5-Methyl-3-Phenyl-4-Isoxazolylboronic Acid

Base Information

• Chemical Name: 5-Methyl-3-Phenyl-4-Isoxazolylboronic Acid
• CAS No.: 491876-01-8
• Molecular Formula: C10H10BNO3
• Molecular Weight: 203.005
• DSSTox Substance ID: DTXSID00406881
• Nikkaji Number: J1.858.158B
• Wikidata: Q82212013
• Mol file: 491876-01-8.mol

Synonyms:491876-01-8;5-Methyl-3-Phenyl-4-Isoxazolylboronic Acid;(5-methyl-3-phenyl-1,2-oxazol-4-yl)boronic Acid;(5-METHYL-3-PHENYLISOXAZOL-4-YL)BORONIC ACID;Boronic acid, (5-methyl-3-phenyl-4-isoxazolyl)-;Boronic acid, B-(5-methyl-3-phenyl-4-isoxazolyl)-;SCHEMBL3088412;DTXSID00406881;MFCD07368498;ZB1045;AB32029;AS-0190;5-methyl-3-phenylisoxazole-4-boronic acid;5-methyl-3-phenylisoxazol-4-ylboronic acid;3-Phenyl-5-methylisoxazole-4-ylboranic acid;5-Methyl-3-phenyl-4-isoxazolyl boronic acid;FT-0741211;EN300-6486429;(5-METHYL-3-PHENYLISOXAZOL-4-YL)BORONICACID;J-517784;5-methyl-3-phenyl-4-isoxazolylboronic acid, AldrichCPR

Chemical Property of 5-Methyl-3-Phenyl-4-Isoxazolylboronic Acid

Chemical Property:

• Vapor Pressure: 1.99E-08mmHg at 25°C
• Melting Point: 104oC
• Boiling Point: 437.5oC at 760 mmHg
• Flash Point: 218.4oC
• PSA: 66.49000
• Density: 1.28g/cm3
• LogP: 0.32980
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 203.0753733
• Heavy Atom Count: 15
• Complexity: 209

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(ON=C1C2=CC=CC=C2)C)(O)O

Technology Process of 5-Methyl-3-Phenyl-4-Isoxazolylboronic Acid

There total 4 articles about 5-Methyl-3-Phenyl-4-Isoxazolylboronic 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:

4-bromo-5-methyl-3-phenylisoxazole (31295-65-5) → C10H10BNO3 (491876-01-8)

Guidance literature:

4-bromo-5-methyl-3-phenylisoxazole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 30h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h; Further stages.;

DOI:10.1002/1615-4169(200212)344:10<1146::AID-ADSC1146>3.0.CO;2-1

Reference yield:

5-hydroxy-5-methyl-3-phenyl-4,5-dihydro-2-isoxazole (1027564-45-9) → C10H10BNO3 (491876-01-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: conc. H₂SO₄ / 80 °C

2.1: 80 percent / Br₂ / CCl₄ / 0 - 20 °C

3.1: BuLi / tetrahydrofuran; hexane / 30 h / -78 °C

3.2: triisopropyl borate / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

With n-butyllithium; sulfuric acid; bromine; In tetrahydrofuran; tetrachloromethane; hexane;

DOI:10.1002/1615-4169(200212)344:10<1146::AID-ADSC1146>3.0.CO;2-1

Reference yield:

acetophenone oxime (613-91-2) → C10H10BNO3 (491876-01-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BuLi / tetrahydrofuran; hexane / -40 °C

1.2: tetrahydrofuran; hexane / -40 - 20 °C

2.1: conc. H₂SO₄ / 80 °C

3.1: 80 percent / Br₂ / CCl₄ / 0 - 20 °C

4.1: BuLi / tetrahydrofuran; hexane / 30 h / -78 °C

4.2: triisopropyl borate / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

With n-butyllithium; sulfuric acid; bromine; In tetrahydrofuran; tetrachloromethane; hexane;

DOI:10.1002/1615-4169(200212)344:10<1146::AID-ADSC1146>3.0.CO;2-1

upstream raw materials:

4-bromo-5-methyl-3-phenylisoxazole

5-hydroxy-5-methyl-3-phenyl-4,5-dihydro-2-isoxazole

5-methyl-3-phenylisoxazole

acetophenone oxime

Downstream raw materials:

valdecoxib

Refernces