Product Name

  • Name

    m-(1-Cyanoethyl)benzoic acid

  • EINECS 226-897-0
  • CAS No. 5537-71-3
  • Article Data5
  • CAS DataBase
  • Density 1.204 g/cm3
  • Solubility
  • Melting Point 143-148 ºC
  • Formula C10H9NO2
  • Boiling Point 355.8 ºC at 760 mmHg
  • Molecular Weight 175.187
  • Flash Point 169 ºC
  • Transport Information
  • Appearance White crystalline powder
  • Safety 26-36/37/38
  • Risk Codes 22-41-43
  • Molecular Structure Molecular Structure of 5537-71-3 (m-(1-Cyanoethyl)benzoic acid)
  • Hazard Symbols HarmfulXn
  • Synonyms Benzoicacid, m-(1-cyanoethyl)- (7CI,8CI);2-(3-Carboxyphenyl)propionitrile;3-(1-Cyanoethyl)benzoic acid;NSC 113992;
  • PSA 61.09000
  • LogP 1.84098

Synthetic route

3-(cyanomethyl)benzoic acid
5689-33-8

3-(cyanomethyl)benzoic acid

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

Conditions
ConditionsYield
With dimethylamine borane; sodium t-butanolate at 80℃; for 0.833333h; Inert atmosphere;58%
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

3-(1-cyanoethyl)benzoyl chloride
42872-29-7

3-(1-cyanoethyl)benzoyl chloride

Conditions
ConditionsYield
With thionyl chloride for 3h; Heating / reflux;100%
With thionyl chloride Heating;
With thionyl chloride for 3h; Heating;
With thionyl chloride at 0 - 80℃; for 2h; Inert atmosphere;
With thionyl chloride at 0 - 80℃; for 2h;
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-(3-carboxyphenyl)propionic acid
68432-95-1

2-(3-carboxyphenyl)propionic acid

Conditions
ConditionsYield
With sodium hydroxide for 5h; Heating;97%
With water; sodium hydroxide for 7h; Reflux;94.9%
With hydrogenchloride In 1,4-dioxane for 5h; Heating;92%
methanol
67-56-1

methanol

2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-<3-(carboxymethyl)phenyl>propionitrile
146257-39-8

2-<3-(carboxymethyl)phenyl>propionitrile

Conditions
ConditionsYield
With sulfuric acid at 65℃; for 10h; Inert atmosphere;96%
With acetyl chloride for 18h; Reflux;
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-<3-(carboxymethyl)phenyl>propionitrile
146257-39-8

2-<3-(carboxymethyl)phenyl>propionitrile

Conditions
ConditionsYield
With sulfuric acid In methanol89%
1-benzofurane
271-89-6

1-benzofurane

2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-[3-(benzofuran-2-carbonyl)phenyl] propionitrile
891658-41-6

2-[3-(benzofuran-2-carbonyl)phenyl] propionitrile

Conditions
ConditionsYield
With trifluoroacetic anhydride In acetonitrile for 5h;65%
4-(4-chloro-1H-imidazol-1-yl)-3-methoxybenzenamine
1235491-93-6

4-(4-chloro-1H-imidazol-1-yl)-3-methoxybenzenamine

2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-3-(1-cyanoethyl)benzamide
1555543-90-2

N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-3-(1-cyanoethyl)benzamide

Conditions
ConditionsYield
Stage #1: 2-(3-carboxyphenyl)propanenitrile With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 0.166667h;
Stage #2: 4-(4-chloro-1H-imidazol-1-yl)-3-methoxybenzenamine In dichloromethane at 20℃; for 4h;		59%
oxalyl dichloride
79-37-8

oxalyl dichloride

N-[6-(5-amino-2-methoxyphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide
1005780-08-4

N-[6-(5-amino-2-methoxyphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

3-(1-cyanoethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-4-methoxyphenyl]benzamide
1005786-40-2

3-(1-cyanoethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-4-methoxyphenyl]benzamide

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one In tetrahydrofuran; N,N-dimethyl-formamide58%
...Expand
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

