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4-Hydroxybenzoic acid

CAS No.
99-96-7
Chemical Name:
4-Hydroxybenzoic acid
Synonyms
P-HYDROXYBENZOIC ACID;PARA HYDROXY BENZOIC ACID;PHBA;p-hydroxybenzoic;4-hydroxy-benzoicaci;4-hydroxy;p-Salicylic acid;4-Carboxyphenol;PARA-HYDROXYBENZOATE;acidop-idrossibenzoico
CBNumber:
CB1412080
Molecular Formula:
C7H6O3
Molecular Weight:
138.12
MDL Number:
MFCD00002547
MOL File:
99-96-7.mol
MSDS File:
SDS
Last updated:2024-03-13 16:52:01

4-Hydroxybenzoic acid Properties

Melting point 213-217 °C (lit.)
Boiling point 213.5°C (rough estimate)
Density 1,46 g/cm3
vapor pressure 0Pa at 20℃
refractive index 1.4600 (estimate)
FEMA 3986 | 4-HYDROXYBENZOIC ACID
Flash point 199 °C
storage temp. Store below +30°C.
solubility methanol: soluble5%, clear to slightly hazy, colorless to faintly yellow
pka 4.48(at 19℃)
form Crystalline Powder
color White to ivory
PH 3.3 (1g/l, H2O, 20℃)
Odor at 100.00 %. phenolic nutty
Odor Type phenolic
Water Solubility 5 g/L (20 ºC)
Merck 14,4812
JECFA Number 957
BRN 970950
InChIKey FJKROLUGYXJWQN-UHFFFAOYSA-N
LogP 0.878 at 22℃
Substances Added to Food (formerly EAFUS) 4-HYDROXYBENZOIC ACID
CAS DataBase Reference 99-96-7(CAS DataBase Reference)
EWG's Food Scores 3
FDA UNII JG8Z55Y12H
NIST Chemistry Reference Benzoic acid, 4-hydroxy-(99-96-7)
EPA Substance Registry System p-Hydroxybenzoic acid (99-96-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Signal word  Danger
Hazard statements  H318-H335
Precautionary statements  P261-P271-P280-P304+P340+P312-P305+P351+P338-P403+P233
Hazard Codes  Xi
Risk Statements  36-36/37/38
Safety Statements  26-37/39-36
WGK Germany  1
RTECS  DH1925000
Autoignition Temperature >250 °C
TSCA  Yes
HS Code  29182930
Toxicity LD50 orally in Rabbit: > 5000 mg/kg
NFPA 704
0
2 0

4-Hydroxybenzoic acid price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.21814 4-Hydroxybenzoic acid for synthesis 99-96-7 5G $23.9 2024-03-01 Buy
Sigma-Aldrich 8.21814 4-Hydroxybenzoic acid for synthesis 99-96-7 250G $30.8 2024-03-01 Buy
Sigma-Aldrich 8.21814 4-Hydroxybenzoic acid for synthesis 99-96-7 1KG $91.5 2024-03-01 Buy
Sigma-Aldrich 8.21814 4-Hydroxybenzoic acid for synthesis 99-96-7 50KG $2250 2024-03-01 Buy
Sigma-Aldrich 240141 4-Hydroxybenzoic acid ReagentPlus , ≥99% 99-96-7 50g $36.6 2024-03-01 Buy
Product number Packaging Price Buy
8.21814 5G $23.9 Buy
8.21814 250G $30.8 Buy
8.21814 1KG $91.5 Buy
8.21814 50KG $2250 Buy
240141 50g $36.6 Buy

4-Hydroxybenzoic acid Chemical Properties,Uses,Production

Description

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid or PHBA, is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohol and acetone. It is isomeric with salicylic acid (2-hydroxybenzoic acid), a forerunner to aspirin, and 3-hydroxybenzoic acid. The esters of 4-hydroxybenzoic acid, also called parabens, are widely used as preservatives in cosmetics and some ophthalmic solutions.

Chemical Properties

4-Hydroxybenzoic acid is an odorless white crystalline astringent powder. In pure form, it imparts a sweetish taste at first, which quickly becomes acrid and disagreeable

Occurrence

4-Hydroxybenzoic acid is a phenolic acid that has been found in a variety of fruit peels and leaves. It can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in Macrotyloma uniflorum (horse gram), carob and in Phyllanthus acidus (Otaheite gooseberry).

Uses

p-Hydroxybenzoic acid is of significant commercial importance. The most familiar application is the use of several of its esters as preservatives, known as parabens. Also of interest is the use in liquid crystal polymer applications.

Uses

4-Hydroxybenzoic acid is used as an intermediate for dyes, antiseptics and active pharmaceutical ingredients. It is also used as a food preservative, corrosion inhibitor, anti-oxidant and an emulsifier. It reacts with 6-hydroxynaphthalene-2-carboxylic acid to prepare aromatic polyester called Vectran fiber. It acts as a precursor to prepare p-hydroxyphenylbenzoate, p-acetoxybenzoyl chloride and 4,4'-dihydroxybenzophenone. Further, it is used in paint additives, coating additives, processing aids, electrical and electronic products. In addition to this, it acts as a preservative in cosmetics and some ophthalmic solutions.

Uses

In organic. syntheses; intermediate for dyes, fungicides.

Definition

ChEBI: 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate.

