172732-52-4

Basic information

• Product Name: 2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
• Synonyms: AKOS BRN-0170;2-(1,3,2-DIOXABORINAN-2-YL)BENZONITRILE;2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE;(2-CYANOPHENYL)BORONIC ACID, 1,3-PROPANEDIOL CYCLIC ESTER;(2-CYANOPHENYL)BORONIC ACID PROPANE-1,3-DIOL CYCLIC ESTER;2-CYANOPHENYLBORONIC ACID PROPANEDIOL-1,3 CYCLIC ESTER;2-CYANOPHENYLBORONIC ACID PROPANEDIOL ESTER;2-Cyanobenzeneboronic acid propane-1,3-diol cyclic ester
• CAS NO: 172732-52-4
• Molecular Formula: C₁₀H₁₀BNO₂
• Molecular Weight: 187
• Product Categories: blocks;BoronicAcids
• Mol File: 172732-52-4.mol

Chemical Properties

• Melting Point: 46-56 °C(lit.)
• Boiling Point: 372.4 °C at 760 mmHg
• Flash Point: 179 °C
• Appearance: /
• Density: 1.13 g/cm³
• Vapor Pressure: 9.63E-06mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(172732-52-4)
• EPA Substance Registry System: 2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(172732-52-4)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 172732-52-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE is used as a key intermediate in the synthesis of AMPA receptor antagonists for the treatment of neurological diseases. These diseases are characterized by the dysfunction of glutamatergic neurotransmission, and the compound plays a crucial role in developing effective treatments.
Specifically, it is used in the small-scale synthesis of Perampanel (P285520), an AMPA receptor antagonist. Perampanel is a medication used to treat seizures associated with epilepsy, and the compound contributes to its development by providing a stable and efficient synthetic route.

InChI:InChI=1/C10H10BNO2/c12-8-9-4-1-2-5-10(9)11-13-6-3-7-14-11/h1-2,4-5H,3,6-7H2

Synthetic route

2-Cyanophenylboronic acid (138642-62-3) + trimethyleneglycol (504-63-2) → o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4)

Conditions	Yield
at 20℃; for 1h;	82.4%
In dichloromethane	57.2%
In dichloromethane for 20h;	57.2%

o-cyanobromobenzene (2042-37-7) → o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene / 0.5 h / 0 - 5 °C / Inert atmosphere 1.2: 1.5 h / 0 - 5 °C 1.3: 0.75 h / 0 - 25 °C 2.1: hydrogenchloride / water / 0.5 h / 0 - 25 °C 3.1: toluene; tetrahydrofuran; Isopropyl acetate / 2 h / 20 - 25 °C View Scheme

benzonitrile (100-47-0) → o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium chloride; n-butyllithium / tetrahydrofuran; hexane / -10 °C / Inert atmosphere 1.2: -50 °C / Inert atmosphere 1.3: Inert atmosphere 2.1: 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: 2,2,6,6-tetramethyl-piperidine; lithium chloride; n-butyllithium / tetrahydrofuran; hexane / 3 h / -50 - -10 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: 1 h / 20 °C View Scheme

2-bromoanisole (578-57-4) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2'-methoxy-[1,1'-biphenyl]-2-carbonitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In toluene for 1h; Heating;	99%

benzoimidazole (51-17-2) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → salicylonitrile (611-20-1) + benzonitrile (100-47-0) + 2-(1H-benzo[d]imidazol-1-yl)benzonitrile (25699-93-8)

Conditions	Yield
With pyridine; water; copper diacetate In N,N-dimethyl-formamide at 30℃; for 24h; Kinetics; Product distribution; Further Variations:; Reaction partners; amount of water;	A n/a B n/a C 93%

2-Bromo-m-xylene (576-22-7) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2',6'-dimethyl-[1,1'-biphenyl]-2-carbonitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In toluene for 1h; Heating;	92%

tert-butyl N-(3-(3-iodo-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-1-yl)phenyl)carbamate + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → tert-butyl N-(3-(3-(2-cyanophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-1-yl)phenyl)carbamate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere;	90%

tert-butyl N-(3-(3-iodo-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-1-yl)phenyl)carbamate + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) + 2-(1,3,2-dioxaboran-2-yl)benzonitrile → tert-butyl N-(3-(3-(2-cyanophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-1-yl)phenyl)carbamate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere;	90%

(E)-2-methylbut-2-enoyl chloride (35660-94-7) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2-[(E)-2-methylbut-2-enoyl]benzonitrile

Conditions	Yield
With potassium phosphate; bis-triphenylphosphine-palladium(II) chloride In toluene at 80℃; for 4h;	89%

