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234524

Sigma-Aldrich

O-Phenyl chlorothionoformate

99%

Synonym(s):

Phenyl thionochloroformate

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5 G
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About This Item

Linear Formula:
ClC(S)OC6H5
CAS Number:
1005-56-7
Molecular Weight:
172.63
Beilstein:
774830
EC Number:
213-736-4
MDL number:
MFCD00004920
UNSPSC Code:
12352100
PubChem Substance ID:
24854046
NACRES:
NA.22

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Assay

99%

form

liquid

refractive index

n20/D 1.581 (lit.)

bp

81-83 °C/6 mmHg (lit.)

density

1.248 g/mL at 25 °C (lit.)

functional group

chloro
phenoxy

SMILES string

ClC(=S)Oc1ccccc1

InChI

1S/C7H5ClOS/c8-7(10)9-6-4-2-1-3-5-6/h1-5H

InChI key

KOSYAAIZOGNATQ-UHFFFAOYSA-N

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Application

O-Phenyl chlorothionoformate has been used in:
  • stereodirected synthesis of optically active, (−)-mintlactone[1]
  • synthesis of peptide α-thioesters having a variety of C-terminal amino acids[2]
  • synthesis of scyllo-inositol derivatives[3]
  • thionocarbonylation of unprotected thymine nucleosides[4]
  • preparation of phenoxythiocarbonyl esters of protected ribonucleosides[5][6]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

177.8 °F - closed cup

Flash Point(C)

81 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

234524-BULK:
234524-5G:
234524-VAR:
234524-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
1383855V
1383856V
1383857V
1383854V
1383854

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Canadian Journal of Chemistry, 71, 186-186 (1993)
Total synthesis of (-)-mintlactone.
Carda M and Marco JA.
Tetrahedron Letters, 32(38), 5191-5192 (1991)
A synthetic approach to a peptide α-thioester from an unprotected peptide through cleavage and activation of a specific peptide bond by N-acetylguanidine.
Ryo Okamoto et al.
Angewandte Chemie (International ed. in English), 51(1), 191-196 (2011-11-19)
Synlett, 221-221 (1993)
The Journal of Organic Chemistry, 58, 2552-2552 (1993)
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