4-Formylphenylboronic acid supplier

Name
4-Formylphenylboronic acid
EINECS 438-670-5
CAS No. 87199-17-5
Article Data39
CAS DataBase
Density 1.244 g/cm³
Solubility Slightly Soluble in water.
Melting Point 237-242 °C(lit.)
Formula C₇H₇BO₃
Boiling Point 347.584 °C at 760 mmHg
Molecular Weight 149.942
Flash Point 164.013 °C
Transport Information UN 1759 8/PG 3
Appearance white to light yellow crystal powder
Safety 22-26-36/37/39-45-37/39-36
Risk Codes 34-36/37/38
Molecular Structure
Hazard Symbols C,Xi
Synonyms Boronic acid, (4-formylphenyl)-;(4-formylphenyl)boronic acid;(4-formylphenyl) Boronic acid;4-Formylphenyl Boronic Acid;4-Formylbenzeneboronic acid;4-(dihydroxyboryl)benzaldehyde;
PSA 57.53000
LogP -0.82110

Synthetic route

: potassium 4-formylphenyltrifluoroborate

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With iron(III) chloride; water In tetrahydrofuran at 20℃; for 1h;	97%
With aluminum oxide; water at 70℃; for 0.25h; Microwave irradiation;	92%
With water; silica gel at 20℃; for 24h; Inert atmosphere;	88%

: 59016-93-2
p-hydroxymethylphenylboronic acid

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 5h; Inert atmosphere;	90%
With o-iodoxybenzoic acid In dimethylsulfoxide reaction at room temp.; one phase-switch purification used;	90%

: 186497-79-0
4-allylphenylboronic acid

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With Triethoxysilane; iron(III) chloride In methanol for 12h; Reflux;	88%

: 61568-51-2
2-(4-bromophenyl)-1,3-dioxane

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Stage #1: 2-(4-bromophenyl)-1,3-dioxane With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: With Trimethyl borate In tetrahydrofuran; pentane at -78 - 20℃; for 3h; Stage #3: With hydrogenchloride In tetrahydrofuran; water; pentane	81%
Stage #1: 2-(4-bromophenyl)-1,3-dioxane With magnesium; ethylene dibromide In tetrahydrofuran for 0.5h; Metallation; Heating; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - -45℃; for 7.5h; Grignard reaction; Stage #3: With hydrogenchloride; water for 0.25h; Hydrolysis; Heating;	67%
Stage #1: 2-(4-bromophenyl)-1,3-dioxane With magnesium; ethylene dibromide In tetrahydrofuran for 1.66667h; Stage #2: With Trimethyl borate In tetrahydrofuran for 0.666667h; Stage #3: With hydrogenchloride In water for 1h; Reflux;	48%

: 10602-01-4
p-bromobenzaldehyde 1,3-dioxolane

: 5419-55-6
Triisopropyl borate

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Stage #1: p-bromobenzaldehyde 1,3-dioxolane With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 3h; Inert atmosphere; Schlenk technique;	78%
With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere;	71%
Stage #1: p-bromobenzaldehyde 1,3-dioxolane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; for 2h;	64%
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane n-C4H9Li/hexanes added dropwise to a soln. of 2-(4-bromophenyl)-1,3-dioxolane in THF at -78°C, stirred at -78°C for 45 min, B compd. added dropwise, warmed slowly to room temp. and stirred overnight, quenched with HCl at room temp. for 2 h; extd. (EtOAc), the combined org. layers washed (brine), dried (MgSO4), flash-chromd. (silica gel, EtOAc/petroleum ether, then MeOH); elem. anal.;	64%

