4,4'-Diaminobenzanilide Chemical Properties

Melting point:

205-207 °C(lit.)

Boiling point:

384.0±27.0 °C(Predicted)

Density 

1.314±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Water Solubility 

Practically insoluble in water

form 

powder to crystal

pka

13.99±0.70(Predicted)

color 

White to Brown

BRN 

2215469

InChI

InChI=1S/C13H13N3O/c14-10-3-1-9(2-4-10)13(17)16-12-7-5-11(15)6-8-12/h1-8H,14-15H2,(H,16,17)

InChIKey

XPAQFJJCWGSXGJ-UHFFFAOYSA-N

SMILES

C(NC1=CC=C(N)C=C1)(=O)C1=CC=C(N)C=C1

CAS DataBase Reference

785-30-8(CAS DataBase Reference)

EPA Substance Registry System

Benzamide, 4-amino-N-(4-aminophenyl)- (785-30-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HS Code 

29214200

MSDS

• Language:English Provider:4,4'-Diaminobenzanilide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4,4'-Diaminobenzanilide Usage And Synthesis

Chemical Properties

off-white to grey-beige powder

Uses

4,4'-Diaminobenzanilide (DABA) is an organic compound that is used as an intermediate in the synthesis of various dyes, pigments, and other organic compounds used in the textile and printing industries. It is also used as a intermediate in the synthesis of certain types of pharmaceuticals and agrochemicals.

Synthesis

1. 30 g of 4,4'-dinitrobenzanilide obtained in step 1, 150 mL of N,N'-dimethylformamide and 0.8 g of 3 wt% palladium-carbon catalyst were added to an autoclave. The hydrogenation reaction was carried out at a hydrogen pressure of 0.8±0.1 MPa and a temperature of 100±1 °C until the reaction was complete. Upon completion of the reaction, the reaction mixture was filtered and the solvent was evaporated under vacuum to obtain the crude 4,4'-diaminobenzanilide. 2. The crude 4,4'-diaminobenzanilide obtained in step 2 was added to an autoclave with 100 g of n-butanol and 0.96 g of activated carbon, and nitrogen was passed through for three times to ensure that a positive pressure was maintained in the autoclave. Subsequently, the temperature was raised to 135±1 °C and stirred for 20 min. The filtrate was filtered under nitrogen protection, the filtrate was cooled to 25±1 °C, filtered again and dried. Finally, 22.8 g of electronic grade 4,4'-diaminobenzanilide in the form of white crystalline powder was obtained in 96.1% yield and 99.7% purity (HPLC).

References

[1] Patent: CN108329224, 2018, A. Location in patent: Paragraph 0013; 0015-0017; 0026; 0028-0030
[2] Journal of the Serbian Chemical Society, 2011, vol. 76, # 2, p. 177 - 188
[3] ChemMedChem, 2014, vol. 9, # 3, p. 590 - 601
[4] Journal fuer Praktische Chemie (Leipzig), 1958, vol. <4> 6, p. 14,16
[5] Bl. Fac. Eng. Hiroshima Univ., 1956, vol. 5, p. 311,312

4,4'-Diaminobenzanilide(785-30-8)Related Product Information

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