2,4-Dimethoxyphenylboronic acid

Base Information

• Chemical Name: 2,4-Dimethoxyphenylboronic acid
• CAS No.: 133730-34-4
• Molecular Formula: C8H11BO4
• Molecular Weight: 181.984
• Hs Code.: 29420000
• European Community (EC) Number: 679-695-3
• DSSTox Substance ID: DTXSID20370232
• Nikkaji Number: J778.552F
• Wikidata: Q72467621
• Mol file: 133730-34-4.mol

Synonyms:2,4-Dimethoxyphenylboronic acid;133730-34-4;2,4-Dimethoxybenzeneboronic Acid;(2,4-dimethoxyphenyl)boronic Acid;MFCD01074590;Boronic acid, (2,4-dimethoxyphenyl)-;2,4-DIMETHOXYBENZENE BORONIC ACID;2,4-Dimethoxybenzeneboronic acid;2,4-DimethoxyphenylboronicAcid;SCHEMBL203357;2,4-dimethoxy-phenylboronic acid;2,4-dimethoxyphenyl boronic acid;DTXSID20370232;2,4-dimethoxy benzeneboronic acid;SQTUYFKNCCBFRR-UHFFFAOYSA-N;2,4-dimethoxy-phenyl boronic acid;2,4-dimethoxy-phenyl-boronic acid;AM724;BCP26726;CS-D1031;(2,4-dimethoxyphenyl) boronic acid;2,4-Dimethoxyphenylboronic acid (contains varying amounts of Anhydride);AKOS004116550;2,4-Dimethoxyphenylboronic acid, 95%;AB08057;AC-5376;AS-12978;Boronic acid, B-(2,4-dimethoxyphenyl)-;BP-12805;SY016396;D3521;FT-0610134;2-ACRYLOXYETHYLTRIMETHYLAMMONIUMCHLORIDE;EN300-116876;A806667;J-507236;F0001-0447;Z336080000

Chemical Property of 2,4-Dimethoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: white to beige or pink moist powder
• Vapor Pressure: 7.61E-06mmHg at 25°C
• Melting Point: 125-127 °C(lit.)
• Refractive Index: 1.517
• Boiling Point: 361.1 °C at 760 mmHg
• PKA: 8.98±0.58(Predicted)
• Flash Point: 172.2 °C
• PSA: 58.92000
• Density: 1.19 g/cm³
• LogP: -0.61640
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.0750390
• Heavy Atom Count: 13
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

2,4-Dimethoxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=C(C=C1)OC)OC)(O)O
• Uses: 2,4-Dimethoxyphenylboronic acid can be used:?? As a reactant in meatal-catalyzed Suzuki?Miyaura cross-coupling reaction.?? To prepare hydroxy(trimethoxy)phenanthrene by cross-coupling with bromo(benzyloxy)methoxybenzaldehyde followed by condensation and debenzylation reaction.??To synthesize 2,4-dimethoxy-1-(trifluoromethyl)benzene via Cu-catalyzed trifluoromethylation reaction. Reactant for:??Suzuki-Miyaura?and Negishi couplings. suzuki reaction 2,4-Dimethoxyphenylboronic acid can be used: As a reactant in meatal-catalyzed Suzuki?Miyaura cross-coupling reaction. To prepare hydroxy(trimethoxy)phenanthrene by cross-coupling with bromo(benzyloxy)methoxybenzaldehyde followed by condensation and debenzylation reaction. To synthesize 2,4-dimethoxy-1-(trifluoromethyl)benzene via Cu-catalyzed trifluoromethylation reaction.

Technology Process of 2,4-Dimethoxyphenylboronic acid

There total 7 articles about 2,4-Dimethoxyphenylboronic 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: 70.0%

methanol (67-56-1) + diisopropylamine borane (55124-35-1) + 1-Bromo-2,4-dimethoxybenzene (17715-69-4) → 2,4-dimethoxyphenylboronic acid (133730-34-4)

Guidance literature:

diisopropylamine borane; With magnesium; phenylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 0.166667h;

1-Bromo-2,4-dimethoxybenzene; In tetrahydrofuran; at 70 ℃;

methanol; Further stages;

DOI:10.1016/j.tet.2018.11.036

Reference yield: 56.0%

1-Bromo-2,4-dimethoxybenzene (17715-69-4) → 2,4-dimethoxyphenylboronic acid (133730-34-4)

Guidance literature:

1-Bromo-2,4-dimethoxybenzene; With tert.-butyl lithium; In tetrahydrofuran; Cyclopentane; at -78 ℃; for 0.25h;

With Trimethyl borate; In tetrahydrofuran; Cyclopentane; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ol991381s

Reference yield: 52.0%

boric acid tributyl ester (688-74-4) + 2,4-dimethoxyphenylmagnesium bromide (138109-49-6) → 2,4-dimethoxyphenylboronic acid (133730-34-4)

Guidance literature:

In tetrahydrofuran; react. under N2; THF cooled to -60°C, addn. of borate and Grignard reagent in THF simultaneously (equimolar amts. over whole period of react.), then stirred for 30 min at -60°C, warmed to room temp., stirred for 30 min;; treated with water, extd. with Et2O, organic layers extd. with 1M aq. NaOH, aq. layers acidified with 2M aq. HCl, extd. with CH2Cl2, organic layers dried (MgSO4), filtered, concentrated, recrystd. from ethanol/water;;

upstream raw materials:

1-Bromo-2,4-dimethoxybenzene

1,3-Dimethoxybenzene

C₈H₉BF₃O₂^(1-)

boric acid tributyl ester

Downstream raw materials:

4-(2,4-Dimethoxyphenyl)-2H-1-benzopyran-2-one

6-benzyloxy-5-(2,4-dimethoxy-phenyl)-4-methoxy-benzo[1,3]dioxole

6-(2,4-dimethoxyphenyl)nicotinic acid

4-chloro-6-(2,4-dimethoxy-phenyl)-pyrimidin-2-ylamine