4-cyanophenyl acetate
4-cyanophenol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.25h; Hydrolysis; Heating; | 100% |
With potassium hydroxide In ethanol for 0.333333h; Heating; | 88% |
With sodium tetrahydroborate; cobalt(II) chloride In ethanol at 0 - 25℃; for 10h; | 83% |
With N-butylamine; Tetraethylene glycol dimethyl ether In chlorobenzene at 25℃; Rate constant; efficacy of glyme catalysis, other glymes; |
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride at 100℃; for 0.25h; Condensation; microwave irradiation; | 100% |
With oxygen; copper; ammonium chloride In pyridine at 60℃; for 24h; | 99% |
With sodium azide; trifluorormethanesulfonic acid In acetonitrile at 20℃; for 0.0333333h; Schmidt reaction; | 99% |
Conditions | Yield |
---|---|
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h; | 100% |
With sodium methylate; 1-dodecylthiol In N,N-dimethyl-formamide at 100℃; for 1h; | 97% |
With cyclohexa-1,4-diene; 3,6-bis(dimethylamino)-9H-carbazole; caesium carbonate In dimethyl sulfoxide at 23℃; for 48h; Inert atmosphere; Schlenk technique; Irradiation; | 94% |
4-allyloxy-benzonitrile
4-cyanophenol
Conditions | Yield |
---|---|
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h; | 100% |
With tetrabutylammonium tetrafluoroborate; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis: Mg rod anode, carbon fibre cathode, const. current 60 mA; | 99% |
With aniline; (ϖ-allyl)palladium triflate based catalyst at 30℃; for 0.333333h; | 99% |
(E)-4-hydroxybenzaldehyde oxime
4-cyanophenol
Conditions | Yield |
---|---|
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 20℃; for 4h; Beckmann rearrangement; | 100% |
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4 A molecular sieve In acetonitrile at 80℃; for 0.5h; | 99% |
for 0.0583333h; Dehydration; Irradiation; | 82% |
4-cyanophenyl benzoate
4-cyanophenol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.25h; Hydrolysis; debenzoylation; Heating; | 100% |
With potassium fluoride; thiophenol In 1-methyl-pyrrolidin-2-one at 100℃; for 1h; | 85% |
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 90℃; for 0.25h; | 84% |
With potassium carbonate In 1-methyl-pyrrolidin-2-one for 0.333333h; Heating; | 80% |
4-cyanophenyl acetate
2-amino-benzenethiol
A
2-Methylbenzothiazole
B
4-cyanophenol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 0.5h; Hydrolysis; cyclization; | A n/a B 100% |
2-amino-benzenethiol
4-cyanophenyl pivalate
A
2-(tert-butyl)benzo[d]thiazole
B
4-cyanophenol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 1.5h; Hydrolysis; cyclization; | A n/a B 100% |
4-benzyloxybenzonitrile
4-cyanophenol
Conditions | Yield |
---|---|
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h; | 100% |
With hydrogen; palladium on activated charcoal; ethylenediamine In tetrahydrofuran at 20℃; for 24h; atmospheric pressure; | 100% |
With cyclohexa-1,4-diene; 3,6-bis(dimethylamino)-9H-carbazole; caesium carbonate In dimethyl sulfoxide at 23℃; for 18h; Inert atmosphere; Schlenk technique; Irradiation; | 99% |
Conditions | Yield |
---|---|
With nickel dibromide In 1-methyl-pyrrolidin-2-one at 200℃; under 10343 Torr; for 0.333333h; microwave irradiation; | 99% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In water at 170℃; under 10343.2 Torr; for 0.0833333h; microwave irradiation; | 99% |
Conditions | Yield |
---|---|
With β-D-glucose; copper(II) acetate monohydrate; potassium hydroxide In water; dimethyl sulfoxide at 20 - 120℃; for 28h; | 99% |
With bis(η3-allyl-μ-chloropalladium(II)); p-methylbenzaldehyde oxime; caesium carbonate; tert-butyl XPhos In tetrahydrofuran at 75℃; for 2h; Inert atmosphere; | 98% |
With cesiumhydroxide monohydrate; t-BuBrettPhos; C44H62NO5PPdS; water In 1,4-dioxane at 20℃; for 18h; Inert atmosphere; | 97% |
4-cyanophenylboronic acid
