phenyl chloromethanethioate

• ChemBase编号: 140273
• 分子式: C7H5ClOS
• 平均质量: 172.632
• 单一同位素质量: 171.97496346
• SMILES: c1ccc(cc1)OC(=S)Cl
• Canonical SMILES: ClC(=S)Oc1ccccc1
• InChI: InChI=1S/C7H5ClOS/c8-7(10)9-6-4-2-1-3-5-6/h1-5H
• InChIKey: KOSYAAIZOGNATQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: phenyl chloromethanethioate
• IUPAC传统名: phenyl chloromethanethioate
• 别名: 氯甲基硫代苯酯; 硫代氯甲酸苯酯; 氯化硫代甲酸苯酯; Carbonochloridothioic Acid O-Phenyl Ester; Chlorothioformic Acid O-Phenyl Ester; NSC 99103; O-Phenyl Carbonochloridothioate; O-Phenyl Chlorothiocarbonate; O-Phenyl Chlorothioformate; O-Phenyl Chlorothionoformate; Phenoxythiocarbonyl Chloride; Phenyl Chlorothiocarbonate; Phenyl Chlorothionoformate; Phenyl Thiochloroformate; Phenyl Thioxochloroformate; Phenyl Chlorothionoformate; Phenyl thionochloroformate; O-Phenyl chlorothionoformate; Phenyl chlorothionocarbonate; Phenyl chlorothionoformate

登记号

• CAS号: 1005-56-7
• EC号: 213-736-4
• MDL号: MFCD00004920
• Beilstein号: 774830
• PubChem SID: 162234517; 24854046
• PubChem CID: 70498

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 3.477103
• LogD (pH = 7.4): 3.477103
• Log P: 3.477103
• 摩尔折射率: 45.8943 cm^3
• 极化性: 18.151892 Å^3
• 极化表面积: 9.23 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate
• 外观: Clear Yellow Oil
• 沸点: 81-83 °C/6 mmHg(lit.); 81-83°C/6mm
• 闪点: 177.8 °F; 81 °C; 81°C(177°F)
• 密度: 1.248; 1.248 g/mL at 25 °C(lit.)
• 折射率: 1.5804; n20/D 1.581; n20/D 1.581(lit.)

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 3265; UN3265
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 34
• 安全公开号: 26-36/37/39-45
• TSCA收录: 否
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H314; H314-H318-H227
• GHS警示性声明: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2

产品相关信息

• 纯度: ≥99.0% (AT); 98+%; 99%
• 级别: purum
• 线性分子式: ClC(S)OC6H5

详细说明

Sigma Aldrich - 234524

Application
用于无保护的胸腺嘧啶核苷的巯羰基化。1形成保护性核糖核苷（可被三丁基氢化锡（产品号234788）还原为脱氧核苷）的苯氧基硫代羰基酯。2,3
包装
1, 5 g in glass bottle

Sigma Aldrich - 26470

Other Notes
通过硫羰碳酸酯用于 Bu3SnH 介导的醇脱氧反应1,2

Toronto Research Chemicals - P319650

Phenyl Chlorothionoformate is used in the preparation of an bicyclic thymidine analogs as selective inhibitors of Thymidine monophosphate kinase Mycobacterium tuberculosis (TMPKmt).

参考文献

• Vanheusden, V. et al.: J. Med. Chem., 47, 6187 (2004)
• Similarly, amides are dehydrated to nitriles, and formamides to isonitriles under mild conditions: Tetrahedron Lett., 40, 747 (1999).
• Aryl chlorothionoformates react with OH groups to give thiocarbonate esters. These have a much greater tendency to undergo cyclic elimination than their oxygen counterparts, with dehydration as the net result. Thus, e.g. oximes are dehydrated to nitriles under mild conditions: Chem. Commun., 1014 (1970):
  
• Alcohols are converted to alkenes in better yields than in the Chugaev (xanthate pyrolysis) method, succeeding with hindered alcohols which do not readily form xanthates: J. Chem. Soc., Chem. Commun., 1215 (1972); Helv. Chim. Acta, 55, 2277 (1972). Secondary alcohols give thiocarbonate esters which can be reduced to alkanes by tributyltin hydride, in a useful deoxygenation sequence. For use in an enantiospecific synthesis of the antiviral agent ganciclovir phosphonate, see: J. Med. Chem., 37, 1371 (1994).
• Reagent for conversion of imidazoles to imidazole-2-thiones: Synlett, 239 (1995).
• Reagent, alternative to chloroformates, for dealkylation of tertiary amines: Austral. J. Chem., 52, 841 (1999).