ChemicalBook > CAS DataBase List > 4-Hydroxybenzoic acid

4-Hydroxybenzoic acid

Product Name
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
Formula Weight
138.12
MOL File
99-96-7.mol
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4-Hydroxybenzoic acid Property

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
form 
Crystalline Powder
pka
4.48(at 19℃)
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℃
CAS DataBase Reference
99-96-7(CAS DataBase Reference)
NIST Chemistry Reference
Benzoic acid, 4-hydroxy-(99-96-7)
EPA Substance Registry System
p-Hydroxybenzoic acid (99-96-7)
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Safety

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
Hazardous Substances Data
99-96-7(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 5000 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.21814
Product name
4-Hydroxybenzoic acid
Purity
for synthesis
Packaging
5G
Price
$23.9
Updated
2024/03/01
Sigma-Aldrich
Product number
8.21814
Product name
4-Hydroxybenzoic acid
Purity
for synthesis
Packaging
250G
Price
$30.8
Updated
2024/03/01
Sigma-Aldrich
Product number
8.21814
Product name
4-Hydroxybenzoic acid
Purity
for synthesis
Packaging
1KG
Price
$91.5
Updated
2024/03/01
Sigma-Aldrich
Product number
8.21814
Product name
4-Hydroxybenzoic acid
Purity
for synthesis
Packaging
50KG
Price
$2250
Updated
2024/03/01
Sigma-Aldrich
Product number
240141
Product name
4-Hydroxybenzoic acid
Purity
ReagentPlus , ≥99%
Packaging
50g
Price
$36.6
Updated
2024/03/01
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4-Hydroxybenzoic acid Chemical Properties,Usage,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

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

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

In organic. syntheses; intermediate for dyes, fungicides.

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

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.

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.]

4-Hydroxybenzoic acid Preparation Products And Raw materials

Raw materials

Saccharin Potassium hydroxide Phenol Dipotassium rabdosiin Rabdosiin Potassium hydroxide solution Tosyl chloride potassium phenolate Potassium sulfate

Preparation Products

Propylparaben Methylparaben 4-N-BUTOXYBENZOIC ACID Isobutylparaben Bromoxynil Ethylparaben Butylparaben Isopropylparaben 2-Bromobenzonitrile 4-Cyanophenol 4-Methoxybenzoic acid CYANOPHOS Heptyl 4-hydroxybenzoate
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View Lastest Price from 4-Hydroxybenzoic acid manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
4-Hydroxybenzoic acid 99-96-7
Price
US $60.00/kg
Min. Order
1kg
Purity
99
Supply Ability
5000
Release date
2024-05-16
Jinan Finer Chemical Co., Ltd
Product
4-Hydroxybenzoic acid 99-96-7
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
2000mt/year
Release date
2021-08-03
Hebei Yanxi Chemical Co., Ltd.
Product
4-Hydroxybenzoic acid 99-96-7
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 tons
Release date
2024-06-19

99-96-7, 4-Hydroxybenzoic acidRelated Search:

2-Fluoro-4-hydroxybenzoic acid 3,5-Dihydroxybenzoic acid 3-CHLORO-4-HYDROXYBENZOIC ACID 3-Hydroxybenzoic acid 2-Chloro-4-hydroxybenzoic acid 2,3,4-Trihydroxybenzoic acid 4-Hydroxybenzyl alcohol 4-Hydroxybenzaldehyde 3-(4-Hydroxyphenyl)propionic acid 4-Bromophenylacetic acid Sasapyrine Acetylsalicylic acid ACETYLSALICYLSALICYLIC ACID ACETYLSALICYLIC ANHYDRIDE 4-Nitrophenylacetic acid 4-Nitrobenzyl alcohol 4-Bromomethylbenzoic acid 4'-Hydroxyacetophenone

  • 4-hydroxy-benzoicaci
  • acidop-idrossibenzoico
  • Benzoic acid, p-hydroxy-
  • benzoicacid,4-hydroxy
  • Benzoicacid,4-hydroxy-
  • Hydroxybenzoic acid, para
  • Kyselina 4-hydroxybenzoova
  • kyselina4-hydroxybenzoova
  • p-hydroxybenzoic
  • PHBA
  • P-HYDROXYBENZOIC ACID
  • PARA HYDROXY BENZOIC ACID
  • 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
  • 4-Carboxyphenol
  • 4-hydroxy
  • Acetylsalicylic Acid IMpurity A (Aspirin IMpurity A)
  • Salicylic Acid Related CoMpound 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-HYDROXYBENZOATE
  • PARA-CARBOXYPHENOL
  • 4-Hydroxybenzoesure
  • 4-HYDROXYBENZOIC ACID / P-HYDROXYBENZOIC ACID
  • Aspirin EP IMpurity A
  • Aspirin IMpurity A
  • Aspirin Impurity 1
  • P-hydroxybenzoic acid (acetylsalicylic acid impurity A/aspirin impurity A)
  • p-hydroxy-benzoicaci
  • p-oxybenzoesaure
  • p-Salicylic acid
  • p-salicylicacid
  • 4-Hydroyxbenzoic acid
  • NSC 4961
  • Paraben-acid
  • p-Carboxyphenol
  • 4-Hydroxybenzoic acid, 99+% 100GR
  • LR-68
  • Hydroxybenzenecarboxylic acid
  • Salicylic Acid Related Compound A (100 mg) (4-hydroxybenzoic acid)
  • Acetylsalicylic Acid EP Impurity A
  • Acetylsalicylic Acid Impurity 1（Acetylsalicylic Acid EP Impurity A）