Preparation

Prepared from p-bromophenol or p-hydroxybenzaldehyde, or from saponification of methyl salicylate, a major component of oil of wintergreen.
In 1947, H. Gilman and C. E. Arntzen at Iowa State College (Ames) reported the synthesis of 4-HBA from 4-hydroxybenzaldehyde. Several other preparation methods were developed since then. Today it is produced commercially via the Kolbe–Schmitt reaction, which originated in the mid-1800s. Potassium phenoxide and CO2 are heated under pressure; the reaction mixture is then acidified to obtain the product 4-Hydroxybenzoic acid. (Oddly, if the sodium salt is used, the product is 2-hydroxybenzoic acid, or salicylic acid.)
Org. Synth. 1934, 14, 48
DOI: 10.15227/orgsyn.014.0048

Application

4-Hydroxybenzoic acid can be used as a starting material to synthesize organic intermediates such as 4-acetoxybenzoic acid and 4-hydroxy-3,5-diiodobenzoic acid.
4-Hydroxybenzoic acid is used as an intermediate for dyes, antiseptics and active pharmaceutical ingredients. It is also used as a food preservative, corrosion inhibitor, anti-oxidant and an emulsifier. It reacts with 6-hydroxynaphthalene-2-carboxylic acid to prepare aromatic polyester called Vectran fiber. It acts as a precursor to prepare p-hydroxyphenylbenzoate, p-acetoxybenzoyl chloride and 4,4′-dihydroxybenzophenone. Further, it is used in paint additives, coating additives, processing aids, electrical and electronic products. In addition to this, it acts as a preservative in cosmetics and some ophthalmic solutions.

Aroma threshold values

Detection at 5 ppm (water)

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 174, 1984 DOI: 10.1021/ja00313a035
The Journal of Organic Chemistry, 29, p. 3459, 1964 DOI: 10.1021/jo01035a003

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. 4-Hydroxybenzoic acid belongs to the class of aromatic acids, which may be used as a preservative in cosmetics, pharmaceuticals and as a synthetic flavoring agent in food products.

Flammability and Explosibility

Non flammable

Purification Methods

Crystallise the hydroxyacid from water. [Beilstein 10 IV 345.]

1000389-71-8
99-96-7
Synthesis of 4-Hydroxybenzoic acid from Benzenamine, 4-(tri-1H-pyrazol-1-ylmethyl)-
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View Lastest Price from 4-Hydroxybenzoic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4-Hydroxybenzoic acid pictures 2024-03-19 4-Hydroxybenzoic acid
99-96-7
US $0.00 / Kg/Drum 1KG 99% 2000mt/year Jinan Finer Chemical Co., Ltd
4-Hydroxybenzoic acid pictures 2024-03-15 4-Hydroxybenzoic acid
99-96-7
US $100.00 / kg 1kg 99.9% 20tons Hong Kong Excellence Biotechnology Co., Ltd.
4-Hydroxybenzoic acid pictures 2024-03-13 4-Hydroxybenzoic acid
99-96-7
US $3.00-1.00 / kg 1kg 99.9% 10 tons Shanghai Aosiris new Material Technology Co., LTD
Benzoic acid, p-hydroxy- benzoicacid,4-hydroxy Benzoicacid,4-hydroxy- Hydroxybenzoic acid, para Kyselina 4-hydroxybenzoova kyselina4-hydroxybenzoova RARECHEM AL BO 0112 FEMA 3986 HYDROXYBENZOIC ACID, 4- AKOS BBS-00003776 ACETYLSALISYLIC ACID IMP A ACETYLSALICYLIC ACID IMPURITY A 4-Hydroxybenzoic acid Vetec(TM) reagent grade, 99% 4-Hydroxybenzoic acid Solution, 100ppm Acetylsalicylic Acid IMpurity A (Aspirin IMpurity A) 4-Hydroxybenzoic acid ReagentPlus(R), >=99% 4-Hydroxybenzoic acid ReagentPlus(R), 99% p-Hydroxybenzoic acid, Standard for GC,>=99.5%(GC) 4-HYDROXYBENZOIC ACID 4-hydroxybenzenecarboxylic acid PARA HYDROXY BENZONIC ACID PARAHYDROXY BENZOIC ACID (POLYMER GRADE OF 99 4-HYDROXYBENZOIC ACID, 99+% P-HYDROXYBENZOIC ACID 99+% 4-Hydroxybenzoic acid, 99.5% 4-Hydroxybenzoic Acid-carboxyl-13C P-HYDROXYBENZOICACID,REAGENT PARA-CARBOXYPHENOL 4-Hydroxybenzoesure 4-HYDROXYBENZOIC ACID / P-HYDROXYBENZOIC ACID Aspirin EP IMpurity A Aspirin IMpurity A p-hydroxy-benzoicaci p-oxybenzoesaure p-salicylicacid 4-Hydroyxbenzoic acid NSC 4961 Paraben-acid p-Carboxyphenol 4-Hydroxybenzoic acid, 99+% 100GR LR-68 Salicylic Acid Related Compound A (100 mg) (4-hydroxybenzoic acid) Acetylsalicylic Acid EP Impurity A Acetylsalicylic Acid Impurity 1(Acetylsalicylic Acid EP Impurity A) Para Hydroxy Benzoic Acid (PHBA) Salicylic Acid EP Impurityuriy A p-Hydroxybenzoic acid(PHBA) Cefazolin Impurity 3 (1H-Tetrazole-1-Acetic Acid) PHBA 4-Hydroxybenzoic acid 4-Hydroxybenzoic acid (Paraben)@100 μg/mL in AcCN 4-HydroxybenzoicAcid> Salicylic Acid EP Impurity A 4-HYDROXYBENZOIC ACID FOR SYNTHESIS Acetylsalicylic Acid EP Impurity A (Aspirin Impurity A) Propyl Parahydroxybenzoate EP Impurity A Butyl Parahydroxybenzoate EP Impurity A 4-Hydroxybenzoic acid 99-96-7 4-Hydroxybenzoic acid ISO 9001:2015 REACH