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Sigma-Aldrich

Pentafluorophenyl chlorothionoformate

96%

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Linear Formula:
ClC(S)OC6F5
CAS Number:
Molecular Weight:
262.58
MDL number:
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

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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
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

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