4,6-DIMETHYL-1,2-PHENYLENEDIAMINE Chemical Properties

Melting point:

127-129 °C (lit.)

Boiling point:

279.6±35.0 °C(Predicted)

Density 

1.076±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

5.02±0.10(Predicted)

form 

Crystalline Mass, Crystals or Chunks

color 

White to yellow to brownish

Water Solubility 

Slightly soluble in water.

Sensitive 

Air & Light Sensitive

InChI

InChI=1S/C8H12N2/c1-5-3-7(9)8(10)4-6(5)2/h3-4H,9-10H2,1-2H3

InChIKey

XSZYBMMYQCYIPC-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

3171-45-7(CAS DataBase Reference)

EPA Substance Registry System

1,2-Benzenediamine, 4,5-dimethyl- (3171-45-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-36

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29212900

MSDS

• Language:English Provider:SigmaAldrich

4,6-DIMETHYL-1,2-PHENYLENEDIAMINE Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

4, 5-dimethyl-o-phenylenediamine used in the determination of aromatic aldehydes by high performance liquid chromatography after precolumn fluorescent derivatization. For the determination of vanillin.

Uses

Employed in the preparation of transition metal complexes1 and quinoxalinones.2

Synthesis Reference(s)

Tetrahedron Letters, 42, p. 2277, 2001 DOI: 10.1016/S0040-4039(01)00163-0

Synthesis

(4.1) The reducing system was prepared by adding 32 mL of deionized water to 72 mL of anhydrous ethanol solution containing 12.9 g (57.17 mmol; 9.5 eq.) of SnCl2-2H2O. Subsequently, 1 g (6.02 mmol; 1 eq.) of 4,5-dimethyl-2-nitroaniline was added in batches at room temperature and under inert atmosphere. The reaction mixture was heated to reflux for 1 h. The reaction process was monitored by thin layer chromatography (TLC) (unfolding agent: ethyl acetate). After completion of the reaction, it was cooled to room temperature and the reaction mixture was poured into 120 mL of water and neutralized with NaHCO3. The tin salts and NaHCO3 were removed by filtration through filter paper. the filtrate was extracted with dichloromethane (organic phase 1) and the residual solid was continuously extracted with dichloromethane through a Soxhlet extractor for 2 days. The dichloromethane phase after Soxhlet extraction was washed once with water (organic phase 2). Organic phases 1 and 2 were combined, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by silica gel fast column chromatography (elution gradient: cyclohexane/ethyl acetate 2/8; pure ethyl acetate; ethyl acetate/methanol 95/5). The resulting target compound (No. cs 357-1) was an orange solid in quantitative yield. rf = 0.33 (ethyl acetate). 1H NMR (CDCl3, ppm): 2.12 (s, 6H, 2 x CH3); 6.52 (s, 2H, 2 x aromatic CH). 13C NMR (CDCl3, ppm): 18.99 (CH3); 118.64 (aromatic CH); 128.02 (quaternary carbon-CH3); 132.38 (quaternary carbon-N). Mass spectrum (MS): [M + H]+ m/z = 137.1; [M + Na]+ m/z = 159.1; [M + K]+ m/z = 175.2.

References

[1] Patent: WO2011/117830, 2011, A1. Location in patent: Page/Page column 20
[2] Chemistry - A European Journal, 2018, vol. 24, # 36, p. 8989 - 8993
[3] ChemCatChem, 2016, vol. 8, # 15, p. 2461 - 2465
[4] Biochemische Zeitschrift, 1956, vol. 327, p. 422,447
[5] Chemische Berichte, 1901, vol. 34, p. 2255

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