87199-17-5

Basic information

• Product Name: 4-Formylphenylboronic acid
• Synonyms: RARECHEM AH PB 0193;TIMTEC-BB SBB004077;P-FORMYLPHENYLBORONIC ACID;AKOS BRN-0111;4-FORMYLBENZENEBORONIC ACID;4-FORMYLPHENYLBORONIC ACID;4-BORONOBENZALDEHYDE;4-(dihydroxyboryl)benzaldehyde
• CAS NO: 87199-17-5
• Molecular Formula: C₇H₇BO₃
• Molecular Weight: 149.94
• EINECS: 438-670-5
• Product Categories: ALDEHYDE;Aldehydes;blocks;BoronicAcids;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;Boronate Ester;Potassium Trifluoroborate
• Mol File: 87199-17-5.mol
• Article Data: 34

Chemical Properties

• Melting Point: 237-242 °C(lit.)
• Boiling Point: 347.584 °C at 760 mmHg
• Flash Point: 164.013 °C
• Appearance: Clear colorless to yellow-orange/Liquid
• Density: 1.244 g/cm³
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: 0-6°C
• Solubility: <10g/l
• PKA: 7.34±0.10(Predicted)
• Water Solubility: Slightly Soluble in water.
• Sensitive: Air Sensitive
• BRN: 3030770
• CAS DataBase Reference: 4-Formylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Formylphenylboronic acid(87199-17-5)
• EPA Substance Registry System: 4-Formylphenylboronic acid(87199-17-5)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 22-26-36/37/39-45-37/39-36
• RIDADR: UN 1759 8/PG 3
• WGK Germany: 3
• F: 10
• TSCA: T
• HazardClass: IRRITANT, AIR SENSITIVE
• Hazardous Substances Data: 87199-17-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 87199-17-5 differently. You can refer to the following data:
1. suzuki reaction
2. 4-Formylbenzeneboronic acid acts as a reagent used for Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water, copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids, triethylamine-catalyzed three-component Hantzsch condensations, copper-catalyzed nitrations, oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta, palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides, palladium-catalyzed aerobic oxidative cross-coupling reactions. It acts as a reagent used in preparation of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells, a novel protein synthesis inhibitor active against Gram-positive bacteria.
3. 4-Formylphenylboronic acid is a substrate for Suzuki cross-coupling reactions and it can be used as a reagent for:Palladium-catalyzed Suzuki-Miyaura cross-coupling in water. Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides. Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids. Triethylamine-catalyzed three-component Hantzsch condensations. Copper-catalyzed nitrations. Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta. Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides. Palladium-catalyzed aerobic oxidative cross-coupling reactions. The synthesis of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells.The synthesis of a novel protein synthesis inhibitor active against Gram-positive bacteria.The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene.A rhodium-catalyzed cyclization, converting 1,5-enynes to cyclopentenes and spiro-cyclopentenes.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H

Synthetic route

potassium 4-formylphenyltrifluoroborate → 4-formylphenylboronic acid, (87199-17-5)

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%

p-hydroxymethylphenylboronic acid (59016-93-2) → 4-formylphenylboronic acid, (87199-17-5)

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%

4-allylphenylboronic acid (186497-79-0) → 4-formylphenylboronic acid, (87199-17-5)

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

2-(4-bromophenyl)-1,3-dioxane (61568-51-2) → 4-formylphenylboronic acid, (87199-17-5)

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%

p-bromobenzaldehyde 1,3-dioxolane (10602-01-4) + Triisopropyl borate (5419-55-6) → 4-formylphenylboronic acid, (87199-17-5)

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%

boric acid tributyl ester (688-74-4) + 4-bromobenzaldehyde diethyl acetal (34421-94-8) → 4-formylphenylboronic acid, (87199-17-5)

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%

potassium 4-formylphenyltrifluoroborate + water (7732-18-5) → 4-formylphenylboronic acid, (87199-17-5)

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

C41H63BO6 → 4-formylphenylboronic acid, (87199-17-5)

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

(HO)2BC6H4CH(C6H2(OH)2(CH2)10CH3)2 + water (7732-18-5) → 4-formylphenylboronic acid, (87199-17-5)