3-iodo-1-(3-dimethylaminophenyl)-5-(pyrimidin-2-yl)pyridin-2(1H)-one + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2-(1-(3-dimethylaminophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 115℃; for 0.333333h; Inert atmosphere;	89%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate	89%

o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) + 1-{3-bromo-4-chloro-5-[1-(R)-fluoropropyl]}phenylpiperazine (172732-49-9) → 1-{3-(2-cyanophenyl)-4-chloro-5-[1-(R)-fluoropropyl]}phenyl piperazine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In toluene Product distribution; Further Variations:; Reagents;	87%
With trans-bis(triphenylphosphine)palladium dichloride; tripotassium phosphate "n" hydrate In toluene at 20℃; for 1h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere; Large scale;

3-bromo-5-(2-pyridyl)-1-(3-pyridyl)-1,2-dihydropyridin-2-one + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 3-(2-cyanophenyl)-5-(pyridin-2-yl)-1-(pyridin-3-yl)-1,2-dihydropyridin-2-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Suzuki-Miyaura Coupling;	84%

potassium phosphate + 1-(2-trimethylsilyloxyethyl)-4-[3-bromo-4-chloro-5-(1-fluoropropyl)]phenylpiperazine (172732-42-2) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 1-(2-hydroxyethyl)-4-[3-(2-cyanophenyl)-4-chloro-5-(1-fluoropropyl)]phenylpiperazine hydrochloride (172732-18-2)

Conditions	Yield
With hydrogenchloride; tetrakis(triphenylphosphine)palladium (0) In ethanol; water; N,N-dimethyl-formamide	83.9%

3-acetylamino-1-(4-iodo-phenyl)-1H-pyrazole-4-carboxylicacid ethyl ester (1335105-20-8) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 3-acetylamino-1-(2'-cyano-biphenyl-4-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (1335105-40-2)

Conditions	Yield
With potassium phosphate; PdCl2(dppf) In toluene for 2h; Suzuki reaction; Reflux;	83%

iodobenzene (591-50-4) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → biphenyl-2-carbonitrile (24973-49-7)

Conditions	Yield
With tripotassium phosphate "n" hydrate; Pd(PPh3)2Cl2 In toluene at 100℃; for 12h; Schlenk technique; Inert atmosphere;	77%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2',5'-dimethoxy-[1,1'-biphenyl]-2-carbonitrile (75860-41-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In toluene for 1h; Heating;	76%

C16H12BrN3O2 (1415212-92-8) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2-(1-(6-methoxypyridin-3-yl)-2-oxo-5-(pyridin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 110 - 120℃; for 24h; Inert atmosphere;	75%

3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one (381248-06-2) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → [14C]-Perampanel (380917-97-5)

Conditions	Yield
With caesium carbonate; palladium dichloride In N,N-dimethyl-formamide at 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;	73%
Stage #1: 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one; o-cyanophenylboronic acid-1,3-propylene glycol ester With copper(l) iodide; potassium carbonate; palladium diacetate; triphenylphosphine In 1,2-dimethoxyethane at 70℃; for 4.5h; Heating / reflux; Stage #2: With ammonia In water at 60℃; for 0.883333h;
With potassium carbonate; palladium diacetate; copper(l) iodide; triphenylphosphine In 1,2-dimethoxyethane at 70℃; for 4.5h; Heating / reflux;
With copper(l) iodide; potassium carbonate; palladium diacetate; triphenylphosphine In 1,2-dimethoxyethane at 70℃; for 4.5h; Heating / reflux;
With tetrakis(triphenylphosphine) palladium(0); triethylamine In dichloromethane at 25 - 30℃; for 12h; Reagent/catalyst; Temperature; Solvent;

C17H10BrN3O (1415212-90-6) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → C24H14N4O (380919-04-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 110 - 120℃; for 24h; Inert atmosphere;	73%

potassium phosphate + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) + 1-{3-bromo-4-chloro-5-[1-(R)-fluoropropyl]}phenylpiperazine (172732-49-9) → 1-{3-(2-cyanophenyl)-4-chloro-5-[1-(R)-fluoropropyl]}phenyl piperazine

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In water; ethyl acetate; N,N-dimethyl-formamide	71%

5-[acetyl-(4-iodo-phenyl)-amino]-1-butyl-1H-pyrazole-4-carboxylic acid ethyl ester (1335105-43-5) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 5-[acetyl-(2'-cyano-biphenyl-4-yl)-amino]-1-butyl-1H-pyrazole-4-carboxylic acid ethyl ester (1335105-44-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In water; toluene for 1.5h; Suzuki reaction; Reflux;	71%

benzoyl chloride (98-88-4) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2-cyanobenzophenone (37774-78-0)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In toluene at 110℃; for 4h; Product distribution; Further Variations:; Reagents; Solvents; Suzuki-Miyaura coupling recation;	70%

tert-butyl (2-fluoro-5-(3-iodo-2-oxo-5-(pyrimidin-2-yl)pyridin-1(2H)-yl)phenyl)carbamate + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → tert-butyl (5-(3-(2-cyanophenyl)-2-oxo-5-(pyrimidin-2-yl)pyridin-1(2H)-yl)-2-fluorophenyl)carbamate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 110℃; for 1h; Inert atmosphere;	68%

