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Sigma-Aldrich

O-Phenyl chlorothionoformate

99%

Synonym(s):

Phenyl thionochloroformate

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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

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.)

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
  • synthesis of peptide α-thioesters having a variety of C-terminal amino acids
  • synthesis of scyllo-inositol derivatives
  • thionocarbonylation of unprotected thymine nucleosides
  • preparation of phenoxythiocarbonyl esters of protected ribonucleosides

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Total synthesis of (-)-mintlactone.
Carda M and Marco JA.
Tetrahedron Letters, 32(38), 5191-5192 (1991)
Canadian Journal of Chemistry, 71, 186-186 (1993)
Yedi Sun et al.
Bioorganic & medicinal chemistry, 16(15), 7177-7184 (2008-07-19)
scyllo-Inositol has shown promise as a potential therapeutic for Alzheimer's disease, by directly interacting with the amyloid beta (Abeta) peptide to inhibit Abeta42 fiber formation. To explore the molecular details of the inositol-Abeta42 interaction, a series of scyllo-inositol derivatives have
The Journal of Organic Chemistry, 58, 2552-2552 (1993)
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)
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