Dimethylglyoxime

Dimethylglyoxime Basic information
Product Name:Dimethylglyoxime
Synonyms:2,3-DIISONITROSOBUTANE;2,3-BUTANEDIONE DIOXIME;2,3-BUTANEDIONEDIOXIME DISODIUM SALT;2,3-BUTENEDIONDIOXIME;(2E,3E)-2,3-Butanedione dioxime;2,3-Butadione dioxime;DIMETHYLGLYOXIME TECHNICAL;DIMETHYLGLYOXIME 99+% A.C.S. REAGENT
CAS:95-45-4
MF:C4H8N2O2
MW:116.12
EINECS:202-420-1
Product Categories:Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;bc0001;95-45-4
Mol File:95-45-4.mol
Dimethylglyoxime Structure
Dimethylglyoxime Chemical Properties
Melting point 240-241 °C(lit.)
Boiling point 217.15°C (rough estimate)
density 1.2829 (rough estimate)
refractive index 1.4880 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Soluble in alcohol, acetone, ether
form Powder
pkapK1:10.60 (25°C)
color White to off-white
OdorOdorless
Water Solubility INSOLUBLE
Merck 14,3246
BRN 506731
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyJGUQDUKBUKFFRO-GGWOSOGESA-N
CAS DataBase Reference95-45-4(CAS DataBase Reference)
NIST Chemistry Reference2,3-Butanedione, dioxime(95-45-4)
EPA Substance Registry System2,3-Butanedione, dioxime (95-45-4)
Safety Information
Hazard Codes Xn,T,F
Risk Statements 22-20/21/22-25-11
Safety Statements 22-24/25-36-45
RIDADR UN 2926 6.1(4.1) / PGIII
WGK Germany 3
RTECS EK2975000
10
Hazard Note Harmful
TSCA Yes
PackingGroup III
HS Code 29280090
MSDS Information
ProviderLanguage
2,3-Butanedione dioxime English
SigmaAldrich English
ACROS English
ALFA English
Dimethylglyoxime Usage And Synthesis
Chemical PropertiesDimethylglyoxime is a white crystalline powder. Soluble in alcohol, ether, acetone and pyridine. Solubility in water 0.5g/l, insoluble in tolerate chloroform, toluene, xylene. It is one of the first selective organic reagents applied in analytical chemistry. It is an extraordinary sensitive and specific reagent for nickel. under appropriate conditions dimethylglyoxime is specific for nickel(II) and palladium(II), but it also forms coloured water-soluble complexes with iron(II), cobalt(II) and copper(II).
UsesDimethylglyoxime is specific for nickel(II) ions in ammoniacal solution if alkali tartrate is employed as masking agent to keep in solution the possibly interfering hydrolysing salts.
UsesDimethylglyoxime is used as nickel-specific complexing reagent; determination of palladium.
UsesDetection and determination of Ni and its separation from Co and many other metals. Forms a scarlet red ppt with Ni even in dil solutions. Separation of Pd from Sn, Au, Rh, and Ir, also to detect Bi with which it forms a bright yellow color and ppt.
ApplicationDimethylglyoxime is a chelate ligand that can be used as an antimicrobial agent. The compound binds to metals, such as iron and copper, which are found in wastewater and industrial effluents. It can also chelate metal ions that are present in the water supply. This property makes it an effective agent for removing heavy metals from water. Dimethylglyoxime has been shown to react with various metal ions by means of Langmuir adsorption isotherms and fluorescence spectrometry. When this reaction occurs, the compound forms a complex with the metal ion. The model system is a solution of it with sodium citrate and tetramethylammonium chloride (TMA). The reaction mechanism involves protonation and deprotonation of the ligand, which occurs when the pH is changed from acidic to basic conditions.
ReactionsNickel cation reacts with dimethylglyoxime forms an insoluble red precipitate of nickel dimethylglyoxime.
Ni2+ + 2C4H8N2O2 → Ni(C4H7N2O2)2↓(red precipitate) + 2H+
Dimethylglyoxime reacts with ferrous sulphate and ammonium hydroxide forms a complex compound of iron and ammonium sulphate and water is formed.
FeSO4 + 2NH4OH + 2C4H8N2O2 → Fe(C4H7N2O2)2 + (NH4)2SO4 + 2H2O
General DescriptionDimethylglyoxime (DMG) is a complexing ligand. Dimethylglyoxime forms a number of mixed ligand complexes with N-acetylglycine with metals such as VO(IV), Ni(II), Zn(II), Pd(II), Cd(II) and Pb(II). It is a useful reagent for the spectrophotometric determination of Co(II), Fe(II), Ni(II), Pd(II) and Re(VII).
Safety ProfilePoison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Purification MethodsCrystallise it from EtOH (10mL/g) or aqueous EtOH. [Beilstein 1 III 3105.] TOXIC.
Dimethylglyoxime Preparation Products And Raw materials
Raw materialsSodium bisulfite-->2-Butanone-->Congo red paper-->Hydroxylamine-O-sulfonic acid-->2,3-Butanedione monoxime
Preparation Products1,4-DIAMINOBUTANE
DICHLORO(DIMETHYLGLYOXIMATO)(DIMETHYLGLYOXIME)RHODIUM(III) Methylglyoxime Methylglyoxal 1,4-Benzoquinone dioxime (Diacetoxyiodo)benzene Tralkoxydim Acetylferrocene Polyethylene glycol dimethyl ether PYRITHYLDIONE DIMETHYLGLYOXIME DISODIUM SALT OCTAHYDRATE technetium Tc 99m tris(dimethylglyoxime)-3-carboxy-5-isothiocyanatophenylboronic acid DIACETAMIDE DIPHENYLGLYOXIME DIMETHYLGLYOXIME DISODIUM SALT Nickel bis(dimethylglyoxime) Acetohydroxamic acid DIMETHYLGLYOXIME DINICKEL SALT Acetone oxime

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