216393-57-6

Basic information

• Product Name: 3,5-DIFLUOROBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER
• Synonyms: 3,5-DIFLUOROBENZENEBORNOIC ACID NEOPENTYL GLYCOL CYCLIC ESTER;3,5-DIFLUOROBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER;3,5-DIFLUOROBENZENEBORONIC ACID NEOPENTYL GLYCOL ESTER;2-(3,5-Difluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane;3,5-DIFLUOROBENZENEBORONIC ACID NEOPENTYL GLYCOL ESTER, 98+%;3,5-Difluorophenylboronic acidneopentylglycol ester
• CAS NO: 216393-57-6
• Molecular Formula: C₁₁H₁₃BF₂O₂
• Molecular Weight: 226.03
• EINECS: -0
• Mol File: 216393-57-6.mol

Chemical Properties

• Melting Point: 43-45°C
• Boiling Point: 290.9 °C at 760 mmHg
• Flash Point: 129.8 °C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 0.0035mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,5-DIFLUOROBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIFLUOROBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER(216393-57-6)
• EPA Substance Registry System: 3,5-DIFLUOROBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER(216393-57-6)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• Hazardous Substances Data: 216393-57-6(Hazardous Substances Data)

Usage

Uses

3,5-Difluorophenylboronic acid neopentyl glycol ester

InChI:InChI=1/C11H13BF2O2/c1-11(2)6-15-12(16-7-11)8-3-9(13)5-10(14)4-8/h3-5H,6-7H2,1-2H3

Upstream product

• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 156545-07-2 3,5-difluorophenylboronic acid 

Downstream Products

• 139368-37-9 ethyl 2-(3,5-difluorophenyl)acetate 
• 1415045-91-8 1-(3,5-difluorophenyl)-N,N-diethyl-2-naphthamide 
• 1415045-46-3 N,N-diethyl-2-(3,5-difluorophenyl)furan-3-carboxamide 
• 718610-73-2 (R)-iso-propyl 3-(3,5-difluorophenyl)-3-(1-(methylsulfonyl)piperidine-4-yl)propanoate 

Relevant articles and documents

Beyond Directed ortho Metalation: Ruthenium-Catalyzed Amide-Directed CAr-OMe Activation/Cross-Coupling Reaction of Naphthamides with Aryl Boronates

A new and general synthetic methodology for the construction of biaryl, heterobiaryl, and polyaryl molecules by the ruthenium-catalyzed cross-coupling of ortho-methoxy naphthamides with aryl boroneopentylates is described. The isomeric 1-MeO-2-naphthamides and 2-MeO-1-naphthamides furnish an expansive series of arylated naphthamides in excellent yields. Competition experiments showed the higher reactivity of 1-MeO-2-naphthamide over 2-MeO-benzamide. Orthogonality between the C-O activation/cross-coupling and the Suzuki-Miyaura reactions was established. The method provides naphthalenes which are difficult to prepare by directed ortho metalation.

C-H activation by amide chelation control: Ruthenium-catalyzed direct synthesis of 2-Aryl-3-furanamides

A new, catalytic methodology for the synthesis of heterobiaryls by the ruthenium-catalyzed C-H activation/cross-coupling of heterocyclic amides with aryl boroneopentylates is surveyed. From this survey, the highly regioselective reaction of furan-3-carboxamide to give 2-aryl-3-furanamides is optimized and generalized in scope with respect to the aryl boroneopentylate coupling partners. Established thereby is a one-step synthetic method which may supercede the broadly applied two-step directed ortho metalation (DoM)-cross coupling reaction involving cryogenic and strong base conditions and which has potential for further ortho and remote metalation chemistry.

Beyond directed ortho metalation: Ruthenium-catalyzed amide-directed C Ar-N activation/C-C coupling reaction of anthranilamides with organoboronates

A new, catalytic, and general methodology for the synthesis of biaryls and heterobiaryls by the cross coupling of anthranilamide derivatives (o-NMe 2 benzamides) with aryl boroneopentylates is described. The reaction proceeds under catalytic RuH2(CO)(PPh3)3 conditions driven by the activation of the unreactive C-N bond by amide directing group (DG)-Ru catalyst chelation. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, and convenient scale-up are features of these reactions which may lend themselves to industrial applications.

Beyond directed ortho metalation: Ru-catalyzed CAr-O activation/cross-coupling reaction by amide chelation

Disclosed is a new, catalytic, and general methodology for the chemical synthesis of biaryl, heterobiaryl, and polyaryl molecules by the cross-coupling of o-methoxybenzamides with aryl boroneopentylates. The reaction is based on the activation of the unreactive C-OMe bond by the proximate amide directing group using catalytic RuH2(CO)(PPh3)3 conditions. A one-step, base-free coupling process is thereby established that has the potential to supersede the useful two-step directed ortho metalation/cross- coupling reaction involving cryogenic temperature and strong base conditions. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, minimum waste, and convenient scale-up make these reactions suitable for industrial applications.

PROCESS FOR PREPARING BETA- (FLUOROPHENYL) -PROPANOATE ESTER DERIVATIVES

A process for preparing a compound of formula (I) comprising reacting a compound of formula (II) with a fluorinated boron species of formula (III) in the presence of: an alcohol; a rhodium (I) pre-catalyst species; a suitable ligand that binds to the rhodium (I) pre-catalyst species to form a catalyst complex; a base; and, a suitable solvent; the process being carried out at a temperature in the range 40 to 110oC. The compounds of formula (I) are useful in the preparation of pharmaceutically active compounds.