4,4,5,5-Tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane
• CAS No.: 1073339-21-5
• Molecular Formula: C13H16BF3O2
• Molecular Weight: 272.075
• Hs Code.: 2934999090
• European Community (EC) Number: 805-903-0,932-590-9
• DSSTox Substance ID: DTXSID20590413
• Nikkaji Number: J2.708.776K
• Wikidata: Q82484110
• Mol file: 1073339-21-5.mol

Synonyms:1073339-21-5;4,4,5,5-Tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane;2-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER;2-(Trifluoromethyl)phenylboronic acid pinacol ester;2-[2-(Trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-[2-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane;MFCD06795676;2-Trifluoromethylphenylboronic acid pinacol ester;4,4,5,5-Tetramethyl-2-(2-(trifluoromethyl)-phenyl)-1,3,2-dioxaborolane;SCHEMBL9755;DTXSID20590413;AKOS015960087;AB29232;AT16992;AS-55617;SY051384;DB-347346;CS-0175669;T2428;EN300-1425730;A895501;J-001789;Z1336745123;4,4,5,5-tetramethyl-2-(2-trifluoromethyl-phenyl)-[1,3,2]dioxaborolane;4,4,5,5-tetramethyl-2-(2-trifluoromethyl-phenyl)-1,3,2-dioxaborolane;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(trifluoromethyl)benzene;4,4,5,5-Tetramethyl-2-[2-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane, AldrichCPR

Chemical Property of 4,4,5,5-Tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Chemical Property:

• Boiling Point: 73 °C / 2mmHg
• PSA: 18.46000
• Density: 1.15
• LogP: 3.00460
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 272.1195444
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2C(F)(F)F

Technology Process of 4,4,5,5-Tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

There total 12 articles about 4,4,5,5-Tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane 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: 93.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 2-iodo(trifluoromethyl)benzene (444-29-1) → 4,4,5,5-tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (1073339-21-5)

Guidance literature:

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-iodo(trifluoromethyl)benzene; With TurboGrignard; In tetrahydrofuran; at 0 ℃; Cooling with ice; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran;

DOI:10.1021/op2000089

Reference yield: 88.0%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (1073339-21-5)

Guidance literature:

With tris(trimethylphosphine)nickel(II) chloride; (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; In tetrahydrofuran; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol202267t

Reference yield: 49.0%

2-(trifluoromethyl)benzoyl fluoride (312-96-9) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (1073339-21-5)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; potassium fluoride; triphenylphosphine; sodium chloride; In octane; toluene; at 140 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c8cc08504h

upstream raw materials:

α,α,α-trifluorotoluene

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

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

Downstream raw materials:

2-(2-(trifluoromethyl)phenyl)pyridine

1,2-bis(trifluoromethyl)benzene

4-(3-(trifluoromethyl)phenyl)morpholine

methyl (E)-2-(3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2(5H)-ylidene)-2-(2-(trifluoromethyl)phenyl)acetate

Refernces

• 1、 Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie. "Cross-Coupling through Ag(I)/Ag(III) Redox Manifold". supporting information. p. 15396 - 15405. Retrieved 2021/10/12.
• 2、 Pinet, Sandra,Liautard, Virginie,Debiais, Mégane,Pucheault, Mathieu. "Radical Metal-Free Borylation of Aryl Iodides". . p. 4759 - 4768. Retrieved 2017/10/03.