3,5-Diaminobenzoic acid

3,5-Diaminobenzoic acid Property

Melting point:

235-238 °C (dec.) (lit.)

Boiling point:

274.61°C (rough estimate)

Density 

1.2804 (rough estimate)

vapor pressure 

0Pa at 25℃

refractive index 

1.5200 (estimate)

Flash point:

235-240°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Sparingly), Methanol (Slightly)

form 

Powder

pka

pK1:5.30 (25°C)

color 

White to gray

Water Solubility 

Very soluble in water.

Decomposition 

235-240 ºC

Merck 

14,2978

BRN 

2086484

InChIKey

UENRXLSRMCSUSN-UHFFFAOYSA-N

LogP

-0.51

CAS DataBase Reference

535-87-5(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 3,5-diamino- (535-87-5)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

DG6186000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29224995

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H341Suspected of causing genetic defects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

3,5-Diaminobenzoic acid Chemical Properties,Usage,Production

Chemical Properties

White to grey powder

Uses

3,5-diaminobenzoic acid be used as organic intermediates.

Uses

3,5-Diaminobenzoic acid is an analog of diatriazoate, which has been shown to have antigenicity properties towards the monoclonal antibodies. It is used as pharmaceutical intermediate.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 3,5-diaminobenzoic acid from 3,5-dinitrobenzoic acid: 3,5-dinitrobenzoic acid (51 g, 0.24 mol) and 300 mL of water were added to a 1 L stainless steel high-pressure reactor and stirred thoroughly until homogeneous. Subsequently, the pH of the reaction system was adjusted to 7-8 using an aqueous sodium hydroxide solution with a mass percent concentration of 20%. 0.25 g of Ni-Yb-Al triple-acting catalyst was added followed by three nitrogen substitutions to remove air. The hydrogen pressure was controlled at 0.2 MPa and the reaction temperature was maintained at 25-30 °C until the reaction pressure decreased significantly, indicating the completion of the reaction. Upon completion of the reaction, the catalyst was recovered by filtration. The filtrate was adjusted to pH 3 with concentrated hydrochloric acid to precipitate the target product 3,5-diaminobenzoic acid. The solid product was collected by filtration, washed with water and finally dried under vacuum to give 36.5 g of 3,5-diaminobenzoic acid in 98.8% yield and 98.9% HPLC purity. The retention time of the product was consistent with the standard control.

Purification Methods

Crystallise the acid from water. The dihydrochloride has m 226-228o(dec). [Beilstein 14 H 453, 14 III 1179, 14 IV 1304.]

References

[1] Patent: CN105949076, 2016, A. Location in patent: Paragraph 0025; 0026; 0031; 0036; 0040; 0045; 0053
[2] Journal of the Iranian Chemical Society, 2014, vol. 11, # 6, p. 1587 - 1592
[3] Synthetic Communications, 2000, vol. 30, # 20, p. 3639 - 3644
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 9, p. 709 - 711
[5] Synthetic Communications, 2003, vol. 33, # 2, p. 281 - 289