3,5-二氯-4-吡啶酮-1-乙酸 | 56187-37-2

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3,5-二氯-4-吡啶酮-1-乙酸
• 中文别名: 头孢西酮侧链；N,N',N''-三(对甲苯磺酰)二乙撑三胺；N,N,N-三(对甲苯磺酰基)二乙烯三胺
• 英文名称: 3,5-dichloro-4-pyridone-1-acetic acid
• 英文别名: 3,5-dichloro-4-pyridon-1-acetic acid；3,5-dichloro-4-pyridone-N-acetic acid；2-(3,5-Dichloro-4-oxopyridin-1(4H)-yl)acetic acid；2-(3,5-dichloro-4-oxopyridin-1-yl)acetic acid
• CAS: 56187-37-2
• 化学式: C₇H₅Cl₂NO₃
• mdl: MFCD02180547
• 分子量: 222.028
• InChiKey: MFMXEEQESUEMSB-UHFFFAOYSA-N

物化性质

• 熔点：
  259-263 °C
• 沸点：
  364.1±42.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（少量）、甲醇（少量）
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会分解，没有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将贮藏器密封，并存放在阴凉、干燥处。确保工作环境中具备良好的通风或排气设施。

SDS

Name:	3 5-Dichloro-4-pyridone-1-acetic acid Material Safety Data Sheet
Synonym:	3,5-Dichloro-4-oxo-1(4H)-pyridineacetic aci
CAS:	56187-37-2

Section 1 - Chemical Product MSDS Name:3 5-Dichloro-4-pyridone-1-acetic acid Material Safety Data Sheet
Synonym:3,5-Dichloro-4-oxo-1(4H)-pyridineacetic aci

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
56187-37-2	3,5-Dichloro-4-pyridone-1-acetic acid		260-040-1

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.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. 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:
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# 56187-37-2: 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 or liquid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C7H5Cl2NO3
Molecular Weight: 222.02

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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:
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# 56187-37-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,5-Dichloro-4-pyridone-1-acetic acid - 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# 56187-37-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 56187-37-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 56187-37-2 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

3,5-二氯-4-吡啶酮-1-乙酸是一种白色固体，主要用于合成头孢西酮钠的原料。

用途

它被用作制备头孢西酮的中间体。

反应信息

• 作为反应物：
  描述：

  3,5-二氯-4-吡啶酮-1-乙酸 在 N-溴代丁二酰亚胺(NBS) 、 三聚氯氰 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.08h， 生成 头孢西酮
  参考文献：
  名称：

  一种头孢西酮的制备方法

  摘要：

  本发明公开了一种头孢西酮的制备方法，本发明利用起始原料7‑氨基去乙酰氧基头孢烷酸(Ⅱ)，与3,5‑二氯吡啶酮乙酸(Ⅲ)反应制得化合物Ⅳ，化合物Ⅳ经过取代反应制得化合物Ⅴ，化合物Ⅴ与2‑巯基‑5‑甲基‑1,3,4‑噻二唑反应制得终产品头孢西酮。本发明采用廉价的起始原料及缩合剂进行反应，反应过程可控，操作简单，纯度及收率高，适合工业化生产。

  公开号：

  CN106967092B
• 作为产物：
  描述：

  3,5-二氯-4-羟基吡啶 在 氯乙酸 作用下， 以 sodium hydroxide 、 水 为溶剂， 生成 3,5-二氯-4-吡啶酮-1-乙酸
  参考文献：
  名称：

  Pyridone-acetic acid derivative

  摘要：

  新型吡啶酮-乙酸衍生物，即3,5-二氯-4-吡啶酮-1-乙酸（I），用作在生产具有抗革兰氏阴性和革兰氏阳性细菌活性的头孢类衍生物中的中间体。该酸（I）通过通常在艺术上已知的方法制备，例如通过将3,5-二氯-4-吡啶酮与氯乙酸或溴乙酸反应。

  公开号：

  US04243810A1

文献信息

• Cephem Compounds with Latent Reactive Groups
  申请人：Gladius Pharmaceuticals, Inc.

  公开号：US20190100534A1

  公开（公告）日：2019-04-04

  Cephem and penem compounds having a styrylmethylene moiety at the 3-position in the cephem or penem ring to which a positively charged leaving group is bonded and wherein the leaving group contains a vicinal diol or is bonded to a unsubstituted or substituted catechol. The leaving group can be a positively charge nitrogen leaving group. Cephems include cephalosporins, cephamycins, carbacephems, and oxacephems. Penems include penems, carbapenems and oxapenems. Preferred cephems are cephalosporins. Preferred penems are carbapenems. Compounds exhibit antibiotic activity against Gram-negative bacteria and/or Gram-positive bacteria. Compounds exhibit antibiotic activity against bacteria which exhibit multi-drug resistance. Compounds of the invention exhibit antibiotic activity against bacterial strains which produce extended spectrum beta-lactamases (ESBL), which produce AmpC beta-lactamases or which produce a carbapenemase. Pharmaceutical compositions comprising one or more cephems or penems or methods of treatment of bacterial infections with such compounds and compositions.

