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119938 Aldrich

Benzyl chloroformate

≥98%

Synonym: Carbobenzoxy chloride, Z-Chloride

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Properties

Related Categories Amine Protection, Chemical Biology, Chemical Synthesis, Others, Peptide Chemistry,
vapor density   1 (vs air)
vapor pressure   1.39 psi ( 20 °C)
assay   ≥98%
refractive index   n20/D 1.519(lit.)
bp   103 °C/20 mmHg(lit.)
density   1.195 g/mL at 25 °C(lit.)
storage temp.   2-8°C

Description

Application

Cbz-protected anilines were prepared directly from aromatic carboxylic acids, sodium azide and Cbz-Cl.1 Also used in a recently reported 3-step synthesis of 1,2,4-oxadiazoles.2

Protecting reagent in peptide synthesis.

Useful for the introduction of the benzyloxycarbonyl(Cbz,Z) protecting group

Packaging

100, 500 g in Sure/Seal™

2.5 kg in Sure/Seal™

5 g in glass bottle

Price and Availability

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Safety & Documentation

Safety Information

Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 1739 8 / PGI
WGK Germany 
3
Flash Point(F) 
197.6 °F
Flash Point(C) 
92 °C

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Curtius rearrangement of aromatic carboxylic acids to access protected anilines and aromatic ureas. Org. Lett. 8, 5717, (2006)

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2. Synthesis, 3453, (2006)

Highly sensitive determination of chlorpheniramine as fluorescence derivative by high-performance liquid chromatography. Miyamoto Y J. Chromatogr. A 420(1), 63-72, (1987)

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The beta-bend ribbon spiral. Synthesis and conformational analysis in solution and in the crystal state of depsipeptides containing alpha-hydroxyisobutyric acid. Crisma M, Valle G, Bonora GM, et al. Int. J. Pept. Protein Res. 41(6), 553-60, (1993)

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Ames Salmonella/mammalian-microsome testing of peptides and peptide synthesis reagents. Allen JS and Panfili J Mutat. Res. 170(1-2), 23-9, (1986)

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An improved synthesis of a trifurcated newkome-type monomer and orthogonally protected two-generation dendrons. Cardona CM and Gawley RE J. Org. Chem. 67(4), 1411-3, (2002)

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High yield regioselective monobenzyloxycarbonylation of secondary alcohols in glycopyranoside series. Morère A, Mouffouk F, Jeanjean A, et al. Carbohydr. Res. 338(22), 2409-12, (2003)

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Merck 14,1801

Beil. 6,IV,2278

Fieser 1,109 / Fieser 2,59 / Fieser 15,22

Aldrich MSDS 1, 171:D / Corp MSDS 1 (1), 383:D / FT-IR 2 (2), 2957:D / FT-IR 1 (2), 353:C / IR-Spectra (2), 929:G / IR-Spectra (3), 1063:B / NMR-Reference 2 (2), 331:D / RegBook 1 (2), 1985:D / Sax 6, 403 / Sigma FT-IR 1 (2), 367:B / Structure Index 1, 318:E:4

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