4-Cyano-4'-pentylbiphenyl Chemical Properties

Melting point:

34 °C

Boiling point:

140-150 °C0.5 mm Hg(lit.)

Density 

1.008 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.532(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

liquid crystal (nematic)

color 

Off-White

Water Solubility 

insoluble

InChI

InChI=1S/C18H19N/c1-2-3-4-5-15-6-10-17(11-7-15)18-12-8-16(14-19)9-13-18/h6-13H,2-5H2,1H3

InChIKey

HHPCNRKYVYWYAU-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(CCCCC)C=C2)=CC=C(C#N)C=C1

CAS DataBase Reference

40817-08-1(CAS DataBase Reference)

NIST Chemistry Reference

[1,1'-Biphenyl]-4-carbonitrile, 4'-pentyl-(40817-08-1)

EPA Substance Registry System

[1,1'-Biphenyl]-4-carbonitrile, 4'-pentyl- (40817-08-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

23-26-28-36-36/37/39

RIDADR 

3276

WGK Germany 

3

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

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

4-Cyano-4'-pentylbiphenyl Usage And Synthesis

Chemical Properties

white to light yellow crysta

Uses

4-Cyano-4'-n-pentylbiphenyl is used in the preparation of 4'-pentylbiphenyl-4-carboxylic acid by acidic hydrolysis using sulfuric acid as a reagent.

Uses

Intermediates of Liquid Crystals

General Description

4′-Pentyl-4-biphenylcarbonitrile (5CB) is a nematic liquid crystal. 5CB undergoes phase transition from crystalline to nematic then to isotropic state at 18^oC and 35^oC respectively. It may be produced by modifying biphenyl.2

Synthesis

General procedure for the synthesis of 4'-n-pentyl-4-cyanobiphenyl from p-bromopentyl biphenyl: To a dry flask containing magnesium shavings (0.29 g, 12 mmol) was added a solution of 1-bromo-4-methylbenzene (1.37 g, 8.0 mmol) in tetrahydrofuran (THF, 8 mL) at room temperature. After stirring the reaction mixture for 2 h, N,N-dimethylformamide (DMF, 1.3 mL, 12 mmol) was slowly added. The reaction mixture was cooled to 0°C and stirring was continued for 2 hours. Subsequently, ammonia solution (7 mL, 28-30%) and iodine (I2, 4.06 g, 16 mmol) were added to the reaction system. After stirring the reaction mixture for 2 h at room temperature, it was poured into saturated aqueous sodium sulfite (Na2SO3) solution and extracted with chloroform (CHCl3, 3 x 30 mL). The organic layers were combined, dried with anhydrous sodium sulfite (Na2SO4) and filtered. After the solvent was removed by distillation under reduced pressure, the residue was purified by silica gel short column chromatography (eluent: hexane/ethyl acetate = 9:1, v/v) to afford pure 4-methylbenzonitrile (0.77 g) in 82% yield.

References

[1] Tetrahedron, 2013, vol. 69, # 5, p. 1462 - 1469

4-Cyano-4'-pentylbiphenyl(40817-08-1)Related Product Information

• 2,3,3',4,4',5-HEXACHLOROBIPHENYL
• Bifendate
• Benzonitrile
• Cyclopentanecarbaldehyde
• Bifenthrin
• Biphenyl
• TERT-AMYL METHYL ETHER
• 4-Cyanobiphenyl
• CYCLOPENTYLMAGNESIUM CHLORIDE
• 2-Chlorophenyl cyclopentyl ketone
• trans-4'-(4-Pentylcyclohexyl)-4-biphenylcarbonitrile
• 4-CYANO-4'-DODECYLBIPHENYL
• 4'-Octyl[1,1'-biphenyl]-4-carbonitrile
• 4'-HEXYL-4-BIPHENYLCARBONITRILE
• 10CB
• 4'-Heptyl-4-biphenylcarbonitrile
• 4'-(trans-4-Propylcyclohexyl)-[1,1'-biphenyl]-4-carbonitrile
• 4-N-PENTYLBIPHENYL