Product Name

  • Name

    4'-Hydroxy-4-biphenylcarbonitrile

  • EINECS 427-840-4
  • CAS No. 19812-93-2
  • Article Data37
  • CAS DataBase
  • Density 1.24 g/cm3
  • Solubility
  • Melting Point 192-199 °C
  • Formula C13H9NO
  • Boiling Point 379.8 °C at 760 mmHg
  • Molecular Weight 195.221
  • Flash Point 183.5 °C
  • Transport Information 3439
  • Appearance light yellow to beige crystalline powder
  • Safety 36/37/39-26-22-36/37-9-36
  • Risk Codes 36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 19812-93-2 (4'-Hydroxy-4-biphenylcarbonitrile)
  • Hazard Symbols HarmfulXn
  • Synonyms 4-Biphenylcarbonitrile,4'-hydroxy- (8CI);4-(4-Hydroxyphenyl)benzonitrile;4-Cyano-4'-hydroxybiphenyl;4-Hydroxy-4'-cyanobiphenyl;4'-Cyanobiphenyl-4-ol;4'-Hydroxy-4-biphenylylcarbonitrile;4'-Hydroxy-4-cyano-1,1'-biphenyl;4'-Hydroxy[1,1'-biphenyl]-4-carbonitrile;
  • PSA 44.02000
  • LogP 2.93088

Synthetic route

4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

(p-hydroxyphenyl)boronic acid
71597-85-8

(p-hydroxyphenyl)boronic acid

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With potassium phosphate; catacxium A; palladium diacetate In toluene at 100℃; for 20h; Suzuki cross-coupling reaction;99%
4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-4-carbonitrile
406482-72-2

4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-4-carbonitrile

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With potassium phosphate; potassium peroxymonosulphate In tetrahydrofuran; water at 25℃; for 1h;98%
With dihydrogen peroxide In tetrahydrofuran; water at 0 - 20℃; for 3h; Inert atmosphere; chemoselective reaction;39 mg
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-tert-butyl-dimethylsilyloxyphenylboronic acid anhydride
123088-32-4

4-tert-butyl-dimethylsilyloxyphenylboronic acid anhydride

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 95℃; Suzuki reaction;91%
4-cyano-3',5'-di-tert-butyl-4'-hydroxy-1,1'-biphenyl
114460-19-4

4-cyano-3',5'-di-tert-butyl-4'-hydroxy-1,1'-biphenyl

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With aluminium trichloride; toluene at 100℃; for 15h;90%
With aluminium trichloride In toluene
4'-methoxybiphenyl-4-carbonitrile
58743-77-4

4'-methoxybiphenyl-4-carbonitrile

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 20℃; Cooling with ice;90%
With aluminium(III) iodide In acetonitrile for 5h; Heating;80%
With iodine; aluminium In acetonitrile at 20℃; for 4h; Reflux;67%
With boron tribromide In dichloromethane at -78 - 20℃; for 16h;
4'-cyano-[1,1'-biphenyl]-4-yl acetate
127783-75-9

4'-cyano-[1,1'-biphenyl]-4-yl acetate

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 70 - 80℃; for 1h;89.2%
With potassium hydroxide In isopropyl alcohol Heating; Yield given;
4-Iodophenol
540-38-5

4-Iodophenol

4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With lithium hydroxide monohydrate; C29H40N2O3Pd In water; N,N-dimethyl-formamide at 50℃; for 24h; Suzuki-Miyaura Coupling;76%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h; Suzuki Coupling; Microwave irradiation;
With Pd/CaCO3; potassium carbonate In ethanol; water at 50℃; for 7h; Inert atmosphere;
4’-hydroxybiphenyl-4-carboxamide
182318-78-1

4’-hydroxybiphenyl-4-carboxamide

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
at 345℃; for 1h; Temperature;73%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-bromo-phenol
106-41-2

4-bromo-phenol

A

(1,1'-biphenyl)-4,4'-dicarbonitrile
1591-30-6

(1,1'-biphenyl)-4,4'-dicarbonitrile

B

4,4'-Dihydroxybiphenyl
92-88-6

4,4'-Dihydroxybiphenyl

C

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With NaH-t-AmONa-Ni(OAc)2-bpy-KI In tetrahydrofuran; benzene at 63℃; for 4h; Yields of byproduct given;A n/a
B n/a
C 70%
...Expand
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-bromo-phenol
106-41-2

4-bromo-phenol

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With [2,2]bipyridinyl; nickel diacetate; sodium hydride; potassium iodide In tetrahydrofuran; benzene at 63℃; for 4h;70%
4-bromo-phenol
106-41-2

