2-METHYL-5-NITROBENZONITRILE Chemical Properties

Melting point:

103.5-107.5 °C (lit.)

Boiling point:

175°C/10mmHg(lit.)

Density 

1.3264 (rough estimate)

refractive index 

1.5770 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

ethanol: soluble(lit.)

form 

powder to crystal

color 

White to Light yellow

BRN 

1947376

CAS DataBase Reference

939-83-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

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

2-METHYL-5-NITROBENZONITRILE Usage And Synthesis

Chemical Properties

Light yellow crystalline

Uses

2-Methyl-5-nitrobenzonitrile was used in the preparation of 5-(2-methyl-5-nitrophenyl)-1H-tetrazole.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 4971, 1984 DOI: 10.1016/S0040-4039(01)91273-0

General Description

2-Methyl-5-nitrobenzonitrile is an aralkyl nitrile. It is formed by nitration of o-toluonitrile with NO₂⁺BF₄^-. Crystal structure of 2-methyl-5-nitrobenzonitrile is stabilized by van der Waals interactions.

Synthesis

Using 2-bromo-4-nitrotoluene (250.0 g, 1.16 mol) and zinc cyanide (135.0 g, 1.16 mol) as raw materials, both were mixed with tetrakis(triphenylphosphine)palladium (25 g, 0.02 mol) in anhydrous N,N-dimethylformamide (1500 mL) under nitrogen protection. The reaction mixture was stirred at 80°C for 24 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding reagent ratio of petroleum ether:ethyl acetate = 10:1), and after confirming the completion of the reaction, the mixture was poured into toluene (1500 mL) and washed with 2N ammonia (800 mL x 2). The aqueous layer was back-extracted with toluene (800 mL x 2). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography (first eluted with petroleum ether, then with a mixed solvent of petroleum ether:ethyl acetate=10:1) to give 2-methyl-5-nitrobenzonitrile (25.5 g, 42% yield) as a gray solid and recovered unreacted 2-bromo-4-nitrotoluene (170 g) as a yellow solid. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 8.46-8.47 (d, J=3.0 Hz, 1H), 8.31-8.34 (dd, J=9.0 Hz, 1H), 7.53-7.56 (d, J=9.0 Hz, 1H), 2.68 (s, 3H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6273 - 6278
[2] Patent: WO2006/117669, 2006, A1. Location in patent: Page/Page column 41; 113

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