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Benzocyclobutene-4-boronic acid is a boronic acid derivative featuring a benzocyclobutene ring, which serves as a versatile building block in organic synthesis. Its unique molecular structure and ability to engage in various chemical reactions, such as Suzuki-Miyaura cross-coupling, render it a valuable component in the creation of complex organic molecules and the development of novel materials with specific properties.

195730-31-5

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195730-31-5 Usage

Uses

Used in Pharmaceutical Synthesis:
Benzocyclobutene-4-boronic acid is used as a key intermediate in the synthesis of pharmaceuticals for its ability to facilitate the construction of complex organic molecules, contributing to the development of new drugs with enhanced therapeutic properties.
Used in Agrochemical Development:
In the agrochemical industry, Benzocyclobutene-4-boronic acid is utilized as a precursor in the synthesis of various agrochemicals, enabling the creation of effective compounds for crop protection and enhancement of agricultural productivity.
Used in Materials Science:
Benzocyclobutene-4-boronic acid is employed as a component in the development of novel materials with specific properties, leveraging its unique molecular structure to engineer materials with tailored characteristics for diverse applications in science and industry.

Check Digit Verification of cas no

The CAS Registry Mumber 195730-31-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,5,7,3 and 0 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 195730-31:
(8*1)+(7*9)+(6*5)+(5*7)+(4*3)+(3*0)+(2*3)+(1*1)=155
155 % 10 = 5
So 195730-31-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H9BO2/c10-9(11)8-4-3-6-1-2-7(6)5-8/h3-5,10-11H,1-2H2

195730-31-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenylboronic acid

1.2 Other means of identification

Product number -
Other names benzocyclobutene-4-boronic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:195730-31-5 SDS

195730-31-5Synthetic route

4-bromobenzocyclobutene
1073-39-8

4-bromobenzocyclobutene

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

Conditions
ConditionsYield
Stage #1: 4-bromobenzocyclobutene With magnesium In tetrahydrofuran
Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃;		73%
1,3-dibromobenzene
108-36-1

1,3-dibromobenzene

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

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

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

Conditions
ConditionsYield
With borax; tetrabutylammomium bromide; palladium dichloride In ethanol at 20℃; for 3h; Suzuki coupling;98%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

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

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

Conditions
ConditionsYield
With lithium hydroxide; tetrabutylammomium bromide; palladium dichloride In ethanol at 20℃; for 6h; Suzuki coupling;98%
4-(4-bromophenyl)bromobenzene
92-86-4

4-(4-bromophenyl)bromobenzene

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

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

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

Conditions
ConditionsYield
With borax; tetrabutylammomium bromide; palladium dichloride In ethanol at 20℃; for 8h; Suzuki coupling;98%
4-bromobenzocyclobutene
1073-39-8

4-bromobenzocyclobutene

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

4-(benzocyclobuten-4-yl)benzocyclobutene

4-(benzocyclobuten-4-yl)benzocyclobutene

Conditions
ConditionsYield
With borax; tetrabutylammomium bromide; palladium dichloride In ethanol at 20℃; Suzuki coupling;96%
12-bromodehydroabietic acid

12-bromodehydroabietic acid

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

C28H34O2

C28H34O2

Conditions
ConditionsYield
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

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

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

C53H54O2

C53H54O2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 75℃; for 12h; Suzuki Coupling; Inert atmosphere;85%
1-bromo-3,5-dichlorobenzene
19752-55-7

1-bromo-3,5-dichlorobenzene

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

C14H10Cl2

C14H10Cl2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 90℃; for 12h; Inert atmosphere;60%
C37H44Br2O2Si2

C37H44Br2O2Si2

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

C53H58O2Si2

C53H58O2Si2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; for 10.5h; Inert atmosphere;56.5%
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde
33985-40-9

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

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

(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
ConditionsYield
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

C41H52Br2O2Si2

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

C57H66O2Si2

C57H66O2Si2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; for 10.5h; Inert atmosphere;52%
N,N'-didodecyl-1,6,7,12-tetrabromoperylene-3,4,9,10-tetracarboxylic acid bisimide
1158651-91-2

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

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

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

Conditions
ConditionsYield
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

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

Reaxys ID: 33726853

Reaxys ID: 33726853

12-bromodehydroabietic acid
33573-31-8

12-bromodehydroabietic acid

4-bicyclo[4.2.0]octa-1,3,5-trienylboronic acid
195730-31-5

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

12-(benzocyclobutene)dehydroabietic acid

12-(benzocyclobutene)dehydroabietic acid

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

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

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

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

[(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
ConditionsYield
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

195730-31-5Upstream product

195730-31-5Downstream Products

195730-31-5Relevant academic research and scientific papers

An efficient route to biaryl bisbenzocyclobutene monomers based on Suzuki coupling reaction at room temperature

Yang, Jun-Xiao,Ma, Kuo-Yan,Zhu, Fang-Hua,Chen, Wen,Li, Bo,Zhang, Lin,Xie, Ru-Gang

, p. 184 - 186 (2007/10/03)

An efficient and practical preparation of the bisbenzocyclobutene monomers has been developed via the room temperature Suzuki couplings of phenyl-1, 4-diboronic ester with 4-bromobenzocyclobutene or benzocyclobutene-4-boronic acid with aryl dibromides.

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