1,2-乙二硫醇

1,2-乙二硫醇
乙二硫醇的球棍模型
乙二硫醇的空间填充模型
IUPAC名
Ethane-1,2-dithiol
别名 乙二硫醇、二硫代乙二醇
1,2-二巯基乙烷
识别
CAS号 540-63-6  checkY
ChemSpider 13865015
SMILES
 
  • SCCS
InChI
 
  • 1/C2H6S2/c3-1-2-4/h3-4H,1-2H2
InChIKey VYMPLPIFKRHAAC-UHFFFAOYAA
RTECS KI3325000
性质
化学式 C2H6S2
摩尔质量 94.20 g·mol⁻¹
外观 无色液体
密度 1.123 g/cm³ (液)
熔点 -41 °C
沸点 146 °C
63 °C, 46 mmHg
溶解性（水） 微溶
溶解性（其他溶剂） 可溶于多数有机溶剂
pKa ~11
折光度n
D 		1.5589 (D-line, 25 °C)
危险性
警示术语 R：R10, R22
安全术语 S：S16
欧盟分类 有毒 (T)
NFPA 704
2
2
0
 
闪点 50 °C
相关物质
相关硫醇 乙硫醇、苯硫酚
1,3-丙二硫醇、邻苯二硫醇
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

1,2-乙二硫醇，又称乙二硫醇，分子式为C2H4(SH)2，室温下为无色有气味的液体。可用于有机合成试剂和螯合配体。

有机合成应用

1,2-乙二硫醇比乙二醇反应性更强，更易与醛和酮反应生成缩硫醛／酮。后者是有机合成中的重要中间体，也可用于羰基的保护。[1]

C2H4(SH)2 + RR'CO → C2H4S2CRR' + H2O
用1,2-乙二硫醇将其转变为缩硫醛／酮，保护羰基

缩硫醛／酮用加氢的雷尼镍处理，硫原子脱掉，羰基被还原为亚甲基。若需恢复羰基，则要加入Hg2+以与体系中的硫醇反应，沉淀出HgS，使反应平衡移动。

二醇如乙二醇与醛酮反应生成缩醛／缩酮；其他1,2-和1,3-取代的二硫醇也可发生类似反应，分别生成五元和六元缩硫醛／酮。缩硫醛的氢可被脱去，且生成的碳负离子可发生烷基化，缩硫酮则不然，因此可依此区分此二者。

合成

1,2-乙二硫醇可由1,2-二溴乙烷与硫脲反应后水解制得。[2]

参考资料

  1. ^ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
  2. ^ Speziale, A. J. (1963). "Ethanedithiol". Org. Synth.; Coll. Vol. 4: 401. 

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