Name: 5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole
SKU: 906673-24-3

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Basic Information

Molecular Structure:
CAS No.:	906673-24-3
Name:	5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole
Article Data:	28

Formula:	C14H10BNO3
Molecular Weight:	251.049
Synonyms:	AN2728; 4-[(1,3-Dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]benzonitrile
Density:	1.33±0.1 g/cm3(Predicted)
Boiling Point:	425.9±55.0 °C(Predicted)
PSA:	62.48000
LogP:	1.56828

Synthetic route

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 60℃; Reagent/catalyst; Temperature; Solvent;	95%

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h; Reagent/catalyst; Temperature;	95%
With potassium carbonate In dimethyl sulfoxide at 60 - 70℃; for 4h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;	76.9%

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 60℃; Reagent/catalyst; Solvent; Temperature;	93.3%

: 5-(4-cyanophenoxy)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 40℃; Reagent/catalyst; Solvent; Temperature;	93%
With sodium hydroxide at 15 - 45℃;	91%

: 4-(3-(hydroxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzonitrile

Conditions	Yield
With hydrogenchloride In water at 80℃; for 4h;	93%

Conditions	Yield
With methanesulfonic acid In ethanol; water at 20 - 30℃; for 24h; Solvent; Reagent/catalyst;	92%

: 2,6-dichloro-4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)oxy)benzonitrile

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen; potassium hydroxide In ethanol; water under 760.051 - 3800.26 Torr; for 1h;	90%

Conditions	Yield
With water; potassium hydroxide at 55 - 65℃; for 2h; Inert atmosphere;	90%

: 4-(3-formyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzonitrile

Conditions	Yield
Stage #1: 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-formylphenoxy]benzonitrile With sodium tetrahydroborate; ethanol at 0 - 5℃; for 1h; Inert atmosphere; Stage #2: water With hydrogenchloride at 40 - 45℃; for 0.5h; Inert atmosphere;	89.4%
Stage #1: 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-formylphenoxy]benzonitrile With methanol; sodium tetrahydroborate at 0 - 15℃; for 1h; Inert atmosphere; Stage #2: water With hydrogenchloride pH=4 - 6; Temperature;	76.5%