5537-71-3

Basic information

• Product Name: m-(1-Cyanoethyl)benzoic acid
• Synonyms: 3-(1-Cyanethyl)benzoicacid;CEBA;3-(1-cyanoethyl)-benzoicaci;3-(1-Cyanoethyl)benzolcacid;m-(1-Cyanoethyl)benzoic acid;3-(1-CYANOETHYL)BENZOIC ACID;3-(1-Cyanoethyl)benzoophenone;Cyano Ethyl benzoic acid
• CAS NO: 5537-71-3
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• EINECS: 226-897-0
• Product Categories: C10;Carbonyl Compounds;Carboxylic Acids;Pharmaceutical raw material;API;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;(intermediate of ketoprofen)
• Mol File: 5537-71-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 143-145 °C(lit.)
• Boiling Point: 355.8 ºC at 760 mmHg
• Flash Point: 169 ºC
• Appearance: White crystalline powder
• Density: 1.204 g/cm³
• Vapor Pressure: 1.12E-05mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.96±0.10(Predicted)
• CAS DataBase Reference: m-(1-Cyanoethyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: m-(1-Cyanoethyl)benzoic acid(5537-71-3)
• EPA Substance Registry System: m-(1-Cyanoethyl)benzoic acid(5537-71-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41-43
• Safety Statements: 26-36/37/39-36/37/38
• WGK Germany: 3
• Hazardous Substances Data: 5537-71-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 5537-71-3 differently. You can refer to the following data:
1. 3-(1-Cyanoethyl)benzoic Acid is a intermediate for the synthetic preparation of various pharmaceutical compounds. 3-(1-Cyanoethyl)benzoic Acid was used in studies examining the enantioselectivity of n itrile hydratases.
2. 3-(1-Cyanoethyl)benzoic acid was used in screening of cobalt containing nitrile hydratases for their enantioselectivity towards wide range of chiral nitriles.

Definition

ChEBI: Benzoic acid meta-substituted with a 1-cyanoethyl group.

InChI:InChI=1/C10H9NO2/c1-7(6-11)8-3-2-4-9(5-8)10(12)13/h2-5,7H,1H3,(H,12,13)

Synthetic route

3-(cyanomethyl)benzoic acid (5689-33-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-(3-carboxyphenyl)propanenitrile (5537-71-3)

Conditions	Yield
With dimethylamine borane; sodium t-butanolate at 80℃; for 0.833333h; Inert atmosphere;	58%

2-(3-carboxyphenyl)propanenitrile (5537-71-3) → 3-(1-cyanoethyl)benzoyl chloride (42872-29-7)

Conditions	Yield
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)propionic acid (68432-95-1)

Conditions	Yield
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) + 2-(3-carboxyphenyl)propanenitrile (5537-71-3) → 2-<3-(carboxymethyl)phenyl>propionitrile (146257-39-8)

Conditions	Yield
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-(carboxymethyl)phenyl>propionitrile (146257-39-8)

Conditions	Yield
With sulfuric acid In methanol	89%

1-benzofurane (271-89-6) + 2-(3-carboxyphenyl)propanenitrile (5537-71-3) → 2-[3-(benzofuran-2-carbonyl)phenyl] propionitrile (891658-41-6)

Conditions	Yield
With trifluoroacetic anhydride In acetonitrile for 5h;	65%

4-(4-chloro-1H-imidazol-1-yl)-3-methoxybenzenamine (1235491-93-6) + 2-(3-carboxyphenyl)propanenitrile (5537-71-3) → N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-3-(1-cyanoethyl)benzamide (1555543-90-2)

Conditions	Yield
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) + N-[6-(5-amino-2-methoxyphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (1005780-08-4) + 2-(3-carboxyphenyl)propanenitrile (5537-71-3) → 3-(1-cyanoethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-4-methoxyphenyl]benzamide (1005786-40-2)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one In tetrahydrofuran; N,N-dimethyl-formamide	58%

di-tert-butyl dicarbonate (24424-99-5) + 2-(3-carboxyphenyl)propanenitrile (5537-71-3) → 3-{2-[(tert-butoxycarbonyl)amino]-1-methyl-ethyl}-benzoic acid (1011293-78-9)

