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Salicylaldoxime

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  • 2026-07-15
  • CAS:94-67-7
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  • CAS:94-67-7
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  • CAS:94-67-7
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Related articles

  • What is Salicylaldoxime?
  • Salicylaldoxime is an organic compound described by the formula C6H4CH=NOH-2-OH and it is the oxime of salicylaldehyde. This c....
  • Jan 10,2020
Salicylaldoxime Basic information
Uses Elements Extraction
Product Name:Salicylaldoxime
Synonyms:LABOTEST-BB LT00000132;SALICYLALDEHYDE OXIME;SALICYLALDOXIME;2-HYDROXYBENZALDEHYDE OXIME;SALICYLALDOXIME / 2-HYDROXYBENZALDEHYDE OXIME;SalicylaldoxiMe, 98% 100GR;SalicylaldoxiMe, 98% 25GR;SalicylaldoxiMe >=98.0% (NT)
CAS:94-67-7
MF:C7H7NO2
MW:137.14
EINECS:202-353-8
Product Categories:Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
Mol File:94-67-7.mol
Salicylaldoxime Structure
Salicylaldoxime Chemical Properties
Melting point 57-59 °C 59-61 °C (lit.)
Boiling point 251.96°C (rough estimate)
density 1.2528 (rough estimate)
refractive index 1.5030 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility sparingly soluble in water, soluble in ethanol, diethyl ether, acetone, benzene.
form Powder
pkapK1:1.37(+1);pK2:9.18;pK3:12.11 (25°C)
color Bordeaux to purple-red
OdorOdorless
Water Solubility Slightly soluble in water
Merck 14,8327
BRN 1859881
InChI1S/C7H7NO2/c9-7-4-2-1-3-6(7)5-8-10/h1-5,9-10H/b8-5+
InChIKeyORIHZIZPTZTNCU-VMPITWQZSA-N
SMILESO\N=C\c1ccccc1O
CAS DataBase Reference94-67-7(CAS DataBase Reference)
NIST Chemistry ReferenceBenzaldehyde, 2-hydroxy-, oxime(94-67-7)
EPA Substance Registry SystemBenzaldehyde, 2-hydroxy-, oxime (94-67-7)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS VN5775000
TSCA TSCA listed
HazardClass IRRITANT
HS Code 29280000
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
2-Hydroxybenzaldehyde oxime English
SigmaAldrich English
ACROS English
ALFA English
Salicylaldoxime Usage And Synthesis
Uses

Salicylaldoxime is an organic compound described by the formula C6H4CH=NOH-2-OH and it is the oxime of salicylaldehyde. This crystalline, colorless solid is a chelator and sometimes used in the analysis of samples containing transition metal ions, with which it often forms brightly colored coordination complexes.

Elements Extraction

Salicylaldoxime is recognized as a selective precipitant for copper, although it forms water-insoluble chelates with a number of elements. Ingvar Dahl invested the extraction of divalent magnesium, manganese, cobalt, nickel, copper, zinc, cadmium, mercury, and lead with solutions of salicylaldoxime in benzene and the effect of the reagent concentration and particularly the pH of the aqueous phase on the extractability was also studied. The solubility of salicylaldoxime in organic solvents has been utilized in the solvent extraction of carious elements.

Chemical Propertiesoff-white to light beige crystalline powder
UsesAs a reagent for copper and nickel.
UsesSalicylaldoxime reacts with several metal ions to give intensively coloured complexes which are insoluble in water. The structure of the copper(II), nickel(II) and palladium(II) complexes is shown in Fig. 14 (structure I), and that of the manganese(II), iron(II), cobalt(II) and zinc(II) complexes in Fig. 14 (structure II). The copper(Il) and palladium(II) salicylaldoxime complexes are of importance from an analytical point of view. The complexes precipitated from aqueous media are easily filterable and washable and are weighed after drying at 100°C. The precipitates are of stoichiometric composition.
The outstanding stabilities of the copper(II) and palladium(II) complexes make the reagent suitable for the selective determination of these metal ions. These two complexes form quantitatively at low pH values where the complexes of other metal ions do not exist.
Besides the gravimetric method, salicylaldoxime is also useful in the volumetric, amperometric and nephelometric determinations of copper and palladium.
Salicylaldoxime gives a black precipitate with VOs~ in media containing sulfuric acid; this is soluble in chloroform to give an orange solution. The reaction is specific for vanadium which can thus be detected by this method in the presence of almost all other metals.
In neutral medium salicylaldoxime reacts with iron(III) to give a red complex which is soluble in water. The reaction is utilized for the detection of micro amounts of iron.
Synthesis
Salicylaldehyde

90-02-8

Salicylaldoxime

94-67-7

The general procedure for the synthesis of salicylaldehyde oxime from salicylaldehyde is as follows: 30 mmol of 2-hydroxybenzaldehyde, 60 mmol of sodium bicarbonate, and 45 mmol of hydroxylamine hydrochloride were dissolved in a mixed ethanol/water solvent (50 mL of ethanol/5 mL of water) at room temperature. The reaction mixture was stirred for 2 hours, followed by removal of most of the solvent by concentration. The residue was diluted with ethyl acetate and filtered directly. The filtrate was concentrated to give a final 3.99 g (98% yield) of the colorless oily product salicylaldoxime.

References[1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 5, p. 870 - 872
[2] Journal of the Iranian Chemical Society, 2010, vol. 7, # 1, p. 114 - 118
[3] Patent: CN103864754, 2016, B. Location in patent: Paragraph 0378; 0379
[4] Chemical Communications, 2014, vol. 50, # 56, p. 7531 - 7534
[5] Revue Roumaine de Chimie, 2015, vol. 60, # 9, p. 875 - 880
Tag:Salicylaldoxime(94-67-7) Related Product Information
Salicylaldehyde Salicylhydrazide SALICYLALDEHYDE AZINE Methyl salicylate AMMONIUM SALICYLATE Benzyl salicylate Sodium salicylate Salicylic acid Benzaldoxime FORMOXIME Benzoximate 2,3-Dimethoxybenzaldoxime 2,4-Dihydroxybenzaldehyde oxime 3,5-Dibromosalicylaldoxime 2,4-Dihydroxyacetophenone oxime OXIME 2,3,4-Trimethoxybenzaldehyde oxime N-Hydroxy-2,4-dimethoxy-benzamidine