Trichloromethyl chloroformate

Base Information

• Chemical Name: Trichloromethyl chloroformate
• CAS No.: 503-38-8
• Molecular Formula: C2Cl4 O2
• Molecular Weight: 197.833
• Hs Code.: 2915900090
• European Community (EC) Number: 207-965-9
• ICSC Number: 1630
• UNII: PO4Q4R80LV
• DSSTox Substance ID: DTXSID60862065
• Nikkaji Number: J12.981J
• Wikipedia: Diphosgene
• Wikidata: Q419283
• NCI Thesaurus Code: C163651
• Mol file: 503-38-8.mol

Synonyms:diphosgene;trichloromethyl chloroformate

Chemical Property of Trichloromethyl chloroformate

Chemical Property:

• Appearance/Colour: clear, colorless liquid
• Vapor Pressure: 10.8mmHg at 25°C
• Melting Point: -57 ºC
• Refractive Index: n20/D 1.458
• Boiling Point: 128 ºC
• Flash Point: >110°C
• PSA: 26.30000
• Density: 1.64
• LogP: 2.68950
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: may decompose
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 197.862290
• Heavy Atom Count: 8
• Complexity: 94.7

Purity/Quality:

99.9% ^*data from raw suppliers

Trichloromethyl chloroformate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+,Xi
• Statements: 26/28-34-26/27/28-36/37/38
• Safety Statements: 26-28-36/37/39-45-28A-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C(=O)(OC(Cl)(Cl)Cl)Cl
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the respiratory tract, skin and eyes. Lachrymation. Inhalation may cause lung oedema.
• Description: Diphosgene (DP), trichloromethyl chloroformate, is a clear, colorless liquid with an odor similar to phosgene. It is noncombustible, a strong irritant to the eyes and tissues, and is toxic by inhalation and ingestion. DP has a boiling point of 127°C–128°C (263°F) and a vapor pressure of 4.2 at 68°F (20°C). The liquid density is 1.65, which is heavier than water, and a melting/freezing point of 314°F (157°C). Inhalation LC50 is 3600 mg/m3 for 10 min. Effects of exposure are quite similar to phosgene gas. Its molecular formula is ClCOOCCl3, and the structure and molecular formula are shown in Figure 8.38. The DOT lists diphosgene as a 6.1 poison liquid. The NFPA 704 designation for CG is estimated to be health 4, flammability 0, reactivity 1, and special 0. It has a four-digit UN identification number of 2972.
• Uses: In organic synthesis; as war gas. Trichloromethyl chloroformate is used as a reagent in the synthesis of organic compounds. It serves as a source of phosgene used in some laboratory preparations. Also, it is used as a reactant for the synthesis of cyclic carbamimidates, N-alkenyl and cycloalkyl carbamates and prostate-specific membrane antigen-targeted anticancer prodrugs. In addition, it is involved in the preparation of an erythromycin A derivatives and antibody-drug conjugates. It is utilized in the conversion of amines, carboxylic acids, formamides in to isocyanates, acid chlorides and isocyanides respectively. Reactant for preparation of:Cyclic carbamimidates using a monophosphine gold(i) catalystN-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligandsProstate-specific membrane antigen-targeted anticancer prodrugsPotential west nile virus protease inhibitorsAntibody-drug conjugates (ADCs)Erythromycin A derivatives

Technology Process of Trichloromethyl chloroformate

There total 8 articles about Trichloromethyl chloroformate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

methyl chloroformate (79-22-1) → trichloromethyl chloroformate (503-38-8)

Guidance literature:

With chlorine; at 75 - 85 ℃; for 35h;

DOI:10.1021/jo01308a027

Reference yield: 76.0%

carbonochloridic acid, chloromethyl ester (22128-62-7) → dichloromethoxycarbonyl chloride (22128-63-8) + trichloromethyl chloroformate (503-38-8)

Guidance literature:

With chlorine; for 61h;

DOI:10.1055/s-1990-27124

Reference yield:

Methyl formate (107-31-3) → trichloromethyl chloroformate (503-38-8)

Guidance literature:

bei der Chlorierung im UV-Licht; die Bildungsgeschwindigkeit waechst mit steigender Temperatur bis 110-112grad;

upstream raw materials:

Methyl formate

bis(trichloromethyl) carbonate

methyl chloroformate

carbonochloridic acid, chloromethyl ester

Downstream raw materials:

octadecyl isocyanate

ethyl violet

phosgene

benzyl chloride

Refernces

• 1、 -. "Method and device for the production of phosgene from diphosgene and/or triphosgene". . . Retrieved 2008/06/13.
• 2、 -. "Process for preparing cyclopropylacetylene". . . Retrieved 2008/06/13.