3-(Dimethylamino)benzoic acid Chemical Properties

Melting point:

148-150 °C(lit.)

Boiling point:

293.03°C (rough estimate)

Density 

1.1603 (rough estimate)

refractive index 

1.5200 (estimate)

storage temp. 

Store below +30°C.

solubility 

methanol: 50mg/mL, clear to very slightly hazy, yellow to brown

form 

Crystalline Powder

pka

3.36±0.10(Predicted)

color 

Light yellow to yellow-beige

Water Solubility 

Soluble in methanol (50 mg/ml). Insoluble in water.

BRN 

2208586

InChI

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

InChIKey

NEGFNJRAUMCZMY-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=CC(N(C)C)=C1

CAS DataBase Reference

99-64-9(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 3-(dimethylamino)- (99-64-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29224995

MSDS

• Language:English Provider:3-(Dimethylamino)benzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-(Dimethylamino)benzoic acid Usage And Synthesis

Chemical Properties

Light yellow to yellow-beige crystalline powder

Uses

3-Dimethylaminobenzoic acid is used as a benzoic acid derivative.

Uses

3-(Dimethylamino)benzoic acid has been used to analyse glucose content from the extraction of starch and soluble sugars.

Biochem/physiol Actions

3-(Dimethylamino)benzoic acid can be used to quantity the activity of peroxidase and manganese peroxidase.

Synthesis

In a 250 mL three-neck flask, 95 mL of methanol and 3 mL of tetrahydrofuran were added, followed by 16.7 g of m-nitrobenzoic acid and 0.2 g of 5% palladium carbon catalyst. A constant pressure dropping funnel was installed and 15.2 mL of 37% formaldehyde aqueous solution was added to it. The air in the reaction system was replaced with hydrogen via an air pump. The reaction system was warmed up to 64 °C and the reaction was stirred at this temperature until hydrogen uptake stopped. Subsequently, the hydrogenation reaction was continued by slowly adding the formaldehyde solution through a dropping funnel until the hydrogen uptake stopped again. After stopping stirring, the reaction mixture was filtered to recover the catalyst. The filtrate was concentrated to precipitate the product m-dimethylaminobenzoic acid. The precipitate was collected by filtration, washed with a small amount of water and dried at 100 °C to give 15.3 g of m-dimethylaminobenzoic acid in 93% yield. The recovered catalyst was washed with reaction solvent and could be reused in subsequent reactions.

References

[1] Patent: CN107056633, 2017, A. Location in patent: Paragraph 0013; 0014; 0015; 0016
[2] Journal of the Chemical Society, 1950, p. 1342,1345

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