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A17444 Trichloromethyl chloroformate, 98%

CAS Number
503-38-8
Synonyms
Chloroformic acid trichloromethyl ester
Diphosgene

Stock No. Size Price ($) Quantity Availability
A17444-09 10g 44.80
A17444-18 50g 173.00
A17444-30 250g 593.00
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Trichloromethyl chloroformate, 98%

MDL
MFCD00015553
EINECS
207-965-9

Chemical Properties

Formula
C2Cl4O2
Formula Weight
197.83
Melting point
-57°
Boiling Point
128°
Flash Point
>110°(230°F)
Density
1.640
Refractive Index
1.4570
Storage & Sensitivity
Moisture Sensitive. Ambient temperatures.
Solubility
Miscible with ethanol, ether and benzene. Immiscible with water.

Applications

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.

Notes

Special handling precautions required. View MSDS prior to purchase. MSDS are available online at www.alfa.comStore in a cool place. Light and heat sensitive. Incompatible with strong oxidizing agents and bases.

Literature References

Convenient replacement for phosgene in many reactions, for example:

Conversion of amines to isocyanates: J. Org. Chem., 41, 2070 (1976); Org. Synth. Coll ., 6, 715 (1988). For aliphatic amines, best results were obtained in the presence of the hindered amine 1,8-Bis(dimethyl­amino)­naphthalene, L00313: J. Org. Chem., 61, 3883 (1996).

Dehydration of N-monosubstituted formamides to isocyanides: Angew. Chem. Int. Ed., 16, 259 (1977).

Formation of nitriles from oximes Synthesis, 1037 (1986); or carboxamides: Tetrahedron Lett., 27, 2203 (1986).

See also Triphosgene, A14932, and Oxalyl­ chloride, A18012.

Lezama, J.; Domínguez, R. M.; Chuchani, G. Kinetics of the Gas-Phase Elimination Reaction of Benzyl Chloroformate and Neopentyl Chloroformate. Int. J. Chem. Kinet. 2015, 47 (2), 104-112.

Prousis, K. C.; Markopoulos, J.; Mckee, V.; Igglessi-Markopoulou, O. An efficient synthetic approach towards fully functionalized tetronic acids: the use of 1, 3-dioxolane-2, 4-diones as novel protected-activated synthons of α-hydroxy acids. Tetrahedron 2015, 71 (45), 8637-8648.

GHS Hazard and Precautionary Statements

Hazard Statements: H300-H314-H330

Fatal if swallowed. Causes severe skin burns and eye damage. Fatal if inhaled.

Precautionary Statements: P260-P262-P264b-P270-P271-P280-P284-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. Wear respiratory protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,3334
Beilstein
970225
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2915.90
TSCA
Yes
RTECS
LQ7350000

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