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%

p-bromobenzaldehyde 1,3-dioxolane (10602-01-4) + Trimethyl borate (121-43-7) → 4-formylphenylboronic acid, (87199-17-5)

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%

p-bromobenzaldehyde 1,3-dioxolane (10602-01-4) → 4-formylphenylboronic acid, (87199-17-5)

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;

4-bromomethylphenylboronic acid (68162-47-0) → 4-formylphenylboronic acid, (87199-17-5)

Conditions	Yield
With hexamethylenetetramine

<4-dibromomethyl-phenyl>-dihydroxy-borane → 4-formylphenylboronic acid, (87199-17-5)

Conditions	Yield
With sulphurous acid

C11H17BO4 → 4-formylphenylboronic acid, (87199-17-5)

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

4-bromo-benzaldehyde (1122-91-4) + LiPh2InH2 → 4-formylphenylboronic acid, (87199-17-5)

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

4-bromobenzaldehyde diethyl acetal (34421-94-8) → 4-formylphenylboronic acid, (87199-17-5)

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

4-bromo-benzaldehyde (1122-91-4) + 4-acetylbenzoyl-Rink resin → 4-formylphenylboronic acid, (87199-17-5)

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

4-bromo-benzaldehyde (1122-91-4) + decyl magnesium halide → 4-formylphenylboronic acid, (87199-17-5)

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

Trimethyl borate (121-43-7) + 4-bromo-benzaldehyde (1122-91-4) → 4-formylphenylboronic acid, (87199-17-5)

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;

tris(4-dibromomethyl phenyl)boroxine (111561-46-7) + water (7732-18-5) → 4-formylphenylboronic acid, (87199-17-5)

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

m-tolylboronic acid (17933-03-8) → 4-formylphenylboronic acid, (87199-17-5)

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

tris(4-bromomethyl phenyl)boroxine (51239-44-2) → 4-formylphenylboronic acid, (87199-17-5)

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

4-chlorobenzaldehyde (104-88-1) → p-hydroxymethylphenylboronic acid (59016-93-2) + 4-formylphenylboronic acid, (87199-17-5)

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;

4-bromo-benzaldehyde (1122-91-4) → p-hydroxymethylphenylboronic acid (59016-93-2) + 4-formylphenylboronic acid, (87199-17-5)

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;

4-bromo-benzaldehyde (1122-91-4) → 4-formylphenylboronic acid, (87199-17-5)

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

4-Vinylphenylboronic acid (2156-04-9) → 4-(1,2-dihydroxyethyl)phenylboronic acid + 4-formylphenylboronic acid, (87199-17-5) + 4-Vinylphenol (2628-17-3)

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

Trimethyl borate (121-43-7) + 4-bromobenzaldehyde diethyl acetal (34421-94-8) → 4-formylphenylboronic acid, (87199-17-5)

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;

2,4,6-tris(4-bromophenyl)boroxin (7519-94-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 4-formylphenylboronic acid, (87199-17-5)

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

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-formylphenylboronic acid, (87199-17-5) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (128376-64-7)

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

4-bromobenzenecarbonitrile (623-00-7) + 4-formylphenylboronic acid, (87199-17-5) → 4-(4-cyanophenyl)-benzaldehyde (50670-55-8)

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%

4-formylphenylboronic acid, (87199-17-5) + 4-bromopyridine hydrochloride (19524-06-2) → 4-(pyridin-4-yl)benzaldehyde (99163-12-9)

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%

2-bromo-pyridine (109-04-6) + 4-formylphenylboronic acid, (87199-17-5) → 2-(4-formylphenyl)pyridine (127406-56-8)

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 + 4-formylphenylboronic acid, (87199-17-5) → 2'-(4-Methyl-piperazine-1-yl)-biphenyl-4-carboxaldehyde (735333-36-5)

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

2-({4-[(4-fluorophenyl)amino]-1-piperidinyl}carbonyl)-3-pyridinyl trifluoromethanesulfonate (920511-33-7) + 4-formylphenylboronic acid, (87199-17-5) → 4-[2-({4-[(4-fluorophenyl)amino]-1-piperidinyl}carbonyl)-3-pyridinyl]benzaldehyde (920511-34-8)

