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347973

Sigma-Aldrich

Pentafluorophenyl chlorothionoformate

96%

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About This Item

Linear Formula:
ClC(S)OC6F5
CAS Number:
Molecular Weight:
262.58
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

96%

form

liquid

refractive index

n20/D 1.481 (lit.)

bp

98-102 °C/50 mmHg (lit.)

density

1.635 g/mL at 25 °C (lit.)

SMILES string

Fc1c(F)c(F)c(OC(Cl)=S)c(F)c1F

InChI

1S/C7ClF5OS/c8-7(15)14-6-4(12)2(10)1(9)3(11)5(6)13

InChI key

DKFQHZNKNWNZCO-UHFFFAOYSA-N

Application

Pentafluorophenyl chlorothionoformate may be used:
  • as derivatizing agent during radical-chain deoxygenations of primary alcohols
  • as a reagent during the conversion of ribonucleoside to arabinonucleosides
  • as reagent during the conversion of 6,8-diethyl-7-hydroxy-5-propyl-hexahydro-indolizin-3-one to O-6,8-diethyl-octahydro-3-oxo-5-propylindolizin-7-yl benzothioate

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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The invention of radical reactions. Part XXI. Simple methods for the radical deoxygenation of primary alcohols.
Barton DHR, et al.
Tetrahedron, 47(43), 8969-8994 (1991)
Wang et al.
Organic letters, 2(2), 227-230 (2000-05-18)
[structures: see text] A regio- and stereoselective glycosylation of ribose tetraester with persilylated alloxazine to give either beta-N1 or beta-N3 nucleosides is described. The N3 product is potentially of interest as a fluorescent nucleoside and is predicted to have the
Ramaiah Kumareswaran et al.
The Journal of organic chemistry, 69(26), 9151-9158 (2004-12-22)
Starting from succinamide and 1,2-heptadiene-4-ol, a racemic allene-aldehyde substrate, 20, suitable for R(3)SiSnR'(3)-mediated cyclization was synthesized in six steps and in 21% yield. Stereoselective cyclization (relative cis configuration at the new stereogenic centers of the homoallyl alcohol generated) proceeded smoothly

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