(6-Formylbenzo[d][1,3]dioxol-5-yl)boronic acid

Base Information

• Chemical Name: (6-Formylbenzo[d][1,3]dioxol-5-yl)boronic acid
• CAS No.: 94838-88-7
• Molecular Formula: C8H7BO5
• Molecular Weight: 193.952
• Hs Code.: 2932999099
• European Community (EC) Number: 687-045-5
• DSSTox Substance ID: DTXSID20378450
• Nikkaji Number: J1.252.759D
• Wikidata: Q82167949
• Mol file: 94838-88-7.mol

Synonyms:94838-88-7;(6-Formylbenzo[d][1,3]dioxol-5-yl)boronic acid;2-Formyl-4,5-methylenedioxyphenylboronic acid;(2-FORMYL-4,5-METHYLENEDIOXY)BENZENEBORONIC ACID;(2-Formyl-4,5-methylenedioxy)phenylboronic acid;(6-formyl-1,3-benzodioxol-5-yl)boronic acid;Boronic acid,B-(6-formyl-1,3-benzodioxol-5-yl)-;(6-FORMYL-2H-1,3-BENZODIOXOL-5-YL)BORONIC ACID;C8H7BO5;SCHEMBL1128702;DTXSID20378450;MFCD01319005;AKOS015894160;AB08819;AT24748;AS-67191;CS-0173775;FT-0642291;(6-formyl-1,3-dioxaindan-5-yl)boronic acid;4,5-methylenedioxy-2-formylphenylboronic acid;(6-Formyl-1,3-benzodioxole-5-yl)boronic acid;6-formylbenzo[d][1,3]dioxol-5-ylboronic acid;(6-Formylbenzo[d][1,3]dioxol-5-yl)boronicacid;(6-methanoyl-1,3-benzodioxol-5-yl)boronic acid;EN300-7383694;A845112;2-Formyl-4,5-methylenedioxyphenylboronic acid, >=95%

Chemical Property of (6-Formylbenzo[d][1,3]dioxol-5-yl)boronic acid

Chemical Property:

• Vapor Pressure: 2.59E-08mmHg at 25°C
• Melting Point: 231-233 °C
• Refractive Index: 1.598
• Boiling Point: 434.3 °C at 760 mmHg
• PKA: 8.13±0.20(Predicted)
• Flash Point: 216.5 °C
• PSA: 75.99000
• Density: 1.49 g/cm³
• LogP: -1.09240
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 194.0386535
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

97% ^*data from raw suppliers

2-Formyl-4,5-methylenedioxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1C=O)OCO2)(O)O
• Uses: Reactant for:? ;Enantioselective preparation of indenamines by cationic palladium complex-catalyzed tandem annulation with alkynes1? ;Stereoselective preparation of indenol derivatives via cationic palladium complex-catalyzed diastereoselective tandem annulation2? ;Synthesis of oxazoline-substituted potassium organotrifluoroborates3? ;Preparation of aristolactam analogs as an antitumor agent4? ;Suzuki-Miyaura coupling reactions5? ;Suzuki and Negishi cross-coupling reactions6 Reactant for:Enantioselective preparation of indenamines by cationic palladium complex-catalyzed tandem annulation with alkynesStereoselective preparation of indenol derivatives via cationic palladium complex-catalyzed diastereoselective tandem annulationSynthesis of oxazoline-substituted potassium organotrifluoroboratesPreparation of aristolactam analogs as an antitumor agentSuzuki-Miyaura coupling reactionsSuzuki and Negishi cross-coupling reactions

Technology Process of (6-Formylbenzo[d][1,3]dioxol-5-yl)boronic acid

There total 2 articles about (6-Formylbenzo[d][1,3]dioxol-5-yl)boronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxole-5-carbaldehyde → 2-formyl-4,5-(methylenedioxy)benzeneboronic acid (94838-88-7)

Guidance literature:

6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxole-5-carbaldehyde; With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 0.333333h;

With hydrogenchloride; In tetrahydrofuran; water; for 2h;

DOI:10.1016/j.bmcl.2021.127956

Reference yield:

6-bromo-3,4-methylenedioxybenzaldehyde (15930-53-7) → 2-formyl-4,5-(methylenedioxy)benzeneboronic acid (94838-88-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium acetate / 1,4-dioxane / 8 h / 90 °C / Inert atmosphere

2.1: sodium periodate / tetrahydrofuran; water / 0.33 h / 20 °C

2.2: 2 h

With sodium periodate; potassium acetate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1016/j.bmcl.2021.127956

Reference yield: 99.0%

2-bromophenyl methyl ketone (2142-69-0) + 2-formyl-4,5-(methylenedioxy)benzeneboronic acid (94838-88-7) → 6-(2-acetylphenyl)benzo[d][1,3]dioxole-5-carbaldehyde (1149344-88-6)

Guidance literature:

With potassium fluoride; palladium diacetate; di‐tert‐butyl‐(1‐phenylindol‐2‐yl)phosphane; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo900508z

upstream raw materials:

6-bromo-3,4-methylenedioxybenzaldehyde

Downstream raw materials:

anhydrolycorine-7-one

norallonitidine

6-(6-hydroxymethyl-2,3,4-trimethoxy-phenyl)-benzo[1,3]dioxole-5-carbaldehyde

6-(6-bromomethyl-2,3,4-trimethoxy-phenyl)-benzo[1,3]dioxole-5-carbaldehyde