905966-41-8

Basic information

• Product Name: [4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile(SALTDATA: FREE)
• Synonyms: [4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile(SALTDATA: FREE);[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile
• CAS NO: 905966-41-8
• Molecular Formula: C13H16BNO2
• Molecular Weight: 229.08264
• Mol File: 905966-41-8.mol

Chemical Properties

• Boiling Point: 378.7°C at 760 mmHg
• Flash Point: 182.8°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 6.18E-06mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: [4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile(SALTDATA: FREE)(CAS DataBase Reference)
• NIST Chemistry Reference: [4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile(SALTDATA: FREE)(905966-41-8)
• EPA Substance Registry System: [4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile(SALTDATA: FREE)(905966-41-8)

Safety Data

• Hazardous Substances Data: 905966-41-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile(SALTDATA: FREE) is used as a reagent in organic synthesis for its ability to participate in Suzuki-Miyaura cross-coupling reactions. These reactions are significant in the synthesis of pharmaceuticals and agrochemicals, allowing for the creation of complex molecular structures with potential applications in medicine and agriculture.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, [4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile(SALTDATA: FREE) serves as a valuable building block for the development of new drugs. Its unique structure allows for the formation of diverse chemical entities that can be tailored to target specific biological pathways or receptors, potentially leading to the discovery of novel therapeutic agents.
Used as a Solvent:
The acetonitrile group in [4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile(SALTDATA: FREE) makes it a useful solvent in various chemical reactions. Its properties enable it to dissolve a wide range of substances, facilitating reactions and improving overall yields in the synthesis of target compounds.
Used in Chemical Research:
[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]acetonitrile(SALTDATA: FREE) is also utilized in chemical research to explore new reaction pathways, develop innovative synthetic methods, and understand the fundamental principles governing chemical interactions. Its diverse applications in research contribute to the advancement of knowledge in the field of chemistry and related disciplines.

InChI:InChI=1/C13H16BNO2/c1-13(2)9-16-14(17-10-13)12-5-3-11(4-6-12)7-8-15/h3-6H,7,9-10H2,1-2H3

Upstream product

• 668987-38-0 5,5-dimethyl-1,3,2-dioxaborinane 
• 140-53-4 p-chlorobenzyl cyanide 

Relevant articles and documents

Ni(COD)2/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature

Reaction conditions for the Ni(COD)2/PCy3 catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)2/PCy 3 was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature. This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives. In combination with the recently developed Nicatalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible (Figure presented).

Zero-valent metals accelerate the neopentylglycolborylation of aryl halides catalyzed by NiCl2-based mixed-ligand systems

The highly active mixed-ligand catalytic system NiCl2(dppp)/dppf combined with the reducing effect of zerovalent Zn and of other metals was used to demonstrate a method for the dramatic acceleration of the rate and for the enhancement of the yi

Neopentylglycolborylation of aryl chlorides catalyzed by the mixed ligand system NiCl2(dppp)/dppf

The mixed ligand system 10 mol % NICl2(dppp) with 5 mol % dppf was discovered to be an extremely efficient catalyst for the neopentylglycolborylation of a diversity of electron-rich and electron-deficient aryl chlorides. Optimization showed tha