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119490

Sigma-Aldrich

2,4,6-Triisopropylbenzenesulfonyl chloride

97%

Synonym(s):

2,4,6-Tris(1-methylethyl)benzenesulfonyl chloride, Tripsyl chloride

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About This Item

Linear Formula:
[(CH3)2CH]3C6H2SO2Cl
CAS Number:
6553-96-4
Molecular Weight:
302.86
Beilstein:
1218575
EC Number:
229-479-6
MDL number:
MFCD00007433
UNSPSC Code:
12352100
PubChem Substance ID:
24847399
NACRES:
NA.22

Quality Level

200

Assay

97%

form

solid

mp

92-94 °C (lit.)

solubility

ethanol: soluble 5%, clear, colorless to light yellow

SMILES string

CC(C)c1cc(C(C)C)c(c(c1)C(C)C)S(Cl)(=O)=O

InChI

1S/C15H23ClO2S/c1-9(2)12-7-13(10(3)4)15(19(16,17)18)14(8-12)11(5)6/h7-11H,1-6H3

InChI key

JAPYIBBSTJFDAK-UHFFFAOYSA-N

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Application

2,4,6-Triisopropylbenzenesulfonyl chloride can be used in the analysis of phosphonolipids in eggyolk by HPLC/MS technique.
It can also be used to synthesize:
  • Dimeric neomycin-neomycin conjugate with a flexible linker, 2,2′-(ethylenedioxy)bis(ethylamine).
  • Coupling reagents for the synthesis of oligonucleotides.
  • Sulfonates of pyrimidine nucleosides. These sulfonates can be displaced by nucleophiles in the presence of palladium-catalysts.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sunil Kumar et al.
Journal of the American Chemical Society, 133(19), 7361-7375 (2011-04-29)
A dimeric neomycin-neomycin conjugate 3 with a flexible linker, 2,2'-(ethylenedioxy)bis(ethylamine), has been synthesized and characterized. Dimer 3 can selectively bind to AT-rich DNA duplexes with high affinity. Biophysical studies have been performed between 3 and different nucleic acids with varying
A General Route to 4-C-Substituted Pyrimidine Nucleosides
Ulrich Hennecke,et al.
Synthesis, 6, 929-935 (2007)
Studies on Polynucleotides. LII. 1 The Use of 2, 4, 6-Triisopropylbenzenesulfonyl Chloride for the Synthesis of Internucleotide Bonds2.
Lohrmann R and Khorana HG.
Journal of the American Chemical Society, 88(4), 829-833 (1966)
Analysis of glycerophosphonolipids in egg yolk.
Ternes W and Jaekel T.
European Food Research and Technology, 230(4), 559-570 (2010)
A K Seth et al.
Nucleic acids research, 8(22), 5445-5459 (1980-11-25)
The efficiencies and problems of sulfonation of several condensing reagents for deoxyoligoribonucleotide synthesis have been studied. While 2,4,6-triisopropylbenzenesulfonyl chloride (TPSC1) gave very low yield and slow rate of coupling, the new 1:3 mixture of TPSC1 and tetrazole afforded excellent yield
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