2,3-DIAMINOTOLUENE Chemical Properties

Melting point:

59-65 °C (lit.)

Boiling point:

225°C

Density 

1.0343 (rough estimate)

refractive index 

1.5103 (estimate)

Flash point:

225°C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Dichloromethane

pka

4.28±0.10(Predicted)

form 

Powder or Crystals

color 

Brown to dark brown

BRN 

907184

InChI

InChI=1S/C7H10N2/c1-5-3-2-4-6(8)7(5)9/h2-4H,8-9H2,1H3

InChIKey

AXNUJYHFQHQZBE-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(C)=C1N

CAS DataBase Reference

2687-25-4(CAS DataBase Reference)

EPA Substance Registry System

1,2-Benzenediamine, 3-methyl- (2687-25-4)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-36/37/39

RIDADR 

2811

WGK Germany 

3

RTECS 

XS9550000

Hazard Note 

Harmful/Irritant

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29214990

Hazardous Substances Data

2687-25-4(Hazardous Substances Data)

Toxicity

mouse,LD50,intraperitoneal,286mg/kg (286mg/kg),Genetica Polonica. Vol. 26, Pg. 109, 1985.

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,3-DIAMINOTOLUENE Usage And Synthesis

Chemical Properties

brown powder

Uses

Inducer of CYP1A activity, and possible mutagenic carcinogen.

General Description

The antitumour activity of Pd(II) and Pt(II) new complexes with 2,3-diaminotoluene was studied. 2,3-Diaminotoluene induced CYP1A activity.

Synthesis

General procedure for the synthesis of 2,3-diaminotoluene from 2-methyl-6-nitroaniline: 4.0 g of 10% palladium-carbon catalyst (51.5% in water) was added to 200 ml of ethanol solution containing 8.50 g (55.9 mmol) of 2-methyl-6-nitroaniline. The reaction mixture was stirred at room temperature and atmospheric pressure in a hydrogen atmosphere for 4 hours. Upon completion of the reaction, the catalyst was removed by filtration and the solvent was subsequently removed by evaporation from the filtrate to afford 6.64 g (97% yield) of 2,3-diaminotoluene crude product in the form of black crystals. The product could be used directly in the subsequent reaction without further purification.1H-NMR (CDCl3) δ: 2.22 (3H, s), 3.35-3.40 (4H, m), 6.62-6.68 (3H, m).

References

[1] Patent: EP1479681, 2004, A1. Location in patent: Page 110
[2] Polyhedron, 2016, vol. 105, p. 137 - 149
[3] Patent: US2012/130078, 2012, A1. Location in patent: Page/Page column 6
[4] Heterocycles, 1997, vol. 45, # 5, p. 955 - 962
[5] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 543 - 548

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