1708-33-4

Basic information

• Product Name: 4-Hydroxybutyraldehyde 2,4-dinitrophenyl hydrazone
• Synonyms: 4-Hydroxybutyraldehyde 2,4-dinitrophenyl hydrazone
• CAS NO: 1708-33-4
• Molecular Formula: C₁₀H₁₂N₄O₅
• Molecular Weight: 268.23
• Mol File: 1708-33-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Hydroxybutyraldehyde 2,4-dinitrophenyl hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxybutyraldehyde 2,4-dinitrophenyl hydrazone(1708-33-4)
• EPA Substance Registry System: 4-Hydroxybutyraldehyde 2,4-dinitrophenyl hydrazone(1708-33-4)

Safety Data

• Hazardous Substances Data: 1708-33-4(Hazardous Substances Data)

Upstream product

• 89941-77-5 2-methoxy-tetrahydro-furan-3-carboxylic acid methyl ester 
• 5371-52-8 2-hydroxytetrahydrofuran 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 1191-99-7 2,3-dihydro-2H-furan 
• 90726-99-1 5-tetrahydrofuran-2-ylamino-pentan-1-ol 

Relevant articles and documents

A long-range tautomeric effect on a new Schiff isoniazid analogue, evidenced by NMR study and X-ray crystallography

Long-range tautomerism to a N,O-aminal thereby closing a tetrahydrofuran ring was evidenced for an isoniazid analogue, whose accidental synthesis is presented in the paper. The isoniazid analogue was synthesized by the reaction of isoniazid with 2-hydroxy-tetrahydrofuran which was demonstrated to exist in old THF together with other peroxides, especially 2-HOO-THF. The same compound was efficiently obtained from a THF containing 2-HOO-THF, by reducing this peroxide in the presence of isoniazid. The 2,4-dinitrophenylhydrazone was also synthesized. The oxidation of 1,4-butanediol and the reaction of the resulting mono-aldehyde with isoniazid gave the same compound. The existence of the linear tautomer was evidenced in the NMR spectra in DMSO-d6 and was confirmed by X-ray analysis to be the single tautomer in the crystal. The cyclic N,O-aminal tautomer was found in the NMR spectra in CDCl3, resulting from an intramolecular HCl-catalyzed addition of the hydroxyl group to the double bond CHN of the linear tautomer, thereby closing a tetrahydrofuran ring. This is a favoured cyclization according to Baldwin's rules (5-exo-trig). The same tautomerism was also present for two isoniazid analogues obtained from two lactols, used in prostaglandin synthesis. The compounds 1, 4, 6 and INH had no antibacterial or antifungal activity.

Cyclic α-acetoxynitrosamines: Mechanisms of decomposition and stability of α-hydroxynitrosamine and nitrosiminium ion reactive intermediates

A study of the kinetics and mechanism of the decay of α-acetoxy-N- nitrosopyrrolidine and α-acetoxy-N-nitrosopiperidine are reported. The compounds differ in reactivity by more than 2 orders of magnitude at physiological pH. On the basis of thermodynamic