1-(1H-imidazole-1-carbothioyl)-1H-imidazole

• ChemBase编号: 67483
• 分子式: C7H6N4S
• 平均质量: 178.21434
• 单一同位素质量: 178.03131721
• SMILES: C(=S)(n1cncc1)n1cncc1
• Canonical SMILES: S=C(n1cncc1)n1cncc1
• InChI: InChI=1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H
• InChIKey: RAFNCPHFRHZCPS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(1H-imidazole-1-carbothioyl)-1H-imidazole
• IUPAC传统名: 1-(imidazole-1-carbothioyl)imidazole
• 别名: N,N′-硫羰基二咪唑; 1,1'-硫代碳酰基二咪唑; 1,1'-Thiocarbonyldiimidazole; di-1H-Imidazol-1-ylmethanethione; 1,1'-Carbonothioylbis-1H-imidazole; , 1,1'-(Thiocarbonyl)diimidazole; 1,1'-(Thiocarbonyl)bis[imidazole]; 1,1'-(Thiocarbonyl)diimidazole; 1-(1H-Imidazol-1-ylcarbothioyl)-1H-imidazole; Diimidazol-1-ylmethanthione; N,N'-Thiocarbonyldiimidazole; NSC 141692; Thiocarbonylbisimidazole; Thiocarbonyldiimidazole; 1-[(1H-imidazol-1-yl)carbothioyl]-1H-imidazole; 1,1′-Thiocarbonyldiimidazole; Di(1H-imidazol-1-yl)methanethione; 1,1'-Thiocarbonyldi(1H-imidazole) 90%; 1,1'-Thiocarbonyldiimidazole

登记号

• CAS号: 6160-65-2
• EC号: 228-183-4
• MDL号: MFCD00005289
• Beilstein号: 609349
• PubChem SID: 24889110; 24889111; 162033218; 24849589
• PubChem CID: 80264

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.0659748
• LogD (pH = 7.4): -0.06423997
• Log P: -0.06421781
• 摩尔折射率: 48.7679 cm^3
• 极化性: 18.80097 Å^3
• 极化表面积: 35.64 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; DMSO
• 外观: Yellow Solid
• 熔点: 101 - 103°C; 80-82°C; 98-102 °C; 98-102 °C(lit.); 98-102°C; 98-102°C
• 疏水性(logP): 0.978

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• 保存注意事项: Harmful/Moisture Sensitive/Keep Cold/Store under Argon; IRRITANT; Moisture Sensitive
• 欧盟危险性物质标志: X
• 德国WGK号: 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26-36/37
• TSCA收录: false; 否
• GHS危险品标识: GHS06
• GHS危险声明: H301-H315-H319-H335
• GHS警示性声明: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥90% (S); ≥95.0% (S); 90%; 95%; 95+%; 97%; tech 90%
• 级别: technical; technical grade
• Empirical Formula (Hill Notation): C7H6N4S

详细说明

Sigma Aldrich - 88545

Other Notes
用于合成硫酰胺1；用于改进的 Corey-Winter 烯烃合成2；通过醇与 Bu3SnH-AIBN 发生自由基反应制备硫代氨基甲酸酯3,4
包装
1, 5, 25 g in glass bottle

Sigma Aldrich - 156051

Application
本品可用于醇与三丁基氢化锡以及二醇与氢化铝锂发生脱氧反应。
生化合成中的有用试剂。
包装
5, 10 g in glass bottle

Toronto Research Chemicals - T344410

1,1’-Thiocarbonyldiimidazole can be used to deoxygenate carboxylic monosaccharide analogues.

参考文献

• Loke, I., et al.: Tetrahedron, 68, 697 (2012)
• Can be used to deoxygenate carbocyclic monosaccharide analogues: Tetrahedron., 48, 2349 (1992).
• Reacts with diols to give cyclic thionocarbonates which are desulfurized by trialkyl phosphites to give alkenes by cis-elimination of CO₂ from the intermediate carbene (Corey-Winter olefination): J. Am. Chem. Soc., 85, 2677 (1963); Angew. Chem. Int. Ed., 14, 753 (1975). For a modified procedure involving ring-opening of the thionocarbonate intermediate with an alkyl iodide, followed by Zn reduction of the resulting iodo ester, see: Tetrahedron Lett., 3793 (1973). Alternatively, the thionocarbonate of a 1,2-diol can be selectively reduced to the methylenedioxy group with Triphenyltin hydride, L00163, under free-radical conditions: J. Org. Chem., 62, 4159 (1997).