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748684

Sigma-Aldrich

Phosgene solution

15 wt. % in toluene

Sinonimo/i:

Carbon oxychloride, Carbonyl chloride, Phosgen

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About This Item

Formula condensata:
COCl2
Numero CAS:
Peso molecolare:
98.92
Beilstein:
1098367
Numero MDL:
Codice UNSPSC:
12352101
ID PubChem:
NACRES:
NA.22

Stato

liquid

Livello qualitativo

Concentrazione

15 wt. % in toluene

Densità

0.924 g/mL at 25 °C

Gruppo funzionale

chloro

Temperatura di conservazione

2-8°C

Stringa SMILE

ClC(Cl)=O

InChI

1S/CCl2O/c2-1(3)4
YGYAWVDWMABLBF-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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

Confezionamento

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

Note legali

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

Avvertenze

Danger

Classi di pericolo

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

Organi bersaglio

Central nervous system

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

39.2 °F - closed cup

Punto d’infiammabilità (°C)

4 °C - closed cup


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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)
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
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
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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