ChemicalBook CAS DataBase List 32315-10-9

32315-10-9

Name	Triphosgene
CAS	32315-10-9
EINECS(EC#)	250-986-3
Molecular Formula	C3Cl6O3
MDL Number	MFCD00062848
Molecular Weight	296.75
MOL File	32315-10-9.mol

Chemical Properties

Appearance	White solid
Melting point	79-83 °C (lit.)
Boiling point	203-206 °C (lit.)
density	1.78
vapor pressure	16 hPa (90 °C)
Fp	203-206°C
storage temp.	2-8°C
solubility	Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form	Crystalline Powder, Crystals and/or Chunks
color	White to off-white
Water Solubility	practically insoluble
Sensitive	Moisture Sensitive
BRN	1787583
InChI	1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9
InChIKey	UCPYLLCMEDAXFR-UHFFFAOYSA-N
SMILES	ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl
CAS DataBase Reference	32315-10-9(CAS DataBase Reference)
EPA Substance Registry System	32315-10-9(EPA Substance)

Safety Data

Symbol(GHS)	GHS05,GHS06
Signal word	Danger
Hazard statements	H314-H330
Precautionary statements	P260-P271-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Hazard Codes	T+,Xn
Risk Statements	R26:Very Toxic by inhalation. R34:Causes burns. R29:Contact with water liberates toxic gas. R36/37/38:Irritating to eyes, respiratory system and skin . R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . less more
Safety Statements	S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . S9:Keep container in a well-ventilated place . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . S7/9:Keep container tightly closed and in a well-ventilated place . less more
RIDADR	UN 2928 6.1/PG 2
WGK Germany	2
F	10-19-21
TSCA	Yes
REACH Registrations	Active
HazardClass	6.1
PackingGroup	II
HS Code	29209010
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 1 Inhalation Skin Corr. 1B

Raw materials And Preparation Products

Hazard Information

Description

Triphosgene is also known as solid phosgene. Its chemical name is bis (Trichloromethyl) carbonate, and its English name is bisgriehloromethyl) carbonate or triphosgene, abbreviated as BTC. Triphosgene is a white crystal, similar to the smell of phosgene. It is mainly used to synthesize chloroformate, isocyanate, polycarbonate and acyl chloride. It is widely used as an intermediate in plastics, medicine, herbicides and pesticides.

Chemical Properties

White solid

Uses

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

Reactions

The Triphosgene reaction is quenched very carefully by dropwise addition of 75 mL of saturated aqueous sodium sulfate solution (Notes 5 and 6). The resulting white granular precipitate or slurry is removed by vacuum filtration through Celite, and the filter cake is washed with three portions of 75 mL of chloroform .

General Description

Triphosgene [Bis(trichloromethyl)carbonate] is a versatile organic reagent used in organic synthesis alternative to phosgene. A catalytic amount of triphosgene is particularly used in chloroformylations, carbonylations, chlorinations, and dehydration reactions.

reaction suitability

reaction type: Coupling Reactions

Safety

Triphosgene's low vapor pressure makes it possible for it to reach concentrations that are considered toxicologically unsafe. While several properties of triphosgene are not yet readily available, it is known that it is extremely toxic if inhaled. A toxic gas is emitted if it comes in contact with water. There is a lack of information and variability regarding the proper handling of triphosgene. It is assumed to have the same risks as phosgene.

Synthesis

Triphosgene is synthesized by exhaustive free radical chlorination of dimethyl carbonate:
CH₃OCO₂CH₃ + 6 Cl₂ → CCl₃OCO₂CCl₃ + 6 HCl
Triphosgene can be easily recrystallized from hot hexanes.

Purification Methods

It is a good solid substitute for phosgene (using a third mol per mol). Crystallise it from pet ether (b 60-80o), wash it with anhydrous cold Et2O, de-gas it at 200mm then dry at 0.1mm (over H2SO4). It has IR: max 900 and 1900 cm-1 . It is a lachrymator, is TOXIC and should be handled with gloves and in an efficient fume hood. [Hales et al. J Chem Soc 620 1957, Eckert & Forster Angew Chem, Int Ed Engl 26 894 1987, Aldrichimica Acta 21 47 1988, Beilstein 3 H 17, 3 I 8, 3 II 16, 3 III 36, 3 IV 33.]

Material Safety Data Sheet(MSDS)

Questions And Answer

Spectrum Detail

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32315-10-9

Chemical Properties

Safety Data

Raw materials And Preparation Products

Raw materials

Preparation Products

Hazard Information

Description

Chemical Properties

Uses

Reactions

General Description

reaction suitability

Safety

Synthesis

Purification Methods

Material Safety Data Sheet(MSDS)

Questions And Answer

Toxicity

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Related Products