trichloromethyl chloroformate

• ChemBase编号: 123315
• 分子式: C2Cl4O2
• 平均质量: 197.8322
• 单一同位素质量: 195.86523996
• SMILES: C(OC(=O)Cl)(Cl)(Cl)Cl
• Canonical SMILES: ClC(=O)OC(Cl)(Cl)Cl
• InChI: InChI=1S/C2Cl4O2/c3-1(7)8-2(4,5)6
• InChIKey: HCUYBXPSSCRKRF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: trichloromethyl chloroformate; chloro(trichloromethoxy)methanone
• IUPAC传统名: trichloromethyl chloroformate; diphosgene
• 别名: 双光气; 氯代甲酸三氯甲酯; 氯甲酸三氯甲酯; trichloromethyl carbonochloridate; Diphosgene; trichloromethyl chloroformate; Diphosgene; di-Phosgene; Trichloromethyl chloroformate; Chloroformic acid trichloromethyl ester

登记号

• CAS号: 503-38-8
• EC号: 207-965-9
• MDL号: MFCD00015553
• Beilstein号: 970225
• 默克索引号: 143334
• PubChem SID: 24853917; 162217668
• PubChem CID: 10426
• Chemspider ID: 21154424
• 维基百科标题: Diphosgene

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 3.3808258
• LogD (pH = 7.4): 3.3808258
• Log P: 3.3808258
• 摩尔折射率: 14.7329 cm^3
• 极化性: 13.222563 Å^3
• 极化表面积: 26.3 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: insol. in water
• 外观: liquid at room temperature
• 熔点: -57 °C; -57°C
• 沸点: 128 °C; 128°C; 20 °C/10 mmHg(lit.)
• 闪点: >110°C(230°F); 32°C
• 密度: 1.639 g/mL at 20 °C; 1.640; 1.65 g/cm^3
• 折射率: 1.4570; n20/D 1.458

安全信息

• 保存注意事项: Moisture Sensitive
• RTECS编号: LQ7350000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 3277; UN3390
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2; I
• 危险公开号: 26/28-34; 26-34
• 安全公开号: 26-27/28-36/37/39-45; 26-28-36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS06
• GHS警示词: Danger
• 主要危害: toxic
• GHS危险声明: H300-H314-H330; H330-H314-H318
• GHS警示性声明: P260-P264-P280-P284-P301 + P310-P305 + P351 + P338; P280-P303+P361+P353-P305+P351+P338-P304+P340-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 3277 6.1/PG 2
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97.0% (GC); 98%
• 线性分子式: ClCOOCCl3

详细说明

Sigma Aldrich - 23261

Other Notes
光气的易处理替代品7,8,9；可通过原位炭催化分解成光气，并可与氨基酸反应生成 N-羧酸酐10
包装
10, 50 mL in glass bottle
Application
Reactant for preparation of:
• Cyclic carbamimidates using a monophosphine gold(i) catalyst1
• N-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligands2
• Prostate-specific membrane antigen-targeted anticancer prodrugs3
• Potential west nile virus protease inhibitors4
• Antibody-drug conjugates (ADCs)5
• Erythromycin A derivatives6

参考文献

• Convenient replacement for phosgene in many reactions, for example:
• Conversion of amines to isocyanates: J. Org. Chem., 41, 2070 (1976); Org. Synth. Coll ., 6, 715 (1988). For aliphatic amines, best results were obtained in the presence of the hindered amine 1,8-Bis(dimethylamino)naphthalene, L00313: J. Org. Chem., 61, 3883 (1996).
• Dehydration of N-monosubstituted formamides to isocyanides: Angew. Chem. Int. Ed., 16, 259 (1977).
• Formation of nitriles from oximes Synthesis, 1037 (1986); or carboxamides: Tetrahedron Lett., 27, 2203 (1986).
• See also Triphosgene, A14932, and Oxalyl chloride, A18012.