Triphosgene 三光气溶液

CAS 32315-10-9 MFCD00062848

化学结构图

32315-10-9
SMILES: O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl

化学属性

Mol. FormulaC3Cl6O3
Mol. Weight297
Melting Point79-83
Density1.78
TSCAYes
Boiling Point203-206
Flash Point203-206°C
Appearance 是一种稳定的白色晶体，熔点78-82℃，沸点203-206℃。有类似光气的气味，分子式为CO(OCCl 3 ) 2 ,分子量为296.75，固体比重为1.78g/cm 3 ，熔融状态下比重为1.629g/cm 3 由于一摩尔BTC在一定条件下可产生三摩尔光气，所以又叫“三光气”，因该产品是固体的，所以又叫“固体光气”。 BTC不溶于水，可溶于苯、甲苯、乙醇、乙醚、氯仿、四氢呋喃、二氯乙烷等有机溶剂，遇热水及氢氧化钠则分解。BTC的反应活性与光气类似，可以和醇、醛、胺、酰胺、羧酸、酚、羟胺等多种化合物反应，还可环化缩合制备杂环化合物。总之，BTC在化学反应中完全可替代剧毒的光气和双光气，合成相关的化工产品。
Stability对湿度敏感
pH:A

别名和识别编码

Chemical NameTriphosgene
CAS Number32315-10-9
Synonym 1,1,1-Trichloromethanol 1,1'-Carbonate BTC Bis(trichlormethyl)-carbonat Bis(trichlormethyl)carbonat Bis(trichloromethyl)carbonate Bis-(trichlormethyl)-carbonat Kohlensäure-bistrichchlormethylester Kohlensäurebistrichlormethylester Triphosgene bis(trichloromethyl) carbonate carbonic acid bis-trichloromethyl ester 三光气，Cartridge for Phosgene Generation 光气制备药筒 固体光气
PubChem Substance ID87577229
EC Number250-986-3
Beilstein Registry Number1787583
MDL NumberMFCD00062848
Reaxys-RN1787583
Chemical Name Translation三光气溶液
LabNetwork Molecule IDLN00195971
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分类

  • {uni_hamburg} no charge; carbonate; 1fragment
  • {SNA} Chemical Synthesis, Coupling, Greener Alternatives and Technologies, Greener Alternatives: Reagents, Phosgene Derivatives, Phosgene Generation Kit, Synthetic Reagents
  • {SNA} Chemical Synthesis, Coupling, Phosgene Derivatives, Synthetic Reagents
  • Building Blocks, Carbonates, Carbonyl Compounds, Chemical Synthesis, Organic Building Blocks

产品应用

  • ⑴ 医药合成：用于氯甲酸酯、异氰酸酯、聚碳酸酯、酰氯等精细化学品及阿洛西林、美洛西林、派拉西林及依那普利、降压等药物的合成。是生产抗生素类及其它药物的重要中间体。
  • ⑵ 农药制造：用于制造氨基甲酸酯类农药、脲类除草剂、合成除草剂、杀虫剂。
  • ⑶ 高分子材料合成：是合成聚氨酯类泡沫塑料的重要原料。

相关文献及参考

  • Merck: 14,10355
  • 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).
  • Merck: 14,10355 Beilstein:3(4)33
  • Ferrari, B., et al.: Bioorg. Med. Chem. Lett., 4, 45
  • 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).
  • Short: III/10a
  • 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.

安全信息

GHS Symbol
WGK Germany2
Hazard statements
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H330 Fatal if inhaled 吸入致命
Personal Protective Equipment 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
Hazard Codes 6.1 T T+
Precautionary statements
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P301+P330+P331
  • P303+P361+P353+P310+P363
  • P304+P340+P310
  • P305+P351+P338
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Storage condition Moisture Sensitive 0-10 密封保存，禁止与碱性化合物混放。 0-10°C
UN Number 2928
Safety Statements
  • S20 When using do not eat or drink 使用时，不得进食，饮水；
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S4 Keep away from living quarters 远离生活区；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S7/8 Keep container tightly closed and dry 保存在严格密闭容器中，保持干燥；
  • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所；
Risk Statements
  • R23 Toxic by inhalation 吸入有毒
  • R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入，皮肤接触及吞食都有毒
  • R26 Very toxic by inhalation 吸入极毒
  • R29 Contact with water liberates toxic gas. 遇水释放出有毒气体
  • R34 Causes burns 会导致灼伤
Packing GroupII
Hazard Class6.1/8
Warnings 危化品目录(2015)
Restrict 危险品

其他信息

  • 有类似光气味，溶于乙醇、苯、乙醚、氯仿及二氯甲烷等有机溶剂。遇热水及氢氧化碱则分解，遇冷水基本无作用。实际上不溶于水，可能形成光气，二氯甲烷中溶解度：588 g/L CH2Cl2 (20°C)。

系列性分类

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Halogenated Hydrocarbons 卤代烃
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Halogenated Hydrocarbons 卤代烃
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Coupling - Synthetic Reagents
  4. Phosgene Derivatives - Coupling
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Coupling - Synthetic Reagents
  4. Others - Coupling
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Esters - Carbonyl Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Carbonates - Carbonyl Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Amides
  1. Functional Group 官能团索引
  2. carbonic acid derivative