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Merck

748684

Phosgene solution

15 wt. % in toluene

Synonym(s):

Carbon oxychloride, Carbonyl chloride, Phosgen

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About This Item

Linear Formula:
COCl2
CAS Number:
75-44-5
Molecular Weight:
98.92
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
329765925
MDL number:
MFCD00036119
Beilstein/REAXYS Number:
1098367

Key Documents

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InChI

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

SMILES string

ClC(Cl)=O

InChI key

YGYAWVDWMABLBF-UHFFFAOYSA-N

form

liquid

concentration

15 wt. % in toluene

density

0.924 g/mL at 25 °C

functional group

chloro

storage temp.

2-8°C

Quality Level

200

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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

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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

3 - Flammable liquids

wgk

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

108-88-3

CAS No.

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR7440
SHBQ7121
SHBM1001
SHBL6678
SHBK2424

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An Efficient Synthesis of N-Protected b-Amino-ethanesulfonylchlorides: Versatile Building Blocks for the Synthesis of Oligopeptidosulfonamides.
Brouwer AJ, et al.
Synthesis, 2000, 1579=84-1579=84 null
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)
The effect of side-chain functionality and hydrophobicity on the gene delivery capabilities of cationic helical polypeptides.
Zhang R, et al.
Biomaterials, 35(10), 3443-3454 (2014)
Polypeptide vesicles with densely packed multilayer membranes.
Song Z, et al.
Soft Matter, 11(20), 4091-4098 (2015)
UV?responsive degradable polymers derived from 1?(4?aminophenyl) ethane?1, 2?diol.
Ma L, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 53(9), 1161-1168 (2015)
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