: 688-74-4
boric acid tributyl ester

: 34421-94-8
4-bromobenzaldehyde diethyl acetal

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With Mg; aq. H2SO4; KOH In tetrahydrofuran; diethyl ether byproducts: BuOH, Mg(OH)2, MgBr2; dropwise addn. of the grignard compd. of the acetal in THF to mixt. of B(OC4H9)3 in THF (under N2, -68°C, under stirring), stirred after thawing (1 h), evapn. of volatiles (20°C, 1 Torr), addn. of 1 M H2SO4 to soln. of the residue in ether; extn. with ether, evapn. of ether (vac.), addn. of KOH to aq. phase, after addn. of water azeotropic distn. of H2O/ BuOH in vac., residue acidified with 1 M H2SO4, refluxed (30 min), filtered, cooling of the filtrate, recrystn. from hot H2O; elem. anal.;	78%

Yield

With Mg; aq. H2SO4; KOH In tetrahydrofuran; diethyl ether byproducts: BuOH, Mg(OH)2, MgBr2; dropwise addn. of the grignard compd. of the acetal in THF to mixt. of B(OC4H9)3 in THF (under N2, -68°C, under stirring), stirred after thawing (1 h), evapn. of volatiles (20°C, 1 Torr), addn. of 1 M H2SO4 to soln. of the residue in ether; extn. with ether, evapn. of ether (vac.), addn. of KOH to aq. phase, after addn. of water azeotropic distn. of H2O/ BuOH in vac., residue acidified with 1 M H2SO4, refluxed (30 min), filtered, cooling of the filtrate, recrystn. from hot H2O; elem. anal.;

78%

: potassium 4-formylphenyltrifluoroborate

: 7732-18-5
water

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With montmorillonite K10 at 25℃; for 24h;	75%

: C41H63BO6

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
In water; dimethyl sulfoxide at 219.85℃; for 120h;	72%

: (HO)2BC6H4CH(C6H2(OH)2(CH2)10CH3)2

: 7732-18-5
water

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
In dimethyl sulfoxide thermolysis of mixt. of boron compound, DMSO and water at 493 K, 5 d, cooling; filtration, evapn. in vac., washing with ethyl acetate, drying;	72%

: 10602-01-4
p-bromobenzaldehyde 1,3-dioxolane

: 121-43-7
Trimethyl borate

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Stage #1: p-bromobenzaldehyde 1,3-dioxolane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere;	63%

: 10602-01-4
p-bromobenzaldehyde 1,3-dioxolane

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Stage #1: p-bromobenzaldehyde 1,3-dioxolane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: With boric acid tributyl ester In tetrahydrofuran; hexane at -78℃; for 1h;	54%
Stage #1: p-bromobenzaldehyde 1,3-dioxolane With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride; water; sodium chloride In tetrahydrofuran for 0.5h;

: 68162-47-0
4-bromomethylphenylboronic acid

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With hexamethylenetetramine

<4-dibromomethyl-phenyl>-dihydroxy-borane: <4-dibromomethyl-phenyl>-dihydroxy-borane

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With sulphurous acid

: C11H17BO4

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With hydrogenchloride; water at 20℃; for 7h;

: 1122-91-4
4-bromo-benzaldehyde

LiPh2InH2: LiPh2InH2

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 89 percent / p-TsOH / toluene / 20 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C 2.2: tetrahydrofuran; hexane / 20 °C 2.3: 64 percent / aq. HCl / hexane; tetrahydrofuran / 2 h / 20 °C View Scheme

: 34421-94-8
4-bromobenzaldehyde diethyl acetal

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nBuLi; B(O-iPr)3 / tetrahydrofuran; hexane / 20 °C 2: HCl; water / 7 h / 20 °C View Scheme

: 1122-91-4
4-bromo-benzaldehyde

4-acetylbenzoyl-Rink resin: 4-acetylbenzoyl-Rink resin

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 89 percent / p-TsOH*H2O / ethanol / 20 °C 2: nBuLi; B(O-iPr)3 / tetrahydrofuran; hexane / 20 °C 3: HCl; water / 7 h / 20 °C View Scheme