4-cyanophenol
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In water; acetonitrile for 30h; Irradiation; | 99% |
With oxygen; triethylamine In acetonitrile at 20℃; under 760.051 Torr; for 4h; Reagent/catalyst; Irradiation; | 99% |
With water; caesium carbonate; hydrazine hydrate at 80℃; for 12h; | 98% |
4-(dimethylsilyl)benzonitrile
4-cyanophenol
Conditions | Yield |
---|---|
With water; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol at 20℃; for 5h; | 99% |
Multi-step reaction with 2 steps 1: (p-cymene)ruthenium(II) chloride / 0.08 h / 20 °C 2: tetrabutyl ammonium fluoride; water; dihydrogen peroxide; potassium hydrogencarbonate / tetrahydrofuran; methanol / 0.5 h / 20 °C View Scheme | |
With dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran-d8; d(4)-methanol at 20℃; Kinetics; Mechanism; |
Conditions | Yield |
---|---|
With 0.5%Pd/TiO2; isopropyl alcohol In water at 24.84℃; for 2h; Inert atmosphere; Sealed tube; Irradiation; | A 99% B 99% |
Conditions | Yield |
---|---|
With phosphorus pentoxide; urea at 160℃; for 1h; Temperature; | 98.2% |
With hydroxyammonium sulfate; zinc for 0.316667h; Microwave irradiation; | 91% |
With phosphoramide; sodium chloride at 450℃; for 1.5h; | 68% |
Multi-step reaction with 2 steps 1: ammonia / 0.5 h / 250 °C 2: 1 h / 325 °C View Scheme | |
Multi-step reaction with 3 steps 1: sulfuric acid / cyclohexane / 10 h / 90 °C 2: ammonium hydroxide / 5 h / 100 °C / Autoclave 3: resin catalyst supported with palladium salt / water; acetonitrile / 7 h / 50 °C View Scheme |
4-hydroxybenzaldehyde oxime
4-cyanophenol
Conditions | Yield |
---|---|
With thionyl chloride; sodium sulfite at 0℃; for 0.0166667h; | 98% |
With thionyl chloride; silica gel In dichloromethane at 0℃; for 0.116667h; | 98% |
With acetonitrile for 1h; Reflux; Green chemistry; | 98% |
potassium (4-cyanophenyl)trifluoroborate
4-cyanophenol
Conditions | Yield |
---|---|
With Oxone; water In acetone at 20℃; for 0.0333333h; | 98% |
Conditions | Yield |
---|---|
With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 6h; Sealed tube; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique; | 97% |
Conditions | Yield |
---|---|
With diethylenetriaminopentaacetic acid In aq. phosphate buffer; acetonitrile at 37℃; pH=7.4; | A n/a B 97% |
Conditions | Yield |
---|---|
With ammonia; boron phosphate at 400℃; for 0.000277778h; | A 96% B 5% |
A 95% B n/a | |
A 93.8% by weight. B n/a |
Conditions | Yield |
---|---|
With resin catalyst supported with palladium salt In water; acetonitrile at 50℃; for 7h; Temperature; | 96% |
With trichloromethyl chloroformate In various solvent(s) 0-5 deg C then heated to 60 deg C, 5 min; | 94% |
Stage #1: p-hydroxybenzamide With C39H45N2 In acetonitrile at 20℃; Schlenk technique; Glovebox; Inert atmosphere; Stage #2: With phenylsilane In acetonitrile at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 94% |
4-cyanophenyl propyl ether
4-cyanophenol
Conditions | Yield |
---|---|
With 1-n-butyl-3-methylimidazolim bromide at 200 - 220℃; for 0.5h; Microwave irradiation; Inert atmosphere; | 96% |
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; Kinetics; Electrolysis; |
Conditions | Yield |
---|---|
With trichloroisocyanuric acid; ammonia In water at 20 - 60℃; | 96% |
With potassium hydroxide; ammonium bicarbonate; (Bu4N)2S2O8; copper(II) formate; nikel(II) formate In isopropyl alcohol at 25℃; for 1.5h; | 91% |
With ammonia; oxygen In 1,4-dioxane for 2.5h; Reflux; | 91% |
Conditions | Yield |
---|---|
With ammonia; boron phosphate at 400℃; for 0.00111111h; | A 95% B 5% |
Conditions | Yield |
---|---|
With 2-(methylsulfonyl)ethyl alcohol; sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; | 95% |
With acetylhydroxamic acid; potassium carbonate In dimethyl sulfoxide at 80℃; for 16h; Sealed tube; | 93% |
