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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:
5418-86-0
Molecular Weight:
154.32
Beilstein/REAXYS Number:
1733825
MDL number:
MFCD00009851
UNSPSC Code:
12352100
PubChem Substance ID:
24855282
NACRES:
NA.22

Quality Level

100

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

186.8 °F - closed cup

flash_point_c

86 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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
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

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