2,3-Diaminobenzoic acid Chemical Properties

Melting point:

198-204 °C

Boiling point:

274.61°C (rough estimate)

Density 

1.2804 (rough estimate)

refractive index 

1.5200 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

5.10±0.10(Predicted)

color 

Brown to dark brown

CAS DataBase Reference

603-81-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

29224999

2,3-Diaminobenzoic acid Usage And Synthesis

Uses

2,3-Diaminobenzoic acid (23DBA) is an important organic reagent mainly used in scientific research and laboratory experiments. 23DBA can undergo polycondensation with terephthalic acid dichloro anhydride^[1]. 23DBA isomer is also used in the study of luminescence mechanism of red luminescent carbon dots (RCDs)^[2]. In addition, 2,3-Diaminobenzoic acid also possesses antioxidant properties that help reduce the formation of free radicals in the body. It is also used as a chelating agent that effectively binds to metal ions and prevents them from forming insoluble complexes.

Synthesis

2,3-Diaminobenzoic acid is synthesised using 3-nitroanthranilic acid as a raw material by chemical reaction. The specific synthesis steps are as follows:
2-amino-3-nitrobenzoic acid (9.36 g, 51.4 mmol) was dissolved in MeOH (100 mL) and there was added 10% Pd/C (2.0g). The reaction was stirred under H2-atmosphere (ambient pressure) until absorption ceased. The reaction was filtered through a pad of Celite and the filtrate was evaporated under reduced pressure. The product was purified by flash chromatography (CH2Cl2/MeOH 5:1) and the collected fractions were evaporated to give 2,3-Diaminobenzoic acid (5.40 g, 69%) as a dark brown solid. mp. 199 °C dec. (Litt4. 201 °C dec.). 1H NMR (300 MHz, DMSO-d6) δ 7.09 (dd, J = 8.0, 1.5 Hz, 1H), 6.67 (dd, J = 7.4, 1.5 Hz, 1H), 6.34 (dd, J = 8.0, 7.4 Hz, 2H), 6.32 (br s, 4H). 13C NMR (75 MHz, DMSO-d6) δ 170.5, 139.6, 135.6, 119.4, 117.0, 114.9, 110.3.

References

[1] V. N. ODNORALOVA. The polycondensation reaction of 2,4-diaminobenzoic acid with dichloroanhydride of terephthalic acid[J]. Fibre Chemistry, 1974. DOI:10.1007/BF00542946.
[2] LIU Y, DING H, ZHANG S, et al. Photoluminescence mechanism of red emissive carbon dots from a diaminobenzoic acid isomer?[J]. Materials Advances, 2023. DOI:10.1039/D3MA00836C.

2,3-Diaminobenzoic acid(603-81-6)Related Product Information

• 3-Aminobenzoic acid
• Benzocaine
• 4-Aminobenzoic acid
• 4-Amino-3-methylbenzoic acid
• Citric acid
• Folic acid
• Methyl anthranilate
• 4-Dimethylaminobenzoic acid
• Hyaluronic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Ascoric Acid
• 3,4-DIAMINOBENZOIC ACID,3,4-DIAMINOBENZOIC ACID GRAY TO BROWNPOW DER,3,4-DIAMINOBENZOIC ACID 98%,3,4-Diaminobenzoic acid, 97%,
• Anthranilic acid
• 3,5-DIAMINOBENZOIC ACID,3,5-DIAMINOBENZOIC ACID FREE ACID
• 2-NITRO-3-ACETYLAMINO-4-METHYLBENZOIC ACID
• sulfachrysoidine
• 2-NITRO-3-AMINOBENZOIC ACID
• 2-AMINO-6-FLUORO-3-NITROBENZOIC ACID ETHYL ESTER