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177989

Sigma-Aldrich

Isobutyl chloroformate

98%

Synonym(s):

Chloroformic acid isobutyl ester, IBCF

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About This Item

Linear Formula:
ClCO2CH2CH(CH3)2
CAS Number:
543-27-1
Molecular Weight:
136.58
Beilstein/REAXYS Number:
956590
EC Number:
208-840-1
MDL number:
MFCD00000642
UNSPSC Code:
12352100
PubChem Substance ID:
24850706
NACRES:
NA.22

vapor pressure

0.33 mmHg ( 20 °C)

Quality Level

200

assay

98%

form

liquid

refractive index

n20/D 1.407 (lit.)

bp

128.8 °C (lit.)

solubility

benzene: miscible
chloroform: miscible
diethyl ether: miscible

density

1.053 g/mL at 25 °C (lit.)

functional group

chloro

SMILES string

CC(C)COC(Cl)=O

InChI

1S/C5H9ClO2/c1-4(2)3-8-5(6)7/h4H,3H2,1-2H3

InChI key

YOETUEMZNOLGDB-UHFFFAOYSA-N

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General description

Isobutyl chloroformate is used as a peptide reagent. In oligonucleotide synthesis, IBCF blocks the 5′-hydroxyl function of deoxyribosides. It also serves as condensing reagent.

Application

  • Preparation of a volatile derivative of taurine and application to gas chromatographic determination of urinary taurine.: Demonstrates the utility of isobutyl chloroformate in preparing volatile derivatives of taurine for gas chromatographic analysis, offering a methodological advancement in clinical biochemistry (Masuoka et al., 1989).
  • Quinazoline antifolates inhibiting thymidylate synthase: synthesis of four oligo(L-gamma-glutamyl) conjugates of N10-propargyl-5,8-dideazafolic acid and their enzyme inhibition.: This article investigates the synthesis and biological activity of quinazoline antifolates, using techniques including isobutyl chloroformate, relevant in medicinal chemistry and drug development (Pawelczak et al., 1989).
  • Coupling of peptides to protein carriers by mixed anhydride procedure.: Discusses a novel technique using isobutyl chloroformate for peptide coupling to proteins, useful in bioconjugate chemistry and vaccine development (Samokhin & Filimonov, 1985).
  • Folate analogues altered in the C9-N10 bridge region. 18. Synthesis and antitumor evaluation of 11-oxahomoaminopterin and related compounds.: Investigates the role of isobutyl chloroformate in synthesizing folate analogues for cancer research, showing its importance in therapeutic chemistry (Nair et al., 1981).

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

96.8 °F - closed cup

flash_point_c

36 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ7368
BCCD4305
MKCL3086
BCCB2109
SHBJ1418

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J Wang et al.
Journal of chromatography. A, 663(1), 71-78 (1994-03-04)
The one-step ethyl chloroformate derivatization of amino acids in an aqueous medium is extended with the use of a variety of alkyl chloroformate reagents. This provides a new and convenient procedure for preparing esters with different alkoxy groups. A new
Isobutyl Chloroformate
Ray T
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
A new family of highly potent inhibitors of microbes: synthesis and conjugation of elastin based peptides to piperazine derivative
Suhas R, et al.
International Journal of Peptide Research and Therapeutics, 18(2), 89-98 (2012)
S Matsumura et al.
Biomedical chromatography : BMC, 9(5), 205-210 (1995-09-01)
A simple and rapid method for the determination of the 22 protein amino acids by capillary gas chromatography is described. The amino acids were converted into their N(O,S)-isobutoxycarbonyl (isoBOC) methyl ester derivatives and measured by GC with flame ionization detection
S C Cunha et al.
Journal of agricultural and food chemistry, 59(16), 8742-8753 (2011-07-08)
A simple, reliable, and sensitive gas chromatography-mass spectrometry method for the quantification of volatile and nonvolatile biogenic amines in Port wines and grape juices was developed and evaluated. The method was based on a previously reported two-phase derivatization procedure with
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