2,4,6-Triisopropylbenzenesulfonyl chloride Chemical Properties

Melting point:

92-94 °C (lit.)

Boiling point:

378C

Density 

1.1012 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

ethanol: 50 mg/mL, clear

form 

Crystalline Solid

color 

White to slightly beige

Water Solubility 

decomposes

Sensitive 

Moisture Sensitive

BRN 

1218575

InChI

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

InChIKey

JAPYIBBSTJFDAK-UHFFFAOYSA-N

SMILES

C1(S(Cl)(=O)=O)=C(C(C)C)C=C(C(C)C)C=C1C(C)C

CAS DataBase Reference

6553-96-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34-29

Safety Statements 

26-36/37/39-45-27

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

21

Hazard Note 

Corrosive

HazardClass 

8

PackingGroup 

II

HS Code 

29049020

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Skin Corr. 1B

MSDS

• Language:English Provider:2,4,6-Triisopropylbenzenesulfonyl chloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,4,6-Triisopropylbenzenesulfonyl chloride Usage And Synthesis

Chemical Properties

White to cream solid

Uses

2,4,6-Triisopropylbenzenesulfonyl chloride is used for the synthesis of glycerophospholipids as a condensing agent and in the analysis of phosphonolipids in egg yolk by HPLC/MS technique. It acts as a coupling reagent for the synthesis of oligonucleotides and as sulfonates of pyrimidine nucleosides. It also serves as a condensing agent in the synthesis of hydrogen-phosphonate diesters.

Uses

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.

Synthesis

1) 1000mL four-necked bottle, add 2,4,6-triisopropylbenzene 72.0g, add sodium sulfate 3.6g under stirring, ice bath cooling to below 5 ??, control the reaction temperature of 5-15 ??, control 1.5-2.0 hours, from the dropping funnel slowly added primary chlorosulfuric acid 77.0g, add the graduation, at 10-15 ?? holding reaction 0.5 hours.

2) control the reaction temperature for 15-25 ??, control 0.5-1.0 hours, from the drop funnel slowly add 145.0g of secondary chlorosulfonic acid, add, at 20-25 ?? insulation reaction 2.0 hours to produce sulfonated material;

3) 1000mL beaker, add 150g of ice and water mixture, start stirring, the above sulfonated material slowly added to the ice and water, at 15 ?? below the role of 15 minutes to maintain the material placed in the liquid funnel static for 30 minutes, separated out the lower organic layer of the system 2,4,6-triisopropylbenzenesulfonyl chloride 128.8g, yield 98.3%.

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