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255068

Sigma-Aldrich

Tris(methylthio)methane

98%

Synonym(s):

Trimethyl trithioorthoformate

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About This Item

Linear Formula:
(CH3S)3CH
CAS Number:
Molecular Weight:
154.32
Beilstein:
1733825
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

refractive index

n20/D 1.577 (lit.)

bp

102 °C/15 mmHg (lit.)
225-227 °C (lit.)

mp

16 °C (lit.)

density

1.16 g/mL at 25 °C (lit.)

SMILES string

CSC(SC)SC

InChI

1S/C4H10S3/c1-5-4(6-2)7-3/h4H,1-3H3

InChI key

YFMZQCCTZUJXEB-UHFFFAOYSA-N

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General description

Tris(methylthio)methane is a carboxylic anion equivalent.

Application

Tris(methylthio)methane has been used in synthesis of:
  • (−)-nephrosteranic acid and (−)-roccellaric acid
  • (4R,5R)-5-({[1-(tert-butyl)-1,1-diphenylsilyl]oxy}methyl)4-[tri(methylthio)methyl]tetrahydro-furan-2-one
  • terminal difluoromethylenes

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Claudia Mugnaini et al.
Bioorganic & medicinal chemistry, 11(3), 357-366 (2003-01-09)
Novel nucleoside analogues of both D and L enantiomeric series were prepared by coupling reaction between a 2',3'-dideoxy-3'-modified furanose moiety and four different nucleobases. Though in all cases anomeric mixtures of nucleosides were obtained, the presence of the sterically bulky
From ketones, aldehydes or alkyl halides to terminal 1, 1-difluoroolefins using BrF3.
Hagooly A and Rozen S.
Journal of Fluorine Chemistry, 126(8), 1239-1245 (2005)
Bin Mao et al.
Organic letters, 13(5), 948-951 (2011-01-28)
An efficient catalytic asymmetric synthesis of chiral γ-butenolides was developed based on the hetero-allylic asymmetric alkylation (h-AAA) in combination with ring closing metathesis (RCM). The synthetic potential of the h-AAA-RCM protocol was illustrated with the facile synthesis of (-)-whiskey lactone

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