: 1122-91-4
4-bromo-benzaldehyde

decyl magnesium halide: decyl magnesium halide

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 96 percent / BF3*OEt2 / toluene / 4.5 h / Heating 2.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 0.5 h / Heating 2.2: B(OCH3)3 / tetrahydrofuran / 7.5 h / -78 - -45 °C 2.3: 67 percent / HCl; H2O / 0.25 h / Heating View Scheme

: 121-43-7
Trimethyl borate

: 1122-91-4
4-bromo-benzaldehyde

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran N2; BuLi dropping into org. compd. soln. at -78°C, mixt. keeping 3 h, B-compd. soln. addn. dropwise at -78°C, mixt. allowing to warm to room temp. overnight , stirring 1 h with 10% HCl, extn. (Et2O); org. extracts washing (water), drying, solvent vac. removal;

: 111561-46-7
tris(4-dibromomethyl phenyl)boroxine

: 7732-18-5
water

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
In water hydrolysis on boiling in SO2-satd. H2O (10min);;
In water hydrolysis on boiling in SO2-satd. H2O (10min);;

: 17933-03-8
m-tolylboronic acid

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: benzoyl peroxide / tetrachloromethane 2: benzoyl peroxide / tetrachloromethane 3: water View Scheme

: 51239-44-2
tris(4-bromomethyl phenyl)boroxine

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzoyl peroxide / tetrachloromethane 2: water View Scheme

: 104-88-1
4-chlorobenzaldehyde

A: 59016-93-2
p-hydroxymethylphenylboronic acid

B: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With tetrahydroxydiboron; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); potassium acetate; XPhos In ethanol at 80℃; for 20h; Inert atmosphere;

: 1122-91-4
4-bromo-benzaldehyde

A: 59016-93-2
p-hydroxymethylphenylboronic acid

B: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
With tetrahydroxydiboron; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); potassium acetate; XPhos In methanol at 80℃; for 4h; Inert atmosphere;

: 1122-91-4
4-bromo-benzaldehyde

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / toluene / 20 h / Reflux; Dean-Stark 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C 2.2: 1 h / -78 °C View Scheme
With tetrahydroxydiboron; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 20℃; for 6h; Miyaura Borylation Reaction; Inert atmosphere; Sealed tube;
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 24 h / Dean-Stark; Reflux 2: n-butyllithium / tetrahydrofuran; hexane / 2 h / 20 °C / Inert atmosphere View Scheme

: 2156-04-9
4-Vinylphenylboronic acid

A: 4-(1,2-dihydroxyethyl)phenylboronic acid

B: 87199-17-5
4-formylphenylboronic acid,

C: 2628-17-3
4-Vinylphenol

Conditions

Conditions	Yield
With [(hydrotris(3,5-diphenyl-pyrazol-1-yl)borate)FeII(benzilate)]; oxygen In benzene at 20℃; for 0.333333h;

...Expand

: 121-43-7
Trimethyl borate

: 34421-94-8
4-bromobenzaldehyde diethyl acetal

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Stage #1: 4-bromobenzaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor;

: 7519-94-0
2,4,6-tris(4-bromophenyl)boroxin

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 87199-17-5
4-formylphenylboronic acid,

Conditions

Conditions	Yield
Stage #1: 2,4,6-tris(4-bromophenyl)boroxin; N,N-dimethyl-formamide With n-butyllithium In tetrahydrofuran; hexane at -60 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃; pH=2 - 3;	112.4 g

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 87199-17-5
4-formylphenylboronic acid,

: 128376-64-7
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Conditions

Conditions	Yield
In tetrahydrofuran; toluene	100%
In diethyl ether at 20℃; cyclocondensation;	100%
Inert atmosphere;	100%

: 623-00-7
4-bromobenzenecarbonitrile

: 87199-17-5
4-formylphenylboronic acid,

: 50670-55-8
4-(4-cyanophenyl)-benzaldehyde

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 80℃; Schlenk technique; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 80℃; Schlenk technique; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water Suzuki Coupling; Reflux; Inert atmosphere;	100%

