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278076

Sigma-Aldrich

Tris(phenylthio)methane

98%

Synonym(s):

Triphenyl trithioorthoformate

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About This Item

Linear Formula:
(C6H5S)3CH
CAS Number:
4832-52-4
Molecular Weight:
340.53
Beilstein:
1914230
MDL number:
MFCD00010396
UNSPSC Code:
12352100
PubChem Substance ID:
24856504
NACRES:
NA.22

Assay

98%

form

solid

mp

39-41 °C (lit.)

functional group

thioether

SMILES string

S(C(Sc1ccccc1)Sc2ccccc2)c3ccccc3

InChI

1S/C19H16S3/c1-4-10-16(11-5-1)20-19(21-17-12-6-2-7-13-17)22-18-14-8-3-9-15-18/h1-15,19H

InChI key

YOQHDHPBEXTHCP-UHFFFAOYSA-N

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Application

Tris(phenylthio)methane has been used in the preparation of:
  • 1-phenylthio-tetrahydroisoquinolines via activated Pictet-Spengler cyclization
  • homoallylchalcogenoacetals via reaction with allylsilanes in the presence of a Lewis acid

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBG8436V
MKBD5913V
MKBD5913
03923HJ
08428CE

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Thioorthoesters in the activated Pictet-Spengler cyclization. Synthesis of 1-thiosubstituted tetrahydroisoquinolines and carbon? carbon bond formation via sulfonyl iminium ions generated from N,S-sulfonyl acetals.
Silveira CC, et al.
Tetrahedron Letters, 44(32), 6137-6140 (2003)
Lewis acid-catalyzed coupling reactions of allylsilanes with tris (phenylchalcogeno) methane. Synthesis of homoallylchalcogenoacetals.
Silveira CC, et al.
Tetrahedron Letters, 37(34), 6085-6088 (1996)

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