1309982-16-8

Basic information

• Product Name: 5-fluoro-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)aniline
• Synonyms: 5-fluoro-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)aniline;5-Fluoro-2-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-phenylaMine
• CAS NO: 1309982-16-8
• Molecular Formula: C₁₂H₁₇BFNO₂
• Molecular Weight: 237.0782832
• Mol File: 1309982-16-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 5-fluoro-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-fluoro-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)aniline(1309982-16-8)
• EPA Substance Registry System: 5-fluoro-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)aniline(1309982-16-8)

Safety Data

• Hazardous Substances Data: 1309982-16-8(Hazardous Substances Data)

Upstream product

• 1003-99-2 2-bromo-5-fluoroaniline 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 372-19-0 meta-fluoroaniline 

Downstream Products

• 1611447-04-1 2-azido-4-fluorophenylboronic acid pinacolate ester 
• 1611447-10-9 C₁₅H₁₆FN₃O₃ 
• 1611447-16-5 C₁₈H₂₁FN₄O₅ 

Relevant articles and documents

Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids

A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.

Achieving High Ortho Selectivity in Aniline C-H Borylations by Modifying Boron Substituents

High ortho selectivity for Ir-catalyzed C-H borylations (CHBs) of anilines results when B2eg2 (eg = ethylene glycolate) is used as the borylating reagent in lieu of B2pin2, which is known to give isomeric mixtures with anilines lacking a blocking group at the 4-position. With this modification, high selectivities and good yields are now possible for various anilines, including those with groups at the 2- and 3-positions. Experiments indicate that ArylN(H)Beg species are generated prior to CHB and support the improved ortho selectivity relative to B2pin2 reactions arising from smaller Beg ligands on the Ir catalyst. The lowest-energy transition states (TSs) from density functional theory computational analyses have N-H···O hydrogen-bonding interactions between PhN(H)Beg and O atoms in Beg ligands. Ir-catalyzed CHB of PhN(H)Me with B2eg2 is also highly ortho-selective. 1H NMR experiments show that N-borylation fully generates PhN(Me)Beg prior to CHB. The TS with the lowest Gibbs energy was the ortho TS, in which the Beg unit is oriented anti to the bipyridine ligand.

Rh2(II)-catalyzed ester migration to afford 3 H-indoles from trisubstituted styryl azides

Rh2(II)-Complexes trigger the formation of 3H-indoles from ortho-alkenyl substituted aryl azides. This reaction occurs through a 4π-electron-5-atom electrocyclization of the rhodium N-aryl nitrene followed by a [1,2]-migration to afford only 3H-indoles. The selectivity of the migration is dependent on the identity of the β-styryl substituent.