N,N-DIMETHYL-PHENYLENEDIAMINE

N,N-DIMETHYL-PHENYLENEDIAMINE Property

Boiling point:

240.49°C (rough estimate)

Density 

1.049

refractive index 

1.5914 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

7.19±0.18(Predicted)

Appearance

Colorless to light pink Liquid

EPA Substance Registry System

1,2-Benzenediamine, N,N-dimethyl- (2836-03-5)

Safety

HazardClass 

IRRITANT

HS Code 

2921519090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P271Use only outdoors or in a well-ventilated area.

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

N,N-DIMETHYL-PHENYLENEDIAMINE Chemical Properties,Usage,Production

Synthesis

(a) Synthesis of N,N-dimethyl-o-phenylenediamine. N,N-dimethyl-2-nitroaniline (1.00 g, 6.02 mmol), ethanol (22 mL) and ethyl acetate (60 mL) were added to a hydrogenation reaction flask. To the resulting orange solution was added 5% palladium/carbon catalyst (0.67 g), followed by triple degassing of the black suspension and charging with hydrogen (50 psi). After shaking the reaction mixture for 5 h at room temperature, it was filtered through a diatomaceous earth pad (2 in. x 1.5 in.), the filter cake was washed with ethyl acetate (50 mL), and the filtrate was concentrated to obtain an orange residue. Purification by fast column chromatography (silica gel, eluent ethyl acetate:hexane = 1:15) afforded 0.73 g (89% yield) of N,N-dimethyl-o-phenylenediamine as an orange oil: 1H-NMR (CDCl3) δ 7.00 (dd, J = 7.8 and 1.5 Hz, 1H), 6.90 (td, J = 7.6 and 1.5 Hz, 1H). 6.76-6.68 (m, 2H), 3.93 (br s, 2H), 2.65 (s, 6H). (b) Synthesis of N-(2-dimethylaminophenyl)-9-oxo-9H-fluorene-1-carboxamide. Referring to the method of Example 9, the reaction of N,N-dimethylphthalimide (0.281 g, 2.06 mmol) with 9-oxo-9H-fluorene-1-carbamoyl chloride (0.500 g, 2.06 mmol) afforded 0.356 g (50% yield) of the target product as a brown solid: melting point 152-155°C; 1H-NMR (CDCl3) δ 10.77 (br s, 1H), 8.42-8.40 (m, 1H), 8.06 (d, J=8.2Hz, 1H), 7.72-7.54 (m, 5H), 7.36-7.33 (m, 1H), 7.18-7.12 (m, 3H), 2.70 (s, 6H).

References

[1] Dalton Transactions, 2011, vol. 40, # 35, p. 8906 - 8911
[2] Organic Letters, 2012, vol. 14, # 24, p. 6366 - 6369
[3] Patent: WO2006/39356, 2006, A2. Location in patent: Page/Page column 36
[4] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 9, p. 2730 - 2734
[5] Patent: US2007/254894, 2007, A1. Location in patent: Page/Page column 22