: 87199-17-5
4-formylphenylboronic acid,

: 19524-06-2
4-bromopyridine hydrochloride

: 99163-12-9
4-(pyridin-4-yl)benzaldehyde

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 4h; Suzuki Coupling; Reflux; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; isopropyl alcohol; toluene for 7h; Inert atmosphere; Reflux;	94%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; isopropyl alcohol; toluene for 7h; Inert atmosphere; Reflux;	84%

: 109-04-6
2-bromo-pyridine

: 87199-17-5
4-formylphenylboronic acid,

: 127406-56-8
2-(4-formylphenyl)pyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 8h; Suzuki coupling; Reflux;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	100%
Stage #1: 2-bromo-pyridine; 4-formylphenylboronic acid, With potassium carbonate In 1,4-dioxane; water for 0.5h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water Inert atmosphere; Reflux;	100%

: N-(2-bromophenyl)-N'-methylpiperazine

: 87199-17-5
4-formylphenylboronic acid,

: 735333-36-5
2'-(4-Methyl-piperazine-1-yl)-biphenyl-4-carboxaldehyde

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine)palladium (0) In ethanol; water at 90℃; for 18h;	100%

: 920511-33-7
2-({4-[(4-fluorophenyl)amino]-1-piperidinyl}carbonyl)-3-pyridinyl trifluoromethanesulfonate

: 87199-17-5
4-formylphenylboronic acid,

: 920511-34-8
4-[2-({4-[(4-fluorophenyl)amino]-1-piperidinyl}carbonyl)-3-pyridinyl]benzaldehyde

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 50℃; Suzuki-Miyaura coupling;	100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 60℃; for 4h;
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 20 - 60℃;

: 87199-17-5
4-formylphenylboronic acid,

: 504-63-2
trimethyleneglycol

: 4-(1,3,2-dioxaborinan-2-yl)-benzaldehyde

Conditions

Conditions	Yield
In toluene at 135℃; for 5h; Inert atmosphere; Dean-Stark;	100%
In toluene for 12h; Reflux;

: 87199-17-5
4-formylphenylboronic acid,

: 107-21-1
ethylene glycol

: 328063-34-9
4-(OCH2CH2O-B)C6H4C(H)=O

Conditions

Conditions	Yield
In toluene for 2.5h; Reflux;	100%
In toluene for 8h; Reflux;	43%
In toluene 1:1 molar ratio, mixt. refluxed for 8 h; cooled, evapd., elem. anal.;	43%

: 98027-84-0
2,6-dichloro-4-iodopyridine

: 87199-17-5
4-formylphenylboronic acid,

: 1628606-70-1
4-(2,6-dichloropyridin-4-yl)benzaldehyde

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 4h; Suzuki Coupling; Reflux; Inert atmosphere;	100%

: 1206522-04-4
5-ethyl-3-iodo-2,5-dihydrofuran-2-one

: 87199-17-5
4-formylphenylboronic acid,

: 5-ethyl-3-(4-formylphenyl)furan-2(5H)-one

Conditions

Conditions	Yield
With 1,1',1'',1'''-benzene-1,2,4,5-tetrayltetrakis(methylene)tetrakis-(piperidin-4-ol); palladium diacetate; potassium carbonate In ethanol; water at 20℃; for 0.25h; Suzuki-Miyaura Coupling;	100%

: 87199-17-5
4-formylphenylboronic acid,

: 126-30-7
2,2-Dimethyl-1,3-propanediol

: 128376-65-8
5,5-dimethyl-2-(4-formylphenyl)-1,3,2-dioxaborinane

Conditions

Conditions	Yield
In benzene 4-formylphenylboronic acid and 2,2-dimethylpropane-1,3-diol were refluxed in benzene for 2 h 30 min; soln. was evapd. to dryness;	99%
In tetrahydrofuran at 20℃; for 0.166667h; Esterification;	98%
In tetrahydrofuran	97%