Conditions	Yield
With hydrogen; triethylamine; nickel In tetrahydrofuran at 20℃;	57%

3-amino benzophenone (2835-78-1) + 2-(3-carboxyphenyl)propanenitrile (5537-71-3) → N-(3-Benzoyl-phenyl)-3-(cyano-methyl-methyl)-benzamide

Conditions	Yield
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) → bis(3-carboxyphenyl)ethane (693780-98-2)

Conditions	Yield
With sodium hydroxide In water for 4h; Heating;

2-(3-carboxyphenyl)propanenitrile (5537-71-3) → 2-(3-propionylphenyl) propionitrile

Conditions	Yield
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) → C12H14O3

Conditions	Yield
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-(isobutyryl)phenyl]propionitrile (891657-73-1)

Conditions	Yield
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) → C13H16O3

Conditions	Yield
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) → C15H17NO

Conditions	Yield
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) → C15H18O3

Conditions	Yield
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) → C16H19NO

Conditions	Yield
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) → C16H20O3

Conditions	Yield
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-(thiophene-2-carbonyl)phenyl)propanenitrile (52986-65-9)

Conditions	Yield
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) → C14H11NO2 (80313-08-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 3 h / Heating View Scheme

2-(3-carboxyphenyl)propanenitrile (5537-71-3) → C14H12O4

Conditions	Yield
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-(oxazole-2-carbonyl)phenyl] propionitrile (891658-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 3 h / Heating View Scheme

2-(3-carboxyphenyl)propanenitrile (5537-71-3) → C13H11NO4

Conditions	Yield
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) → C13H10N2OS

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 3 h / Heating View Scheme

2-(3-carboxyphenyl)propanenitrile (5537-71-3) → C13H11NO3S

Conditions	Yield
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-trifluoroacetylamino)phenyl]propanenitrile (891657-42-4)

Conditions	Yield
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-aminophenyl)propanenitrile (97844-30-9)

Conditions	Yield
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-iodophenyl)propanenitrile (891657-58-2)

Conditions	Yield
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

Upstream product

• 5689-33-8 ethyl 3-cyanomethylbenzoate 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 68432-95-1 2-(3-carboxyphenyl)propionic acid 
• 693780-98-2 bis(3-carboxyphenyl)ethane 
• 42872-29-7 3-(1-cyanoethyl)benzoyl chloride 
• 1011293-78-9 3-{2-[(tert-butoxycarbonyl)amino]-1-methyl-ethyl}-benzoic acid 
• 891657-73-1 2-[3-(isobutyryl)phenyl]propionitrile 
• 52986-65-9 2-(3-(thiophene-2-carbonyl)phenyl)propanenitrile 
• 80313-08-2 C₁₄H₁₁NO₂ 
• 77614-38-1 C₁₄H₁₂O₄ 
• 891658-02-9 2-[3-(oxazole-2-carbonyl)phenyl] propionitrile 
• 891657-42-4 2-[(3-trifluoroacetylamino)phenyl]propanenitrile 
• 97844-30-9 2-(3-aminophenyl)propanenitrile 
• 891657-58-2 2-(3-iodophenyl)propanenitrile 
• 52779-89-2 suprofen 

Relevant articles and documents

Selective α-Monomethylation by an Amine-Borane/N,N-Dimethylformamide System as the Methyl Source

A new and practical α-monomethylation strategy using an amine-borane/N,N-dimethylformamide (R3N-BH3/DMF) system as the methyl source was developed. This protocol has been found to be effective in the α-monomethylation of arylacetonitriles and arylacetamides. Mechanistic studies revealed that the formyl group of DMF delivered the carbon and one hydrogen atoms of the methyl group, and R3N-BH3 donated the remaining two hydrogen atoms. Such a unique reaction pathway enabled controllable assemblies of CDH2-, CD2H-, and CD3- units using Me2NH-BH3/d7-DMF, Me3N-BD3/DMF and Me3N-BD3/d7-DMF systems, respectively. Further application of this method to the facile synthesis of anti-inflammatory flurbiprofen and its varied deuterium-labeled derivatives was demonstrated.