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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:
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.)

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).

Signal Word

Danger

Hazard Statements

H226,H302,H314,H330

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

96.8 °F

Flash Point(C)

36 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Isobutyl Chloroformate
Ray T
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Journal of Chromatography. B, Biomedical Sciences and Applications, 617, 191-191 (1993)
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)
C H Paik et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 24(10), 932-936 (1983-10-01)
Diethylenetriaminepentaacetic acid (DTPA) was conjugated with antibody to human serum albumin (Ab) at low concentration (300 micrograms/ml, 2.0 microM) via the DTPA carboxycarbonyl mixed-anhydride method. To study parameters determining the balance between the degree of conjugation and the antibody-binding activity
Sh Kh Khalikov et al.
Bioorganicheskaia khimiia, 20(4), 393-405 (1994-04-01)
Fragments 134-145 and 150-159 of the antigenic-region of the VP1 protein of the A22 foot-and-mouth disease virus were synthesized by classic methods of peptide chemistry with isobutyl chloroformate as a coupling reagent. After purification by HPLG and amino acid analysis
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