1,4-Benzodioxane-6-boronic acid

Base Information

• Chemical Name: 1,4-Benzodioxane-6-boronic acid
• CAS No.: 164014-95-3
• Molecular Formula: C₈H₉BO₄
• Molecular Weight: 179.968
• Hs Code.: 29163990
• European Community (EC) Number: 625-755-9
• DSSTox Substance ID: DTXSID00379869
• Nikkaji Number: J1.915.077A
• Wikidata: Q72445395
• Mol file: 164014-95-3.mol

Synonyms:1,4-Benzodioxane-6-boronic acid;164014-95-3;2,3-dihydro-1,4-benzodioxin-6-ylboronic acid;(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)boronic acid;MFCD01009696;BORONIC ACID, (2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)-;1,4-Benzodioxan-6-boronic acid;3,4-(ethylenedioxy)benzeneboronic acid;(2,3-dihydro-1,4-benzodioxin-6-yl)boronic acid;2,3-dihydro-1,4-(benzodioxin-6-yl)boronic acid;2,3-dihydrobenzo[b][1,4]dioxin-6-ylboronic acid;1,4-Benzodioxane-6-boronicacid;SCHEMBL121851;DTXSID00379869;SQDUGGGBJXULJR-UHFFFAOYSA-N;1,4-Benzodioxane-6-ylboronic acid;3,4-ethylenedioxyphenylboronic acid;BCP23246;CS-D1714;(1,4-benzodioxan-6-yl)boronic acid;AKOS002659294;AB07964;1,4-Benzodioxane-6-boronic acid, 96%;3H-benzo[e]1,4-dioxin-6-boronic acid;NCGC00249476-01;AS-15068;BP-10782;SY021600;2H,3H-benzo[e]1,4-dioxin-6-boronic acid;2h,3h-benzo[e] 1,4-dioxin-6-boronic acid;A3641;AM20030103;B4181;FT-0604574;EN300-212569;2,3-Dihydro-1,4-benzodioxin-6-yl boronic acid;(2,3-dihydrobenzo[1,4]dioxine-6-yl)boronic acid;Q-103514;Boronic acid, B-(2,3-dihydro-1,4-benzodioxin-6-yl)-;Z381541022

Chemical Property of 1,4-Benzodioxane-6-boronic acid

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 7.64E-06mmHg at 25°C
• Melting Point: 187 °C
• Refractive Index: 1.575
• Boiling Point: 361 °C at 760 mmHg
• PKA: 8.52±0.20(Predicted)
• Flash Point: 172.2 °C
• PSA: 58.92000
• Density: 1.35 g/cm³
• LogP: -0.86240
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 180.0593889
• Heavy Atom Count: 13
• Complexity: 176

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,4-Benzodioxane-6-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)OCCO2)(O)O
• Uses: Reactant involved in:Addition reactions with 1,8-naphthyridine N-oxidesIodocyclization and palladium-catalyzed coupling reactions for synthesis of pyranoquinolinesSuzuki coupling reactions for synthesis of combretastatin analogsSuzuki-Miyaura coupling reactions for synthesis of aryl-substituted oxabenzindoles and methanobenzindolesPalladium-catalyzed oxyarylation of Heck reaction intermediatesC-H functionalization of quinones

Technology Process of 1,4-Benzodioxane-6-boronic acid

There total 2 articles about 1,4-Benzodioxane-6-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: 92.1%

2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5,5-dimethyl-1,3,2-dioxaborinane → 2.3-dihydro-1,4-benzodioxin-6-ylboronic acid (164014-95-3)

Guidance literature:

With hydrogenchloride; at 30 ℃; for 3h;

Reference yield:

6-bromo-1,4-benzodioxane (52287-51-1) → 2.3-dihydro-1,4-benzodioxin-6-ylboronic acid (164014-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / dimethyl sulfoxide / 0.25 h / 90 °C

2: hydrogenchloride / 3 h / 30 °C

With hydrogenchloride; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In dimethyl sulfoxide;

Reference yield: 98.0%

3-bromo-2-methylbenzyl alcohol (83647-43-2) + 2.3-dihydro-1,4-benzodioxin-6-ylboronic acid (164014-95-3) → (3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-methylphenyl)methanol

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium acetate; In tetrahydrofuran; Reflux;

DOI:10.1021/acs.jmedchem.0c01329

upstream raw materials:

6-bromo-1,4-benzodioxane

Downstream raw materials:

C₃₃H₃₉NO₆

3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-methoxybenzaldehyde

C₂₄H₂₄N₄O₃

6-(3-methoxy-5-prop-2-ynylphenyl)-2,3-dihydro-benzo[1,4]dioxine

Refernces