With methyl propargyl alcohol; potassium tert-butylate In dimethyl sulfoxide at 125℃; for 0.0333333h; microwave irradiation; | 90% |
4-(tert-butoxycarbonyloxy)benzonitrile
4-cyanophenol
Conditions | Yield |
---|---|
With methanol; carbon tetrabromide; triphenylphosphine for 1h; Reflux; | 95% |
Conditions | Yield |
---|---|
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere; | 95% |
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere; | 95% |
With copper(I) oxide; tetra(n-butyl)ammonium hydroxide; 1,10-phenanthroline-4,7-diol In water at 110℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry; | 88% |
Conditions | Yield |
---|---|
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 95℃; for 16h; Green chemistry; | 95% |
With 1,10-Phenanthroline; oxygen; copper(II) oxide; potassium ferrocyanide In dimethyl sulfoxide at 120℃; under 11251.1 Torr; for 40h; Autoclave; | 36% |
Conditions | Yield |
---|---|
With caesium carbonate In water; N,N-dimethyl-formamide at 20℃; for 12h; | 100% |
With potassium carbonate In acetone at 20℃; for 24h; | 99% |
With potassium carbonate In acetone at 20℃; for 20h; Reflux; | 98% |
Conditions | Yield |
---|---|
With ammonium formate; palladium on activated charcoal In methanol for 2h; Ambient temperature; | 100% |
With 20 % Pd(OH)2/C; hydrogen In methanol at 20℃; under 760.051 Torr; for 3h; | 92% |
With kieselguhr; nickel-copper at 453℃; Hydrogenation; | |
With ethanol at 24.84℃; for 48h; Photolysis; Inert atmosphere; | 99 %Chromat. |
With [RuCl2(p-cymene)(P(Fur)3)] In water at 80℃; for 2h; Catalytic behavior; Green chemistry; | >99 %Chromat. |
Conditions | Yield |
---|---|
With magnesium(II) perchlorate at 80℃; for 0.25h; | 100% |
With thalium(III) chloride tetrahydrate at 20℃; for 0.0333333h; | 97% |
With aluminum triflate at 20℃; for 0.00833333h; | 96% |
Conditions | Yield |
---|---|
With sodium carbonate In acetone for 16h; Reflux; | 100% |
With potassium carbonate In acetone for 5h; Heating; | 98% |
With potassium carbonate In acetone Reflux; | 98% |
Conditions | Yield |
---|---|
With sodium In ethanol for 24h; Heating; | 100% |
With potassium carbonate In acetone Reflux; | 100% |
trifluoromethylsulfonic anhydride
4-cyanophenol
4-cyanophenyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In dichloromethane at 20℃; for 16h; | 100% |
With pyridine In dichloromethane at 20℃; for 1h; | 96% |
With potassium phosphate In water; toluene at 0 - 20℃; | 96% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 12h; | 100% |
In benzene Heating; | |
With pyridine In diethyl ether | |
With triethylamine In dichloromethane at 0 - 5℃; |
Conditions | Yield |
---|---|
With cesium fluoride/clinoptilolite In dimethyl sulfoxide at 110℃; for 0.5h; Ullmann Condensation; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; | 99% |
With potassium hydroxide In dimethyl sulfoxide at 55℃; | 98% |
Conditions | Yield |
---|---|
In potassium carbonate | 100% |
With sodium hydride In N,N-dimethyl-formamide 1.) rt, 1 h, 2.) reflux, 12 h; | 90% |
With potassium carbonate In cyclohexanone for 24h; Heating; | 70% |
Conditions | Yield |
---|---|
With magnesium(II) perchlorate at 80℃; for 0.75h; | 100% |
With potassium tropolonato In acetonitrile at 70℃; for 4h; | 80% |
Conditions | Yield |
---|---|
With bis-(2-(1-adamantyl)ethyl) azodicarboxylate; triphenylphosphine Mitsunobu reaction; | 100% |
ethyl 2-bromoisobutyrate
4-cyanophenol
2-(4-cyanophenoxy)-2-methylpropionic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-cyanophenol With potassium carbonate In acetonitrile for 1h; Heating / reflux; Stage #2: ethyl 2-bromoisobutyrate With potassium carbonate for 72h; Heating / reflux; | 100% |
Stage #1: 4-cyanophenol With potassium carbonate In N,N-dimethyl-formamide for 0.166667h; Stage #2: ethyl 2-bromoisobutyrate In N,N-dimethyl-formamide at 20℃; for 16h; | 69% |
