5-Formyl-2-methoxyphenylboronic acid

Base Information

• Chemical Name: 5-Formyl-2-methoxyphenylboronic acid
• CAS No.: 127972-02-5
• Molecular Formula: C8H9BO4
• Molecular Weight: 179.968
• Hs Code.: 29319090
• European Community (EC) Number: 626-939-1
• DSSTox Substance ID: DTXSID20370257
• Nikkaji Number: J1.127.094H
• Wikidata: Q72489920
• Mol file: 127972-02-5.mol

Synonyms:127972-02-5;5-Formyl-2-methoxyphenylboronic acid;2-Methoxy-5-formylphenylboronic acid;(5-formyl-2-methoxyphenyl)boronic acid;5-Formyl-2-methoxybenzeneboronic Acid;(5-formyl-2-methoxy-phenyl)boronic Acid;SCHEMBL67899;3-borono4-methoxybenzaldehyde;3-BORONO-P-ANISALDEHYDE;DTXSID20370257;NKKNXLPHCRLBDY-UHFFFAOYSA-N;MFCD01319044;2-Methoxy-5-formylbenzeneboronic acid;(5-formyl-2-methoxyphenyl)boronicacid;2-methoxy-5-formylphenyl boronic acid;3-BORONO-4-METHOXYBENZALDEHYDE;5-formyl-2-methoxyphenyl boronic acid;AKOS004116322;AB08873;AM90037;CS-W017245;PS-9582;5-formyl 2-methoxy phenyl boronic acid;5-formyl-2-methoxy phenyl boronic acid;BP-11847;F0834;FT-0620435;Boronic acid, B-(5-formyl-2-methoxyphenyl)-;EN300-7373078;A805770;J-501588

Chemical Property of 5-Formyl-2-methoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: light orange powder
• Vapor Pressure: 1.03E-07mmHg at 25°C
• Melting Point: 154-157 °C(lit.)
• Refractive Index: 1.537
• Boiling Point: 417.4 °C at 760 mmHg
• PKA: 7.86±0.58(Predicted)
• Flash Point: 206.2 °C
• PSA: 66.76000
• Density: 1.25 g/cm³
• LogP: -0.81250
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 180.0593889
• Heavy Atom Count: 13
• Complexity: 174

Purity/Quality:

98% ^*data from raw suppliers

5-Formyl-2-methoxyphenylboronic Acid (contains varying amounts of Anhydride) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, C
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 22-26-36/37/39-45-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC(=C1)C=O)OC)(O)O
• Uses: suzuki reaction

Technology Process of 5-Formyl-2-methoxyphenylboronic acid

There total 4 articles about 5-Formyl-2-methoxyphenylboronic 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: 78.0%

2-(3-bromo-4-methoxyphenyl)-1,3-dioxane (208399-74-0) → 5-formyl-2-methoxyphenyl boronic acid (127972-02-5)

Guidance literature:

2-(3-bromo-4-methoxyphenyl)-1,3-dioxane; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 4h;

With Trimethyl borate; In tetrahydrofuran; hexane; at -70 - 20 ℃; Further stages;

DOI:10.3762/bjoc.5.71

Reference yield:

3-bromo-4-methoxybenzylaldehyde (34841-06-0) → 5-formyl-2-methoxyphenyl boronic acid (127972-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / toluene-4-sulfonic acid / toluene / 24 h / Heating

2: 1.) 2.5 M nBuLi; 2.) tributyl borate; 3.) 2M HCl / 1.) diethyl ether, hexane, -70 deg C, 4 h; 2.) 12 h, 20 deg C; 3.) water

With hydrogenchloride; n-butyllithium; boric acid tributyl ester; toluene-4-sulfonic acid; In toluene;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<877::AID-EJOC877>3.0.CO;2-S

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → 5-formyl-2-methoxyphenyl boronic acid (127972-02-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: bromine; aluminum (III) chloride / 1,2-dichloro-ethane

2.1: orthoformic acid triethyl ester; tetra-N-butylammonium tribromide

3.1: n-butyllithium / -70 °C

3.2: Acidic conditions

With aluminum (III) chloride; n-butyllithium; bromine; tetra-N-butylammonium tribromide; orthoformic acid triethyl ester; In 1,2-dichloro-ethane;

upstream raw materials:

2-(3-bromo-4-methoxyphenyl)-1,3-dioxane

3-bromo-4-methoxybenzylaldehyde

Trimethyl borate

4-methoxy-benzaldehyde

Downstream raw materials:

3-(1H-benzo[d]imidazol-2-yl)-4-methoxybenzaldehyde

2-[4'-tert-butyl-6-methoxybiphenyl-3-yl]-9-hydroxy-3H-naphtho[1,2-d]imidazole-7-carboxylic acid

3-(2-chloropyrimidin-4-yl)-4-methoxybenzaldehyde

[3-(2-chloropyrimidin-4-yl)-4-methoxyphenyl]methanol

Refernces

• 1、 Joshi, Vidya,Hatim, Jaywant Govind. "A facile and convenient synthesis of new substituted heteroarylchalcones and flavones by microwave irradiated suzuki-miyaura cross coupling reaction in aqueous medium". . p. 281 - 288. Retrieved 2013/09/24.
• 2、 Eicher, Theophil,Fey, Sabine,Puhl, Werner,Buechel, Edwin,Speicher, Andreas. "Syntheses of Cyclic Bisbibenzyl Systems". . p. 877 - 888. Retrieved 2007/10/03.