4883-67-4

Basic information

• Product Name: 2-NITROCYCLOHEXANONE
• Synonyms: alpha-Nitrocyclohexanone;2-NITROCYCLOHEXANONE;Cyclohexanone, 2-nitro- (6CI, 7CI, 8CI, 9CI);2-Nitrocyclohexan-1-one;2-Nitrocyclohexanone 99%
• CAS NO: 4883-67-4
• Molecular Formula: C₆H₉NO₃
• Molecular Weight: 143.14
• Product Categories: NITRO;C3 to C6;Carbonyl Compounds;Ketones
• Mol File: 4883-67-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 39-43 °C(lit.)
• Boiling Point: 272.7°C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 0.00598mmHg at 25°C
• Refractive Index: 1.479
• PKA: 5.84±0.20(Predicted)
• CAS DataBase Reference: 2-NITROCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROCYCLOHEXANONE(4883-67-4)
• EPA Substance Registry System: 2-NITROCYCLOHEXANONE(4883-67-4)

Safety Data

• Hazard Codes: Xi
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 4883-67-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 357, 1966 DOI: 10.1021/jo01340a002Tetrahedron Letters, 36, p. 7149, 1995 DOI: 10.1016/0040-4039(95)01421-D

General Description

The tautomerization rates of 2-nitrocyclohexanone (2-NCH) has been studied spectrophotometrically in several organic aprotic solvents and their binary mixtures.

InChI:InChI=1/C6H9NO3/c8-6-4-2-1-3-5(6)7(9)10/h5H,1-4H2

Upstream product

• 4050-48-0 2-nitrocyclohexanol 
• 108-94-1 cyclohexanone 
• 1424-22-2 1-cyclohexenyl acetate 
• 110-83-8 cyclohexene 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 509-14-8 tetranitromethane 
• 25176-13-0 2-Nitro-cyclohex-1-enol 
• 6925-09-3 2-Nitro-cyclohexylacetat 
• 6925-10-6 2-nitro-1-cyclohexyl nitrate 

Downstream Products

• 6782-77-0 cyclohexane-1,2-dione-bis-phenylhydrazone 
• 10269-96-2 6-nitrohexanoic acid 
• 39764-69-7 1-amino-2-nitrocyclohexene 
• 40930-08-3 (2-Nitro-cyclohex-1-enyl)-phenyl-amine 
• 39764-67-5 Methyl-(2-nitro-cyclohex-1-enyl)-amine 
• 39764-66-4 (2-Nitro-cyclohex-1-enyl)-o-tolyl-amine 
• 88226-39-5 2-Hydroxymethyl-2-nitro-cyclohexanone 
• 115033-03-9 (3R)-3-n-butyl-1-nitrocyclohexene 
• 146347-17-3 1-Methylthio-2-nitro-cyclohexen 
• 146347-18-4 1,1-Bis(methylthio)-2-nitrocyclohexan 
• 133732-74-8 1-(1'-Nitro-2'-oxocyclohexyl)heptan-3-on 
• 100820-08-4 2-allyl-2-nitrocyclohexanone 
• 115032-88-7 2-[(S)-(1-naphthyl)ethylimino]-aci-1-nitrocyclohexane 
• 98435-94-0 (+/-)-1-methyl-2t-nitro-cyclohexan-r-ol 

Relevant articles and documents

Solvent effects on the rate of the keto-enol interconversion of 2-nitrocyclohexanone

The rates of tautomerization of 2-nitrocyclohexanone (2-NCH) have been measured spectrophotometrically at 25.0 ± 0.1 °C in several organic aprotic solvents and their binary mixtures. In cyclohexane the reaction is effectively catalyzed by bases and inhibi

Ionization and tautomerization of 2-nitrocyclohexanone in aqueous solution

(Chemical Equation Presented) The keto-enol tautomerism of 2-nitrocyclohexanone (2-NCH) was studied in aqueous solution under different experimental conditions. Ketonization rate constants were measured spectrophotometrically at 25°C at an ionic strength of 0.4 mol dm -3 (NaCl) in diluted hydrochloric acid, in diluted sodium hydroxide, and in several buffers by using NaHSO3 as the scavenger of the keto form. A value of pKaEH = 4.78 for the enol form was obtained from the rate-pH profile of the reaction. A value of pK aKH = 5.97 for the keto form was directly obtained from the UV-vis spectra of 2-NCH recorded at different pHs. The equilibrium constant for the keto-enol tautomerism, pKT = -log([enol]/[ketone]) = 1.19, was obtained by combining the two pKa values (pKT = pKaKH - pKaEH). A comparison of these results with the corresponding values (Keefe, J. R.; Kresge, A. J. In The Chemistry of Enols; Rappoport, Z., Ed.; Wiley & Sons: New York, 1990; pp 399-480) for cyclohexanone shows the dramatic effects of an α-nitro substituent on the keto-enol acidities and the tautomerization constant of alicyclic ketones. Rates and equilibria were discussed in the light of the Bronsted equation, the principle of nonperfect synchronization, and the Marcus theory. It turns out that, on passing from nitroalkanes to nitroketones, the resonance contribution to pKa and deprotonation rate decreases, being overwhelmed by steric and inductive effects.

Practical and User-Friendly Procedure for Michael Reactions of α-Nitroketones in Water

A variety of α,β-unsaturated carbonyl derivatives gave selective Michael additions with several α-nitrocycloalkanones in water, at room temperature without any added catalyst, or in very dilute, aqueous solutions of potassium carbonate. Both preparative methods constitute new, environmentally benign and more efficient alternatives to previous procedures.