19812-93-2

Basic information

• Product Name: 4'-Hydroxy-4-biphenylcarbonitrile
• Synonyms: 4'-HYDROXYBIPHENYL-4-CARBONITRIL;4'-HYDROXYBIPHENYL-4-CARBONITRILE;4'-HYDROXY[1,1'-BIPHENYL]-4-CARBONITRILE;4'-HYDROXY-4-BIPHENYLCARBONITRILE;4-HYDROXY-4'-CYANOBIPHENYL;4-CYANO-4'-HYDROXY-1,1'-BIPHENYL;4-CYANO-4'-HYDROXYBIPHENYL;4-CYAN-4'-HYDROXYBIPHENYL
• CAS NO: 19812-93-2
• Molecular Formula: C₁₃H₉NO
• Molecular Weight: 195.22
• EINECS: 427-840-4
• Product Categories: 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
• Mol File: 19812-93-2.mol
• Article Data: 35

Chemical Properties

• Melting Point: 192-199 °C
• Boiling Point: 331.88°C (rough estimate)
• Flash Point: 183.5 °C
• Appearance: Light yellow to beige/Crystalline Powder
• Density: 1.1266 (rough estimate)
• Vapor Pressure: 0.022 hPa (20 °C)
• Refractive Index: 1.6060 (estimate)
• Storage Temp.: Room temperature.
• Solubility: 12.7g/l no data available
• PKA: 9.43±0.26(Predicted)
• CAS DataBase Reference: 4'-Hydroxy-4-biphenylcarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Hydroxy-4-biphenylcarbonitrile(19812-93-2)
• EPA Substance Registry System: 4'-Hydroxy-4-biphenylcarbonitrile(19812-93-2)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22-36/37-9-36
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 19812-93-2(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to beige crystalline powder

Uses

Intermediates of Liquid Crystals

Synthetic route

4-Cyanochlorobenzene (623-03-0) + (p-hydroxyphenyl)boronic acid (71597-85-8) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
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-Cyano-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
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-tert-butyl-dimethylsilyloxyphenylboronic acid anhydride (123088-32-4) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
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-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
With aluminium trichloride; toluene at 100℃; for 15h;	90%
With aluminium trichloride In toluene

4'-methoxybiphenyl-4-carbonitrile (58743-77-4) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
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-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
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-cyanophenylboronic acid (126747-14-6) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
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-Cyano-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
at 345℃; for 1h; Temperature;	73%

4-Cyanochlorobenzene (623-03-0) + 4-bromo-phenol (106-41-2) → (1,1'-biphenyl)-4,4'-dicarbonitrile (1591-30-6) + 4,4'-Dihydroxybiphenyl (92-88-6) + 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
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%

4-Cyanochlorobenzene (623-03-0) + 4-bromo-phenol (106-41-2) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
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-cyanophenylboronic acid (126747-14-6) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Conditions	Yield
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-Cyano-4'-hydroxybiphenyl (19812-93-2) + 4-(3'-hydroxyphenyl)benzenecarbonitrile (127703-35-9) + phenol (108-95-2)

Conditions	Yield
In ethanol for 2h; Ambient temperature; Irradiation;	A 30% B 43% C 13%

4-Cyanochlorobenzene (623-03-0) + sodium phenoxide (139-02-6) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2) + 4-(3'-hydroxyphenyl)benzenecarbonitrile (127703-35-9)

Conditions	Yield
With ammonia; potassium bromide at -40℃; electrochemical reduction; Title compound not separated from byproducts;

4-amino-4'-cyanobiphenyl (4854-84-6) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

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

Upstream product

• 4854-84-6 4-amino-4'-cyanobiphenyl 
• 111278-47-8 C₁₃H₉N₃S 
• 16909-23-2 tetra-n-butylammonium phenolate 
• 127783-75-9 4'-cyano-[1,1'-biphenyl]-4-yl acetate 
• 29577-88-6 (Z)-tert-Butyl (4-cyanophenyl)azo sulfide 
• 108-95-2 phenol 
• 132555-11-4 (E)-(4-Cyanophenyl)azo phenyl sulfide 
• 540-38-5 p-Iodophenol 
• 126747-14-6 4-cyanophenylboronic acid 
• 106-41-2 4-bromo-phenol 
• 58666-77-6 (4-cyanophenyl)trimethylstannane 
• 873-74-5 4-Aminobenzonitrile 
• 106-37-6 1.4-dibromobenzene 
• 58743-77-4 4'-methoxybiphenyl-4-carbonitrile 

Downstream Products

• 58743-77-4 4'-methoxybiphenyl-4-carbonitrile 
• 52364-73-5 4-octyloxy-4'-cyanobiphenyl 
• 115498-57-2 4-Propyl-cyclohex-1-enecarboxylic acid 4'-cyano-biphenyl-4-yl ester 
• 174660-49-2 4'-[6-(2-Nitro-phenoxy)-hexyloxy]-biphenyl-4-carbonitrile 
• 323208-14-6 propynoic acid 4'-cyano-biphenyl-4-yl ester 

Relevant articles and documents

Design of a facile fluorescent probe with a large Stokes shift for hydrogen peroxide imaging in vitro and in vivo

By modifying 4′?hydroxybiphenyl?4?carbonitrile (BPN-OH) with 2?(4?(bromo?methyl)phenyl)?4,4,5,5?tetramethyl?1,3,2?dioxaborolane group, a facile fluorescent probe, BPN-TOB, for sensitively tracing H2O2 was designed and synthesized. BPN-TOB displayed a low detection limit (67 nM), fast response time (10 min), low cytotoxicity, a mega Stokes shift (170 nm) and a remarkable fluorescence enhancement (72-fold) in the detection of H2O2. Additionally, probe BPN-TOB could monitor exogenous and endogenous H2O2 in living MGC-803 cells (human gastric cancer cells) and RAW264.7 cells (leukemia cellsin mouse macrophage). In particular, this probe BPN-TOB was successfully utilized for imaging H2O2 in zebrafish.

A simple but effective fluorescent probe with large stokes shift for specific detection of cysteine in living cells

A novel 4′-hydroxybiphenyl-4-carbonitrile-based fluorescent probe, 1, for selective detection of cystein (Cys) over homocystein (Hcy) and glutathione (GSH) was developed. This probe had simple structure and could be easily synthesized with good yield from commercially available materials. Moreover, probe 1 showed a remarkable large Stokes shift (180 nm) and displayed a rapid (5 min) and highly sensitive response (the detection limit was 0.15 μM) for Cys with fluorescence turn-on signal changes (142-fold fluorescence enhancement). Importantly, probe 1 could be used to detect and image both exogenous and endogenous Cys in living A549 cells.

A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls

A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described. The tandem reaction proceeds efficiently at room temperature, and various biaryls and biaryl fluorosulfates were obtained in good to excellent yields. Furthermore, biaryl fluorosulfates were utilized as versatile building blocks for the preparation of terphenyls. The Royal Society of Chemistry 2020.

Synthesis of Aryl Trimethylstannane via BF3·OEt2-Mediated Cross-Coupling of Hexaalkyl Distannane Reagent with Aryl Triazene at Room Temperature

BF3·OEt2-mediated cross-coupling of (SnMe3)2 with aryl triazene offers a new strategy for the synthesis of aryl stannane. A variety of synthetically useful aryl trimethylstannanes were produced in moderate to good yields with this metal-free approach. One-pot sequential Stille cross-coupling with different aryl bromides provides a short entry to both symmetrical and unsymmetrical biaryl compounds.