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℃;

4-formylphenylboronic acid, (87199-17-5) + trimethyleneglycol (504-63-2) → 4-(1,3,2-dioxaborinan-2-yl)-benzaldehyde

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

4-formylphenylboronic acid, (87199-17-5) + ethylene glycol (107-21-1) → 4-(OCH2CH2O-B)C6H4C(H)=O (328063-34-9)

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%

2,6-dichloro-4-iodopyridine (98027-84-0) + 4-formylphenylboronic acid, (87199-17-5) → 4-(2,6-dichloropyridin-4-yl)benzaldehyde (1628606-70-1)

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

5-ethyl-3-iodo-2,5-dihydrofuran-2-one (1206522-04-4) + 4-formylphenylboronic acid, (87199-17-5) → 5-ethyl-3-(4-formylphenyl)furan-2(5H)-one

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%

4-formylphenylboronic acid, (87199-17-5) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 5,5-dimethyl-2-(4-formylphenyl)-1,3,2-dioxaborinane (128376-65-8)

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%

4-formylphenylboronic acid, (87199-17-5) + para-nitrophenyl bromide (586-78-7) → 4-(4'-nitrophenyl)benzaldehyde (98648-23-8)

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%

4-formylphenylboronic acid, (87199-17-5) + 2.3-butanediol (513-85-9) → 2-(4-formylphenyl)-4,5-dimethyl-1,3,2-dioxaborolane (215876-82-7)

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

iodobenzene (591-50-4) + 4-formylphenylboronic acid, (87199-17-5) → 4-Phenylbenzaldehyde (3218-36-8)

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%

4-formylphenylboronic acid, (87199-17-5) + 4-bromo-benzaldehyde (1122-91-4) → 4,4'-diformylbiphenyl (66-98-8)

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%

p-nitrobenzene iodide (636-98-6) + 4-formylphenylboronic acid, (87199-17-5) → 4-(4'-nitrophenyl)benzaldehyde (98648-23-8)

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%

bromobenzene (108-86-1) + 4-formylphenylboronic acid, (87199-17-5) → 4-Phenylbenzaldehyde (3218-36-8)

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%

4-tolyl iodide (624-31-7) + 4-formylphenylboronic acid, (87199-17-5) → 4-(4-methylphenyl)benzaldehyde (36393-42-7)

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%

4-formylphenylboronic acid, (87199-17-5) + 1,7-dibromo-N,N'-bis(2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic acid diimide (331861-94-0) → N,N'-bis(2,6-diisopropylphenyl)-1,7-di(4-formylphenyl)perylene-3,4,9,10-tetracarboxydiimide

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%

5-bromopyrimidine (4595-59-9) + 4-formylphenylboronic acid, (87199-17-5) → 4-(pyrimidin-5-yl)benzaldehyde (198084-12-7)

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) + 4-formylphenylboronic acid, (87199-17-5) → bis-(σ-(4-formylphenyl))-tetrakis-μ-(caprolactamato)dirhodium(III) (1039763-74-0, 1158952-16-9)

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%

1-Bromonaphthalene (90-11-9) + 4-formylphenylboronic acid, (87199-17-5) → 4-(naphthalene-1-yl)benzaldehyde (56432-18-9)

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.

benzoimidazole (51-17-2) + 4-formylphenylboronic acid, (87199-17-5) → 4-(1H-benzo[d]imidazol-1-yl)benzaldehyde (90514-72-0)

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%

pinanediol (18680-27-8) + 4-formylphenylboronic acid, (87199-17-5) → 4-(2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0(2,6)]dec-4-yl)-benzaldehyde

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%

(R)-1-(2-bromo-benzenesulfonyl)-2-methyl-pyrrolidine (1202647-41-3) + 4-formylphenylboronic acid, (87199-17-5) → 2'-((R)-2-Methyl-pyrrolidine-1-sulfonyl)-biphenyl-4-carbaldehyde (1202647-44-6)

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%

4-formylphenylboronic acid, (87199-17-5) → 4-hydroxy-benzaldehyde (123-08-0)

