2-Cyanophenylboronic acid 1,3-propanediol ester supplier

Name
2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
EINECS
CAS No. 172732-52-4
Article Data10
CAS DataBase
Density 1.13 g/cm³
Solubility
Melting Point 46-56 °C(lit.)
Formula C₁₀H₁₀BNO₂
Boiling Point 372.4 °C at 760 mmHg
Molecular Weight 187.006
Flash Point 179 °C
Transport Information 3439
Appearance
Safety 26-36/37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-(1,3,2-Dioxaborinan-2-yl)benzonitrile;2-(2-Cyanophenyl)-1,3,2-dioxaborinane;2-(1,3,2-dioxaborinan-2-yl)benzonitrile;Benzonitrile, 2-(1,3,2-dioxaborinan-2-yl)-;
PSA 42.25000
LogP 0.69038

Synthetic route

: 138642-62-3
2-Cyanophenylboronic acid

: 504-63-2
trimethyleneglycol

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

Conditions

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

: 2042-37-7
o-cyanobromobenzene

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

Conditions

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

: 100-47-0
benzonitrile

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

Conditions

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

: 578-57-4
2-bromoanisole

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 2'-methoxy-[1,1'-biphenyl]-2-carbonitrile

Conditions

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

: 51-17-2
benzoimidazole

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

A: 611-20-1
salicylonitrile

B: 100-47-0
benzonitrile

C: 25699-93-8
2-(1H-benzo[d]imidazol-1-yl)benzonitrile

Conditions

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%

...Expand

: 576-22-7
2-Bromo-m-xylene

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 2',6'-dimethyl-[1,1'-biphenyl]-2-carbonitrile

Conditions

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

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: tert-butyl N-(3-(3-(2-cyanophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-1-yl)phenyl)carbamate

Conditions

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

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

2-(1,3,2-dioxaboran-2-yl)benzonitrile: 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

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

...Expand

: 35660-94-7
(E)-2-methylbut-2-enoyl chloride

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 2-[(E)-2-methylbut-2-enoyl]benzonitrile

Conditions

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

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 2-(1-(3-dimethylaminophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions

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%

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 172732-49-9
1-{3-bromo-4-chloro-5-[1-(R)-fluoropropyl]}phenylpiperazine

: 1-{3-(2-cyanophenyl)-4-chloro-5-[1-(R)-fluoropropyl]}phenyl piperazine

Conditions

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

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 3-(2-cyanophenyl)-5-(pyridin-2-yl)-1-(pyridin-3-yl)-1,2-dihydropyridin-2-one

Conditions

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

: potassium phosphate

: 172732-42-2
1-(2-trimethylsilyloxyethyl)-4-[3-bromo-4-chloro-5-(1-fluoropropyl)]phenylpiperazine

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 172732-18-2
1-(2-hydroxyethyl)-4-[3-(2-cyanophenyl)-4-chloro-5-(1-fluoropropyl)]phenylpiperazine hydrochloride

Conditions

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

...Expand

: 1335105-20-8
3-acetylamino-1-(4-iodo-phenyl)-1H-pyrazole-4-carboxylicacid ethyl ester

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 1335105-40-2
3-acetylamino-1-(2'-cyano-biphenyl-4-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

Conditions

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

: 591-50-4
iodobenzene

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 24973-49-7
biphenyl-2-carbonitrile

Conditions

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

: 25245-34-5
1-bromo-2,5-dimethoxybenzene

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 75860-41-2
2',5'-dimethoxy-[1,1'-biphenyl]-2-carbonitrile

Conditions

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

: 1415212-92-8
C16H12BrN3O2

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 2-(1-(6-methoxypyridin-3-yl)-2-oxo-5-(pyridin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions

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

: 381248-06-2
3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 380917-97-5
[14C]-Perampanel

Conditions

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;

: 1415212-90-6
C17H10BrN3O

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 380919-04-0
C24H14N4O

Conditions

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

: potassium phosphate

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 172732-49-9
1-{3-bromo-4-chloro-5-[1-(R)-fluoropropyl]}phenylpiperazine

: 1-{3-(2-cyanophenyl)-4-chloro-5-[1-(R)-fluoropropyl]}phenyl piperazine

Conditions

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

...Expand

: 1335105-43-5
5-[acetyl-(4-iodo-phenyl)-amino]-1-butyl-1H-pyrazole-4-carboxylic acid ethyl ester

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 1335105-44-6
5-[acetyl-(2'-cyano-biphenyl-4-yl)-amino]-1-butyl-1H-pyrazole-4-carboxylic acid ethyl ester

Conditions

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

: 98-88-4
benzoyl chloride

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 37774-78-0
2-cyanobenzophenone

Conditions

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

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: tert-butyl (5-(3-(2-cyanophenyl)-2-oxo-5-(pyrimidin-2-yl)pyridin-1(2H)-yl)-2-fluorophenyl)carbamate

Conditions

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

: 381248-05-1
5-(2-pyridyl)-3-bromo-2-methoxypyridine

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 3-(2-cyanophenyl)-5-(2-pyridyl)-2-methoxypyridine

Conditions

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

: 51605-98-2
2-bromo-4-butylaniline

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 946147-28-0
2-(n-butyl)-6-aminophenanthridine

Conditions

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

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 2-(1-(3-fluorophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions

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

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 2-(1-(3-fluorophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions

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

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 381233-77-8
5-bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one

Conditions

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

: 1415212-89-3
C15H9BrFN3O

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 3-(2-cyanophenyl)-5-(pyridin-2-yl)-1-(2-fluoropyridin-5-yl)-1,2-dihydropyridin-2-one

Conditions

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

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 2-(2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)benzonitrile

Conditions

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

: 946147-25-7
2-bromo-4-n-hexylaniline

: 172732-52-4
o-cyanophenylboronic acid-1,3-propylene glycol ester

: 2-(n-hexyl)-6-aminophenanthridine

Conditions

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%

2-Cyanophenylboronic acid 1,3-propanediol ester Specification

The Benzonitrile,2-(1,3,2-dioxaborinan-2-yl)-, with the CAS registry number 172732-52-4, has the systematic name of 2-(1,3,2-dioxaborinan-2-yl)benzonitrile. It belongs to the product categories of Blocks and BoronicAcids. And the molecular formula of the chemical is C₁₀H₁₀BNO₂.

The characteristics of Benzonitrile,2-(1,3,2-dioxaborinan-2-yl)- are as followings: (1)#H bond acceptors: 3; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 42.25 Å²; (5)Index of Refraction: 1.519; (6)Molar Refractivity: 50.12 cm³; (7)Molar Volume: 165 cm³; (8)Polarizability: 19.86×10^-24cm³; (9)Surface Tension: 40.6 dyne/cm; (10)Density: 1.13 g/cm³; (11)Flash Point: 179 °C; (12)Enthalpy of Vaporization: 61.96 kJ/mol; (13)Boiling Point: 372.4 °C at 760 mmHg; (14)Vapour Pressure: 9.63E-06 mmHg at 25°C.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin, and it is also harmful by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: N#Cc1ccccc1B2OCCCO2
(2)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
(3)InChIKey: REQZFVYFYAZUMG-UHFFFAOYAH

Product Name

2-(1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE

Synthetic route

2-Cyanophenylboronic acid 1,3-propanediol ester Specification

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