3271-62-3

Basic information

• Product Name: Formaldehyde, (4-nitrophenyl)hydrazone
• CAS NO: 3271-62-3
• Molecular Formula: C7H7N3O2
• Molecular Weight: 165.151
• Mol File: 3271-62-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Formaldehyde, (4-nitrophenyl)hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Formaldehyde, (4-nitrophenyl)hydrazone(3271-62-3)
• EPA Substance Registry System: Formaldehyde, (4-nitrophenyl)hydrazone(3271-62-3)

Safety Data

• Hazardous Substances Data: 3271-62-3(Hazardous Substances Data)

Upstream product

• 3385-78-2 trimethyl indium 
• 50-00-0 formaldehyd 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 7732-18-5 water 

Downstream Products

• 109496-67-5 5-(3-methyl-3H-benzothiazol-2-ylidene)-1-(4-nitro-phenyl)-formazan 
• 63655-98-1 1-(4-nitro-phenyl)-5-thiazol-2-yl-formazan 
• 63656-02-0 1-(5-bromo-thiazol-2-yl)-5-(4-nitro-phenyl)-formazan 
• 63656-04-2 1-(4-nitro-phenyl)-5-(5-nitro-thiazol-2-yl)-formazan 
• 34278-09-6 6,8-bis-(4-nitro-phenyl)-3-oxa-1,5,6,8-tetraaza-bicyclo[3.2.2]nonane 
• 33722-56-4 2,7-bis-(4-nitro-phenyl)-4-oxa-1,2,6,7-tetraaza-bicyclo[4.2.1]nonane 
• 88246-29-1 (4-Nitro-phenyl)-(4,5,6,7-tetrahydro-benzo[1,3]dithiol-2-ylidenemethyl)-diazene 

Relevant articles and documents

Reactions of arenediazonium o-benzenedisulfonimides with aliphatic triorganoindium compounds

The reaction of various arenediazonium o-benzenedisulfonimides with aliphatic triorganoindium compounds is described. Surprisingly, with triethyl- or tributylindium we obtained N-ethyl- or N-butylanilines, respectively. This is the first case in which, at least formally, the reactive site of a diazonium salt is the nitrogen atom directly bonded to the aromatic ring. In contrast, with trimethylindium we obtained only formaldehyde (aryl)hydrazones. In order to explain the difference between trimethyl- and triethylindium we have proposed some reaction mechanisms, supported by detailed density functional (DFT) calculations. The possible role of diazene/hydrazone tautomerism initially assumed was discarded and therefore three mechanisms for the key step (nucleophilic addition of the trialkylindium to the N=N double bond of diazene) were studied. For the favoured mechanism there is a difference in the energy barriers of 2 kcalmol-1 between the reactions with trimethyl- and triethylindium. This difference is explained on the basis of the different C-In bond energies in the two organometallics and it is assumed to be enough to explain their different behaviour under the experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.