4'-(Octyloxy)-4-biphenylcarbonitrile Chemical Properties

Melting point:

51-77 °C (lit.)

Boiling point:

447.93°C (rough estimate)

Density 

1.0505 (rough estimate)

refractive index 

1.5614 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

liquid crystal (Nematic)

color 

White to Almost white

InChI

InChI=1S/C21H25NO/c1-2-3-4-5-6-7-16-23-21-14-12-20(13-15-21)19-10-8-18(17-22)9-11-19/h8-15H,2-7,16H2,1H3

InChIKey

GPGGNNIMKOVSAG-UHFFFAOYSA-N

SMILES

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

NIST Chemistry Reference

Octyloxycyanobiphenyl(52364-73-5)

EPA Substance Registry System

[1,1'-Biphenyl]-4-carbonitrile, 4'-(octyloxy)- (52364-73-5)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DV1764500

TSCA 

TSCA listed

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich

4'-(Octyloxy)-4-biphenylcarbonitrile Usage And Synthesis

Chemical Properties

White Crysstalline

Uses

8CB may be used in the preparation of asymmetrical zinc phthalocyanine (aZnPc)-functional photocurable copolymer.

Uses

Intermediates of Liquid Crystals

General Description

4′-octyl-4- biphenylcarbonitrile (8CB) is a low molar mass liquid crystal (LCs), which shows different liquid crystalline phases depending on temperature conditions. Under normal temperature conditions 8CB exists only as bulk smectic-A phase. LCs are responsive to minor changes in temperature, shear, electric (or magnetic) fields, and the structure of solid surfaces with which they are in contact.

Synthesis

GENERAL STEPS: 4'-hydroxybiphenyl-4-carbonitrile (20.0 g, 0.1 mol), potassium carbonate (28.0 g, 0.2 mol) and N,N-dimethylformamide (600 mL) were added sequentially in a 1000 mL three-necked flask with magnetic stirring turned on. Subsequently, 1-bromooctane (23.0 g, 0.12 mol) was slowly added dropwise, and the reaction system was warmed to 120 °C and kept for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature, slowly poured into ice water (1000 mL) and allowed to stand overnight. The precipitated solid product was collected by filtration and purified by recrystallization with ethanol to afford the target compound 4'-octyloxy-[1,1'-biphenyl]-4-carbonitrile.

References

[1] Molecular Crystals and Liquid Crystals, 2008, vol. 480, # 1, p. 287 - 294
[2] Tetrahedron, 2012, vol. 68, # 39, p. 8172 - 8180
[3] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 268, p. 21 - 44
[4] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1192 - 1195
[5] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1310 - 1314

4'-(Octyloxy)-4-biphenylcarbonitrile(52364-73-5)Related Product Information

• 4-Aminobenzotrifluoride
• FIREMASTER BP-6
• BIFENAZATE
• Thiamethoxam
• trans-4-(4-Pentylcyclohexyl)benzonitrile
• 4-(4-ETHYLCYCLOHEXYL)BENZONITRILE
• trans-4-(4-Propylcyclohexyl)benzonitrile
• 4'-Butyl-4-biphenylcarbonitrile
• EBBA
• 4'-Heptyloxy-4-cyanobiphenyl
• Biphenyl
• 4-Cyanobiphenyl-4'-Trans-Propylcyclohexylcarboxylate
• 4'-(decyloxy)[1,1'-biphenyl]-4-carbonitrile
• 4'-(dodecyloxy)[1,1'-biphenyl]-4-carbonitrile
• 4'-(nonyloxy)[1,1'-biphenyl]-4-carbonitrile
• 4'-(Octyloxy)-4-biphenylcarbonitrile