2,3,4-Trimethoxyphenylboronic acid

Base Information

• Chemical Name: 2,3,4-Trimethoxyphenylboronic acid
• CAS No.: 118062-05-8
• Molecular Formula: C9H13BO5
• Molecular Weight: 212.01
• Hs Code.: 29163990
• European Community (EC) Number: 681-179-8
• DSSTox Substance ID: DTXSID80378572
• Nikkaji Number: J331.439A
• Wikidata: Q72513830
• Mol file: 118062-05-8.mol

Synonyms:2,3,4-Trimethoxyphenylboronic acid;118062-05-8;(2,3,4-trimethoxyphenyl)boronic Acid;2,3,4-Trimethoxybenzeneboronic acid;Boronic acid, (2,3,4-trimethoxyphenyl)-;MFCD01318183;2,3,4-TRIMETHOXYLPHENYLBORONIC ACID;(2,3,4-Trimethoxyphenyl)boronicacid;trimethoxyphenyl boronic acid;SCHEMBL23439;2,3,4-Trimethoxyphenylboronsaure;DTXSID80378572;LDQLSQRFSNMANA-UHFFFAOYSA-N;AMY29788;2,3,4-trimethoxyphenyl boronic acid;AKOS004116552;AB08680;CS-W015030;NCGC00249492-01;AC-16696;BP-10169;DS-13627;SY109490;FT-0609399;H11780;J-506875

Chemical Property of 2,3,4-Trimethoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 3.65E-06mmHg at 25°C
• Melting Point: 74-79 °C
• Refractive Index: 1.513
• Boiling Point: 371.1 °C at 760 mmHg
• PKA: 8.50±0.58(Predicted)
• Flash Point: 178.3 °C
• PSA: 68.15000
• Density: 1.21 g/cm³
• LogP: -0.60780
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 212.0856037
• Heavy Atom Count: 15
• Complexity: 189

Purity/Quality:

98% ^*data from raw suppliers

2,3,4-Trimethoxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C(=C(C=C1)OC)OC)OC)(O)O
• Uses: (2,3,4-Trimethoxyphenyl)boronic Acid is a reagent used in the synthesis of heteroaryl, mono and bicyclic compounds which may be used as inhibitors for EGF and PDGF receptor tyrosine kinases. Also used in the synthesis of non-steroidal CYP 17 inhibitors in the treatment of prostate cancer suzuki reaction

Technology Process of 2,3,4-Trimethoxyphenylboronic acid

There total 2 articles about 2,3,4-Trimethoxyphenylboronic 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: 73.0%

boric acid tributyl ester (688-74-4) + 2,3,4-trimethoxyphenylmagnesium bromide (114605-54-8) → 2,3,4-trimethoxyphenylboronic acid (118062-05-8)

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 water; elem. anal.;;

Reference yield:

2,3,4-trimethoxybromobenzene (10385-36-1) → 2,3,4-trimethoxyphenylboronic acid (118062-05-8)

Guidance literature:

2,3,4-trimethoxybromobenzene; With tert.-butyl lithium; In diethyl ether; at -95 ℃; for 0.5h;

With Triisopropyl borate; In diethyl ether; at -95 ℃; for 0.333333h;

With silica gel;

DOI:10.1081/SCC-200066658

Reference yield: 99.0%

(S)-5-bromo-6-(p-tolylsulfinyl)benzo[d][1,3]dioxole + 2,3,4-trimethoxyphenylboronic acid (118062-05-8) → (S)-5-(p-tolylsulfinyl)-6-(2,3,4-trimethoxyphenyl)benzo[d][1,3]dioxole

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 119 ℃; for 10h; Reagent/catalyst; Sealed tube; Inert atmosphere;

DOI:10.1016/j.tet.2016.03.060

upstream raw materials:

2,3,4-trimethoxybromobenzene

boric acid tributyl ester

2,3,4-trimethoxyphenylmagnesium bromide

Downstream raw materials:

2,3,4-trimethoxybiphenyl

1,2-(methylenedioxy)-4-(2',3',4'-trimethoxyphenyl)benzene

methyl 4-(2',3',4'-trimethoxyphenyl)benzoate

2-methoxy-5-(2',3',4'-trimethoxyphenyl)-2,4,6-cycloheptatrien-1-one

Refernces

• 1、 Hernández-Ruiz, Raquel,Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Fernández-Rodríguez, Manuel A.,Tapia, M. José,Sanz, Roberto. "Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties". supporting information. p. 13613 - 13623. Retrieved 2021/08/23.