3-{2-[(tert-butoxycarbonyl)amino]-1-methyl-ethyl}-benzoic acid
1011293-78-9

3-{2-[(tert-butoxycarbonyl)amino]-1-methyl-ethyl}-benzoic acid

Conditions
ConditionsYield
With hydrogen; triethylamine; nickel In tetrahydrofuran at 20℃;57%
3-amino benzophenone
2835-78-1

3-amino benzophenone

2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

N-(3-Benzoyl-phenyl)-3-(cyano-methyl-methyl)-benzamide

N-(3-Benzoyl-phenyl)-3-(cyano-methyl-methyl)-benzamide

Conditions
ConditionsYield
With polymer-bound EDC 1.) CH2Cl2, room temperature, 30 min, 2.) 50 deg C; Yield given. Multistep reaction;
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

bis(3-carboxyphenyl)ethane
693780-98-2

bis(3-carboxyphenyl)ethane

Conditions
ConditionsYield
With sodium hydroxide In water for 4h; Heating;
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-(3-propionylphenyl) propionitrile

2-(3-propionylphenyl) propionitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: SOCl2 / 3 h / Heating
2.1: PdCl2(dppf); ZnCl2 / diethyl ether / 0.33 h / 0 °C
2.2: 81 percent / diethyl ether; tetrahydrofuran / 4 h / 0 - 20 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C12H14O3

C12H14O3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: SOCl2 / 3 h / Heating
2.1: PdCl2(dppf); ZnCl2 / diethyl ether / 0.33 h / 0 °C
2.2: 81 percent / diethyl ether; tetrahydrofuran / 4 h / 0 - 20 °C
3.1: 85 percent / aq. HCl / dioxane / 4 h / 70 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-[3-(isobutyryl)phenyl]propionitrile
891657-73-1

2-[3-(isobutyryl)phenyl]propionitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: SOCl2 / 3 h / Heating
2.1: PdCl2(dppf); ZnCl2 / diethyl ether / 0.33 h / 0 °C
2.2: diethyl ether; tetrahydrofuran / 4 h / 0 - 20 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C13H16O3

C13H16O3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: SOCl2 / 3 h / Heating
2.1: PdCl2(dppf); ZnCl2 / diethyl ether / 0.33 h / 0 °C
2.2: diethyl ether; tetrahydrofuran / 4 h / 0 - 20 °C
3.1: 85 percent / aq. HCl / dioxane / 4 h / 70 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C15H17NO

C15H17NO

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: SOCl2 / 3 h / Heating
2.1: PdCl2(dppf); ZnCl2 / diethyl ether / 0.33 h / 0 °C
2.2: diethyl ether; tetrahydrofuran / 4 h / 0 - 20 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C15H18O3

C15H18O3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: SOCl2 / 3 h / Heating
2.1: PdCl2(dppf); ZnCl2 / diethyl ether / 0.33 h / 0 °C
2.2: diethyl ether; tetrahydrofuran / 4 h / 0 - 20 °C
3.1: 74 percent / aq. HCl / dioxane / 4 h / 70 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C16H19NO

C16H19NO

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: SOCl2 / 3 h / Heating
2.1: PdCl2(dppf); ZnCl2 / diethyl ether / 0.33 h / 0 °C
2.2: diethyl ether; tetrahydrofuran / 4 h / 0 - 20 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C16H20O3

C16H20O3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: SOCl2 / 3 h / Heating
2.1: PdCl2(dppf); ZnCl2 / diethyl ether / 0.33 h / 0 °C
2.2: diethyl ether; tetrahydrofuran / 4 h / 0 - 20 °C
3.1: 80 percent / aq. HCl / dioxane / 4 h / 70 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-(3-(thiophene-2-carbonyl)phenyl)propanenitrile
52986-65-9

2-(3-(thiophene-2-carbonyl)phenyl)propanenitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 3 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: iodine; carbon monoxide / 1,2-dichloro-ethane / 24 h / 20 °C / 3040.2 Torr / Sealed tube
2: 0.5 h / 20 °C / Glovebox
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C14H11NO2
80313-08-2

C14H11NO2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 3 h / Heating
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C14H12O4

