3-Fluorophenylacetonitrile Chemical Properties

Melting point:

21 °C

Boiling point:

113-114 °C18 mm Hg(lit.)

Density 

1.163 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.502(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

powder to lump to clear liquid

color 

White or Colorles to Yellow to Orange

Specific Gravity

1.163

BRN 

1861071

Exposure limits

NIOSH: IDLH 25 mg/m3

InChI

InChI=1S/C8H6FN/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6H,4H2

InChIKey

DEJPYROXSVVWIE-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

501-00-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneacetonitrile, 3-fluoro-(501-00-8)

EPA Substance Registry System

Benzeneacetonitrile, 3-fluoro- (501-00-8)

Safety Information

Hazard Codes 

Xn,Xi,T

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39-24/25-36

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Toxic

TSCA 

T

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:3-Fluorobenzeneacetonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Fluorophenylacetonitrile Usage And Synthesis

Chemical Properties

clear light yellow to slightly brown liquid

Uses

3-Fluorophenylacetonitrile is a phenylacetonitrile derivative that is mainly used in pharmaceutical manufacturing or organic synthesis. It is used as a pharmaceutical intermediate for Lemborexant. The drug is a dual receptor orexin antagonist (DORA) approved for the treatment of primary insomnia.

Synthesis

General procedure for the synthesis of m-fluorophenylacetonitrile from compound (CAS: 773837-37-9) and 3-fluorobenzyl bromide: Compound 36-1 (1.0 g, 5.3 mmol) and sodium cyanide (520 mg, 10.6 mmol) were dissolved in dimethylsulfoxide (10 mL), and the reaction was stirred at 30 °C overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (50 mL). The organic phase was washed sequentially with water (10 mL x 5) and saturated sodium bicarbonate solution (20 mL), dried over anhydrous sodium sulfate and concentrated. The residue was purified by fast column chromatography to give product 36-2 as a colorless oil (360 mg, yield: 50%).

References

[1] Patent: WO2011/11522, 2011, A2. Location in patent: Page/Page column 57
[2] Patent: WO2012/79079, 2012, A1. Location in patent: Page/Page column 63

3-Fluorophenylacetonitrile(501-00-8)Related Product Information

• Copper(I) Cyanide
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• 3-NITROPHENYLACETONITRILE
• Florfenicol
• 3-Fluoroanisole
• 1,3-Difluorobenzene
• (3-Methoxyphenyl)acetonitrile
• Iminodiacetonitrile
• 3-Fluorophenethylamine
• 3'-Fluoroacetophenone
• POTASSIUM CYANIDE
• 2,5-DIFLUOROPHENYLACETONITRILE
• 2,3,4,5,6-PENTAFLUOROPHENYLACETONITRILE
• 3-FLUORO-5-(TRIFLUOROMETHYL)PHENYLACETONITRILE
• 3,4-Difluorophenylacetonitrile
• 5-FLUORO-2-NITROPHENYLACETONITRILE
• 3-FLUORO-4-METHOXYPHENYLACETONITRILE
• 2,4,5-Trifluorophenylacetonitrile