4-bromo-phenol

4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
Stage #1: 4-bromo-phenol; 4-cyanophenylboronic acid With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran
Stage #2: With tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 48h;		55%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In water; isopropyl alcohol at 70℃; for 15h; Suzuki-Miyaura Coupling; Inert atmosphere;51%
Suzuki-Miyaura Coupling;
Stage #1: 4-bromo-phenol; 4-cyanophenylboronic acid With potassium carbonate In water at 25℃; for 0.25h; Suzuki-Miyaura Coupling;
Stage #2: With palladium dichloride In water at 25℃;
With palladium diacetate; potassium carbonate In ethanol; water at 25℃; for 2h; Suzuki-Miyaura Coupling;
4-phenoxybenzonitrile
3096-81-9

4-phenoxybenzonitrile

A

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

B

4-(3'-hydroxyphenyl)benzenecarbonitrile
127703-35-9

4-(3'-hydroxyphenyl)benzenecarbonitrile

C

phenol
108-95-2

phenol

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature; Irradiation;A 30%
B 43%
C 13%
...Expand
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

sodium phenoxide
139-02-6

sodium phenoxide

A

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

B

4-(3'-hydroxyphenyl)benzenecarbonitrile
127703-35-9

4-(3'-hydroxyphenyl)benzenecarbonitrile

Conditions
ConditionsYield
With ammonia; potassium bromide at -40℃; electrochemical reduction; Title compound not separated from byproducts;
...Expand
4-amino-4'-cyanobiphenyl
4854-84-6

4-amino-4'-cyanobiphenyl

4-Cyano-4'-hydroxybiphenyl
19812-93-2

4-Cyano-4'-hydroxybiphenyl

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite In acetic acid Heating;

4'-Hydroxy-4-biphenylcarbonitrile Specification

The IUPAC name of 4'-Hydroxy-4-biphenylcarbonitrile is 4-(4-hydroxyphenyl)benzonitrile. With the CAS registry number 19812-93-2, it is also named as 4-Cyano-4'-hydroxybiphenyl. The product's categories are Aromatic Compounds; Liquid Crystal Intermediates; Biphenyl Derivatives; Biphenyl & Diphenyl Ether; Heterocyclic Compounds; Benzonitriles (Building Blocks for Liquid Crystals); Biphenyls (Building Blocks for Liquid Crystals); Building Blocks for Liquid Crystals; Functional Materials; Building Block; Liquid Crystals; Organic Electronics and Photonics. It is light yellow to beige crystalline powder which should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.52; (4)ACD/LogD (pH 7.4): 2.51; (5)ACD/BCF (pH 5.5): 48.32; (6)ACD/BCF (pH 7.4): 47.88; (7)ACD/KOC (pH 5.5): 558.61; (8)ACD/KOC (pH 7.4): 553.47; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.652; (13)Molar Refractivity: 57.55 cm3; (14)Molar Volume: 157.3 cm3; (15)Polarizability: 22.81×10-24 cm3; (16)Surface Tension: 61.2 dyne/cm; (17)Enthalpy of Vaporization: 65.24 kJ/mol; (18)Vapour Pressure: 2.62E-06 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 2; (21)Exact Mass: 195.068414; (22)MonoIsotopic Mass: 195.068414; (23)Topological Polar Surface Area: 44; (24)Heavy Atom Count: 15; (25)Complexity: 239.

Preparation of 4'-Hydroxy-4-biphenylcarbonitrile: It can be obtained by 4-chloro-benzonitrile and 4-bromo-phenol. This reaction needs reagents NaH, Ni(OAc)2, bipyridyl, KI and solvents benzene, tetrahydrofuran at temperature of 63 °C. The reaction time is 4.0 hours. The yield is 70%.

Uses of 4'-Hydroxy-4-biphenylcarbonitrile: It is used as intermediate of liquid crystal. And it can react with 1-bromo-butane to get 4-butoxy-4'-cyano-biphenyl. This reaction needs reagent sodium isopropoxide and solvent propan-2-ol by heating. The reaction time is 1 hours. The yield is 71%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. 

People can use the following data to convert to the molecule structure.
1. SMILES:N#Cc1ccc(cc1)c2ccc(O)cc2
2. InChI:InChI=1/C13H9NO/c14-9-10-1-3-11(4-2-10)12-5-7-13(15)8-6-12/h1-8,15H
3. InChIKey:ZRMIETZFPZGBEB-UHFFFAOYAU

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