4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole

Base Information

• Chemical Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole
• CAS No.: 928664-98-6
• Molecular Formula: C9H14BNO3
• Molecular Weight: 195.026
• Hs Code.: 2934999090
• European Community (EC) Number: 689-432-4
• DSSTox Substance ID: DTXSID50585938
• Nikkaji Number: J2.954.192B
• Wikidata: Q82477958
• Mol file: 928664-98-6.mol

Synonyms:928664-98-6;4-Isoxazoleboronic acid pinacol ester;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole;ISOXAZOLE-4-BORONIC ACID PINACOL ESTER;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoxazole;MFCD06657891;Isoxazol-4-ylboronic acid pinacol ester;4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1,2-OXAZOLE;LXCICYRNWIGDQA-UHFFFAOYSA-N;4-isooxazolylboronic acid pinacol ester;Isoxazole, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;SCHEMBL142345;DTXSID50585938;AKOS006293858;4-Isoxazoleboronic acid, pinacol ester;AB25740;AM85030;CS-W001065;DS-13033;SY025655;4-Isoxazoleboronic acid pinacol ester, 95%;EN300-212573;A851174;J-513440;Z1198169385

Chemical Property of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole

Chemical Property:

• Vapor Pressure: 3.63E-05mmHg at 25°C
• Melting Point: 110-115℃
• Boiling Point: 339.2oC at 760 mmHg
• PKA: -2.02±0.50(Predicted)
• Flash Point: 158.9oC
• PSA: 44.49000
• Density: 1.13g/cm3
• LogP: 0.97380
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 195.1066735
• Heavy Atom Count: 14
• Complexity: 216

Purity/Quality:

98% ^*data from raw suppliers

4-Isoxazoleboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CON=C2
• Uses: 4-?Isoxazoleboronic Acid Pinacol Ester is a reagent used in the preparation of potent and selective in vivo probe (GNE-272) for bromodomains of CBP/EP300 involved in cancer and immune system regulation.

Technology Process of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole

There total 2 articles about 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole 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: 90.0%

4-iodoisoxazole (847490-69-1) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 4-isoxazoleboronic acid pinacol ester (928664-98-6)

Guidance literature:

4-iodoisoxazole; With TurboGrignard; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at 0 ℃; for 4.5h; Inert atmosphere;

DOI:10.1002/anie.201608039

Reference yield:

(isoxazol-4-yl)boronic acid (1008139-25-0) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 4-isoxazoleboronic acid pinacol ester (928664-98-6)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja201743j

Reference yield: 90.0%

4-isoxazoleboronic acid pinacol ester (928664-98-6) + 2-iodonaphthalene (612-55-5) → 2-naphthaleneacetonitrile (7498-57-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; water; In dimethyl sulfoxide; at 130 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja201743j

upstream raw materials:

(isoxazol-4-yl)boronic acid

2,3-dimethyl-2,3-butane diol

4-iodoisoxazole

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

(S)-3-[4-(2-amino-6-{(S)-2,2,2-trifluoro-1-(4-isoxazol-4-yl-phenyl)ethoxy}pyrimidin-4-yl)phenyl]-2-tert-butoxycarbonylaminopropionic acid

[4-(5-isoxazol-4-yl-thiophen-2-yl)-5-methyl-pyrimidin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

3-t-butyl-5-(4-isoxazol-4-ylphenyl)-4-(2-methoxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazol-6-one

tert-butyl 4-(2-(3-fluorophenylamino)-6-(isoxazol-4-yl)quinazolin-7-yloxy) piperidin-1-carboxylate

Refernces

• 1、 Velcicky, Juraj,Soicke, Arne,Steiner, Roland,Schmalz, Hans-Guenther. "Palladium-catalyzed cyanomethylation of aryl halides through domino Suzuki coupling-isoxazole fragmentation". supporting information; experimental part. p. 6948 - 6951. Retrieved 2011/06/19.