2-CHLORO-4-TRIFLUOROMETHOXYBENZENEBORONIC ACID

Base Information

• Chemical Name: 2-CHLORO-4-TRIFLUOROMETHOXYBENZENEBORONIC ACID
• CAS No.: 345226-20-2
• Molecular Formula: C7H5BClF3O3
• Molecular Weight: 240.37200
• Hs Code.: 2931900090
• Mol file: 345226-20-2.mol

Synonyms:(2-Chloro-4-(trifluoromethoxy)phenyl)boronic acid;[2-chloro-4-(trifluoromethoxy)phenyl]boronic acid;

Chemical Property of 2-CHLORO-4-TRIFLUOROMETHOXYBENZENEBORONIC ACID

Chemical Property:

• Melting Point: 150-152 °C
• Boiling Point: 294.1±50.0 °C(Predicted)
• PKA: 8.00±0.58(Predicted)
• PSA: 49.69000
• Density: 1.53±0.1 g/cm3(Predicted)
• LogP: 0.91840
• Storage Temp.: Refrigerated.

Purity/Quality:

98% ^*data from raw suppliers

(2-Chloro-4-trifluoromethoxyphenyl)boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2-Chloro-4-trifluoromethoxyphenyl)boronic Acid is an intermediate used to prepare aza- and diazabiphenyl analogs of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine. It is also used in the synthesis of aryl(alkylamino)nitropyridines via amination of chlorohydroxynitropyridine with aliphatic amines followed by chlorination, and Suzuki-coupling with arylboronic acids.

Technology Process of 2-CHLORO-4-TRIFLUOROMETHOXYBENZENEBORONIC ACID

There total 2 articles about 2-CHLORO-4-TRIFLUOROMETHOXYBENZENEBORONIC 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: 77.0%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-2-chloro-4-(trifluoromethoxy)benzene (892845-59-9) → (2-chloro-4-(trifluoromethoxy)phenyl)boronic acid (345226-20-2)

Guidance literature:

1-bromo-2-chloro-4-(trifluoromethoxy)benzene; With TurboGrignard; In tetrahydrofuran; at 0 - 23 ℃;

Trimethyl borate; In tetrahydrofuran; at 0 - 23 ℃;

With hydrogenchloride; In tetrahydrofuran;

Reference yield: 64.0%

2-chloro-1-iodo-4-(trifluoromethoxy)benzene (345226-19-9) → (2-chloro-4-(trifluoromethoxy)phenyl)boronic acid (345226-20-2)

Guidance literature:

2-chloro-1-iodo-4-(trifluoromethoxy)benzene; With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; toluene; at -78 - -20 ℃; for 6.5h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; hexane; water; toluene; at -20 - 20 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1021/jm101288t

Reference yield: 69.0%

(6R)-6-[(5-bromopyridin-2-yl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine + (2-chloro-4-(trifluoromethoxy)phenyl)boronic acid (345226-20-2) → (6R)-6-({5-[2-chloro-4-(trifluoromethoxy)phenyl]pyridin-2-yl}methoxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 70 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01581

upstream raw materials:

2-chloro-1-iodo-4-(trifluoromethoxy)benzene

Trimethyl borate

1-bromo-2-chloro-4-(trifluoromethoxy)benzene

Refernces

• 1、 -. "PYRAZOLYL-BASED CARBOXAMIDES II AS CRAC CHANNEL INHIBITORS". Page/Page column 52; 53. . Retrieved 2014/07/23.