| 109-06-8

• 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
• CAS: 109-06-8
• 化学式: C₆H₇N
• 分子量: 93.1283
• InChiKey: KMQJWNDIJGRBFI-UHFFFAOYSA-N

物化性质

• 熔点：
  -70 °C (lit.)
• 沸点：
  128-129 °C (lit.)
• 密度：
  0.942-0.946 at 20 °C 0.943 g/mL at 25 °C (lit.)
• 蒸气密度：
  3.2 (vs air)
• 闪点：
  79 °F
• 溶解度：
  易溶于水
• 介电常数：
  9.8000000000000007
• LogP：
  1.11 at 20℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  7.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  14.1
• 氢给体数：
  0.0
• 氢受体数：
  0.0

安全信息

• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22,R10,R36/37
• WGK Germany：
  1
• 海关编码：
  29333999
• 危险品运输编号：
  UN 2313 3/PG 3
• 危险类别：
  3
• RTECS号：
  TJ4900000
• 包装等级：
  III
• 危险标志：
  GHS02,GHS06
• 危险性描述：
  H226,H302 + H332,H311,H319,H335
• 危险性防范说明：
  P261,P280,P305 + P351 + P338,P312

制备方法与用途

化学性质
这是一种无色油状液体，具有强烈不愉快的吡啶气味。它溶于丙酮和乙醚，并能与水及乙醇混溶。

用途
2-甲基吡啶用作溶剂和色层分析试剂，广泛应用于有机合成工业。此外，它是植物生长调节剂吡啶醇的重要中间体。它还可用于制备多种化学品，如2-乙烯基吡啶、氮肥增效剂（N-Serve）、长效磺胺药物、抗矽肺病药、牲畜驱虫药、家禽用药、有机磷解毒剂、局部麻醉药、泻药、胶片感光剂的添加物、染料中间体和橡胶促进剂等。作为合成医药、染料、树脂的原料，它可以制备化肥增效剂、除草剂、牲畜驱虫剂、橡胶促进剂及染料中间体等多种产品。此外，它还用于药品、染料、橡胶等化学品的合成，并可用作溶剂和实验试剂。

2-甲基吡啶还可用于检定钴、氰酸盐和铁，进行有机合成。

生产方法
吡啶和甲基吡啶过去主要从煤焦化副产品中回收。这些化合物分布在焦炉煤气、粗苯和焦油中。通常，吡啶类水合物在硫铵母液中的沸点较低，在95-97℃之间。通过精馏可以从中提取2-甲基吡啶。

随着2-甲基吡啶用途的扩大，合成法生产逐渐发展起来。目前国外约95%的2-甲基吡啶及类似化合物是通过合成方法生产的。主要的合成方法有乙醛法、乙炔法和丙烯腈法等。乙醛法涉及乙醛、甲醛与氨反应生成2-甲基吡啶、3-甲基吡啶和4-甲基吡啶。乙炔法则通过乙炔与氨反应，得到2-甲基吡啶和4-甲基吡啶。乙烯法则在乙烯与氨反应时产生2-甲基吡啶及2-甲基-5-乙基吡啶。丙烯腈法则是在过量丙酮参与下与丙烯腈反应生成2-甲基吡啶，同时丙烯醛与氨反应主要生成3-甲基吡啶。

生产方法
以乙醛为原料，在催化剂存在下进行气相反应，温度控制在350～500℃之间，即可得到2-甲基吡啶。副产物包括4-甲基吡啶。

类别
易燃液体

毒性分级
中毒

急性毒性
大鼠口服LD50：790毫克/公斤；小鼠口服LD50：674毫克/公斤

刺激数据
兔子皮肤接触10毫克/24小时，表现为轻度刺激；兔子眼睛接触0.75毫克，表现为重度刺激

爆炸物危险特性
与空气混合可爆

可燃性危险特性
遇明火、高温或氧化剂较易燃，受热会产生有毒的氧化氮气体

储运特性
应存放在通风、低温和干燥的库房中，并与其他氧化剂、酸类分开存放

灭火剂
干粉、干砂、二氧化碳、泡沫以及1211灭火剂

反应信息

• 作为反应物：
  描述：

  碳酸甲丙酯 、 以 gas 为溶剂， 生成 2-methylpyridine conjugate acid 、 6-Methyl-2-pyridyl-Radikal
  参考文献：
  名称：

