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543-27-1 - Isobutyl chloroformate, 98% - Chloroformic acid isobutyl ester - A14692 - Alfa Aesar

A14692 Isobutyl chloroformate, 98%

CAS Number
543-27-1
Synonyms
Chloroformic acid isobutyl ester

Size Price ($) Quantity Availability
25g 14.04
100g 26.64
500g 98.10
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Isobutyl chloroformate, 98%

MDL
MFCD00000642
EINECS
208-840-1

Chemical Properties

Formula
C5H9ClO2
Formula Weight
136.58
Melting point
-80°
Boiling Point
128-129°
Flash Point
30°(86°F)
Density
1.048
Refractive Index
1.4060
Sensitivity
Moisture Sensitive
Solubility
Immiscible with water.

Applications

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.

Notes

Store in a cool place. Incompatible with strong oxidizing agents, acids, bases, alcohols and amines. Moisture sensitive.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H300-H310-H330-H314-H318-H226

Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Flammable liquid and vapour.

Precautionary Statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,5139
Beilstein
956590
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2915.90
TSCA
Yes

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