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N-(4-Cyanophenyl)glycine

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Name

N-(4-Cyanophenyl)glycine

EINECS 459-560-3
CAS No. 42288-26-6 Density 1.3 g/cm3
PSA 73.12000 LogP 1.12778
Solubility N/A Melting Point 237 °C(dec.)
Formula C9H8N2O2 Boiling Point 447.2 °C at 760 mmHg
Molecular Weight 176.175 Flash Point 224.3 °C
Transport Information N/A Appearance Off-white solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 42288-26-6 (N-(4-CYANO-PHENYL)-GLYCINE) Hazard Symbols N/A
Synonyms

Glycine,N-(p-cyanophenyl)- (6CI,7CI);2-(4-Cyanophenylamino)acetic acid;4-(((Carboxy)methyl)amino)benzonitrile;N-(p-Cyanophenyl)glycine;[(4-Cyanophenyl)amino]acetic acid;

Article Data 18

N-(4-Cyanophenyl)glycine Synthetic route

79-08-3

bromoacetic acid

873-74-5

4-Aminobenzonitrile

42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
In water at 100 - 110℃; for 3h;88%
In water at 100℃; for 16h;
In water at 20 - 100℃; for 16.4h;
In water at 100℃; for 5h;
In water at 100℃;
623-00-7

4-bromobenzenecarbonitrile

56-40-6

glycine

42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid In water; dimethyl sulfoxide at 25℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction;88%
3926-62-3

sodium monochloroacetic acid

873-74-5

4-Aminobenzonitrile

42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
In water for 6.5h; Product distribution / selectivity; Reflux;73.2%
With water at 0℃; Product distribution / selectivity; Reflux;73.2%
Stage #1: sodium monochloroacetic acid; 4-Aminobenzonitrile With tetrabutylammomium bromide; sodium hydrogencarbonate; potassium iodide In water at 90 - 95℃; for 24h;
Stage #2: With ammonia In water at 20 - 30℃; for 0.333333h; pH=7.5;
Stage #3: With hydrogenchloride In water at 20 - 30℃; for 3h; pH=2.5; Product distribution / selectivity;
With tetrabutylammomium bromide; sodium hydrogencarbonate; potassium iodide In water at 90 - 95℃; for 24h;131 g
With tetrabutylammomium bromide; sodium hydrogencarbonate; potassium iodide In water at 85 - 90℃; for 24h;120 g
79-11-8

chloroacetic acid

873-74-5

4-Aminobenzonitrile

42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
In water Reflux;73%
In water Heating / reflux;58%
In water Reflux;47%
With water
298-12-4

Glyoxilic acid

873-74-5

4-Aminobenzonitrile

42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
With sodium cyanoborohydride for 2h; Milling;56%
144656-11-1

(4-cyanophenylamino)-acetic acid tert-butyl ester

42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
With methoxybenzene; trifluoroacetic acid
With trifluoroacetic acid In dichloromethane for 24h; Ambient temperature;
873-74-5

4-Aminobenzonitrile

42288-26-6

(4-cyanophenyl)glycine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3 / dimethylformamide / 16 h / 80 °C
2: TFA / CH2Cl2; various solvent(s) / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: K2CO3
2: TFA, anisole
View Scheme
253796-98-4

(R)-2-(4-methylamino-3-amino-phenyl)-2-tert.butyloxycarbonylamino-1-pyrrolidino-propanone

42288-26-6

(4-cyanophenyl)glycine

530-62-1

1,1'-carbonyldiimidazole

(R)-2-(4-cyanophenylaminomethyl)-1-methyl-5-[1-(N-tert-butyloxycarbonylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole

Conditions
ConditionsYield
In tetrahydrofuran; acetic acid100%
42288-26-6

(4-cyanophenyl)glycine

212322-56-0

ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate

948551-71-1

3-({3-[2-(4-cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-pyridin-2-yl-amino)-ethyl propanoate

Conditions
ConditionsYield
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 5℃; for 6h; Large scale;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In dichloromethane at 20℃; for 24h; Solvent; Reagent/catalyst; Large scale;
99.3%
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran at 20℃;
93.8%
Stage #1: (4-cyanophenyl)glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 0 - 10℃; for 0.5h; Large scale;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran at 20 - 25℃; for 6h; Large scale;
84.33%
Stage #1: (4-cyanophenyl)glycine With 1,1'-carbonyldiimidazole In tetrahydrofuran at 50℃;
Stage #2: ethyl 3-{[{2-amino-1-(methylamino)phen-4-yl}carbonyl](pyridyn-2-yl)amino}propanoate In tetrahydrofuran for 24h; Heating; Further stages.;
42288-26-6

(4-cyanophenyl)glycine

73874-95-0

(piperidin-4-yl)carbamic acid tert-butyl ester

tert-butyl N-[1-[2-(4-cyanoanilino)acetyl]-4-piperidyl]carbamate

Conditions
ConditionsYield
With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;99%

N-(4-Cyanophenyl)glycine Chemical Properties

Product Name: N-(4-Cyanophenyl)glycine (CAS NO.42288-26-6)

Molecular Formula: C9H8N2O2
Molecular Weight: 176.17g/mol
Mol File: 42288-26-6.mol
Boiling point: 447.2 °C at 760 mmHg
Flash Point: 224.3 °C 
Density: 1.3 g/cm3
Index of Refraction: 1.593 
Molar Refractivity: 45.87 cm3 
Molar Volume: 135.2 cm3 
Surface Tension: 63.4 dyne/cm
Enthalpy of Vaporization: 74.35 kJ/mol
Vapour Pressure: 8.8E-09 mmHg at 25°C

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