6-吡咯啉烟酸甲酯 | 210963-94-3

• 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: 6-吡咯啉烟酸甲酯
• 中文别名: 6-(1-吡咯烷基)-3-吡啶羧酸甲酯
• 英文名称: 6-(N-pyrrolidinyl)nicotinic acid methyl ester
• 英文别名: methyl 6-(pyrrolidine-1-yl)nicotinate；Methyl 6-pyrrolidinonicotinate；methyl 6-pyrrolidin-1-ylpyridine-3-carboxylate
• CAS: 210963-94-3
• 化学式: C₁₁H₁₄N₂O₂
• mdl: MFCD05664433
• 分子量: 206.244
• InChiKey: OWOKTZZFJFFUKY-UHFFFAOYSA-N

物化性质

• 熔点：
  119 °C
• 沸点：
  349.7±27.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090

SDS

Name:	Methyl 6-(1-pyrrolidinyl)nicotinate Material Safety Data Sheet
Synonym:	Methyl-2-pyrrolidinylnicotinate
CAS:	210963-94-3

Section 1 - Chemical Product MSDS Name:Methyl 6-(1-pyrrolidinyl)nicotinate Material Safety Data Sheet
Synonym:Methyl-2-pyrrolidinylnicotinate

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
210963-94-3	Methyl 6-(1-pyrrolidinyl)nicotinate	97+	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
No information found.

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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.
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:
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. 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 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# 210963-94-3: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 119-120 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: C11H14N2O2
Molecular Weight: 209.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, bases.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 210963-94-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 6-(1-pyrrolidinyl)nicotinate - 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: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 24/25 Avoid contact with skin and eyes.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 210963-94-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 210963-94-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 210963-94-3 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

制备

6-甲苯磺酰基烟酸甲酯的合成如下：

1. 按照通用程序A。向装有隔膜、氮气入口接头和热电偶的三颈圆底烧瓶中加入氯吡啶（1当量）、亚磺酸钠（1.5当量）、氯化四丁基铵（0.3当量）和DMAc（每1g氯吡啶10mL）。将反应混合物在100℃下搅拌24小时，然后用水（每1g氯吡啶30mL）稀释。使所得反应混合物冷却至室温，得到稠浆液。收集晶体，用水洗涤，并在氮气吹扫下真空干燥24小时。

2. 6-（甲苯-4-磺酰基）烟酸甲酯（11）：按照通用方法A，用对甲苯甲酸钠（2）（2.08g，11.66mmol）处理氯吡啶10（1.0g，5.83mmol）、四丁基氯化铵（0.52g，1.75mmol），DMAc（10mL）和水（30mL）。得到1.59g（94%）的白色晶体：熔点122-123℃。核磁共振氢谱（DMSO-d6, 400MHz）δ2.39（s，3H），3.91（s，3H），7.46（d，2H，J = 8.3Hz），7.88（d，2H，J = 8.3Hz），8.33 （d，1H，J = 8.2Hz），8.59（dd，1H，J = 8.2和2.0Hz），9.12（d，1H，J = 2.0Hz）；核磁共振碳谱（DMSO-d6, 100MHz）δ21.6, 53.4, 122.4, 129.1, 129.2, 130.6, 135.4, 140.5, 145.9, 151.2, 161.5, 164.4。

应用

6-吡咯啉烟酸甲酯是一种有机中间体，可由2-氯烟酸甲酯通过两步制备得到。

反应信息

• 作为反应物：
  描述：

  6-吡咯啉烟酸甲酯 在 盐酸 、 title compound 作用下， 以 盐酸 为溶剂， 反应 16.0h， 生成 6-(1-吡咯烷)烟酸
  参考文献：
  名称：

  Benzamidine derivatives

  摘要：

  以下化学式或其类似物的苯甲酰胺衍生物，即其药学上可接受的盐，被提供。这些化合物或其盐具有抗血凝作用，基于抑制活化的血凝因子X的作用具有优异的效果，它们可用作抗凝剂。

  公开号：

  US07396844B1
• 作为产物：
  描述：

  香豆灵酸甲酯 在 四氯化钛 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 6-吡咯啉烟酸甲酯
  参考文献：
  名称：

  吡啶的狄尔斯-阿尔德合成

  摘要：

  在这种情况下，当甲苯磺酰氰与香豆酸甲酯 (la) 在 165°C 下纯加热并对反应产物进行色谱分析时，以 54% 的产率形成了烟酸甲苯磺酰酯 (2a)？其他几种可用的吡喃酮也在 125180°C 的温度下经受这些条件，结果不一，总结在表 P 中。使用更稳定的 6 活化腈亲二烯体（如氰草酸酯）进行的试验即使在 210°C 下也不会产生环加成产物（方程式 2）。

  DOI：

  10.1080/00304940309355365

文献信息

• Benzamidine derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：US07396844B1

  公开（公告）日：2008-07-08

  Benzamidine derivatives of the following formulae or analogs thereof, i.e., pharmaceutically acceptable salts thereof, are provided. These compounds or salts thereof have a blood-coagulation inhibiting effect based on an excellent effect of inhibiting the action of activated blood coagulation factor X, and they are useful as anticoagulants

  以下化学式或其类似物的苯甲酰胺衍生物，即其药学上可接受的盐，被提供。这些化合物或其盐具有抗血凝作用，基于抑制活化的血凝因子X的作用具有优异的效果，它们可用作抗凝剂。
• Conversion of Aryl Azides to Aminopyridines
  作者：Sajan C. Patel、Noah Z. Burns

  DOI：10.1021/jacs.2c08464

  日期：2022.10.5

  transformation of benzene into pyridine via nitrogen insertion and carbon deletion. Herein, we report a protocol for the transformation of aryl azides, easily accessible from their corresponding anilines, to 2-aminopyridines using blue light and oxygen. Mechanistic studies corroborate that the arene to pyridine conversion is achieved by nitrogen insertion into the benzene ring followed by oxidative carbon extrusion

  基本官能团相互转化的长期挑战是通过氮插入和碳缺失将苯直接转化为吡啶。在这里，我们报告了一种使用蓝光和氧气将芳基叠氮化物转化为 2-氨基吡啶的方案，该方案很容易从相应的苯胺中获得。机理研究证实，芳烃向吡啶的转化是通过将氮插入苯环，然后进行氧化碳挤出来实现的。
• [EN] PYRAZOLO[1,5-A]PYRIDINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND COMPOSITION AND USE THEREOF<br/>[FR] DÉRIVÉ DE PYRAZOLO[1,5-A]PYRIDINE, SON PROCÉDÉ DE PRÉPARATION ET COMPOSITION ET UTILISATION ASSOCIÉES<br/>[ZH] 一种吡唑并[1,5-a]吡啶类衍生物及其制备方法，组合物以及用途
  申请人：SHENZHEN JINGTAI TECH CO LTD

  公开号：WO2021213476A1

  公开（公告）日：2021-10-28

  本发明涉及一种吡唑并[1,5-a]吡啶类衍生物及其制备方法，组合物以及用途。具体地，本发明涉及式(I)化合物及其在用于治疗和/或预防与野生型、基因融合型(包括但不限于KIF5B、CCDC6和NCOA4)及突变型(包括但不限于G804、G810和M918)RET激酶相关的疾病，包括由RET激酶介导的疾病或病症。
• BENZAMIDINE DERIVATIVES
  申请人：Ajinomoto Co., Inc.

  公开号：EP0976722B1

  公开（公告）日：2009-03-11
• US7396844B1
  申请人：——

  公开号：US7396844B1

  公开（公告）日：2008-07-08