: 87199-17-5
4-formylphenylboronic acid,

: 586-78-7
para-nitrophenyl bromide

: 98648-23-8
4-(4'-nitrophenyl)benzaldehyde

Conditions

Conditions	Yield
With bis(1,1'-ethylene-3,3'-divinylimidazole-2,2'-diylidene)nickel(II) dibromide dihydrate; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	99%
With potassium carbonate In ethanol; water at 50℃; for 19h; Reagent/catalyst; Suzuki-Miyaura Coupling;	98%
With potassium carbonate In ethanol; water at 80℃; for 0.166667h; Reagent/catalyst; Suzuki Coupling;	95%

: 87199-17-5
4-formylphenylboronic acid,

: 513-85-9
2.3-butanediol

: 215876-82-7
2-(4-formylphenyl)-4,5-dimethyl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With magnesium sulfate In ethyl acetate at 20℃;	99%

: 591-50-4
iodobenzene

: 87199-17-5
4-formylphenylboronic acid,

: 3218-36-8
4-Phenylbenzaldehyde

Conditions

Conditions	Yield
With bis(1,1'-ethylene-3,3'-divinylimidazole-2,2'-diylidene)nickel(II) dibromide dihydrate; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	99%
With potassium carbonate In water; N,N-dimethyl-formamide at 30℃; for 4h; Suzuki-Miyaura Coupling; Irradiation; Inert atmosphere;	98%
With potassium phosphate In ethanol; water at 80℃; for 3h; Suzuki-Miyaura Coupling;	98%

: 87199-17-5
4-formylphenylboronic acid,

: 1122-91-4
4-bromo-benzaldehyde

: 66-98-8
4,4'-diformylbiphenyl

Conditions

Conditions	Yield
With potassium carbonate In ethanol; water at 50℃; for 19h; Reagent/catalyst; Suzuki-Miyaura Coupling;	99%
With potassium carbonate In ethanol; water at 50℃; for 19h; Suzuki Coupling;	99%
With potassium carbonate In ethanol; water at 60℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Suzuki-Miyaura Coupling;	99%

: 636-98-6
p-nitrobenzene iodide

: 87199-17-5
4-formylphenylboronic acid,

: 98648-23-8
4-(4'-nitrophenyl)benzaldehyde

Conditions

Conditions	Yield
With palladium diacetate; 4-Ph2P-C6H4-2-N-glucosamine; sodium carbonate In tetrahydrofuran; ethanol; water at 60℃; for 1h;	99%
With polyhydroxylated phosphine; sodium carbonate; palladium diacetate In ethanol; water; toluene at 60℃; for 1h;	99%
With triethylamine In ethanol; water at 80℃; for 0.5h; Suzuki-Miyaura Coupling; Microwave irradiation;	97%

: 108-86-1
bromobenzene

: 87199-17-5
4-formylphenylboronic acid,

: 3218-36-8
4-Phenylbenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In ethanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling;	99%
With palladium diacetate In water; isopropyl alcohol at 27℃; for 1h; Suzuki-Miyaura Coupling;	96%
With C12H12Cl2N4O2Pd; caesium carbonate In water at 60℃; for 5h; Suzuki-Miyaura Coupling;	90%

: 624-31-7
4-tolyl iodide

: 87199-17-5
4-formylphenylboronic acid,

: 36393-42-7
4-(4-methylphenyl)benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In ethanol; water at 80℃; for 0.166667h; Reagent/catalyst; Suzuki Coupling;	99%
With potassium carbonate In ethanol; water at 50℃; for 19h; Reagent/catalyst; Suzuki-Miyaura Coupling;	92%
With potassium carbonate In ethanol; water at 50℃; for 19h; Catalytic behavior; Suzuki Coupling;	92%
With sodium carbonate; 1,2-bis(2'-pyrazineethynyl)benzene palladium dichloride In water; acetonitrile at 70℃; for 6h; Suzuki coupling;	89%

: 87199-17-5
4-formylphenylboronic acid,

: 331861-94-0
1,7-dibromo-N,N'-bis(2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic acid diimide

