52709-83-8

Basic information

• Product Name: 4'-Butyl-4-biphenylcarbonitrile
• Synonyms: 4-N-BUTYL-4'-CYANOBIPHENYL;4'-N-BUTYLBIPHENYL-4-CARBONITRILE;4'-BUTYL-4-BIPHENYLCARBONITRILE;4-BUTYL-4'-CYANOBIPHENYL;4CB;4-CYANO-4'-BUTYL BIPHENYL;TIMTEC-BB SBB008623;1’-biphenyl]-4-carbonitrile,4’-butyl-[
• CAS NO: 52709-83-8
• Molecular Formula: C₁₇H₁₇N
• Molecular Weight: 235.32
• EINECS: 258-119-0
• Product Categories: Biphenyl & Diphenyl ether
• Mol File: 52709-83-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 49-51°C
• Boiling Point: 210-212°C 2mm
• Flash Point: 210-212°C/2mm
• Appearance: /
• Density: 1.04 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 4'-Butyl-4-biphenylcarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Butyl-4-biphenylcarbonitrile(52709-83-8)
• EPA Substance Registry System: 4'-Butyl-4-biphenylcarbonitrile(52709-83-8)

Safety Data

• Statements: 20/21/22-36/37/38-65-20/21
• Safety Statements: 26-36/37/39-60-36/37-9
• RIDADR: 3276
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 52709-83-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline

Uses

Intermediates of Liquid Crystals

Synthetic route

Cu2(CN)2 → 4'-n-butyl-4-cyanobiphenyl (52709-83-8)

Conditions	Yield
With iodophenylbis(triphenylphosphine)palladium In N,N-dimethyl-formamide for 2h; Heating;	91%

4'-Butyl-biphenyl-4-carbaldehyde oxime (93972-13-5) → 4'-n-butyl-4-cyanobiphenyl (52709-83-8)

Conditions	Yield
With acetic anhydride for 2h; Heating;	70%

terephthalonitrile (623-26-7) + 1-bromo-butane (109-65-9) + benzonitrile (100-47-0) → (1,1'-biphenyl)-4,4'-dicarbonitrile (1591-30-6) + 1-butylbenzene (104-51-8) + 4'-n-butyl-4-cyanobiphenyl (52709-83-8) + 4-butylbenzonitrile (20651-73-4)

Conditions	Yield
Stage #1: terephthalonitrile With sodium In ammonia at -33℃; Stage #2: benzonitrile In ammonia for 0.5h; Stage #3: 1-bromo-butane In ammonia for 1.5h;	A 15% B 9% C 56% D 8%

terephthalonitrile (623-26-7) + 1-bromo-butane (109-65-9) + benzonitrile (100-47-0) → (1,1'-biphenyl)-4,4'-dicarbonitrile (1591-30-6) + 4'-n-butyl-4-cyanobiphenyl (52709-83-8) + 4-butylbenzonitrile (20651-73-4) + 1-butyl-1-cyanocyclohexa-2,5-diene (134785-03-8)

Conditions	Yield
Stage #1: terephthalonitrile With sodium In ammonia at -33℃; Stage #2: 1-bromo-butane; benzonitrile In ammonia	A 8% B 30% C 10% D 3%

biphenyl (92-52-4) → 4'-n-butyl-4-cyanobiphenyl (52709-83-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: AlCl3 / CH2Cl2 / 5 h / Ambient temperature 2: 1) hydrazine hydrate, 2) KOH / 1) diethylene glycol, 130 deg C, 1 h, 2) diethylene glycol, 130 deg C, 2 h, then 160 deg C, 3 h 3: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 4: 70 percent / acetic anhydride / 2 h / Heating View Scheme

4-butylbiphenyl (37909-95-8) → 4'-n-butyl-4-cyanobiphenyl (52709-83-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 2: 70 percent / acetic anhydride / 2 h / Heating View Scheme

