4-Dimethylaminobenzoic acid Chemical Properties

Melting point:

241-243 °C (dec.)(lit.)

Boiling point:

117-118 C

Density 

1,04 g/cm

refractive index 

1,3715

Flash point:

170 °C

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Crystalline Powder

pka

6.03, 11.49(at 25℃)

color 

White, beige to grayish green

Water Solubility 

Insoluble in water.

Merck 

14,3232

BRN 

386867

Stability:

Stable. Incompatible with strong oxidizing agents.

Major Application

peptide synthesis

InChI

1S/C9H11NO2/c1-10(2)8-5-3-7(4-6-8)9(11)12/h3-6H,1-2H3,(H,11,12)

InChIKey

YDIYEOMDOWUDTJ-UHFFFAOYSA-N

SMILES

CN(C)c1ccc(cc1)C(O)=O

CAS DataBase Reference

619-84-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-(dimethylamino)-(619-84-1)

EPA Substance Registry System

Benzoic acid, 4-(dimethylamino)- (619-84-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

DG8735000

TSCA 

TSCA listed

HS Code 

29224995

Storage Class

13 - Non Combustible Solids

MSDS

• Language:English Provider:4-Dimethylaminobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Dimethylaminobenzoic acid Usage And Synthesis

Chemical Properties

4-Dimethylaminobenzoic acid is light grey powder

Uses

4-(Dimethylamino)benzoic Acid is a substituted benzoic acid that acts as an inhibitor of ultraviolet mediated damage to skin. 4-(Dimethylamino)benzoic Acid is a biotransformation product of 2-ethylhe xyl 4-(N,N-dimethylamino)benzoate (EDP), a widely used UV filters in sunscreen cosmetics and other cosmetic products.

Uses

4-Dimethylaminobenzoic acid a substituted benzoic acid that acts as an inhibitor of ultraviolet mediated damage to skin. It is a biotransformation product of 2-ethylhexyl 4- (N,N-dimethylaminobenzo)benzoate(EDP), a widely used UV filters in sunscreen cosmetics and other cosmetic products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 1807, 1960 DOI: 10.1021/jo01080a035

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

a, weigh 1g of ethyl p-aminobenzoate in a two-port round-bottomed flask, add 40 ml of acetone to dissolve, then add 3.6g of anhydrous potassium carbonate and 14.1g of iodomethane, the reaction under nitrogen protection at 80 ?? stirring reflux for 24 hours, the reaction is complete, filtration of the reaction solution, take the filtrate, extracted with dichloromethane, the organic phase dewatered with magnesium sulfate, filtration and removal of magnesium sulfate, evaporation and concentration of the product with a The product was separated and purified by chromatographic column (mobile phase dichloromethane: methanol = 20:1) to obtain the product ethyl 4-dimethylaminobenzoate.

b, in step a of the proceeds of 4-dimethylaminobenzoic acid ethyl ester, add 10% sodium hydroxide, not more than the reaction can be, 95% ethanol as a solvent, reflux reaction at 85 ?? C for 6 hours, with 1M hydrochloric acid to adjust the PH to a weak acidic reaction, the reaction solution is concentrated, add anhydrous acetone to dissolve, filtration, take the precipitate, vacuum drying to get 4-dimethylaminobenzoic acid;

Purification Methods

Crystallise the acid from EtOH/water. [Beilstein 14 IV 1164.]

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