: N,N'-bis(2,6-diisopropylphenyl)-1,7-di(4-formylphenyl)perylene-3,4,9,10-tetracarboxydiimide

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 70℃; for 15h; Inert atmosphere;	99%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; benzene at 80℃; for 96h; Suzuki coupling;	72%

: 4595-59-9
5-bromopyrimidine

: 87199-17-5
4-formylphenylboronic acid,

: 198084-12-7
4-(pyrimidin-5-yl)benzaldehyde

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 90℃; for 18h; Suzuki Coupling;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate monohydrate In 1,2-dimethoxyethane; water at 90℃; Suzuki Coupling; Inert atmosphere;

: tetrakis(μ-caprolactamato)dirhodium(Rh-Rh)

: 87199-17-5
4-formylphenylboronic acid,

: 1039763-74-0, 1158952-16-9
bis-(σ-(4-formylphenyl))-tetrakis-μ-(caprolactamato)dirhodium(III)

Conditions

Conditions	Yield
With sodium methylate; copper(I) trifluoromethanesulfonate benzene In methanol; dichloromethane room temp., 10 equiv. of 4-HOCC6H4B(OH)2, 15 mol% (CuOTf)2*C6H6, 10 equiv. of NaOMe, 12 h, in 4:1 CH2Cl2-MeOH; column chromy. on silica gel or recrystn. from react. soln. by titrn. with MeOH;	99%
With sodium methylate; copper(ll) sulfate pentahydrate In methanol; dichloromethane room temp., 10 equiv. of 4-HOCC6H4B(OH)2, 10 mol% CuSO4*5H2O, 10 equiv. of NaOMe, 12 h, in 4:1 CH2Cl2-MeOH; column chromy. on silica gel;	95%

: 90-11-9
1-Bromonaphthalene

: 87199-17-5
4-formylphenylboronic acid,

: 56432-18-9
4-(naphthalene-1-yl)benzaldehyde

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Inert atmosphere; Reflux;	99%
With potassium phosphate; sodium tetrachloropalladate(II); sodium dodecyl-sulfate In water at 100℃; for 0.0833333h; Suzuki coupling;	90%
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 8h; Suzuki-Miyaura cross-coupling;	56 %Chromat.

: 51-17-2
benzoimidazole

: 87199-17-5
4-formylphenylboronic acid,

: 90514-72-0
4-(1H-benzo[d]imidazol-1-yl)benzaldehyde

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; oxygen; copper(II) nitrate In methanol at 20℃; under 760.051 Torr; for 24h;	99%
With copper diacetate; tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin In water at 50℃; for 4h; Chan-Lam Coupling; chemoselective reaction;	81%

: 18680-27-8
pinanediol

: 87199-17-5
4-formylphenylboronic acid,

: 4-(2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl)-benzaldehyde

Conditions

Conditions	Yield
In diethyl ether at 20℃; for 24h; Inert atmosphere;	99%
In diethyl ether (Ar); mixt. of boronic acid and pinandiol was stirred in Et2O at room temp. for 24 h; dried over MgSO4, concd., elem. anal.;	99%

: 1202647-41-3
(R)-1-(2-bromo-benzenesulfonyl)-2-methyl-pyrrolidine

: 87199-17-5
4-formylphenylboronic acid,

: 1202647-44-6
2'-((R)-2-Methyl-pyrrolidine-1-sulfonyl)-biphenyl-4-carbaldehyde

Conditions

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 2-Methyl-1,2-propanediol; ISOPROPYLAMIDE at 100℃; Suzuki Coupling;	99%

: 87199-17-5
4-formylphenylboronic acid,

: 123-08-0
4-hydroxy-benzaldehyde

Conditions

Conditions	Yield
With copper(II) ferrite; water; sodium hydroxide at 40℃; for 24h; Green chemistry;	99%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 48h; Reagent/catalyst; Irradiation; Green chemistry;	99%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile for 48h; Irradiation;	99%

