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748684

Sigma-Aldrich

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:
Molecular Weight:
98.92
Beilstein:
1098367
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

form

liquid

Quality Level

concentration

15 wt. % in toluene

density

0.924 g/mL at 25 °C

functional group

chloro

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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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.[1] Determination of phosgene in air samples using thermal desorption (TD) followed by gas chromatography-mass spectrometry (GC-MS) has been reported.[2]

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)[3]
  • γ-(4,5-dimethoxy-2-nitrobenzyl)-L-glutamate N-carboxyanhydride (DMNB-L-Glu-NCA)[4]
  • γ-(4,5-dimethoxy-2-nitrobenzyl)-D-glutamate N-carboxyanhydride (DMNB-D-Glu-NCA)[4]
  • 2-nitrobenzyl(4-vinylphenyl)carbamate[5]

Phosgene solution may be used in the synthesis of:
  • sulfonyl chlorides[6]
  • Fmoc (Fluorenylmethyloxycarbonyl chloride)-taurylsulfonyl chloride[6]
  • O-benzyl-L-serine carboxyanhydrides[7]

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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Certificates of Analysis (COA)

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A kinetic study of the hydrolysis of phosgene in aqueous solution by pulse radiolysis.
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Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    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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