492-99-9

Basic information

• Product Name: 1,2-CYCLOHEXANEDIONE DIOXIME
• Synonyms: 1,2-CYCLOHEXANEDIONE DIOXIME;NIOXIME;NIOXIME(R);(1Z,2Z)-1,2-Cyclohexanedione dioxime;1,2-Bis(hydroxyimino)cyclohexane;1,2-Cyclohexadione dioxime;Cyclohexan-1,2-dion-dioxim;Cyclohexan-1,2-dion-dioxime
• CAS NO: 492-99-9
• Molecular Formula: C₆H₁₀N₂O₂
• Molecular Weight: 142.16
• EINECS: 207-769-3
• Mol File: 492-99-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 188-190 °C (dec.)
• Boiling Point: 259.72°C (rough estimate)
• Flash Point: 210.1 °C
• Appearance: beige to brown crystalline powder or needles
• Density: 1.36
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5010 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 0.8% in water, readily soluble in alcohol, diethyl ether and acetone.
• PKA: 10.70±0.20(Predicted)
• Water Solubility: Soluble in water.
• Merck: 14,6559
• BRN: 1909047
• CAS DataBase Reference: 1,2-CYCLOHEXANEDIONE DIOXIME(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-CYCLOHEXANEDIONE DIOXIME(492-99-9)
• EPA Substance Registry System: 1,2-CYCLOHEXANEDIONE DIOXIME(492-99-9)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 492-99-9(Hazardous Substances Data)

Usage

Chemical Properties

beige to brown crystalline powder or needles

Uses

Different sources of media describe the Uses of 492-99-9 differently. You can refer to the following data:
1. Analytical reagent for nickel and palladium.
2. Nioxime is an analogue of dimethylglyoxime, with which, in general, the same determinations can be accomplished as with dimethylglyoxime. It is, however, more soluble in water than dimethylglyoxime so that it can be applied as an aqueous solution for the precipitation of metal complexes. In this way the potential error caused by the increased solubility of the complex in the presence of alcohol is eliminated. In gravimetric determinations the higher molecular weight of nioxime presents a further advantage (the molecular weight of the nioxime complex of nickel is 340.99, while that of the nickel complex of dimethylglyoxime is 288.91). Recently nioxime has been successfully applied for the gravimetric determination of bismuth/34 , 477) The bismuth nioxime complex was precipitated selectively from a solution containing about 30 cations (among them nickel and palladium) using the masking action of EDTA at about pH 12.
3. 1,2-Cyclohexanedione dioxime acts as a chelating ligand forming complexes with many transition metal ions like Co, Fe and Ni. It is used in photometric detection of metal ions.

Purification Methods

Crystallise Nioxime from alcohol/water and dry it in a vacuum at 40o. Also 2.5g of oxime have been recrystallised from 550mL of H2O using Fe free Norit. It forms complexes with Ni and Pd. [Hach et al. Org Synth 32 35 1952.] [Beilstein 7 IV 1982.]

InChI:InChI=1/C6H10N2O2/c9-7-5-3-1-2-4-6(5)8-10/h9-10H,1-4H2/b7-5-,8-6+

Upstream product

• 1056477-06-5 2-bromocyclohexanone 
• 2209-36-1 4,5,6,7-tetrahydro-2,1,3-benzoxadiazol-N-oxide 
• 64-17-5 ethanol 
• 822-87-7 2-Chlorocyclohexanone 
• 20439-47-8 (1R,2R)-1,2-diaminocyclohexane 
• 51425-61-7 2-Nitrosocyclohexanon-Dimer 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 110-83-8 cyclohexene 
• 2209-34-9 2-nitro-cyclohexanone oxime 
• 34006-70-7 2,6-dibromocyclohexanone 
• 27992-37-6 1-hydroxy-2,2-dimethyl-4,5,6,7-tetrahydrobenzimidazoline 3-oxide 
• 66927-19-3 2,2-dimethyl-4,5,6,7-tetrahydro-2H-benzimidazole 1,3-dioxide 
• 51425-62-8 C₁₂H₂₀N₄O₄ 
• 765-87-7 cyclohexane-1,2-dione 

Downstream Products

• 2209-36-1 4,5,6,7-tetrahydro-2,1,3-benzoxadiazol-N-oxide 
• 91385-99-8 cyclohexane-1,2-dione-bis-(O-deuterio oxime ) 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 2258-73-3 1,2-cyclohexanedione dioxime 
• 4340-74-3 α-Amino-cyclohexanon-trans-oxim 
• 765-87-7 cyclohexane-1,2-dione 
• 4006-50-2 1,2,3,4,6,7,8,9-octahydrophenazine 
• 108-91-8 cyclohexylamine 
• 60514-57-0 tetradecahydro-phenazine 
• 75258-07-0 1,2-diacetamido-4-acetoxybenzene 
• 75258-08-1 1-hydroxy-3,4-diacetamidobenzene 
• 31980-12-8 2,2-dimethyl-2H-benzimidazole 1,3-dioxide 
• 73411-50-4 bis(cyclohexane-1,2-dione glyoximato)bis(triphenylphosphine)ruthenium(II) 

Relevant articles and documents

Green and highly selective protocol for the synthesis of oximes

A green and efficient protocol has been developed for the synthesis of either exclusively a monoxime or exclusively a dioxime from a host of 1,2-dicarbonyl compounds on silica.

Oxidoperoxidotungsten(VI) complexes with secondary hydroxamic acids: Synthesis, structure and catalytic uses in highly efficient, selective and ecologically benign oxidation of olefins, alcohols, sulfides and amines with H2O2 as a terminal oxidant

The reaction of a solution of freshly precipitated WO3 in H 2O2 separately with the secondary hydroxamic acids N-benzoyl-N-phenylhydroxamic acid (BPHAH), N-benzoyl-Northo-tolylhydroxamic acid (BOTHAH), N-benzoyl-N-meta-tolylhydroxamic acid (BMTHAH), N-benzoyl-N-para- tolyl-hydroxamic acid (BPTHAH) and N-cinnamyl-N-phenylhy-droxamic acid (CPHAH) afforded [WO(O2)(BPHA)2] (1), [WO(O2)(BOTHA) 2] (2), [WO(O2)(BMTHA)2] (3), [WO(O 2)-(BPTHA)2] (4) and [WO(O2)(CPHA)2] (5), respectively. Aqueous tungstate solution, on reaction with all these hydroxamic acids, produced [W(O)2(hydroxamato)2] (6). The complexes show excellent catalytic functions in the oxidation of (a) olefins at room temperature in the presence of NaHCO3 as promoter, (b) alcohols, sulfides and amines, at reflux, with H2O2 as a terminal oxidant, yielding a high turnover number (TON), the highest being for olefin-to-epoxide conversion. An attempt to synthesize peroxide-rich complexes of the type PPh4[WO(O2)2(hydroxamato)] (7), for example PPh4[WO-(O2)2BMTHA] (7C), resulted in the isolation of PPh4[WO-(O2)2(C 6H5COO)] (8), which was probably obtained by the hydrolysis of coordinated BMTHA. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Kit for the preparation of technetium TC 99m teboroxime myocardial perfusion agent

A kit containing a solution of boronic acid adducts of technetium-99 m dioxime complexes; and hydroxypropyl gamma cyclodextrin to maintain the solution free of particulate matter originating from the formulation.