5-(2-pyridyl)-3-bromo-2-methoxypyridine (381248-05-1) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 3-(2-cyanophenyl)-5-(2-pyridyl)-2-methoxypyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 140℃; for 5h; Inert atmosphere;	66%

2-bromo-4-butylaniline (51605-98-2) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2-(n-butyl)-6-aminophenanthridine (946147-28-0)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine)palladium (0) In ethanol; toluene	65.9%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 38h; Reflux; Inert atmosphere;	65.9%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 38h; Reflux; Inert atmosphere;	65.9%

3-bromo-1-(3-fluorophenyl)-5-(pyrimidin-2-yl)pyridin-2(1H)-one + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2-(1-(3-fluorophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Inert atmosphere;	60%

3-iodo-1-(3-fluorophenyl)-5-(pyrimidin-2-yl)pyridin-2(1H)-one + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2-(1-(3-fluorophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate	60%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide Suzuki-Miyaura Coupling;	28%

5-bromo-1-phenyl-3-iodo-1,2-dihydropyridin-2-one + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one (381233-77-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	52%

C15H9BrFN3O (1415212-89-3) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 3-(2-cyanophenyl)-5-(pyridin-2-yl)-1-(2-fluoropyridin-5-yl)-1,2-dihydropyridin-2-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 110 - 120℃; for 24h; Inert atmosphere;	42%

tert-butyl 3-iodo-2-oxo-5-(pyrimidin-2-yl)pyridine-1(2H)-carboxylate + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2-(2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 110℃; Inert atmosphere;	41%

2-bromo-4-n-hexylaniline (946147-25-7) + o-cyanophenylboronic acid-1,3-propylene glycol ester (172732-52-4) → 2-(n-hexyl)-6-aminophenanthridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 20h; Reflux; Inert atmosphere;	39.8%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 20h; Reflux; Inert atmosphere;	39.8%

Upstream product

• 100-47-0 benzonitrile 
• 2042-37-7 o-cyanobromobenzene 
• 138642-62-3 2-Cyanophenylboronic acid 
• 504-63-2 trimethyleneglycol 

Downstream Products

• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 380917-97-5 [14C]-Perampanel 
• 946147-07-5 5-(4-isopropylphenyl)imidazo[1,2-f]phenanthridine 
• 24061-14-1 1,4-dimethoxy-9H-fluoren-9-one 
• 157366-46-6 2-(o-Tolyl)benzonitrile 
• 1355247-46-9 3',5'-dimethyl-[1,1'-biphenyl]-2-carbonitrile 
• 1433967-20-4 2-(p-tolyl)-9H-fluoren-9-one 
• 125610-78-8 4'-methoxybiphenyl-2-carbonitrile 
• 91748-21-9 4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carbonitrile 
• 3096-56-8 2-bromofluoren-9-one 
• 168072-17-1 4'-bromo-[1,1'-biphenyl]-2-carbonitrile 
• 89346-58-7 4′-chloro-1,1′-biphenyl-2yl-carbonitrile 
• 343-01-1 2-fluoro-9H-fluoren-9-one 
• 486-25-9 9-fluorenone 

Relevant articles and documents

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METHOD OF PRODUCING 2-CYANOPHENYLBORONIC ACID DERIVATIVE

PROBLEM TO BE SOLVED: To provide a synthesis method for a 2-cyanophenylboronic acid derivative (2). SOLUTION: In the synthesis method, in the presence of alkali metal salt and lithium 2,2,6,6-tetramethylpiperidido, aromatic nitrile (1) and trialkoxyborane are reacted with each other. COPYRIGHT: (C)2015,JPOandINPIT

PROCESS FOR THE PREPARATION OF 2-CYANOPHENYLBORONIC ACID AND ESTERS THEREOF

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2-Cyanophenylboronic Acid or Ester Thereof in Which Impurities Are Decreased, and Production Method Thereof

A method for producing high-purity 2-cyanophenylboronic acid, characterized by reacting benzonitrile, lithium 2,2,6,6-tetramethylpiperidide, and trialkoxyborane, adding an aqueous acidic solution to a reaction solution containing the obtained 2-cyanophenylboronic acid, carrying out a contact treatment at a pH of below 7 in the presence of a water-immiscible organic solvent, and then obtaining the 2-cyanophenylboronic acid from the organic layer.

BIPHENYL DERIVATIVES

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