1-([1,1'-biphenyl]-4-yl)butan-1-one (13211-01-3) → 4'-n-butyl-4-cyanobiphenyl (52709-83-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) hydrazine hydrate, 2) KOH / 1) diethylene glycol, 130 deg C, 1 h, 2) diethylene glycol, 130 deg C, 2 h, then 160 deg C, 3 h 2: 1) TiCl4, 2) hydroxylamine hydrochloride, pyridine / 1) CH2Cl2, 0 deg C, 30 min, 2) ethanol, reflux, 2 h 3: 70 percent / acetic anhydride / 2 h / Heating View Scheme

1-bromo-butane (109-65-9) + C14H9N2(1-) → 4'-n-butyl-4-cyanobiphenyl (52709-83-8)

Conditions	Yield
at -33℃; for 1.5h;

4'-n-butyl-4-cyanobiphenyl (52709-83-8) → 4-butylbiphenyl (37909-95-8)

Conditions	Yield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; ethanol; potassium hexamethylsilazane In toluene at 150℃; for 8h; Inert atmosphere; Molecular sieve;	73%

4'-n-butyl-4-cyanobiphenyl (52709-83-8) → 4’-butyl-[1,1 ‘-biphenyl]-4-carboxylic acid (59662-46-3)

Conditions	Yield
With sodium hydroxide

4'-n-butyl-4-cyanobiphenyl (52709-83-8) → 4'-butyl-[1,1'-biphenyl]-4-carbaldehyde (93972-06-6)

Conditions	Yield
With formic acid; aluminum nickel for 8h; Heating;

4'-n-butyl-4-cyanobiphenyl (52709-83-8) → 4-(4-n-butylphenyl)-benzoic acid 4'-methoxyphenyl ester (61733-31-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide 2: (i) SOCl2, (ii) /BRN= 507924/, Py View Scheme

4'-n-butyl-4-cyanobiphenyl (52709-83-8) → 4'-Butyl-biphenyl-4-carboxylic acid 4-pentyl-phenyl ester (61733-14-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide 2: sulfuric acid; boric acid View Scheme

4'-n-butyl-4-cyanobiphenyl (52709-83-8) → 4-butylbiphenyl (37909-95-8) + 4-butyl-1,1'-biphenyl-4'-d

Conditions	Yield
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; ethanol-d6; potassium hexamethylsilazane In toluene at 150℃; Inert atmosphere; Molecular sieve;

Upstream product

• 623-26-7 terephthalonitrile 
• 109-65-9 1-bromo-butane 
• 100-47-0 benzonitrile 
• 13211-01-3 1-([1,1'-biphenyl]-4-yl)butan-1-one 
• 37909-95-8 4-butylbiphenyl 
• 92-52-4 biphenyl 
• 93972-13-5 4'-Butyl-biphenyl-4-carbaldehyde oxime 

Downstream Products

• 59662-46-3 4’-butyl-[1,1 ‘-biphenyl]-4-carboxylic acid 
• 93972-06-6 4'-butyl-[1,1'-biphenyl]-4-carbaldehyde 

Relevant articles and documents

One-pot synthesis of 4?-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling

A convenient one-pot approach to alkylcyanobiaryls is described. The method is based on biaryl cross-coupling between the sodium salt of the terephthalonitrile dianion and a neutral aromatic nitrile in liquid ammonia, and successive alkylation of the long

Synthesis of Mesogenic Compounds, Catalyzed by Metal Complexes. I. Monoalkylation and Monoarylation of 1,4-Dibromobenzene in the Synthesis of 4-n-Alkyl- and 4-n-Alkoxy-4'-Cyanobiphenyls Catalyzed by Palladium

New methods of synthesis of mesomorphic 4-n-alkyl- and 4-n-alkoxy-4'-cyanobiphenyls are developed, based on the palladium catalyzed highly selective reactions of 1,4-dibromobenzene with alkyl and aryl Grignard reagents.