C14H12O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / 3 h / Heating
2: 1.48 g / aq. HCl / dioxane / 4 h / 70 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-[3-(oxazole-2-carbonyl)phenyl] propionitrile
891658-02-9

2-[3-(oxazole-2-carbonyl)phenyl] propionitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 3 h / Heating
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C13H11NO4

C13H11NO4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / 3 h / Heating
2: 1.21 g / aq. HCl / dioxane / 4 h / 70 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C13H10N2OS

C13H10N2OS

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / 3 h / Heating
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

C13H11NO3S

C13H11NO3S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SOCl2 / 3 h / Heating
2: 1.43 g / aq. HCl / dioxane / 4 h / 70 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-[(3-trifluoroacetylamino)phenyl]propanenitrile
891657-42-4

2-[(3-trifluoroacetylamino)phenyl]propanenitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: SOCl2 / 3 h / Heating
2.1: NaN3 / tetrabutylammonium bromide / CH2Cl2; H2O / 2 h / 0 - 5 °C
2.2: 48 h / Heating
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-(3-aminophenyl)propanenitrile
97844-30-9

2-(3-aminophenyl)propanenitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: SOCl2 / 3 h / Heating
2.1: NaN3 / tetrabutylammonium bromide / CH2Cl2; H2O / 2 h / 0 - 5 °C
2.2: 48 h / Heating
3.1: 1.2 g / K2CO3 / methanol; H2O / 16 h / 60 °C
View Scheme
2-(3-carboxyphenyl)propanenitrile
5537-71-3

2-(3-carboxyphenyl)propanenitrile

2-(3-iodophenyl)propanenitrile
891657-58-2

2-(3-iodophenyl)propanenitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: SOCl2 / 3 h / Heating
2.1: NaN3 / tetrabutylammonium bromide / CH2Cl2; H2O / 2 h / 0 - 5 °C
2.2: 48 h / Heating
3.1: 1.2 g / K2CO3 / methanol; H2O / 16 h / 60 °C
4.1: NaNO2; aq. HCl / 0.33 h
4.2: 80 percent / KI / H2O / 3 h
View Scheme

m-(1-Cyanoethyl)benzoic acid Specification

The m-(1-Cyanoethyl)benzoic acid, with the CAS registry number 5537-71-3, has the IUPAC name of 3-(1-cyanoethyl)benzoic acid. And its product categories are including Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids; (intermediate of ketoprofen); C10; Carbonyl Compounds; Carboxylic Acids.

The physical properties of this chemical are as below: (1)ACD/LogP: 1.47; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.07; (4)ACD/LogD (pH 7.4): -1.5; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 4.35; (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: 50.09; (13)Index of Refraction: 1.563; (14)Molar Refractivity: 47.28 cm3; (15)Molar Volume: 145.4 cm3; (16)Polarizability: 18.74 ×10-24 cm3; (17)Surface Tension: 53.2 dyne/cm; (18)Density: 1.204 g/cm3; (19)Flash Point: 169 °C; (20)Enthalpy of Vaporization: 63.41 kJ/mol; (21)Boiling Point: 355.8 °C at 760 mmHg; (22)Vapour Pressure: 1.12E-05 mmHg at 25°C; (23)Exact Mass: 175.063329; (24)MonoIsotopic Mass: 175.063329; (25)Topological Polar Surface Area: 61.1; (26)Heavy Atom Count: 13; (27)Complexity: 241.

When you are dealing with this chemical, you should be much more cautious. For being a kind of harmful chemical, it may cause damage to health and it will be very dangerous if swallowed. And it may cause sensitisation by skin contact and will have risk of serious damage to eyes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection and wear the suitable respiratory equipment if in case of insufficient ventilation. In addition, if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(C#N)C1=CC=CC(=C1)C(=O)O
(2)InChI: InChI=1S/C10H9NO2/c1-7(6-11)8-3-2-4-9(5-8)10(12)13/h2-5,7H,1H3,(H,12,13)
(3)InChIKey: IRYIYPWRXROPSX-UHFFFAOYSA-N 

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