  具有在头孢菌素或青霉烷素环中3位处具有苯乙烯亚甲基基团的头孢菌素和青霉烷素化合物，其中正电离子离去基团与离去基团中含有邻二醇或连接到未取代或取代过的邻苯二酚。离去基团可以是正电离子离去基团。头孢菌素包括头孢菌素、头孢菌烷、卡巴头孢菌素和氧头孢菌素。青霉烷素包括青霉烷素、碳青霉烷素和氧青霉烷素。首选头孢菌素是头孢菌素。首选青霉烷素是碳青霉烷素。化合物对革兰氏阴性细菌和/或革兰氏阳性细菌表现出抗生素活性。化合物对表现出多重耐药性的细菌表现出抗生素活性。本发明的化合物表现出抗生素活性，对产生扩展谱β-内酰胺酶（ESBL）、产生AmpCβ-内酰胺酶或产生碳青霉烷酶的细菌菌株表现出抗生素活性。包括一种或多种头孢菌素或青霉烷素的制药组合物或使用这些化合物和组合物治疗细菌感染的方法。
• 一种头孢类抗感染药物的合成工艺
  申请人：山东罗欣药业集团股份有限公司

  公开号：CN105017285B

  公开（公告）日：2017-08-15

  本发明涉及一种新型头孢类抗感染药物的合成工艺，采用以3,5‑二氯‑4‑吡啶酮‑1‑乙酸和2‑巯基‑5‑甲基‑1,3,4‑噻二唑为原料合成的硫酯化合物(式Ⅲ)直接与7‑ACA一步反应成功制备了头孢西酮钠。本发明的合成方法不仅简化了操作步骤，使生产条件更温和、减少副产物发生、生产工艺更简单，而且在产品收率和纯度上都有很大提高，降低了成本，对环境污染小，具有更好的环保性，使工艺符合产业化的要求。
• 一种3,5-二卤代-4-吡啶酮-1-乙酸的制备方 法
  申请人：新发药业有限公司

  公开号：CN110483384B

  公开（公告）日：2021-05-14

  本发明提供一种3,5‑二卤代‑4‑吡啶酮‑1‑乙酸的制备方法，尤其是3,5‑二氯‑4‑吡啶酮‑1‑乙酸的制备方法。本方法利用哌啶‑4‑酮盐酸盐(Ⅱ)和氯乙酸于合适的溶剂和缚酸剂存在下，经取代反应得到4‑哌啶酮‑1‑乙酸(Ⅲ)，然后4‑哌啶酮‑1‑乙酸和卤代试剂经卤代反应得到3,3,5,5‑四卤代‑4‑哌啶酮‑1‑乙酸(Ⅳ)，再于碱存在下经消除反应脱去卤化氢、盐酸酸化得到3,5‑二卤代‑4‑吡啶酮‑1‑乙酸(Ⅰ)。本发明方法原料价廉易得，成本低，操作简便易于实现，废水产生量少，绿色环保，反应选择性高，产品收率和纯度高，适于工业化生产。
• 一种头孢西酮钠的制备工艺
  申请人：山东罗欣药业集团股份有限公司

  公开号：CN109651402B

  公开（公告）日：2021-01-01

  本发明属于医药技术领域，公开了一种头孢西酮钠的制备工艺。以3,5‑二氯吡啶酮乙酸和特戊酰氯为原料合成混合酸酐，再与7‑氨基头孢烷酸和巯基四氮唑生成的中间体反应，经成盐得到头孢西酮钠。本发明在3‑取代中使用混合溶剂，使反应更加平稳柔和，减少副产物的产生，在酰化反应中使用混合酸酐，活性高，有利于7‑位酰化反应进行，所得头孢西酮钠收率和纯度均较高。
• 一种头孢类抗感染药物的制备方法
  申请人：山东罗欣药业集团股份有限公司

  公开号：CN105017286B

  公开（公告）日：2017-11-28

  本发明属于药物合成领域，涉及一种头孢类抗感染药物头孢西酮钠的制备方法。本发明方法以GCLE替代7‑ACA为原料，克服了现有技术存在的收率低、污染大等缺陷，提供了一种反应条件温和，副反应少，工艺简单的制备方法，该方法原料廉价易得、成本较低，且产品收率高、纯度高，适合工业化生产。