4-acetamidobenzoic acid Chemical Properties

Melting point:

259-262 °C (dec.)(lit.)

Boiling point:

311.69°C (rough estimate)

Density 

1.2822 (rough estimate)

refractive index 

1.5600 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Powder

pka

pK1: 4.28 (25°C)

color 

Off-white to slightly beige

Water Solubility 

<0.1 g/100 mL at 21 ºC

BRN 

390602

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

CAS DataBase Reference

556-08-1(CAS DataBase Reference)

NIST Chemistry Reference

N-(4-Carboxyphenyl)acetic acid amide(556-08-1)

EPA Substance Registry System

Benzoic acid, 4-(acetylamino)- (556-08-1)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29242995

MSDS

• Language:English Provider:Acetylated PABA
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-acetamidobenzoic acid Usage And Synthesis

Description

4-Acetamidobenzoic acid (PAcBA) is a naturally occurring acetylated metabolite of 4-aminobenzoic acid and is a component of the antiviral and immunostimulatory drug inosine pranobex (Inosiplex; Isoprinosine; Methisoprinol).

Chemical Properties

white or off-white powder or crystals

Originator

4-Acetamidobenzoic acid ,ARIAC

Uses

immune stimulant (component)

Uses

Acedoben is the acetylated derivative of p-aminobenzoic acid (PABA). Acedoben is a metabolite of the anesthetic Benzocaine (B202970).

Definition

ChEBI: 4-acetamidobenzoic acid is a amidobenzoic acid that consists of benzoic acid bearing an acetamido substituent at position 4. It is functionally related to a 4-aminobenzoic acid. It is a conjugate acid of a 4-acetamidobenzoate.

Manufacturing Process

Into a 2 L, 3-necked flask set in a tub and equipped with a stirrer, an air condenser (drying tube), thermometer, was placed 860 ml of water, 43.0 g of MgSO4 and 43.0 g of sodium acetate and heated on water bath. Into heated solution to 70°C stirring 43.0 g of N-p-tolylacetamide were added. Then 136.0 g of KMnO4 by small portions were added at 75°-80°C. The reaction mixture allow to stand for 6 h and stirring was continue till the solution became colorless. Hot solution was filtered and filtrate treated hydrochloric acid to slightly acidic pH. After that 44.0 g (85%) of p-acetoaminobenzoic acid was obtained as white precipitate, melting point 250°C.

Therapeutic Function

Antiviral

General Description

Needles or off-white powder.

Air & Water Reactions

Water insoluble.

Reactivity Profile

Simultaneously an amide and a carboxylic acid.

Fire Hazard

Flash point data for p-Acetylamino benzoic acid are not available; however, p-Acetylamino benzoic acid is probably combustible.

reaction suitability

reaction type: solution phase peptide synthesis

References

[1] Synthetic Communications, 2008, vol. 38, # 7, p. 1028 - 1035
[2] Applied Catalysis A: General, 2013, vol. 456, p. 118 - 125
[3] Green Chemistry, 2012, vol. 14, # 3, p. 847 - 854
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 9, p. 1274 - 1281
[5] Synthetic Communications, 2008, vol. 38, # 17, p. 2929 - 2940

4-acetamidobenzoic acid(556-08-1)Related Product Information

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