  Benzene as a selective chemical ionization reagent gas

  摘要：

  AbstractDilute mixtures of C6H6 or C6D6 in He provide abundant [C6H6]+· or [C6D6]+· ions and small amounts of [C6H7]+ or [C6D7]+ ions as chemical ionization (CI) reagent ions. The C6H6 or C6D6 CI spectra of alkylbenzenes and alkylanilines contain predominantly M+· ions from reactions of [C6H6]+· or [C6D6]+· and small amounts of MH+ or MD+ ions from reactions of [C6H7]+ or [C6D7]+. Benzene CI spectra of aliphatic amines contain M+·, fragment ions and sample‐size‐dependent MH+ ions from sample ion‐sample molecules reactions. The C6D6 CI spectra of substituted pyridines contain M+· and MD+ ions in different ratios depending on the substituent (which alters the ionization energy of the substituted pyridine), as well as sample‐size‐dependent MH+ ions from sample ion‐sample molecule reactions. Two mechanisms are observed for the formation of MD+ ions: proton transfer from [C6D6]+· or charge transfer from [C6D6]+· to give M+·, followed by deuteron transfer from C6D6 to M+·. The mechanisms of reactions were established by ion cyclotron resonance (ICR) experiments. Proton transfer from [C6H6]+· or [C6D6]+· is rapid only for compounds for which proton transfer is exothermic and charge transfer is endothermic. For compounds for which both charge transfer and proton transfer are exothermic, charge transfer is the almost exclusive reaction.

  DOI：

  10.1002/oms.1210251003
• 作为产物：
  描述：

  碳酸甲丙酯 、 benzene-d6 radical cation 以 gas 为溶剂， 生成 氘代苯 、
  参考文献：
  名称：

  Benzene as a selective chemical ionization reagent gas

  摘要：

  AbstractDilute mixtures of C6H6 or C6D6 in He provide abundant [C6H6]+· or [C6D6]+· ions and small amounts of [C6H7]+ or [C6D7]+ ions as chemical ionization (CI) reagent ions. The C6H6 or C6D6 CI spectra of alkylbenzenes and alkylanilines contain predominantly M+· ions from reactions of [C6H6]+· or [C6D6]+· and small amounts of MH+ or MD+ ions from reactions of [C6H7]+ or [C6D7]+. Benzene CI spectra of aliphatic amines contain M+·, fragment ions and sample‐size‐dependent MH+ ions from sample ion‐sample molecules reactions. The C6D6 CI spectra of substituted pyridines contain M+· and MD+ ions in different ratios depending on the substituent (which alters the ionization energy of the substituted pyridine), as well as sample‐size‐dependent MH+ ions from sample ion‐sample molecule reactions. Two mechanisms are observed for the formation of MD+ ions: proton transfer from [C6D6]+· or charge transfer from [C6D6]+· to give M+·, followed by deuteron transfer from C6D6 to M+·. The mechanisms of reactions were established by ion cyclotron resonance (ICR) experiments. Proton transfer from [C6H6]+· or [C6D6]+· is rapid only for compounds for which proton transfer is exothermic and charge transfer is endothermic. For compounds for which both charge transfer and proton transfer are exothermic, charge transfer is the almost exclusive reaction.

  DOI：

  10.1002/oms.1210251003

文献信息

• Benzene as a selective chemical ionization reagent gas
  作者：Charles Allgood、Yi Lin、Yee-Chung Ma、Burnaby Munson

  DOI：10.1002/oms.1210251003

  日期：1990.10

  AbstractDilute mixtures of C6H6 or C6D6 in He provide abundant [C6H6]+· or [C6D6]+· ions and small amounts of [C6H7]+ or [C6D7]+ ions as chemical ionization (CI) reagent ions. The C6H6 or C6D6 CI spectra of alkylbenzenes and alkylanilines contain predominantly M+· ions from reactions of [C6H6]+· or [C6D6]+· and small amounts of MH+ or MD+ ions from reactions of [C6H7]+ or [C6D7]+. Benzene CI spectra of aliphatic amines contain M+·, fragment ions and sample‐size‐dependent MH+ ions from sample ion‐sample molecules reactions. The C6D6 CI spectra of substituted pyridines contain M+· and MD+ ions in different ratios depending on the substituent (which alters the ionization energy of the substituted pyridine), as well as sample‐size‐dependent MH+ ions from sample ion‐sample molecule reactions. Two mechanisms are observed for the formation of MD+ ions: proton transfer from [C6D6]+· or charge transfer from [C6D6]+· to give M+·, followed by deuteron transfer from C6D6 to M+·. The mechanisms of reactions were established by ion cyclotron resonance (ICR) experiments. Proton transfer from [C6H6]+· or [C6D6]+· is rapid only for compounds for which proton transfer is exothermic and charge transfer is endothermic. For compounds for which both charge transfer and proton transfer are exothermic, charge transfer is the almost exclusive reaction.