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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
Trichloromethyl chloroformate

Synonyms:diphosgene;trichloromethyl chloroformate

Suppliers and Price of Trichloromethyl chloroformate
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Trichloromethyl chloroformate
  • 25g
  • $ 105.00
  • Sigma-Aldrich
  • Trichloromethyl chloroformate ≥97.0% (GC)
  • 50ml
  • $ 508.00
  • Sigma-Aldrich
  • Trichloromethyl chloroformate ≥97.0% (GC)
  • 10ml
  • $ 112.00
  • Oakwood
  • Trichloromethyl chloroformate 98%
  • 1Kg
  • $ 993.00
  • Oakwood
  • Trichloromethyl chloroformate 98%
  • 5g
  • $ 15.00
  • Medical Isotopes, Inc.
  • Trichloromethyl chloroformate
  • 25 g
  • $ 625.00
  • Biosynth Carbosynth
  • Diphosgene
  • 25 g
  • $ 75.00
  • Biosynth Carbosynth
  • Diphosgene
  • 500 g
  • $ 600.00
  • Biosynth Carbosynth
  • Diphosgene
  • 250 g
  • $ 450.00
  • Biosynth Carbosynth
  • Diphosgene
  • 100 g
  • $ 200.00
Total 23 raw suppliers
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:
  • Pictogram(s):  
  • 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:
Guidance literature:
With chlorine; at 75 - 85 ℃; for 35h;
DOI:10.1021/jo01308a027
Guidance literature:
bei der Chlorierung im UV-Licht; die Bildungsgeschwindigkeit waechst mit steigender Temperatur bis 110-112grad;
Refernces

Novel synthesis of 2-chloroquinolines from 2-vinylanilines in nitrile solvent

10.1021/jo016196i

The study presents a novel method for synthesizing 2-chloroquinolines from 2-vinylanilines using diphosgene in acetonitrile as the solvent. The researchers detail a three-step reaction mechanism involving the generation of phenylisocyanate, quinoline ring formation, and chlorination at the C2 position of the quinoline. The purpose of the chemicals used in the study was to facilitate these steps, with diphosgene reacting with 2-vinylanilines to produce phenyl isocyanate, which then reacts with the acetonitrile to form the quinoline ring. The final step involves the chlorination of the C2 position. This new method eliminates the need for the hazardous use of excess phosphorus oxychloride, which was previously required in the synthesis of 2-chloroquinolines from 2(1H)-quinolinones. The study also discusses the role of acetonitrile as a reactive solvent in the process and provides evidence that the third step, chlorination, is likely the rate-determining step in the reaction.

Isocyanide Synthesis with Phosphoryl Chloride and Diisopropylamine

10.1055/s-1985-31216

The research aims to improve the yield and purity of isocyanide synthesis using phosphoryl chloride and disopropylamine. Traditionally, isocyanides are synthesized by dehydrating formamides, often using reagents like phosgene or diphosgene, which are highly toxic and costly. This study explores an alternative method using phosphoryl chloride combined with disopropylamine as a base. The researchers found that replacing the commonly used triethylamine with disopropylamine significantly enhances the yield and purity of isocyanides, often eliminating the need for chromatographic purification. The method is particularly effective for synthesizing ferrocenylalkyl isocyanides, where other methods fail or produce impurities. The study concludes that this new method is milder, more reproducible, and yields higher purity isocyanides compared to traditional methods, making it a valuable improvement in the field of isocyanide synthesis.

A Preparative Method for o-Diisocyanoarenes

10.1055/s-1988-27683

Yoshibiko Ito et al. describe the preparation of o-di(formamido)arenes through formylation of o-diaminoarenes using phenyl formate, which yielded better results than other formylating agents. The key step involves the dehydration of o-di(formamido)arenes with trichloromethyl chloroformate at low temperatures (-78°C to 0°C) in the presence of triethylamine, resulting in significantly higher yields compared to previous methods. The study reports the synthesis of several new o-disocyanoarenes with yields ranging from 51% to 92%, as detailed in a table that includes product yields, melting points, molecular formulas, IR spectra, and 'H-NMR data. The authors also note that the reaction temperature is crucial for achieving high yields. The synthesized compounds are being investigated for potential applications in polymerization processes.

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