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| CAS No.: | 19812-93-2 |
|---|---|
| Name: | [1,1'-Biphenyl]-4-carbonitrile,4'-hydroxy- |
| Article Data: | 37 |
| Cas Database | |
| Molecular Structure: | |
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| Formula: | C13H9NO |
| Molecular Weight: | 195.221 |
| 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; |
| EINECS: | 427-840-4 |
| Density: | 1.24 g/cm3 |
| Melting Point: | 192-199 °C |
| Boiling Point: | 379.8 °C at 760 mmHg |
| Flash Point: | 183.5 °C |
| Solubility: | N/A |
| Appearance: | light yellow to beige crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 36/37/38-20/21/22 |
| Safety: | 36/37/39-26-22-36/37-9-36 |
| Transport Information: | 3439 |
| PSA: | 44.02000 |
| LogP: | 2.93088 |
4-Cyanochlorobenzene
(p-hydroxyphenyl)boronic acid
4-Cyano-4'-hydroxybiphenyl
| 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
4-Cyano-4'-hydroxybiphenyl
| 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
4-tert-butyl-dimethylsilyloxyphenylboronic acid anhydride
4-Cyano-4'-hydroxybiphenyl
| 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
4-Cyano-4'-hydroxybiphenyl
| Conditions | Yield |
|---|---|
| With aluminium trichloride; toluene at 100℃; for 15h; | 90% |
| With aluminium trichloride In toluene |
4'-methoxybiphenyl-4-carbonitrile
4-Cyano-4'-hydroxybiphenyl
| 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
4-Cyano-4'-hydroxybiphenyl
| Conditions | Yield |
|---|---|
| With sodium hydroxide In ethanol at 70 - 80℃; for 1h; | 89.2% |
| With potassium hydroxide In isopropyl alcohol Heating; Yield given; |
| 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
4-Cyano-4'-hydroxybiphenyl
| Conditions | Yield |
|---|---|
| at 345℃; for 1h; Temperature; | 73% |
4-Cyanochlorobenzene
4-bromo-phenol
A
(1,1'-biphenyl)-4,4'-dicarbonitrile
B
4,4'-Dihydroxybiphenyl
C
4-Cyano-4'-hydroxybiphenyl
| 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% |
| Conditions | Yield |
|---|---|
| With [2,2]bipyridinyl; nickel diacetate; sodium hydride; potassium iodide In tetrahydrofuran; benzene at 63℃; for 4h; | 70% |
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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%.
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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%.
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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
