N,N-dimethyl-m-phenylenediamine Chemical Properties

Melting point:

<-20 °C

Boiling point:

240.49°C (rough estimate)

Density 

0.9950

refractive index 

1.5914 (estimate)

storage temp. 

2-8°C(protect from light)

pka

5.11±0.10(Predicted)

Appearance

Brown to black Liquid

EPA Substance Registry System

1,3-Benzenediamine, N,N-dimethyl- (2836-04-6)

Safety Information

Risk Statements 

25-36/37/38-43

Safety Statements 

36/37/39-45

RIDADR 

2810

HS Code 

29215900

N,N-dimethyl-m-phenylenediamine Usage And Synthesis

Chemical Properties

Light yellow to black liquid

Synthesis

Step 2: Synthesis of N1,N1-dimethylbenzene-1,3-diamine N,N-dimethyl-3-nitroaniline (1.0 g, 6.08 mmol) prepared in Step 1 was dissolved in methanol (25 mL) and 10% palladium carbon (Pd/C, 100 mg) was added. The reaction mixture was hydrogenated in a hydrogen atmosphere for 15 hours at room temperature. Upon completion of the reaction, the palladium carbon catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated to dryness under reduced pressure. The resulting residue was purified by fast column chromatography (eluent: hexane/ethyl acetate=1:1, v/v) to afford N1,N1-dimethylbenzene-1,3-diamine (700 mg, yield: 90%, colorless liquid). 1H NMR (400MHz, CDCl3) δ: 7.04 (t, J=7.6Hz, 1H), 6.2 (d, J=8.0Hz, 1H), 6.11-6.08 (m, 1H), 3.60 (br s, 2H), 2.92 (s, 6H).

References

[1] Journal of Organic Chemistry, 1992, vol. 57, # 19, p. 5254 - 5255
[2] Patent: EP2364983, 2011, A2. Location in patent: Page/Page column 51-52
[3] Patent: US2011/218193, 2011, A1. Location in patent: Page/Page column 42
[4] Journal fuer Praktische Chemie (Leipzig), 1986, vol. 328, # 4, p. 497 - 514
[5] Patent: WO2010/67078, 2010, A2. Location in patent: Page/Page column 79

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