收率和良好的官能团耐受性，为合成3-链烯基吡啶甲酸酰胺提供了便利的策略。
• Synthesis of Fluorogenic Arylureas and Amides and Their Interaction with Amines: A Competition between Turn-on Fluorescence and Organic Radicals on the Way to a Smart Label for Fish Freshness
  作者：Javier García-Tojal、José V. Cuevas、María-Josefa Rojo、Borja Díaz de Greñu、Carla Hernando-Muñoz、José García-Calvo、Mateo M. Salgado、Tomás Torroba

  DOI：10.3390/molecules26051404

  日期：——

  and their interaction with primary or secondary amines under air and light in organic-aqueous mixtures to give rise to a new class of persistent organic radicals, described on the basis of their electron paramagnetic resonance (EPR), as well as UV–vis, fluorescence, NMR, and quantum mechanics calculations, and their prospective use as multi-signal reporters in a smart label for fish freshness.

  我们描述了有机芳基混合物中空气和光照下含氟芳基脲和酰胺的合成以及它们与伯胺或仲胺的相互作用，从而产生了一类新型的持久性有机基团，在其电子顺磁共振（EPR）的基础上进行了描述，以及紫外可见，荧光，核磁共振和量子力学计算，以及它们在鱼类新鲜度智能标签中作为多信号报告物的预期用途。
• Rational Tuning of Melting Entropies for Designing Luminescent Lanthanide-Containing Thermotropic Liquid Crystals at Room Temperature
  作者：Aude Escande、Laure Guénée、Homayoun Nozary、Gérald Bernardinelli、Frédéric Gumy、Annina Aebischer、Jean-Claude G. Bünzli、Bertrand Donnio、Daniel Guillon、Claude Piguet

  DOI：10.1002/chem.200700560

  日期：2007.10.26

  room-temperature mesomorphism is detected. An enthalpically unbalanced large melting entropy (DeltaSmL11=226 J mol(-1) K(-1)) results from the programmed microsegregation induced in the crystalline phase, a phenomenon which is maintained in the associated lanthanide complexes [Ln(L11)(NO3)3] and [Ln(L11)(CF3CO2)3]2. Low-temperature melting processes (-43

  十二个外围和发散的十二烷氧基链与中央三齿芳族结合单元的连接提供了十二碳烷配体L11，其检测到室温的同构。焓不平衡的大熔化熵（DeltaSmL11 = 226 J mol（-1）K（-1））是由结晶相中诱导的程序性微偏析引起的，该现象在相关的镧系元素络合物[Ln（L11）（NO3）中保持）3]和[Ln（L11）（CF3CO2）3] 2。低温熔融工艺（-43

表征谱图