171364-82-2

Basic information

• Product Name: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE
• Synonyms: 4-Cyanophenylboronic acid pinacol ester 97%;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE;4-CYANOPHENYLBORONIC ACID PINACOL ESTER;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE 97%;4-Cyanobenzeneboronic acid, pinacol ester;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile,97%;4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)benzonitrile;Benzonitrile, 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
• CAS NO: 171364-82-2
• Molecular Formula: C₁₃H₁₆BNO₂
• Molecular Weight: 229.08
• Mol File: 171364-82-2.mol
• Article Data: 108

Chemical Properties

• Melting Point: 95-99 °C(lit.)
• Boiling Point: 345.782 °C at 760 mmHg
• Flash Point: 162.923 °C
• Appearance: Light yellow to orange or light tan/Crystalline Powder
• Density: 1.066 g/cm³
• Vapor Pressure: 6.02E-05mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: Refrigerator (+4°C)
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(171364-82-2)
• EPA Substance Registry System: 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE(171364-82-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 171364-82-2(Hazardous Substances Data)

Usage

Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, also known as (Cyanophenyl)boronic Acid Pinacol Ester, is a light yellow to orange or light tan crystalline powder. It is a chemical compound with a unique structure that has various applications in different industries.

Uses

Used in Pharmaceutical Industry:
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows for the preparation of arylparacyclophanes via Suzuki aryl cross-coupling of bromoparacyclophane with arylboronic acid and arylboronates.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is used as a key building block for the preparation of tyrosine-modified analogs of α4β7 integrin inhibitor biotin-R8ERY. This application highlights its importance in the development of novel bioactive compounds with potential therapeutic applications.
Used in Research and Development:
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile is also utilized in research and development for the synthesis of various organic compounds and materials. Its unique structure and reactivity make it a valuable tool for chemists working on the design and synthesis of new molecules with specific properties and functions.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 7508, 1995 DOI: 10.1021/jo00128a024

InChI:InChI=1/C13H16BNO2/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-8H,1-4H3

Upstream product

• 128376-64-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 190788-58-0 4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-[1,3,2]-dioxaborolane 
• 557-21-1 zinc(II) cyanide 
• 302348-51-2 (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol 
• 73183-34-3 bis(pinacol)diborane 
• 1197-19-9 4-cyano-N,N-dimethylaniline 
• 100-47-0 benzonitrile 
• 195062-57-8 p-tolylboronic pinacol ester 
• 3058-39-7 4-iodobenzonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 1416881-52-1 (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile 
• 90819-57-1 4-butyrylbenzonitrile 

Downstream Products

• 1379575-22-0 1,7-bis(4-cyanophenyl)-N,N'-dioctyl-3:4,9:10-perylenetetracarboxydiimide 
• 1379575-23-1 1,6-bis(4-cyanophenyl)-N,N'-dioctyl-3:4,9:10-perylenetetracarboxydiimide 
• 51238-46-1 4-(phenylthio)benzonitrile 

Relevant articles and documents

Two Symmetrically Bis-substituted Pyrene Derivatives: Synthesis, Photoluminescence, and Electroluminescence

Two kinds of cyanophenyl terminated pyrene derivatives for organic light-emitting diodes were synthesized and characterized by UV/Vis, fluorescence (FL), 1H NMR, MALDI-TOF, CV and TGA. Both compounds exhibited blue photoluminescence and high fluorescent quantum yield of 85% and 75% in solutions. Due to the presence of acetylene spacer, the compound distinguishes itself by high coplanarity, high thermal stability, little Stokes' shift and clear excimer formation in the solid state from the acetylene-free compound. In order to suppress the molecular aggregation, the electroluminescent properties were studied by doing the materials in PVK. The result proved that energy transfer happened from the host PVK to the materials. Two kinds of cyanophenyl terminated pyrene derivatives for OLEDs were synthesized and characterized. Both compounds exhibited blue photoluminescence and high fluorescent quantum yield of 85% and 75% in solutions. The result proved that energy transfer happened from the host PVK to the materials.

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Nickel-Catalyzed Cyanation of Aryl Thioethers

A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.