Salicylhydroxamic acid Chemical Properties

Melting point:

177 °C (dec.) (lit.)

Boiling point:

276.03°C (rough estimate)

Density 

1.3585 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Fine Crystalline Powder

pka

pK (25°) 4.19

color 

Beige-pink

Water Solubility 

It is soluble in water.

Merck 

14,8331

BRN 

1210520

Stability:

Stable. Incompatible with strong bases, strong oxidizing agents. Combustible.

CAS DataBase Reference

89-73-6(CAS DataBase Reference)

EPA Substance Registry System

N,2-Dihydroxybenzamide (89-73-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-40

Safety Statements 

22-26-36-24/25

WGK Germany 

3

RTECS 

VO6870000

HS Code 

29242990

MSDS

• Language:English Provider:2-Hydroxybenzohydroxamic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Salicylhydroxamic acid Usage And Synthesis

Chemical Properties

It is a white needle crystal or off-white powder with a slow-heating melting point of 168°C. It is soluble in alcohol and ether and can be sublimated. When exposed to air, it progressively turns red. It is synthesized by combining methyl salicylate and hydroxylamine hydrochloride with sodium hydroxide, followed by acidification.

Uses

Salicylhydroxamic acid is a collector with efficient chelating effect on rare metal oxide minerals. It is used in rare metal beneficiation and has the advantages of good selectivity and strong collecting power. Salicylhydroxamic acid is mainly used as a complexing agent or extractant for rare earth ore, copper oxide ore, lead-zinc oxide ore, gold ore, kaolin, etc., as well as organic synthesis intermediates.

Definition

ChEBI: Salicylhydroxamic acid is a hydroxamic acid that is N-hydroxybenzamide carrying a phenolic hydroxy group at position 2. It has a role as an antibacterial drug, a trypanocidal drug, an EC 3.5.1.5 (urease) inhibitor and an EC 1.11.2.2 (myeloperoxidase) inhibitor. It is a member of phenols and a hydroxamic acid.

Application

Salicylhydroxamic acid has various applications, such as:
Synthesizing phenylboronic acid-based bioconjugates for chromatographic use.
Acting as a ligand to create complexes of Fe(III), Cu(II), Ni(II), and Zn(II).
Acting as a selective collector during the flotation technique for segregating oxide minerals.

Preparation

The synthesis of salicylhydroxamic acid involved a two-step process. In the first step, methyl salicylate was prepared by esterifying salicylic acid with methanol using 28g (0.2 mol) of salicylic acid, 81 ml of methanol, and 8 ml of concentrated sulfuric acid. In the second step, hydroxylamine was coupled with the methyl salicylate. 13.9 g (0.2mol) of hydroxylamine was mixed with 200 ml of 10% sodium hydroxide solution and cooled. To this, 152.3g (0.1mol) of methyl salicylate was added in small portions with vigorous shaking after each addition to ensure complete dissolution. The mixture was allowed to stand for 36 hours, then acidified with 2M sulphuric acid and cooled. The precipitate was filtered, recrystallized from hot water containing a drop of acetic acid, recooled, and filtered. The yield of white precipitate collected and weighed was 14g of salicylhydroxamic acid.
Preparation and Characterization of Salicylhydroxamic acid and its Complexes with Iron (III), Cobalt (II) and Manganese (II)

Purification Methods

Crystallise the hydroxamic acid from acetic acid. [Beilstein 10 H 98.]

Salicylhydroxamic acid(89-73-6)Related Product Information

• Salicylaldoxime
• Benzohydroxamic acid
• Acetohydroxamic acid
• Folic acid
• Glycine
• Citric acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Alkyl hydroxy oximido acid
• Ascoric Acid
• 2-(2-CHLOROETHYL)-3-HYDROXY-3,4-DIHYDRO-2H-1,3-BENZOXAZIN-4-ONE
• N-METHOXY-2,5-BIS(2,2,2-TRIFLUOROETHOXY)BENZENECARBOXAMIDE
• Salicylhydroxamic acid
• phosphoric acid
• N-HYDROXY-2,5-BIS(2,2,2-TRIFLUOROETHOXY)BENZENECARBOXAMIDE
• 2-(([2,5-BIS(2,2,2-TRIFLUOROETHOXY)BENZOYL]AMINO)OXY)ACETIC ACID
• N-[(3,4-DICHLOROBENZYL)OXY]-2,5-BIS(2,2,2-TRIFLUOROETHOXY)BENZENECARBOXAMIDE
• 2-(2-CHLOROETHYL)-4-OXO-3,4-DIHYDRO-2H-1,3-BENZOXAZIN-3-YL N-(4-CHLOROPHENYL)CARBAMATE
• 2-(2-CHLOROETHYL)-4-OXO-3,4-DIHYDRO-2H-1,3-BENZOXAZIN-3-YL N-PHENYLCARBAMATE