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Isobutyl chloroformate is used as a peptide reagent. It is also used in the preparation of phenethyl-carbamic acid isobutyl ester by reaction with phenethylamine.
Superior to ethyl chloroformate in the mixed anhydride method of peptide synthesis: Org. Prep. Proced. Int., 7, 215 (1975); review: Org. React., 12, 157 (1962). Use in combination with 1-Methylpiperidine, L03398, minimizes competing urethane formation, arising from cleavage of the mixed anhydride in the wrong sense: J. Org. Chem., 48, 2939 (1983). Addition of CuCl2 is reported to suppress racemization completely: Chem. Lett., 2125 (1989). For peptide reagents, see Appendix 6.
Has been used to protect a nucleoside OH group as its isobutyl carbonate. Cleavage was by hydrolysis with 80% AcOH: J. Org. Chem., 32, 2365 (1967). Protection of amino groups as their isobutyl carbamates has also been reported: J. Am. Chem. Soc., 91, 3356 (1969).
Giráldez, I.; Ruiz-Azcona, P.; Vidal, A.; Morales, E. Speciation of selenite and selenoamino acids in biota samples by dual stir bar sorptive extraction-single desorption-capillary gas chromatography/mass spectrometry. Microchem. J. 2015, 122, 197-204.
Pan, X.; Dong, J.; Shao, R.; Su, P.; Shi, Y.; Wang, J.; He, L. Expanding the structural diversity of Bcr-Abl inhibitors: Hybrid molecules based on GNF-2 and Imatinib. Bioorg. Med. Chem. Lett. 2015, 25 (19), 4164-4168.
Hazard Statements: H226-H302-H314-H331-H335
Flammable liquid and vapour. Harmful if swallowed. Causes severe skin burns and eye damage. Toxic if inhaled. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. 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. 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. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant