Conditions | Yield |
---|---|
With 2C6H15N*C49H47Cl2Fe2N2O8P2PdS2; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; sodium carbonate; caesium carbonate In N,N-dimethyl-formamide at 25 - 30℃; for 26h; Schlenk technique; Glovebox; Sealed tube; Irradiation; | 84% |
Conditions | Yield |
---|---|
Stage #1: 4-aminophenylacetic acid With hydrogenchloride; sodium nitrite In water; acetic acid at 0 - 40℃; for 0.75h; Stage #2: With sodium cyanide; copper(l) cyanide In water; acetic acid at 0 - 5℃; for 3.66667h; | 78.9% |
Conditions | Yield |
---|---|
With palladium hydroxide, 20 wt% on carbon; tetrabutylammomium bromide; water In tetrahydrofuran at 110℃; under 7500.75 Torr; for 4h; Sealed tube; Autoclave; | 76% |
With cobalt(II) pyridine-2-carboxylate; palladium diacetate; sodium hydroxide In methanol at 150℃; under 11251.1 Torr; for 6h; Reagent/catalyst; Autoclave; | 54% |
4-(cyanomethyl)benzonitrile
A
4-cyanophenylacetic acid
B
4-(cyanomethyl)benzoic acid
Conditions | Yield |
---|---|
With water for 24h; Rhodococcus rhodochrous AJ270; | A 65% B 16% |
With potassium phosphate buffer; Rhodococcus sp. AJ270 at 30℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
carbon dioxide
4-cyanobenzyl 2-methoxyacetate
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With manganese; dichlorobis(trimethylphosphine)nickel In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 24h; Schlenk technique; | 64% |
4-(2-oxo-2-(pyrrolidin-1-yl)ethyl)benzonitrile
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane for 12h; Heating; | 61% |
Conditions | Yield |
---|---|
With potassium ethoxide In 1,4-dioxane at 100℃; for 24h; | 60% |
carbon monoxide
4-cyanobenzyl bromide
A
4-cyanophenylacetic acid
B
2-(4-carbamoylphenyl)-acetic acid
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide In formic acid at 60℃; under 760 Torr; for 18h; Carbonylation; | A 51% B n/a |
Conditions | Yield |
---|---|
With hydrogenchloride for 0.0666667h; Heating; | 46% |
With hydrogenchloride | |
With hydrogenchloride In methanol; acetic acid; ethyl acetate |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 18h; | 42% |
Conditions | Yield |
---|---|
With hydrogenchloride; water; copper(II) sulfate Diazotization.Erwaermen des Reaktionsgemisches; |
methanol
1-Naphthylmethyl 4-cyanophenylacetate
A
4-cyanophenylacetic acid
B
1-(methoxymethyl)naphthalene
Conditions | Yield |
---|---|
Irradiation; | A n/a B 77 % Chromat. C 24 % Chromat. |
Rate constant; Quantum yield; Irradiation; rate of decarboxylation k(CO2); | A n/a B 77 % Chromat. C 24 % Chromat. |
4-cyanophenylketene
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With water at 26℃; Rate constant; |
2,2-dibromo-1-(4-cyanophenyl)ethene
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / H2O / ethyl acetate / 0.3 h / 20 °C 2: 61 percent / aq. HCl / dioxane / 12 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 73 percent / PPh3 / CH2Cl2 / 1 h / 0 °C 2: 90 percent / H2O / ethyl acetate / 0.3 h / 20 °C 3: 61 percent / aq. HCl / dioxane / 12 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous alcohol 2: fuming hydrochloric acid View Scheme |
4-(2-hydroxyethyl)benzonitrile
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With Jones reagent In acetone at 20℃; for 0.166667h; | |
With sodium periodate; ruthenium trichloride In tetrachloromethane; water; acetonitrile at 20℃; | |
With Jones reagent In acetone at 20℃; for 0.166667h; |
carbon dioxide
p-cyanobenzyl methyl carbonate
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In acetonitrile at 0℃; under 760.051 Torr; Electrochemical reaction; |
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In acetonitrile at 0℃; under 760.051 Torr; Electrochemical reaction; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h / 20 °C 2: manganese; dichlorobis(trimethylphosphine)nickel / N,N-dimethyl-formamide / 24 h / 100 °C / 760.05 Torr / Schlenk technique View Scheme |
tert-butyl acetylenyl ether
4-iodobenzonitrile
A
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 80℃; Reagent/catalyst; Sonogashira Cross-Coupling; Inert atmosphere; | A n/a B 54 %Spectr. C n/a D n/a |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 0℃; Solvent; Temperature; Electrochemical reaction; | 78 %Spectr. |
Conditions | Yield |
---|---|
Stage #1: 4-cyanophenylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h; Stage #3: With oxone In acetone at 50℃; for 12h; | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: oxone||potassium monopersulfate triple salt; water / acetone / 12 h / 50 °C / Inert atmosphere View Scheme |
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With oxone||potassium monopersulfate triple salt; water In acetone at 50℃; for 12h; Inert atmosphere; | 516 mg |
Conditions | Yield |
---|---|
With N,N,N,N-tetraethylammonium tetrafluoroborate In acetonitrile Electrochemical reaction; Inert atmosphere; |
4-cyanophenylacetic acid
N4-methyl-[1,1'-biphenyl]-3,4-diamine
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In tetrahydrofuran | 100% |
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In tetrahydrofuran | 100% |
Conditions | Yield |
---|---|
With thionyl chloride for 12h; Cooling with ice; | 100% |
With thionyl chloride at 20℃; for 23h; Cooling with ice; Inert atmosphere; | 99% |
With sulfuric acid at 75℃; for 4h; | 98% |
With thionyl chloride at 0 - 20℃; for 21.5h; | |
With thionyl chloride for 3h; Reagent/catalyst; Reflux; |
morpholine
4-cyanophenylacetic acid
4-[2-(morpholin-4-yl)-2-oxoethyl]benzonitrile
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 1h; | 99% |
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃; for 5h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With ammonium hydroxide; hydrogen In water at 20℃; for 48h; | 94% |
Conditions | Yield |
---|---|
Stage #1: 4-cyanophenylacetic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.166667h; Stage #2: 2-thiophenethanol In dichloromethane at 20℃; | 93% |
4-cyanophenylacetic acid
(4-Cyan-2-nitrophenyl)essigsaeure
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at -9 - 15℃; for 2h; | 92% |
With sulfuric acid; nitric acid at 5 - 10℃; for 2h; | 68% |
4-cyanophenylacetic acid
4-bromo-2-iodoaniline
Conditions | Yield |
---|---|
With triethylamine; HATU In dichloromethane at 20℃; for 22h; | 92% |
Conditions | Yield |
---|---|
With iron(III) sulfate; bis[(2-pyridyl)methyl]amine In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation; | 92% |
4-cyanophenylacetic acid
4-chlorobenzoylmethyl bromide
4-(4-(4-chlorophenyl)-2-oxo-2,5-dihydrofuran-3-yl)benzonitrile
Conditions | Yield |
---|---|
Stage #1: 4-cyanophenylacetic acid With potassium tert-butylate In N,N-dimethyl-formamide at -15 - -10℃; Stage #2: 4-chlorobenzoylmethyl bromide In N,N-dimethyl-formamide at -10 - 0℃; for 1.5h; Stage #3: With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h; | 91% |
Conditions | Yield |
---|---|
With hydrogenchloride for 3h; Reflux; | 89% |
With sulfuric acid for 2h; Inert atmosphere; Reflux; | 88% |
With sulfuric acid at 80℃; Inert atmosphere; Schlenk technique; | 85% |
With sulfuric acid for 2h; Inert atmosphere; Reflux; | |
With sulfuric acid for 24h; Reflux; |
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
