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748684

Sigma-Aldrich

Phosgene solution

15 wt. % in toluene

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Synonym(s):
Carbon oxychloride, Carbonyl chloride, Phosgen
Linear Formula:
COCl2
CAS Number:
Molecular Weight:
98.92
Beilstein:
1098367
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

concentration

15 wt. % in toluene

density

0.924 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

ClC(Cl)=O

InChI

1S/CCl2O/c2-1(3)4

InChI key

YGYAWVDWMABLBF-UHFFFAOYSA-N

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This Item
606251662143618519
Phosgene solution 15 wt. % in toluene

Sigma-Aldrich

748684

Phosgene solution

Phosgene-13C solution ~1 M in benzene, 99 atom % 13C

Sigma-Aldrich

606251

Phosgene-13C solution

Phosgene-13C solution 20% in toluene, 99 atom % 13C

Sigma-Aldrich

662143

Phosgene-13C solution

Phosgene-12C solution ~1 M in benzene, 99.9 atom % 12C

Sigma-Aldrich

618519

Phosgene-12C solution

density

0.924 g/mL at 25 °C

density

-

density

-

density

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

form

liquid

form

-

form

-

form

-

General description

Phosgene is used as a reagent in organic synthesis for various reactions such as carbonylation reaction and synthesis of isocyanates. Phosgene is formed during the free radical induced degradation of chlorinated hydrocarbons. Determination of phosgene in air samples using thermal desorption (TD) followed by gas chromatography-mass spectrometry (GC-MS) has been reported.

Application

Phosgene solution (15 wt. % in toluene) has been used to synthesize the following peptide monomers:
  • γ-(4-propargyloxybenzyl)-L-glutamic acid N-carboxyanhydride (POB-L-Glu-NCA)
  • γ-(4,5-dimethoxy-2-nitrobenzyl)-L-glutamate N-carboxyanhydride (DMNB-L-Glu-NCA)
  • γ-(4,5-dimethoxy-2-nitrobenzyl)-D-glutamate N-carboxyanhydride (DMNB-D-Glu-NCA)
  • 2-nitrobenzyl(4-vinylphenyl)carbamate

Phosgene solution may be used in the synthesis of:
  • sulfonyl chlorides
  • Fmoc (Fluorenylmethyloxycarbonyl chloride)-taurylsulfonyl chloride
  • O-benzyl-L-serine carboxyanhydrides

Packaging

The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

39.2 °F - closed cup

Flash Point(C)

4 °C - closed cup


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Journal of Polymer Science Part A: Polymer Chemistry, 53(9), 1161-1168 (2015)
Polypeptide vesicles with densely packed multilayer membranes.
Song Z, et al.
Soft Matter, 11(20), 4091-4098 (2015)
Yanbing Lu et al.
ACS macro letters, 1(4), 441-444 (2013-01-30)
O-benzyl-L-serine carboxyanhydrides were synthesized via diazotization of O-benzyl-L-serine with sodium nitrite in aqueous sulfuric acid solution followed by cyclization of the resulting serine-based α-hydroxy acid with phosgene. Degradable, water-soluble poly(α-hydroxy acids) bearing pendant hydroxyl groups were readily prepared under mild
A kinetic study of the hydrolysis of phosgene in aqueous solution by pulse radiolysis.
Mertens R, et al.
Angewandte Chemie (International Edition in English), 33(12), 1259-1261 (1994)

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