4-Aminobenzaldehyde Property

Melting point:

77-79°C

Boiling point:

138-139 C

Density 

0,868 g/cm

refractive index 

1.5323 (estimate)

pka

1.88±0.10(Predicted)

form 

Solid

color 

Light yellow to yellow

CAS DataBase Reference

556-18-3(CAS DataBase Reference)

EPA Substance Registry System

Benzaldehyde, 4-amino- (556-18-3)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-43-22

Safety Statements 

26-36/37/39-36-36/37

RIDADR 

UN 1307

WGK Germany 

3

RTECS 

CU4400000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

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

4-Aminobenzaldehyde Chemical Properties,Usage,Production

Description

4-Aminobenzaldehyde can be made into polymer with a certain conductivity and corrosion resistance, and the combination of stainless steel is better than the epoxy resin. It can be used as intermediate of pharmaceutical and dye. It is also used in organic synthesis. Additionally, it can react with Carbonyl dichloride to get 4-Formylphenyl isocyanate.

Chemical Properties

Yellow crystalline powder. Melting point 71-72℃. Soluble in alcohol, benzene, insoluble in water, very easy to polymerize.

Uses

4-Aminobenzaldehyde (p-aminobenzaldehyde) is a useful synthetic reagent and monomer that can be used to synthesize monoazo dyes and photocurable ion exchange resins. 4-Aminobenzaldehyde is also a corrosion inhibitor of metals.

Preparation

4-aminobenzaldehyde is obtained from p-nitrotoluene by oxidation, reduction, sodium sulfide, and sodium hydroxide dissolved in water, filtration, and filtrate heated to 68 ° C to add sulfur powder, at 98 ° C reaction for 18min to get more sodium sulfide solution. Add 65% ethanol and p-nitrotoluene, reaction at 80-86 ℃ for 1.5h, recovery of ethanol, and steam distillation to remove by-products p-aminotoluene. The reaction solution is extracted with benzene, distilled by water vapor, cooled, filtered, and dried to obtain the finished product.

Definition

ChEBI: P-aminobenzaldehyde is a member of benzaldehydes.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 31, 1963
Tetrahedron Letters, 30, p. 251, 1989 DOI: 10.1016/S0040-4039(00)95173-6

References

[1] O. A. NURKENOV. Synthesis, structure and chemical transformations of 4-aminobenzaldehyde[J]. Russian Journal of General Chemistry, 2013, 83 10: 1864-1868. DOI:10.1134/S1070363213100113.
[2] MD. J. SHARIF Tatsuya T Seiji Yamazoe. Selective Hydrogenation of 4-Nitrobenzaldehyde to 4-Aminobenzaldehyde by Colloidal RhCu Bimetallic Nanoparticles[J]. Topics in Catalysis, 2014, 57 10-13: 1049-1053. DOI:10.1007/s11244-014-0269-5.
[3] KUNIO KIMURA. Self-Assembling Polycondensation of 4-Aminobenzaldehyde. Preparation of Star-Like Aggregates of Cone-Shaped Poly(azomethine) Crystals[J]. Polymer Journal, 2003, 35 5: 455-459. DOI:10.1295/polymj.35.455.
[4] A. HALSTIANYe. Yu V A S Вushuiev. Ozonation of 4-aminotoluene as a new method of synthesis of 4-aminobenzaldehyde – an intermediate for the production of anti-tuberculosis drugs[J]. Current issues in pharmacy and medicine: science and practice, 2022, 18 1. DOI:10.14739/2409-2932.2022.1.249620.
[5] Lei Z U .Preparation and Application of 4-Aminobenzaldehyde and Its Polymer[J].Journal of Yanbian University(Natural Science), 2008.