Product Name

  • Name

    4-Cyano-4'-ethylbiphenyl

  • EINECS 261-414-7
  • CAS No. 58743-75-2
  • Article Data12
  • CAS DataBase
  • Density 1.07 g/cm3
  • Solubility insoluble in water
  • Melting Point 74-76°C
  • Formula C15H13N
  • Boiling Point 354 °C at 760 mmHg
  • Molecular Weight 207.275
  • Flash Point 168.7 °C
  • Transport Information UN 3276
  • Appearance White crystalline powder
  • Safety 26-36/37/39
  • Risk Codes 20/21-36/37/38-41-20/21/22
  • Molecular Structure Molecular Structure of 58743-75-2 (4-Cyano-4'-ethylbiphenyl)
  • Hazard Symbols HarmfulXn
  • Synonyms 4-Ethyl-4'-cyanobiphenyl;CB 2;CB 2 (nematogen);
  • PSA 23.79000
  • LogP 3.78768

Synthetic route

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-ethylphenylboronic acid
63139-21-9

4-ethylphenylboronic acid

4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

Conditions
ConditionsYield
With potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 2.3h; Suzuki Coupling;98%
Stage #1: 4-bromobenzenecarbonitrile; 4-ethylphenylboronic acid With potassium carbonate In dimethyl sulfoxide at 70℃; for 0.583333h; Suzuki Coupling;
Stage #2: for 0.583333h; Catalytic behavior;		98%
With potassium carbonate In ethanol; water at 100℃; for 0.666667h; Suzuki-Miyaura Coupling;97%
With palladium on activated charcoal at 100℃; for 2h; Suzuki Coupling;95%
With potassium carbonate In dimethyl sulfoxide at 80℃; for 2h; Catalytic behavior; Suzuki Coupling;84%
4'-vinyl-[1,1'-biphenyl]-4-carbonitrile
94315-55-6

4'-vinyl-[1,1'-biphenyl]-4-carbonitrile

4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

Conditions
ConditionsYield
With 1,4-dioxane; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(dicyclohexylphosphino)ethane at 130℃; for 10h; Inert atmosphere; Sealed tube; chemoselective reaction;98%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-ethylphenylboronic acid
63139-21-9

4-ethylphenylboronic acid

4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

Conditions
ConditionsYield
With potassium carbonate In water at 100℃; for 0.916667h; Suzuki-Miyaura Coupling;95%
4-ethylphenylboronic acid
63139-21-9

4-ethylphenylboronic acid

4-cyanophenol
767-00-0

4-cyanophenol

4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

Conditions
ConditionsYield
Stage #1: 4-cyanophenol With fluorosulfonyl fluoride; triethylamine In ethanol; water at 20℃; for 4h;
Stage #2: 4-ethylphenylboronic acid With palladium diacetate; triethylamine In ethanol; water at 20℃; for 6h;		95%
4-ethyl-1-iodobenzene
25309-64-2

4-ethyl-1-iodobenzene

4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 50℃; for 1.1h; Catalytic behavior; Suzuki-Miyaura Coupling;95%
With potassium carbonate In ethanol; water at 50℃; for 1.4h; Catalytic behavior; Suzuki-Miyaura Coupling;90%
With potassium carbonate In ethanol; water at 70℃; for 9h; Catalytic behavior; Suzuki-Miyaura Coupling;72%
p-ethylphenylmagnesium bromide
22873-28-5

p-ethylphenylmagnesium bromide

4-halobenzonitrile

4-halobenzonitrile

4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

Conditions
ConditionsYield
With palladium diacetate; zinc dibromide; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 20 - 25℃; for 2.5h; Inert atmosphere;84%
1-bromo-4-(4'-ethylphenyl)benzene
58743-79-6

1-bromo-4-(4'-ethylphenyl)benzene

copper(I) cyanide
544-92-3

copper(I) cyanide

4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one
4-bromo-4'-acetylbiphenyl
5731-01-1

