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3-Hydroxybenzoic acid

CAS No.99-06-9
Chemical Name:3-Hydroxybenzoic acid
CBNumber:CB4854760
Molecular Formula:C7H6O3
Formula Weight:138.12
MOL File:99-06-9.mol

3-Hydroxybenzoic acid Property

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)
pka 4.06(at 19℃)
form Powder
color White to off-white
PH 3 (H2O)Aqueous solution
Water Solubility slightly soluble
BRN 508160
InChIKey IJFXRHURBJZNAO-UHFFFAOYSA-N
LogP 1.50
CAS DataBase Reference 99-06-9(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS) 3-HYDROXYBENZOIC ACID
EWG's Food Scores 1
FDA UNII 2ZFW40OJ7U
NIST Chemistry Reference Benzoic acid, 3-hydroxy-(99-06-9)
EPA Substance Registry System m-Hydroxybenzoic acid (99-06-9)
UNSPSC Code 12352100
NACRES NA.22

Safety

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

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302-H315-H319-H335
Precautionary statements P261-P264-P270-P301+P312-P302+P352-P305+P351+P338

3-Hydroxybenzoic acid Price More Price(11)

Brand: Sigma-Aldrich(India)
Product number: H20008
Product name : 3-Hydroxybenzoic acid
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Brand: Sigma-Aldrich(India)
Product number: H20008
Product name : 3-Hydroxybenzoic acid
Purity: ReagentPlus?, 99%
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Brand: Sigma-Aldrich(India)
Product number: H20008
Product name : 3-Hydroxybenzoic acid
Purity: ReagentPlus?, 99%
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Brand: Sigma-Aldrich(India)
Product number: 36333
Product name : 3-Hydroxybenzoic acid
Purity: analytical standard
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Product number: ALF-A13628-36
Product name : 3-Hydroxybenzoic acid, 99%
Purity:
Packaging: 500g
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3-Hydroxybenzoic acid Chemical Properties,Usage,Production

Chemical Properties White to light yellow crystal powder. 3-Hydroxybenzoic acid does not undergo decarboxylation at elevated temperature and is stable up to 300℃. This is in contrast to 2- and 4-hydroxybenzoic acids. Electrophilic substitution (e.g., nitration, halogenation, sulfonation) occurs ortho or para to the hydroxyl group. Thus, nitration with 62 % aqueous nitric acid gives 2-nitro-3-hydroxybenzoic acid as the main product, along with 4-nitro- and 6-nitro-3-hydroxybenzoic acids.
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.]