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3-Hydroxybenzoic acid

3-Hydroxybenzoic acid Structure
CAS No.
99-06-9
Chemical Name:
3-Hydroxybenzoic acid
Synonyms
M-HYDROXYBENZOIC ACID;3-hydroxybenzoate;Benzoic acid, 3-hydroxy-;m-Salicylic acid;meta-Hydroxybenzoic acid;m-Hba;m-salicylicacid;m-Salicylic Aci;3-Carboxyphenol;m-Hydroxybenzoic
CBNumber:
CB4854760
Molecular Formula:
C7H6O3
Molecular Weight:
138.12
MOL File:
99-06-9.mol
MSDS File:
SDS
Modify Date:
2024/5/23 18:06:45

3-Hydroxybenzoic acid 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)
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)
NIST Chemistry Reference Benzoic acid, 3-hydroxy-(99-06-9)
EPA Substance Registry System m-Hydroxybenzoic acid (99-06-9)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
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

3-Hydroxybenzoic acid price More Price(11)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) H20008 3-Hydroxybenzoic acid ReagentPlus?, 99% 99-06-9 5G ₹2413.98 2022-06-14 Buy
Sigma-Aldrich(India) H20008 3-Hydroxybenzoic acid ReagentPlus?, 99% 99-06-9 100G ₹3323.28 2022-06-14 Buy
Sigma-Aldrich(India) H20008 3-Hydroxybenzoic acid ReagentPlus?, 99% 99-06-9 500G ₹9677.55 2022-06-14 Buy
Sigma-Aldrich(India) 36333 3-Hydroxybenzoic acid analytical standard 99-06-9 100MG ₹6375.93 2022-06-14 Buy
ALFA India ALF-A13628-36 3-Hydroxybenzoic acid, 99% 99-06-9 500g ₹6542 2022-05-26 Buy
Product number Packaging Price Buy
H20008 5G ₹2413.98 Buy
H20008 100G ₹3323.28 Buy
H20008 500G ₹9677.55 Buy
36333 100MG ₹6375.93 Buy
ALF-A13628-36 500g ₹6542 Buy

3-Hydroxybenzoic acid Chemical Properties,Uses,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.

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.

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.

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.

Purification Methods

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

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