257298-93-4

Basic information

• Product Name: 4,4,5,5-tetramethyl-2-[(1S)-1-phenyethyl]-1,3,2-dioxaborolane
• Synonyms: 4,4,5,5-tetramethyl-2-[(1S)-1-phenyethyl]-1,3,2-dioxaborolane
• CAS NO: 257298-93-4
• Molecular Weight: 232.131
• Mol File: 257298-93-4.mol
• Article Data: 29

Chemical Properties

• CAS DataBase Reference: 4,4,5,5-tetramethyl-2-[(1S)-1-phenyethyl]-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,5,5-tetramethyl-2-[(1S)-1-phenyethyl]-1,3,2-dioxaborolane(257298-93-4)
• EPA Substance Registry System: 4,4,5,5-tetramethyl-2-[(1S)-1-phenyethyl]-1,3,2-dioxaborolane(257298-93-4)

Safety Data

• Hazardous Substances Data: 257298-93-4(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 143825-84-7 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 156575-60-9 2-(1-phenyl-ethyl)-benzo[1,3,2]dioxaborole 
• 14900-39-1 phenylvinylboronic acid 
• 672-65-1 (1-chloroethyl)benzene 
• 1445-91-6 (S)-1-phenylethanol 
• 133038-74-1 (S)-(-)-1-phenylethyl N,N-diisopropylcarbamate 
• 174090-36-9 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane 

Downstream Products

• 257299-06-2 2-((S)-1-Chloro-2-phenyl-propyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 779-54-4 phenyl(1-phenylethyl)amine 

Relevant articles and documents

Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation

The enantioselective carbon-boron bond oxidation of several chiral boron-containing compounds by Baeyer-Villiger monooxygenases was evaluated. PAMO and M446G PAMO conveniently oxidized 1-phenylethyl boronate into the corresponding 1-(phenyl)ethanol (ee = 82-91%). Cyclopropyl boronic esters were also oxidized but with no enantioselectivity. β-Boryl carboxylic esters were not oxidized by any BVMOs.

Chiral 2-imidazoline aniline compound as well as preparation method and application thereof

The invention provides a chiral 2-imidazoline aniline compound as well as a preparation method and application thereof. The preparation method comprises the following steps: reacting an o-nitrobenzoic acid compound as shown in a formula (1), oxalyl chloride and N, N-dimethylformamide to obtain an o-nitrobenzoyl chloride compound as shown in a formula (7); adding the hydroxyl amide derivative into a mixed solution of an amino alcohol compound as shown in a formula (2) and triethylamine to obtain a hydroxyl amide derivative as shown in a formula (3); reacting with thionyl chloride to obtain a dichloro compound as shown in a formula (4); then adding triethylamine and primary amine R2NH2 to prepare a nitroimidazoline derivative; and finally, reducing to obtain the chiral 2-imidazoline aniline compound as shown in a formula (6). The chiral 2-imidazoline aniline compound is easy to prepare, the raw materials are cheap and easy to obtain, the preparation method is simple, and the synthesized chiral ligand containing the 2-imidazoline aniline fragment can be used as a catalyst for catalyzing asymmetric hydroboration reaction of cobalt-catalyzed olefin and asymmetric hydroamination reaction of cobalt-catalyzed non-activated terminal olefin.

Ring-Opening Lithiation–Borylation of 2-Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters

Stereogenic trifluoromethyl-substituted carbon centers are highly sought-after moieties in pharmaceutical and agrochemical discovery. Here, we show that lithiation–borylation reactions of 2-trifluoromethyl oxirane give densely functionalized and highly versatile trifluoromethyl-substituted α-tertiary boronic esters. The intermediate boronate complexes undergo the desired 1,2-rearrangement of the carbon-based group with complete retentive stereospecificity, a process that was only observed in non-polar solvents in the presence of TESOTf. Although the trifluoromethyl group adversely affects subsequent transformations of the α-boryl group, Zweifel olefinations provide trifluoromethyl-bearing quaternary stereocenters substituted with alkenes, alkynes and ketones.