5-Fluoro-2-methylbenzonitrile

5-Fluoro-2-methylbenzonitrile Property

Melting point:

43-45 °C (lit.)

Boiling point:

230°C (rough estimate)

Density 

1.1203 (estimate)

Flash point:

175 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Light yellow to Light orange

BRN 

7700578

InChI

InChI=1S/C8H6FN/c1-6-2-3-8(9)4-7(6)5-10/h2-4H,1H3

InChIKey

IBRODYNXELBTJC-UHFFFAOYSA-N

SMILES

C(#N)C1=CC(F)=CC=C1C

CAS DataBase Reference

77532-79-7(CAS DataBase Reference)

NIST Chemistry Reference

5-Fluoro-2-methylbenzonitrile(77532-79-7)

Safety

Hazard Codes 

Xi,T

Risk Statements 

37/38-41

Safety Statements 

26-39

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

5-Fluoro-2-methylbenzonitrile Chemical Properties,Usage,Production

Uses

5-Fluoro-2-methylbenzonitrile is a yellow, low-melting-point solid that can be used as an intermediate in organic and pharmaceutical synthesis.

Chemical Properties

yellow low melting solid

General Description

5-Fluoro-2-methylbenzonitrile is an aryl fluorinated building block.

Synthesis

The general procedure for the synthesis of 5-fluoro-2-methylbenzonitrile from the compound (CAS: 953422-44-1) was as follows: aldoxime (1 mmol) and imidazole (3 mmol) were dissolved in anhydrous dichloromethane (10-15 mL) under nitrogen protection, added to a pre-oven-dried round-bottomed flask, and the reaction mixture was stirred at room temperature.After 20 min, the reaction mixture was stirred via syringe under After 20 min, trifluoromethanesulfonic anhydride (0.4-1.0 mmol) was slowly added dropwise via syringe under nitrogen protection and the reaction mixture was continued to be stirred at room temperature for a specific time (see Table 1). The reaction process was monitored by thin layer chromatography (TLC) and/or gas chromatography-mass spectrometry (GC-MS). Upon completion of the reaction, the reaction was quenched with dilute sodium bicarbonate (NaHCO3) solution and the product was extracted with dichloromethane. The solvent was removed by concentration under reduced pressure to give the crude product, which was subsequently purified by preparative thin-layer chromatography (TLC) using a solvent mixture of ethyl acetate-hexane (80:20) to give the target nitrile analogs in 61-88% yield. The structure of the products was confirmed by melting point (mp) or boiling point (bp), TLC, infrared spectroscopy (IR), GC-MS, 1H nuclear magnetic resonance (NMR), and 13C NMR data in comparison with authentic samples commercially purchased or prepared by literature methods.

References

[1] Tetrahedron Letters, 2011, vol. 52, # 40, p. 5184 - 5187