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503-38-8 - Trichloromethyl chloroformate, 98% - Chloroformic acid trichloromethyl ester - Diphosgene - A17444 - Alfa Aesar

A17444 Trichloromethyl chloroformate, 98%

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

Size Price ($) Quantity Availability
10g 41.80
50g 161.00
250g 553.00
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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
Sensitivity
Moisture Sensitive
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: H330-H314-H318

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

Precautionary Statements: P280-P303+P361+P353-P305+P351+P338-P304+P340-P310a

Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER/doctor

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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