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%

4-formylphenylboronic acid, (87199-17-5) + 4-fluoroaniline (371-40-4) → (E)-(4-(((4-fluorophenyl)imino)methyl)phenyl)boronic acid

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

4-formylphenylboronic acid, (87199-17-5) + sodium 4-iodo-benzoate (1005-30-7) → 4′-formyl-(1,1′-biphenyl)-4-carboxylic Acid (70916-98-2)

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

3-Chloropyridine (626-60-8) + 4-formylphenylboronic acid, (87199-17-5) → 4-(pyridin-3-yl)benzaldehyde (127406-55-7)

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%

N-(phenylmethyl)-di(p-toluenesulfonyl)amine (61079-82-1) + 4-formylphenylboronic acid, (87199-17-5) → 4-benzylbenzaldehyde (67468-65-9)

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%

Upstream product

• 61568-51-2 2-(4-bromophenyl)-1,3-dioxane 
• 10602-01-4 p-bromobenzaldehyde 1,3-dioxolane 
• 5419-55-6 Triisopropyl borate 
• 34421-94-8 4-bromobenzaldehyde diethyl acetal 
• 59016-93-2 p-hydroxymethylphenylboronic acid 
• 68162-47-0 4-bromomethylphenylboronic acid 
• 2156-04-9 4-Vinylphenylboronic acid 
• 186497-79-0 4-allylphenylboronic acid 
• 24856-58-4 1,1-dimethoxy-1-(4-bromophenyl)methane 
• 7732-18-5 water 
• 10294-34-5 boron trichloride 
• 13675-18-8 tetrahydroxydiboron 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 155701-60-3 (Z)-1,2-Diphenyl-1-(4-formylphenyl)-1-butene 
• 193280-82-9 7-(4-Formyl-phenyl)-9,10-dihydro-phenanthrene-2-carboxylic acid methyl ester 
• 196811-07-1 2-<2-(4-formylbenzoyl)phenylamino>-3-<4-<2-(5-methyl-2-phenyloxazol-4-yl)ethoxy>phenyl>propionic acid methyl ester 
• 210686-42-3 4'-biphenylmethyl-(4-thiomorpholin-4-ylmethyl-phenyl)amine 
• 215876-82-7 2-(4-formylphenyl)-4,5-dimethyl-1,3,2-dioxaborolane 
• 43153-12-4 ethyl 2-(4-formylphenyl)acetate 
• 342889-39-8 4-(benzo[d][1,3]dioxol-5-yl)benzaldehyde 
• 169831-24-7 4-(anthracene-9-yl)benzaldehyde 
• 324750-99-4 4,4'-(anthracene-9,10-diyl)dibenzaldehyde 
• 50670-55-8 4-(4-cyanophenyl)-benzaldehyde 
• 3218-36-8 4-Phenylbenzaldehyde 

Relevant articles and documents

Space-group revision for 4-formylphenylboronic acid

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Hydroxyl radical-mediated oxidative cleavage of CC bonds and further esterification reaction by heterogeneous semiconductor photocatalysis

A hydroxyl radical-mediated aerobic cleavage of alkenes and further sequence esterification reaction for the preparation of carbonyl compounds have been developed by using tubular carbon nitride (TCN) as a general heterogeneous photocatalyst under an oxygen atmosphere with visible light irradiation. This protocol has an excellent substrate scope and gives the desired aldehydes, ketones and esters in moderate to high yields. Importantly, this metal-free procedure employed photogenerated hydroxyl radicals in situ as green oxidation active species, avoiding the present additional initiators. The reaction could be carried out under solar light irradiation and was applicable to large-scale reactions. Furthermore, the recyclable TCN catalyst could be used several times without a significant loss of activities.

Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions

Asymmetric conjugate addition of aryl halides or aryl triflates to electron-deficient olefins was realized by sequential Miyaura borylation and Hayashi-Miyaura conjugate addition in one pot. A nickel-catalyzed borylation of aryl halides or triflates and a rhodium-chiral diene complex catalyzed enantioselective conjugate addition was executed as a pair of relay reactions as a more efficient and greener protocol.