3-Amino-4-hydroxybenzoic acid Chemical Properties

Melting point:

208 °C (dec.) (lit.)

Boiling point:

276.03°C (rough estimate)

Density 

1.3585 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in solvents.

form 

Crystalline Powder

pka

9.06±0.18(Predicted)

color 

Beige-gray to brown

λmax

308nm(H2O (pH 11))(lit.)

Sensitive 

Light Sensitive

BRN 

972238

InChI

InChI=1S/C7H7NO3/c8-5-3-4(7(10)11)1-2-6(5)9/h1-3,9H,8H2,(H,10,11)

InChIKey

MRBKRZAPGUCWOS-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(O)C(N)=C1

CAS DataBase Reference

1571-72-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, AIR SENSITIVE, LIGHT SENSITIVE

HS Code 

29225090

MSDS

• Language:English Provider:3-Amino-4-hydroxybenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Amino-4-hydroxybenzoic acid Usage And Synthesis

Chemical Properties

beige-grey to brown crystalline powder

Uses

3-Amino-4-hydroxybenzoic acid is used to produce 4-acetoxy-3-acetylamino-benzoic acid with acetic acid anhydride at temperature of 0 - 20°C. This reaction will need reagents aq. HCl and NaOAc.

Application

3-Amino-4-hydroxybenzoic acid is the first matrix to be used specifically for carbohydrates. The other most commonly used matrices are α-cyano-4-hydroxycinnamic acid, 2,5-dihydroxybenzoic acid, and sinapinic acid. Matrix and sample solutions are mixed prior to laser exposure, spotted on a solid metallic surface, and allowed to dry before submitting them to MALDI. These matrices are characterized by high absorptivity of the laser radiation and the capability of forming fine crystalline solids during sample/matrix drying. In general, the more fine-grained and homogeneous the morphology of crystals formed with the analyte/matrix mixture, the more intense the MALDI mass spectrum of the analyte. 3-Amino-4-hydroxybenzoic acid produced [M+Na]+ ions from as little as 1 pmol of dextran hydrolysate and N-linked glycans released from glycoproteins.

Definition

ChEBI: A monohydroxybenzoic acid that is 4-hydroxybenzoic acid carrying an additional amino substitutent at position 3.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 3740, 1989 DOI: 10.1021/jo00276a044

3-Amino-4-hydroxybenzoic acid(1571-72-8)Related Product Information

• Salicylic acid
• Methylparaben
• 6-Aminocaproic acid
• 4-Aminobenzoic acid
• Glycine
• 3-Hydroxybenzoic acid
• 3-Aminobenzoic acid
• 4-Hydroxybenzoic acid
• 4-HYDROXY-3-IODO-5-NITROBENZOIC ACID
• 4-Methoxy-3-nitrobenzoic acid
• METHYL 4-METHOXY-3-NITROBENZOATE
• Methyl 3-amino-4-methoxybenzoate
• Methyl 3-amino-4-hydroxybenzoate
• 4-Hydroxy-3-nitrobenzoic acid
• Methyl 3-nitro-4-hydroxybenzoate
• 3,4-DIMETHOXY-5-NITRO-BENZOIC ACID
• ETHYL 4-HYDROXY-3-NITROBENZOATE
• Anthranilic acid