4-bromo-4'-acetylbiphenyl

4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3, LiAlH4
2: 1-methyl-pyrrolidin-2-one
View Scheme
methanesulfonamide
3144-09-0

methanesulfonamide

4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

N-(1-(4'-cyano-[1,1'-biphenyl]-4-yl)ethyl)methanesulfonamide

N-(1-(4'-cyano-[1,1'-biphenyl]-4-yl)ethyl)methanesulfonamide

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In 1,2-dichloro-ethane at 20℃; for 2.5h; Electrochemical reaction; Inert atmosphere; regioselective reaction;66%
4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

4-(4-ethylphenyl)benzoic acid
5731-13-5

4-(4-ethylphenyl)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide
4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

4-(4-ethylphenyl)-benzoic acid 4'-methoxyphenyl ester

4-(4-ethylphenyl)-benzoic acid 4'-methoxyphenyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide
2: (i) SOCl2, (ii) /BRN= 507924/, Py
View Scheme
4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

4-(4-ethylphenyl)-benzoic acid 4'-ethoxyphenyl ester

4-(4-ethylphenyl)-benzoic acid 4'-ethoxyphenyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide
2: (i) SOCl2, (ii) /BRN= 1907114/, Py
View Scheme
4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

4-(4-ethylphenyl)-benzoic acid 4'-n-butylphenyl ester

4-(4-ethylphenyl)-benzoic acid 4'-n-butylphenyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide
2: sulfuric acid; boric acid
View Scheme
4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

N-butyl-11-(4-ethylphenyl)-5H-isochromeno[3,4-c]isoquinolin-8-amine

N-butyl-11-(4-ethylphenyl)-5H-isochromeno[3,4-c]isoquinolin-8-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aluminum (III) chloride / 0.75 h / 140 °C / Inert atmosphere; Schlenk technique; Sealed tube
2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate / acetonitrile / 12 h / 120 °C / Inert atmosphere; Schlenk technique; Sealed tube
View Scheme
4-ethyl-4'-cyanobiphenyl
58743-75-2

4-ethyl-4'-cyanobiphenyl

N-butylamine
109-73-9

N-butylamine

C19H24N2

C19H24N2

Conditions
ConditionsYield
With aluminum (III) chloride at 140℃; for 0.75h; Inert atmosphere; Schlenk technique; Sealed tube;

4-Cyano-4'-ethylbiphenyl Chemical Properties


IUPAC Name: 4-(4-Ethylphenyl)benzonitrile  
Empirical Formula: C15H13N
Molecular Weight: 207.2704
Canonical SMILES: CCC1=CC=C(C=C1)C2=CC=C(C=C2)C#N
InChI: InChI=1S/C15H13N/c1-2-12-3-7-14(8-4-12)15-9-5-13(11-16)6-10-15/h3-10H,2H2,1H3
EINECS: 261-414-7 
Water Solubility: insoluble 
Index of Refraction: 1.593
Molar Refractivity: 65.28 cm3
Molar Volume: 192.5 cm3
Surface Tension: 46.6 dyne/cm
Density: 1.07 g/cm3
Flash Point: 168.7 °C
Enthalpy of Vaporization: 59.9 kJ/mol
Boiling Point: 354 °C at 760 mmHg
Vapour Pressure: 3.45E-05 mmHg at 25 °C
Product Categories: Biphenyl derivatives; Biphenyl & Diphenyl ether 
Melting Point of 4-Cyano-4'-ethylbiphenyl (CAS NO.58743-75-2): 74-76 °C

4-Cyano-4'-ethylbiphenyl Uses

  4-Cyano-4'-ethylbiphenyl (CAS NO.58743-75-2) is used as intermediates of liquid crystals.

4-Cyano-4'-ethylbiphenyl Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 20/21-36/37/38-41-20/21/22 
R20/21:Harmful by inhalation and in contact with skin. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R41:Risk of serious damage to the eyes. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: 3276
HazardClass: 6.1
PackingGroup of 4-Cyano-4'-ethylbiphenyl (CAS NO.58743-75-2): III

4-Cyano-4'-ethylbiphenyl Specification

  4-Cyano-4'-ethylbiphenyl (CAS NO.58743-75-2), its Synonyms are (1,1'-Biphenyl)-4-carbonitrile, 4'-ethyl- ; 4'-Ethyl(1,1'-biphenyl)-4-carbonitrile ; 1'-Biphenyl-4-carbonitrile,4'-ethyl- . It is white crystalline powder.

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