: 87199-17-5
4-formylphenylboronic acid,

: 371-40-4
4-fluoroaniline

: (E)-(4-(((4-fluorophenyl)imino)methyl)phenyl)boronic acid

Conditions

Conditions	Yield
In toluene for 24h; Reflux;	99%

: 87199-17-5
4-formylphenylboronic acid,

: 1005-30-7
sodium 4-iodo-benzoate

: 70916-98-2
4′-formyl-(1,1′-biphenyl)-4-carboxylic Acid

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate In water at 70℃; for 2h;	99%

: 626-60-8
3-Chloropyridine

: 87199-17-5
4-formylphenylboronic acid,

: 127406-55-7
4-(pyridin-3-yl)benzaldehyde

Conditions

Yield

Stage #1: 3-Chloropyridine; 4-formylphenylboronic acid, With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 0.0833333h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;
Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 80℃; for 4h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;

99%

With Pd(Cy*Phine)2Cl2 ; potassium hydroxide In butan-1-ol at 100℃; for 1h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere; Schlenk technique;

91%

: 61079-82-1
N-(phenylmethyl)-di(p-toluenesulfonyl)amine

: 87199-17-5
4-formylphenylboronic acid,

: 67468-65-9
4-benzylbenzaldehyde

Conditions

Conditions	Yield
With tetrakis(acetonitrile)palladium(II) tetrafluoroborate; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl-formamide at 60℃; for 1.5h; Inert atmosphere;	99%

4-Formylphenylboronic acid Specification

The 4-Formylphenylboronic acid is an organic compound with the formula C₇H₇BO₃. The IUPAC name of this chemical is (4-formylphenyl)boronic acid. With the CAS registry number 87199-17-5, it is also named as Boronic acid, (4-formylphenyl)-. The product's categories are Aldehyde; Aldehydes; Blocks; Boronic Acids; Boronic Acid Series; Boron, Nitrile, Thio & TM-Cpds; Carbonyl Compounds; Substituted Boronic Acids; Pharmacetical; Boronic Acids & Esters; Phenyls & Phenyl-Het; Boronic Acids; Boronic Acid; Aryl; Organoborons; B (Classes of Boron Compounds); Chiral Chemicals; Boronic Acids & Esters; Phenyls & Phenyl-Het. Besides, it is a white to light yellow crystal powder, which should be stored in a closed and dry place.

Physical properties about 4-Formylphenylboronic acid are: (1)ACD/LogP: 0.51; (2)ACD/LogD (pH 5.5): 0.506; (3)ACD/LogD (pH 7.4): 0.183; (4)ACD/BCF (pH 5.5): 1.423; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 44.622; (7)ACD/KOC (pH 7.4): 21.187; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 57.53 Å²; (12)Index of Refraction: 1.548; (13)Molar Refractivity: 38.257 cm³; (14)Molar Volume: 120.525 cm³; (15)Polarizability: 15.166×10^-24cm³; (16)Surface Tension: 49.006 dyne/cm; (17)Density: 1.244 g/cm³; (18)Flash Point: 164.013 °C; (19)Enthalpy of Vaporization: 62.462 kJ/mol; (20)Boiling Point: 347.584 °C at 760 mmHg.

Uses of 4-Formylphenylboronic acid: it can be used to produce 4-iodo-benzaldehyde at temperature of 81 °C. It will need reagent NIS and solvent acetonitrile with reaction time of 14 hours. The yield is about 94%.

When you are using this chemical, please be cautious about it as the following:
It can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection and do not breathe dust. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: B(c1ccc(cc1)C=O)(O)O
(2)InChI: InChI=1/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
(3)InChIKey: VXWBQOJISHAKKM-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
(5)Std. InChIKey: VXWBQOJISHAKKM-UHFFFAOYSA-N

Product Name

4-Formylphenylboronic acid

Synthetic route

4-Formylphenylboronic acid Specification

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