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3-Hydroxybenzoic acid

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3-Hydroxybenzoic acid Basic information

Product Name:
3-Hydroxybenzoic acid
Synonyms:
  • kyselina3-hydroxybenzoova
  • meta-Hydroxybenzoic acid
  • m-Hba
  • m-hydroxy-benzoicaci
  • m-Salicylic acid
  • m-salicylicacid
  • m-Hydroxybenzoic Acid 3-Hydroxybenzoic Acid
  • m-HydroxybenzoicacidM-HydroxybenzoicAcid
CAS:
99-06-9
MF:
C7H6O3
MW:
138.12
EINECS:
202-726-5
Product Categories:
  • Benzoic acid
  • C7
  • Carbonyl Compounds
  • Carboxylic Acids
  • Building Blocks
  • Pyridines
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • Carbonyl Compounds
  • Carboxylic Acids
  • Chemical Synthesis
  • Nutrition Research
  • Organic Building Blocks
  • Phytochemicals by Plant (Food/Spice/Herb)
  • Vaccinium myrtillus (Bilberry)
  • pharmacetical
  • bc0001
  • 99-06-9
Mol File:
99-06-9.mol
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3-Hydroxybenzoic acid Chemical Properties

Melting point:
200-203 °C (lit.)
Boiling point:
213.5°C (rough estimate)
Density 
1.4850
refractive index 
1.4600 (estimate)
FEMA 
4431 | 3-HYDROXYBENZOIC ACID
Flash point:
220 °C
storage temp. 
Store below +30°C.
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Powder
pka
4.06(at 19℃)
color 
White to off-white
PH
3 (H2O)Aqueous solution
Water Solubility 
slightly soluble
BRN 
508160
InChIKey
IJFXRHURBJZNAO-UHFFFAOYSA-N
CAS DataBase Reference
99-06-9(CAS DataBase Reference)
NIST Chemistry Reference
Benzoic acid, 3-hydroxy-(99-06-9)
EPA Substance Registry System
m-Hydroxybenzoic acid (99-06-9)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
RTECS 
DH1924980
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29182990

MSDS

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3-Hydroxybenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

3-Hydroxybenzoic acid is used as an intermediate in the manufacture of germicides, plasticizers, preservatives, light stabiliziers, petroleum additives, pharmaceuticals, and plasticizer. It can also be used for the synthesis of azo dyes and herbicide fomesafen.

Definition

ChEBI: 3-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc. It has a role as a bacterial metabolite and a plant metabolite. It derives from a benzoic acid. It is a conjugate acid of a 3-hydroxybenzoate.

Application

3-Hydroxybenzoic acid is used in perfumery. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Preparation

3-Hydroxybenzoic acid is synthesized from benzoic acid by sulfonation, alkali melting and hydrolysis.
122kg of benzoic acid was put into the reactor, and 100kg of oleum was added under stirring. The temperature was raised to about 100 °C, and the reaction was carried out for 2h to obtain Sodium 3-sulfobenzoate. Then the sulfonated liquid was transferred to an alkali melting pot, 45 kg of solid sodium hydroxide was added, the temperature was raised to melting, and reacted for 4 to 5 hours to obtain sodium m-carboxyphenate, and diluted sulfuric acid was added for acid hydrolysis. Cool and crystallize, filter out sodium sulfate, and decolorize the filter cake with activated carbon to obtain 3-Hydroxybenzoic acid.

Reactions

m-Hydroxybenzoic Acid, of the three hydroxybenzoic acids, the metaisomer is of least commercial importance. Unlike salicylic acid, m-hydroxybenzoic acid does not undergo the Friedel-Crafts reaction. It can be converted in 80% yield to m-aminophenol by the Schmidt reaction, which involves treating the acid with hydrazoic acid in trichloroethylene in the presence of sulfuric acid at 40 °C.

Synthesis Reference(s)

Tetrahedron Letters, 9, p. 3845, 1968 DOI: 10.1016/S0040-4039(01)99116-6

Purification Methods

Crystallise the hydroxyacid from absolute EtOH. [Beilstein 10 IV 315.]

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