3,4-METHYLENEDIOXYPHENYLBORONIC ACID Chemical Properties

Melting point:

224-229 °C(lit.)

Boiling point:

347.3±52.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

8.48±0.20(Predicted)

form 

Powder

color 

White to off-white

BRN 

5523347

InChI

InChI=1S/C7H7BO4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3,9-10H,4H2

InChIKey

CMHPUBKZZPSUIQ-UHFFFAOYSA-N

SMILES

B(C1=CC=C2OCOC2=C1)(O)O

CAS DataBase Reference

94839-07-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,4-METHYLENEDIOXYPHENYLBORONIC ACID Usage And Synthesis

Chemical Properties

3,4-METHYLENEDIOXYPHENYLBORONIC ACID is white powder

Uses

Reactant involved in:• ;Petasis reaction between glyoxylic acid, α-amino phosphonates, and organylboronic acids1• ;Mannich-type multicomponent assembly and 1,3-dipolar cycloaddition for synthesis of tetrahydroisoquinoline fused isoxazolidine scafford2• ;Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides3,4• ;Oxidative Heck reaction for synthesis of functionalized cinnamaldehyde derivatives5• ;Intramolecular Alder-ene and Pictet-Spengler reactions for synthesis of crinine6

Uses

suzuki reaction

Uses

Reactant involved in:

• Petasis reaction between glyoxylic acid, α-amino phosphonates, and organylboronic acids
• Mannich-type multicomponent assembly and 1,3-dipolar cycloaddition for synthesis of tetrahydroisoquinoline fused isoxazolidine scafford
• Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides
• Oxidative Heck reaction for synthesis of functionalized cinnamaldehyde derivatives
• Intramolecular Alder-ene and Pictet-Spengler reactions for synthesis of crinine

Synthesis

General procedure for the synthesis of benzo[d][1,3]dioxol-5-ylboronic acid from 4-bromo-1,2-methylenedioxybenzene and triisopropyl borate: In a 100 mL three-necked round-bottomed flask under nitrogen protection, 5-bromobenzo[d][1,3]dioxolene (2 g, 9.95 mmol, 1.00 eq.) and THF (20 mL) were added, and the flask was cooled to -78 °C. Butyl lithium (BuLi, 5.6 mL, 1.40 eq.) was slowly added dropwise, followed by triisopropyl borate (1.96 g, 14.00 mmol). The reaction mixture was stirred at -78 °C for 1 hour and then slowly warmed to room temperature and continued stirring for 4 hours. Upon completion of the reaction, the reaction was quenched with 10 mL of water and acidified with sulfuric acid (4.9 g, 50.00 mmol, 5.00 equiv). The mixture was heated to reflux overnight. After cooling, it was extracted with ethyl acetate (3 x 50 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid was washed with ethyl acetate (3 x 3 mL) to give 0.5 g (30% yield) of benzo[d][1,3]dioxol-5-ylboronic acid as a white solid.

References

[1] Patent: US2014/128392, 2014, A1. Location in patent: Paragraph 0311; 0312

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