1214264-88-6

Basic information

• Product Name: 1-pinacolato-2-(1,8)diamo-naphthalenylborane
• Synonyms: 1-pinacolato-2-(1,8)diamo-naphthalenylborane;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine;3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4-diaza-3-boratricyclo-[7.3.1.0^{5,13}]trideca-1(13);2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-naphtho[1,8-de][1,3,2]diazaborinane;(Pin)B-B(Dan)
• CAS NO: 1214264-88-6
• Molecular Formula: C₁₆H₂₀B₂N₂O₂
• Molecular Weight: 293.97
• EINECS: -0
• Mol File: 1214264-88-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 186.7-187.4 °C
• Boiling Point: 384.1±25.0 °C(Predicted)
• Appearance: /
• Density: 1.14±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.85±0.20(Predicted)
• CAS DataBase Reference: 1-pinacolato-2-(1,8)diamo-naphthalenylborane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-pinacolato-2-(1,8)diamo-naphthalenylborane(1214264-88-6)
• EPA Substance Registry System: 1-pinacolato-2-(1,8)diamo-naphthalenylborane(1214264-88-6)

Safety Data

• Hazardous Substances Data: 1214264-88-6(Hazardous Substances Data)

Usage

General Description

1-Pinacolato-2-(1,8)diamo-naphthalenylborane is an organoborane compound that contains a boron atom bonded to a naphthalene ring. It is commonly used in organic synthesis as a powerful reducing agent due to its ability to donate a hydride ion. 1-pinacolato-2-(1,8)diamo-naphthalenylborane is highly reactive and can efficiently and selectively reduce a variety of functional groups such as ketones, esters, and amides. Additionally, it is also used in the synthesis of complex organic molecules and as a versatile building block for further chemical transformations. The unique structure and reactivity of 1-pinacolato-2-(1,8)diamo-naphthalenylborane make it a valuable tool in the field of organic chemistry.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1630-79-1 tetrakis(dimethylamido)diborane 
• 479-27-6 naphthalene-1,8-diamine 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1214264-95-5 (E)-1-(4-(2-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)ethanone 
• 1214265-05-0 (Z)-2-(2-phenyl-2-(thiophen-2-yl)vinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1214265-01-6 (Z)-2-(2-phenyl-2-p-tolylvinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1214265-02-7 (Z)-2-(2-(4-methoxyphenyl)-2-phenylvinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1214264-94-4 (E)-ethyl 4-(2-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzoate 
• 1214264-93-3 (E)-2-(2-(4-methoxyphenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1214264-97-7 (E)-2-(2-(3-bromophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1214264-89-7 (E)-2-(2-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1214264-90-0 (CH₃)4C₂O₂BC(C₆H₅)CHB(NH)2C₁₀H₆ 
• 1214265-00-5 (Z)-2-(1-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-en-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1214265-04-9 (Z)-2-(2-phenyl-2-o-tolylvinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1214264-91-1 (E)-2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-p-tolylvinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1214265-03-8 (Z)-ethyl 4-(2-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)-1-phenylvinyl)benzoate 
• 1214264-96-6 (E)-2-(2-(4-bromophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 

Relevant articles and documents

A Boron Activating Effect Enables Cobalt-Catalyzed Asymmetric Hydrogenation of Sterically Hindered Alkenes

Unsymmetric 1,1-diboryl alkenes bearing one -[BPin] (BPin = pinacolatoboryl) and one -[BDan] (BDan = 1,8-diaminonaphthalatoboryl) substituent each were hydrogenated in high yield and enantioselectivity using C1-symmetric pyridine(diimine) (PDI)

Unsymmetrical 1,1-diborated multisubstituted sp3-carbons formed via a metal-free concerted-asynchronous mechanism

We have experimentally proved the unsymmetrical 1,1-diboration of diazo compounds, formed in situ from aldehydes and cyclic and non-cyclic ketones, in the absence of any transition metal complex. The heterolytic cleavage of the mixed diboron reagent, Bpin-Bdan, and the formation of two geminal C-Bpin and C-Bdan bonds has been rationalised based on DFT calculations to occur via a concerted-asynchronous mechanism. Diastereoselection is attained on substituted cyclohexanones and DFT studies provide understanding on the origin of the selectivity. The alkoxide-assisted selective deborylation of Bpin from multisubstituted sp3-carbon and generation of a Bdan stabilized carbanion, easily conducts a selective protodeboronation sequence.

A masked diboron in Cu-catalysed borylation reaction: Highly regioselective formal hydroboration of alkynes for synthesis of branched alkenylborons

The use of a masked diboron as a boron source in the presence of a Cu-N-heterocyclic carbene (NHC) catalyst enables alkyl-, aryl-, heteroatom- and silyl-substituted terminal alkynes to undergo α-selective formal hydroboration to give diverse branched alkenylboron compounds exclusively. Synthetic potential of this α-selective hydroboration has been demonstrated by total synthesis of pharmaceutically significant bexarotene and LG100268. This journal is the Partner Organisations 2014.