4-(1H-BENZOIMIDAZOL-2-YL)-PHENYLAMINE

4-(1H-BENZOIMIDAZOL-2-YL)-PHENYLAMINE Property

Melting point:

248.0 to 252.0 °C

Boiling point:

466.3±47.0 °C(Predicted)

Density 

1.286±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

11.77±0.10(Predicted)

color 

White to Light yellow to Light orange

λmax

314nm(HCl aq.)(lit.)

Safety

Hazard Codes 

Xi

HS Code 

2933.99.8290

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H317May cause an allergic skin reaction

H318Causes serious eye damage

H330Fatal if inhaled

H335May cause respiratory irritation

H351Suspected of causing cancer

H361Suspected of damaging fertility or the unborn child

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

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

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

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

P284Wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

4-(1H-BENZOIMIDAZOL-2-YL)-PHENYLAMINE Chemical Properties,Usage,Production

Synthesis Reference(s)

Journal of Medicinal Chemistry, 39, p. 3375, 1996 DOI: 10.1021/jm9600959

Synthesis

The reaction was carried out with 4-aminobenzoic acid (5 g, 5.78 mmol) and o-phenylenediamine (3.9 g, 3.68 mmol) in polyphosphoric acid (12.5 g) with stirring at 200 °C for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into crushed ice. Subsequently, the precipitate was stirred in cold water. The pH was adjusted with ammonium hydroxide solution to 7. The solid product was collected by filtration and washed several times with methanol. Finally, the target compound 4-(1H-benzimidazol-2-yl)aniline (5) was purified as a white solid by silica gel column chromatography using ethyl acetate: hexane (4:1) as eluent. Yield: 82%; Melting point: 207-209 °C; 1H NMR (400 MHz, DMSO-d6): δ= 7.96 (d, 2H, J = 8.72 Hz, ArH), 7.55-7.51 (m, 2H, ArH), 7.16-7.14 (m, 2H, ArH), 6.75 (d, 2H, J = 8.24 Hz, ArH) , 4.45 (bs, 2H, NH2); 13C NMR (100 MHz, DMSO-d6): δ= 152.2,148.4,127.5,120.9,118.6,113.8 (ArC); MS (ESI), m/z: 210.2 (M++1).

References

[1] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 1, p. 115 - 117
[2] Chinese Chemical Letters, 2011, vol. 22, # 3, p. 296 - 299
[3] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 24 - 35
[4] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 59 - 69
[5] Journal of the Chilean Chemical Society, 2012, vol. 57, # 2, p. 1122 - 1125,4