Stage #1: 4-cyanophenol With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: ethyl 2-bromoisobutyrate In acetone for 16h; Heating / reflux; | 46.9% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone; toluene for 24h; Williamson Ether Synthesis; Reflux; | 100% |
Stage #1: 4-cyanophenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene at 80℃; for 15h; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h; Inert atmosphere; | 95% |
(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol
4-cyanophenol
4-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethoxy)-benzonitrile
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 1.5h; | 100% |
4-cyanophenol
bromoacetic acid methyl ester
methyl 2-(4-cyanophenoxy)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 70℃; for 1.5h; | 100% |
With potassium carbonate In acetonitrile at 20℃; |
di-tert-butyl dicarbonate
4-cyanophenol
4-(tert-butoxycarbonyloxy)benzonitrile
Conditions | Yield |
---|---|
With 6,7-dimethoxyisoquinoline In dichloromethane at 20℃; for 10h; Inert atmosphere; chemoselective reaction; | 100% |
Stage #1: 4-cyanophenol With dmap; triethylamine In dichloromethane for 0.25h; Stage #2: di-tert-butyl dicarbonate In dichloromethane for 2h; | 100% |
triphenylphosphine at 40℃; for 14h; | 97% |
4-cyanophenol
2,4-dinitrophenyl benzoate
A
4-cyanophenyl benzoate
B
potassium 2,4-dinitrophenolate
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 5h; | A 100% B n/a |
4-cyanophenol
2-bromobutyric acid ethyl ester
Ethyl 2-(4-cyanophenoxy)butanoate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; for 3h; | 100% |
With potassium carbonate In acetonitrile at 80℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With potassium iodide In N,N-dimethyl-formamide at 60℃; for 10h; Reagent/catalyst; Solvent; Temperature; | 100% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 6h; | 98.5% |
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 70℃; for 18h; | 98% |
Conditions | Yield |
---|---|
With C45H65FeNO3P2PdS; caesium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Reflux; | 100% |
Molecular formula: C7H5NO
Molecular Weight: 119.12
EINECS: 212-175-2
Melting point: 110-113 °C(lit.)
Water Solubility: Slightly soluble
Index of Refraction: 1.59
Density: 1.22 g/cm3
Flash Point: 123.9 °C
Enthalpy of Vaporization: 54.09 kJ/mol
Boiling Point: 281.2 °C at 760 mmHg
Vapour Pressure: 0.00212 mmHg at 25 °C
Structure of 4-Cyanophenol (CAS NO.767-00-0):
IUPAC Name: 4-Hydroxybenzonitrile
Product Category of 4-Cyanophenol (CAS NO.767-00-0): Liquid Crystal intermediates;Aromatic Nitriles;Phenoles and thiophenoles;Building Blocks for Liquid Crystals;Functional Materials;Benzoic acid Series;Pesticides&Metabolites
4-Cyanophenol (CAS NO.767-00-0) has been used for intermediate of liquid crystals.
1. | orl-mus LD50:450 mg/kg | APFRAD Annales Pharmaceutiques Francaises. 41 (1983),391. | ||
2. | ipr-mus LD50:200 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 . |
4-Cyanophenol (CAS NO.767-00-0) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. And the toxicological properties have not been fully investigated.
Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.
Poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx and CN−. See also NITRILES.
Hazard Codes: Xn,Xi
Risk Statements:
22: Harmful if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
24/25: Avoid contact with skin and eyes
4-Cyanophenol , its cas register number is 767-00-0. It also can be called 4-Hydroxybenzonitrile ; and Benzonitrile, 4-hydroxy- . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately.
In addition, 4-Cyanophenol (CAS NO.767-00-0) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, carbon dioxide.
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