• Name

  Benzocyclobutene-4-boronic acid

• EINECS
• CAS No. 195730-31-5
• Density 1.22 g/cm³
• Solubility
• Melting Point
• Formula C₈H₉BO₂
• Boiling Point 328.5 °C at 760 mmHg
• Molecular Weight 147.969
• Flash Point 152.5 °C
• Transport Information
• Appearance yellow or brown particles
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Bicyclo[4.2.0]octa-1,3,5-trien-3-ylboronic acid;
• PSA 40.46000
• LogP -0.14980

Synthetic route

1073-39-8

4-bromobenzocyclobutene

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

Conditions

Conditions	Yield
Stage #1: 4-bromobenzocyclobutene With magnesium In tetrahydrofuran Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃;	73%

108-36-1

1,3-dibromobenzene

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

1,3-bis(benzocyclobuten-4-yl)benzene

Conditions

Conditions	Yield
With borax; tetrabutylammomium bromide; palladium dichloride In ethanol at 20℃; for 3h; Suzuki coupling;	98%

106-37-6

1.4-dibromobenzene

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

1,4-bis(benzocyclobuten-4-yl)benzene

Conditions

Conditions	Yield
With lithium hydroxide; tetrabutylammomium bromide; palladium dichloride In ethanol at 20℃; for 6h; Suzuki coupling;	98%

92-86-4

4-(4-bromophenyl)bromobenzene

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

4,4'-bis(benzylocyclobuten-4-yl)biphenyl

Conditions

Conditions	Yield
With borax; tetrabutylammomium bromide; palladium dichloride In ethanol at 20℃; for 8h; Suzuki coupling;	98%

1073-39-8

4-bromobenzocyclobutene

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

4-(benzocyclobuten-4-yl)benzocyclobutene

Conditions

Conditions	Yield
With borax; tetrabutylammomium bromide; palladium dichloride In ethanol at 20℃; Suzuki coupling;	96%

12-bromodehydroabietic acid

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

C28H34O2

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water at 60℃; for 10h; Suzuki Coupling; Inert atmosphere;	90%

2,7-dibromo-9,9-bis(4-hexyloxyphenyl)fluorene

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

C53H54O2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 75℃; for 12h; Suzuki Coupling; Inert atmosphere;	85%

19752-55-7

1-bromo-3,5-dichlorobenzene

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

C14H10Cl2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 90℃; for 12h; Inert atmosphere;	60%

C37H44Br2O2Si2

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

C53H58O2Si2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; for 10.5h; Inert atmosphere;	56.5%

33985-40-9

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

(R)-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-(4-bicyclo[4.2.0]octa-1,3,5-trienyl)methanol

Conditions

Conditions	Yield
Stage #1: 4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid With diethylzinc In toluene at 25 - 60℃; for 1h; Stage #2: (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde In toluene at 60℃; for 2h;	55.8%

C41H52Br2O2Si2

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

C57H66O2Si2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; for 10.5h; Inert atmosphere;	52%

1158651-91-2

N,N'-didodecyl-1,6,7,12-tetrabromoperylene-3,4,9,10-tetracarboxylic acid bisimide

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

N,N'-didocananyl-1,6,7,12-tetra(4-benzocyclobutenyl)perylene-3,4,9,10-tetracarboxylic acid bisimide

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; silver(l) oxide In 1,2-dimethoxyethane at 80℃; for 24h; Suzuki coupling; Inert atmosphere;	45%

Reaxys ID: 33726854

Reaxys ID: 33726854

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

Reaxys ID: 33726853

Reaxys ID: 33726853

33573-31-8

12-bromodehydroabietic acid

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

12-(benzocyclobutene)dehydroabietic acid

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water at 60℃; for 10h; Solvent; Reagent/catalyst; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0) In ethanol; water at 60℃; for 10h; Temperature; Suzuki Coupling; Inert atmosphere;
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water at 60℃; for 10h; Temperature; Solvent; Reagent/catalyst; Suzuki Coupling; Inert atmosphere;

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

[(R)-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-(4-bicyclo[4.2.0]octa-1,3,5-trienyl)methyl] 4-phenylbenzoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: diethylzinc / toluene / 1 h / 25 - 60 °C 1.2: 2 h / 60 °C 2.1: triphenylphosphine; diisopropyl (E)-azodicarboxylate / toluene / 3 h / 0 - 25 °C View Scheme

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

[(R)-bicyclo[4.2.0]octa-1,3,5-trien-3-yl-[(2S,3S,4R)-3,4,5-trihydroxytetrahydrofuran-2-yl]methyl] 4-phenylbenzoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diethylzinc / toluene / 1 h / 25 - 60 °C 1.2: 2 h / 60 °C 2.1: triphenylphosphine; diisopropyl (E)-azodicarboxylate / toluene / 3 h / 0 - 25 °C 3.1: trifluoroacetic acid; water / 36 h / 40 °C View Scheme

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

(2R,3R,4S,5R)-2-(4-amino-5-fluoro-pyrrolo[2,3-d]pyrimidin-7-yl)-5-[(R)-4-bicyclo[4.2.0]octa-1,3,5-trienyl(hydroxy)methyl]tetrahydrofuran-3,4-diol hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: diethylzinc / toluene / 1 h / 25 - 60 °C 1.2: 2 h / 60 °C 2.1: triphenylphosphine; diisopropyl (E)-azodicarboxylate / toluene / 3 h / 0 - 25 °C 3.1: trifluoroacetic acid; water / 36 h / 40 °C 4.1: pyridine; tributylphosphine; diisopropyl (E)-azodicarboxylate / tetrahydrofuran / 2 h / 25 °C 5.1: ammonium hydroxide / 1,4-dioxane / 16 h / 120 °C View Scheme

195730-31-5

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid

[(R)-bicyclo[4.2.0]octa-1,3,5-trien-3-yl-[(2S,3S,4R,5R)-5-(4-chloro-5-fluoro-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl] 4-phenylbenzoate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: diethylzinc / toluene / 1 h / 25 - 60 °C 1.2: 2 h / 60 °C 2.1: triphenylphosphine; diisopropyl (E)-azodicarboxylate / toluene / 3 h / 0 - 25 °C 3.1: trifluoroacetic acid; water / 36 h / 40 °C 4.1: pyridine; tributylphosphine; diisopropyl (E)-azodicarboxylate / tetrahydrofuran / 2 h / 25 °C View Scheme

Benzocyclobutene-4-Boronic Acid Chemical Properties

Benzocyclobutene-4-Boronic Acid Specification