Stage #1: 2-amino-N-(3-cyanobenzyl)acetamide hydrochloride With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 4-cyanophenylacetic acid In N,N-dimethyl-formamide at 20℃; | 88% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With iron(III) trifluoromethanesulfonate; sodium nitrite In dimethyl sulfoxide at 50℃; for 10h; Inert atmosphere; Sealed tube; | 82% |
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 24h; Green chemistry; | 66% |
Conditions | Yield |
---|---|
With water; potassium hydroxide at 110℃; for 4h; | 81% |
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
Stage #1: 2-(4-cyanobenzylamino)-2-oxoethanaminium chloride With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 4-cyanophenylacetic acid In N,N-dimethyl-formamide at 20℃; | 81% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere; | 81% |
4-cyanophenylacetic acid
N1-methyl-4-nitrobenzene-1,2-diamine
2-(4-cyano-phenyl)-N-(2-methylamino-5-nitro-phenyl)acetamide
Conditions | Yield |
---|---|
Stage #1: 4-cyanophenylacetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 50℃; for 0.5h; Stage #2: N1-methyl-4-nitrobenzene-1,2-diamine In tetrahydrofuran at 50℃; for 2h; Further stages.; | 79% |
pyrrolidine
4-cyanophenylacetic acid
4-(2-oxo-2-(pyrrolidin-1-yl)ethyl)benzonitrile
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane | 79% |
Stage #1: 4-cyanophenylacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: pyrrolidine In dichloromethane | 79% |
Stage #1: 4-cyanophenylacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.0833333h; Stage #2: pyrrolidine In dichloromethane | 79% |
Conditions | Yield |
---|---|
With ammonium acetate; oxygen; copper diacetate In 1-methyl-pyrrolidin-2-one at 120℃; under 760.051 Torr; for 20h; | 75% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 10 - 35℃; | 75% |
4-cyanophenylacetic acid
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In tetrahydrofuran | 74% |
4-cyanophenylacetic acid
formamidine acetic acid
2-(4-(1,2,4,5-tetrazin-3-yl)phenyl)acetic acid
Conditions | Yield |
---|---|
Stage #1: 4-cyanophenylacetic acid; formamidine acetic acid With nickel(II) triflate; hydrazine at 30℃; for 24h; Microwave irradiation; Stage #2: With hydrogenchloride; sodium nitrite In water at 20℃; pH=3; | 74% |
Conditions | Yield |
---|---|
Stage #1: Grushin’s reagent With dimethyl zinc(II) In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 4-cyanophenylacetic acid With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 40℃; for 10h; Inert atmosphere; Schlenk technique; | 74% |
The cas register number of 4-Cyanophenylacetic acid is 5462-71-5. It also can be called as Benzeneacetic acid, 4-cyano- and the Systematic name about this chemical is 2-(4-cyanophenyl)acetic acid.
Physical properties about 4-Cyanophenylacetic acid are: (1)ACD/LogP: 0.94 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -0.64 ; (4)ACD/LogD (pH 7.4): -2.35 ; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.03; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 50.09Å2; (13)Index of Refraction: 1.576; (14)Molar Refractivity: 42.22 cm3; (15)Molar Volume: 127.5 cm3; (16)Surface Tension: 59.1 dyne/cm; (17)Density: 1.26 g/cm3; (18)Flash Point: 168.6 °C; (19)Enthalpy of Vaporization: 63.34 kJ/mol; (20)Boiling Point: 355.2 °C at 760 mmHg; (21)Vapour Pressure: 1.17E-05 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and irritating to eyes and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
People can use the following data to convert to the molecule structure.
1.SMILES: O=C(O)Cc1ccc(C#N)cc1
2.InChI: InChI=1/C9H7NO2/c10-6-8-3-1-7(2-4-8)5-9(11)12/h1-4H,5H2,(H,11,12)
3.InChIKey: WEBXRQONNWEETE-UHFFFAOYAJ
4.Std. InChI: InChI=1S/C9H7NO2/c10-6-8-3-1-7(2-4-8)5-9(11)12/h1-4H,5H2,(H,11,12).
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