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80-44-4

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80-44-4 Usage

Uses

Butyl Benzenesulfonate is an aryl-sulfonic acid ester found in drug substances. Butyl Benzenesulfonate is also used as a plasticizer in concrete preparation.

Synthesis Reference(s)

Synthesis, p. 822, 1979 DOI: 10.1055/s-1979-28848

Check Digit Verification of cas no

The CAS Registry Mumber 80-44-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 80-44:
(4*8)+(3*0)+(2*4)+(1*4)=44
44 % 10 = 4
So 80-44-4 is a valid CAS Registry Number.

80-44-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Butyl Benzenesulfonate

1.2 Other means of identification

Product number -
Other names Benzenesulfonic acid, butyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:80-44-4 SDS

80-44-4Relevant articles and documents

Sequential C-S and S-N Coupling Approach to Sulfonamides

Chen, Kai,Chen, Wei,Han, Bing,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue

supporting information, p. 1841 - 1845 (2020/03/04)

A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.

ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters

Tamaddon, Fatemeh,Sabeti, Mohammad Reza,Jafari, Abbas Ali,Tirgir, Farhang,Keshavarz, Elham

experimental part, p. 41 - 45 (2012/01/12)

Commercially available and preparative ZnO nanoparticles are reported as efficient and reusable catalysts for the chemoselective synthesis of N-acylsulfonamides and sulfonate esters. A one-pot sequential sulfonylation and acylation of amines took place to afford the N-acylsulfonamides in excellent yields under solvent-free conditions. The ZnO catalyst can be reused for without significant loss of catalytic activity.

Intermediacy of o-sulfonylium arenide ylides in the reactions of arenesulfonyl derivatives with strong bases: Insight into the puzzling rearrangement of N-arylarenesulfonamides into 2-aminodiaryl sulfones

Eisch, John J.,Qian, Yun,Chiu, Chingchen S.

, p. 1392 - 1398 (2007/10/03)

Benzenesulfonyl derivatives, PhSO2E, such as benzenesulfonyl fluoride, phenyl benzenesulfonate, and N-methyl-N-phenylbenzenesulfonamide, have been found to undergo ortho-lithiation with lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF at -78 °C. The resulting lithio derivatives undergo 1,3-elimination of LiE to form the transient o-sulfonylium benzenide. The latter ylide, which may be stabilized by its carbenoid character and its complexation with LiE, can be trapped by benzophenone acting as a 1,3-dipolarophile to form the adduct, 3,3-diphenyl-1,2-benzoxathiole 1,1-dioxide. The alternative formation of the latter cyclic sulfonate by reaction of the initially formed o-lithio derivative with benzophenone and by subsequent cyclization was shown not to occur. If not trapped with benzophenone, such an ylide decomposes partly into SO2 and benzyne and then undergoes self-condensation to yield poly(phenylene-o,o′-biphenylene sulfones). o-Sulfonylium benzenide also can be captured by lithium alkoxides, either present adventitously or intentionally added, to generate the corresponding alkyl benzenesulfonate. However, such alkoxides, unaided by LTMP, are themselves unable to extract an ortho-proton from benzenesulfonyl fluoride or from N-methyl-N-phenylbenzenesulfonamide to yield the corresponding o-lithio derivative. With benzenesulfonyl fluoride the lithium alkoxide can also form the sulfonate ester by direct substitution at the sulfonyl group. The Closson-Hellwinkel rearrangement of N-methyl-N-phenylbenzenesulfonamide into o-(methylamino)diphenyl sulfone by RLi or LTMP is reinterpreted as proceeding by way of the 2-lithio- or 2,6-dilithiobenzenesulfonyl derivative which eliminates lithium N-methylanilide to form the o-sulfonylium benzenide or its 6-lithio derivative. Attack of the latter ylide, acting as an electrophile, upon the ortho-position of the presumably complexed LiNMePh then consummates the rearrangement.

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