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

Description

m-(1-Cyanoethyl)benzoic acid, also known as 3-(1-Cyanoethyl)benzoic acid, is an organic compound characterized by a benzoic acid structure with a meta-substituted 1-cyanoethyl group. m-(1-Cyanoethyl)benzoic acid serves as a crucial intermediate in the synthetic preparation of various pharmaceutical compounds and has been extensively studied for its potential applications in the field of enantioselective catalysis.

Uses

Used in Pharmaceutical Synthesis:
m-(1-Cyanoethyl)benzoic acid is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Enantioselective Catalysis:
m-(1-Cyanoethyl)benzoic acid is utilized in studies examining the enantioselectivity of nitrile hydratases. These enzymes play a vital role in the conversion of nitriles to amides, which are essential for the production of various pharmaceuticals and agrochemicals. m-(1-Cyanoethyl)benzoic acid aids in understanding the selectivity of these enzymes towards chiral nitriles, which is crucial for the development of enantioselective catalysts.
Used in Screening of Enzymes:
m-(1-Cyanoethyl)benzoic acid is employed in the screening of cobalt-containing nitrile hydratases for their enantioselectivity towards a wide range of chiral nitriles. This application is significant for the development of more efficient and selective biocatalysts in the pharmaceutical and chemical industries.

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

• 42872-29-7 3-(1-cyanoethyl)benzoyl chloride 
• 859828-54-9 2-[3-(1-hydroxyethyl)phenyl]propanenitrile 
• 95480-36-7 2-(3-acetylphenyl) propanoic acid 
• 146257-39-8 2-<3-(carboxymethyl)phenyl>propionitrile 
• 1080026-84-1 methyl 3-[1-methyl-2-(2,2,2-trifluoro-acetylamino)-ethyl]-benzoate 
• 1072707-67-5 methyl 3-(1-aminopropan-2-yl)benzoate 
• 1397293-20-7 1-(3-(1-isocyanatoethyl)phenyl)ethanone 
• 1012342-23-2 ethyl 3-(1-cyanoethyl)benzoate 
• 1005786-40-2 3-(1-cyanoethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-4-methoxyphenyl]benzamide 
• 1080026-83-0 3-(2-amino-1-methyl-ethyl)-benzoic acid hydrochloride 
• 891658-41-6 2-[3-(benzofuran-2-carbonyl)phenyl] propionitrile 

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.