849945-21-7

Basic information

• Product Name: Benzeneacetic acid, a-[[(4-methylphenyl)sulfonyl]hydrazono]-, ethyl ester
• CAS NO: 849945-21-7
• Molecular Formula: C17H18N2O4S
• Molecular Weight: 346.407
• Mol File: 849945-21-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzeneacetic acid, a-[[(4-methylphenyl)sulfonyl]hydrazono]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-[[(4-methylphenyl)sulfonyl]hydrazono]-, ethyl ester(849945-21-7)
• EPA Substance Registry System: Benzeneacetic acid, a-[[(4-methylphenyl)sulfonyl]hydrazono]-, ethyl ester(849945-21-7)

Safety Data

• Hazardous Substances Data: 849945-21-7(Hazardous Substances Data)

Upstream product

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 65354-73-6 1-Phenyl-2-isopropylidencyclopropancarbonsaeureethylester 
• 10224-12-1 1,2-diphenylcyclopropanecarboxylic acid ethyl ester 
• 75214-03-8 (±)-ethyl 2-azido-2-phenylacetate 
• 1393473-07-8 (2-azidopropane-1,1-diyl)dibenzene 
• 22065-57-2 ethyl 2-phenyldiazoacetate 

Relevant articles and documents

Copper acetoacetonate [Cu(acac)2]/BINAP-promoted Csp 3-N bond formation via reductive coupling of N-tosylhydrazones with anilines

We report the the copper(II) acetoacetonate [Cu(acac)2]/BINAP- catalyzed synthesis of arylamines from N-tosylhydrazones and anilines. A fine tuning of the reaction conditions was required to accomplish the cross-coupling successfully, including the ligands effect and the addition of small amounts of water. The characteristic feature of this protocol is its functional group compatibility and its chemoselectivity when various aminophenol derivatives were used. Taking into consideration the interest for this copper-reductive coupling in which no stoichiometric metal hydride reagent is employed, this can be considered as an alternative to the conventional reductive amination.

Captodative Rate Enhancements in the Methylenecyclopropane Rearrangement

A series of 2-aryl-2-carbethoxy-3,3-dimethylmethylenecyclopropanes, 7, with substitution in the para position of the aromatic ring, have been prepared.These substrates rearrange thermally to 2-aryl-2-carbethoxyisopropylidenecyclopropanes, 8, by fragmentation of the cyclopropane bond which gives a biradical intermediate.Rates of this rearrangement are substituent-dependent.Electron-donor substituents such as p-OCH3 and p-SCH3 enhance the rearrangement rate to a greater extent than that predicted by their rate-enhancing effect on the "parent" system, 3-aryl-2,2-dimethylmethylenecyclopropane (4).This enhanced rearrangement rate is attributed to the captodative effect in which the acceptor carbethoxy group and the donor group on the aromatic ring exert a synergistic stabilizing effect on the benzylic portion of the biradical intermediate. p-Fluoro and p-methyl substituents are also capable of acting as true donor groups in captodative systems.Rearrangement rates of 7 containing electron-donor groups correlate with ?+ values, which are a measure of the donor abilities of various groups.The captodative effect has been used as a probe for the mechanism of stabilization of free radicals by the sulfinyl group, SOCH3.No captodative rate enhancement is observed when 7-p-SOCH3 is rearranged.This implies that stabilization of free radicals by the sulfinyl group does not involve utilization of the sulfur nonbonding electron pair in a donor fashion, but probably involves this group acting as an acceptor group.