ditrichloromethyl carbonate

• ChemBase编号: 88396
• 分子式: C3Cl6O3
• 平均质量: 296.7483
• 单一同位素质量: 293.79785994
• SMILES: O(C(=O)OC(Cl)(Cl)Cl)C(Cl)(Cl)Cl
• Canonical SMILES: O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl
• InChI: InChI=1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9
• InChIKey: UCPYLLCMEDAXFR-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ditrichloromethyl carbonate
• IUPAC传统名: triphosgene
• 别名: 二(三氯甲基)碳酸酯; 三光气; 三光气; 固体光气; 双(三氯甲基)碳酸酯; Bis(trichloromethyl) carbonate; Triphosgene; Triphosgene; Bis(trichloromethyl) carbonate; tri-Phosgene; Bis(trichloromethyl) carbonate; Triphosgene; 1,1,1-Trichloromethanol 1,1'-Carbonate; Carbonic Acid Bis(trichloromethyl)ester; Bis(trichloromethyl)carbonate; Triphosgene (Technical grade); BTC

登记号

• CAS号: 32315-10-9
• EC号: 250-986-3
• MDL号: MFCD00062848
• Beilstein号: 1787583
• PubChem SID: 24849208; 162075354; 24859885
• PubChem CID: 94429
• Chemspider ID: 85216
• 维基百科标题: Triphosgene

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 5.4449406
• LogD (pH = 7.4): 5.4449406
• Log P: 5.4449406
• 摩尔折射率: 12.2506 cm^3
• 极化性: 19.750893 Å^3
• 极化表面积: 35.53 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Chloroform; Reacts in water
• 外观: White solid
• 熔点: 75-80 °C; 77-91°C; 79-83 °C(lit.); 80°C; 80-82°C
• 沸点: 203-206 °C(lit.); 203-206°C; 206°C
• 密度: 1.600

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• 保存注意事项: Moisture Sensitive; Very Toxic/Corrosive/Keep Cold/Moisture Sensitive/Store under Argon
• 欧盟危险性物质标志: 有毒(Toxic) (T); 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 2928; UN2928
• 德国WGK号: 2
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 23-29-34; 26-34
• 安全公开号: 36/37/39-45; 4-7/8-9-20-26-36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS06
• GHS警示词: Danger
• GHS危险声明: H314-H330; H330-H314-H318
• GHS警示性声明: P260-P280-P284-P305 + P351 + P338-P310; P260-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501A
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2928 6.1/PG 2
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥99.0% (AT); 98%
• 级别: purum; reagent grade
• 线性分子式: Cl3COCOOCCl3

详细说明

InterBioScreen - BB_SC-8946

T. pl.=87,8C

Sigma Aldrich - 15217

Other Notes
易于处理的结晶型光气替代物；1 摩尔试剂的反应性相当于 3 摩尔光气1,2,3,4

Sigma Aldrich - 330752

Application
光气的有用替代品。
具有多种用途的固体光气替代品，这些用途包括由烯丙醇和叠氮化钠通过一锅法制备烯丙基叠氮化物，1以及由 2(5H)-噻吩酮制备酯化偶联剂二-2-噻吩基碳酸酯。2
用于通过对应烯酰胺的环化反应制备 2-氯-3-吡啶甲醛。
包装
5, 25, 100, 500 g in glass bottle

Toronto Research Chemicals - T810500

An efficient carbonylating agent for liquid and solid-phase aza-peptide synthesis.

参考文献

• Ferrari, B., et al.: Bioorg. Med. Chem. Lett., 4, 45 (1994)
• Convenient crystalline alternative to phosgene in many reactions. See also Trichloromethyl chloroformate, A17444. Possible applications include conversion of amines to isocyanates, diols to carbonates, acids to acyl halides, etc.: Angew. Chem. Int. Ed., 26, 894 (1987). For a brief review, see: J. Prakt. Chem./ Chem. Ztg., 337, 516 (1995); for a comprehensive review: Synthesis, 553 (1996).
• In combination with triphenylphosphine, is a mild reagent for the conversions of alcohols to alkyl chlorides: Synth. Commun., 23, 711 (1993), epoxides to vicinal dichlorides: Synth. Commun., 24, 1715 (1994), and acids to acyl chlorides: Tetrahedron Lett., 38, 6489 (1997).
• Trap for titanocycle intermediates in the bicyclization of enynes using the titanocene dichloride (Bis(cyclopentadienyl)titanium dichloride, A11456) - Mg metal system: J. Org. Chem., 63, 9285 (1998):
  
• In combination with triethylamine, dehydrates formamides to isocyanides, and carboxylic acids to their anhydrides: J. Org. Chem., 58, 1646 (1993); 59, 2913 (1994).
• In combination with Dimethyl sulfoxide, A13280, has been used for the low-temperature Swern-type oxidation of alcohols to aldehydes: J. Org. Chem., 56, 5948 (1991); 58, 1646 (1993); Org. Prep. Proced. Int., 24, 363 (1992). Compare Oxalyl chloride, A18012.