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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
form:
liquid
Assay:
98%
Pricing and availability is not currently available.

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.[1]

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

96.8 °F - closed cup

Flash Point(C)

36 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT4290
MKCQ7368
BCCD4305
MKCL3086
BCCB2109

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Journal of Chromatography. B, Biomedical Sciences and Applications, 617, 191-191 (1993)
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)
Veronika Dufková et al.
Journal of chromatography. A, 1216(49), 8659-8664 (2009-10-28)
A rapid and simple derivatization procedure has been developed for gas chromatographic determination of perfluorinated organic acids (PFCAs, C(6)-C(12)), using isobutyl chloroformate (IBCF) to convert the acids into the more volatile isobutyl esters, under catalysis by pyridine. The procedure was
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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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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