287944-10-9

Basic information

• Product Name: 2-CYCLOPENTENYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• Synonyms: 2-CYCLOPENTENYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;1-Cyclopentenyl boronic acid pinacol ester;2-(Cyclopent-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Cyclopenten-1-ylboronic acid, pinacol ester;1,3,2-Dioxaborolane, 2-(1-cyclopenten-1-yl)-4,4,5,5-tetraMethyl-;2-(1-Cyclopenten-1-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane;2-(cyclopent-1-en-1-yl)-4,4,5,5-tetraMethyl-1,3,2- dioxaborolane;1-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1-cyclopentene
• CAS NO: 287944-10-9
• Molecular Formula: C₁₁H₁₉BO₂
• Molecular Weight: 194.07836
• EINECS: 1308068-626-2
• Product Categories: Organoborons
• Mol File: 287944-10-9.mol

Chemical Properties

• Boiling Point: 210 °C at 760 mmHg
• Flash Point: 80.8 °C
• Appearance: /
• Density: 0.96 g/cm³
• Vapor Pressure: 0.284mmHg at 25°C
• Refractive Index: 1.463
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-CYCLOPENTENYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CYCLOPENTENYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(287944-10-9)
• EPA Substance Registry System: 2-CYCLOPENTENYL-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(287944-10-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37
• TSCA: No
• Hazardous Substances Data: 287944-10-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a reagent and building block in organic synthesis for its ability to participate in various reactions, including cross-coupling reactions, and its stability and reactivity in organic transformations.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used as a key intermediate in the synthesis of complex organic molecules, contributing to the development of new pharmaceuticals.
Used in Agrochemical Development:
Similarly, in the agrochemical industry, this compound is utilized as a key intermediate for the synthesis of complex organic molecules, aiding in the development of new agrochemicals.

InChI:InChI=1/C11H19BO2/c1-10(2)11(3,4)14-12(13-10)9-7-5-6-8-9/h7H,5-6,8H2,1-4H3

Upstream product

• 17497-52-8 1-iodocyclopentene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 28075-49-2 1-cyclopentenyl triflate 
• 73183-34-3 bis(pinacol)diborane 
• 930-29-0 1-chlorocyclopent-1-ene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 17529-98-5 cyclopentanone p-tolylsulfonylhydrazone 
• 142-29-0 cyclopentene 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5419-55-6 Triisopropyl borate 
• 120-92-3 cyclopentanone 

Downstream Products

• 847547-03-9 2-cyclopent-1-enyl-5-methanesulfonyl-benzoic acid 
• 1041002-84-9 (4R,5R)-4,5-bis(2-cyclopentenylphenyl)-2,2-dimethyl-1,3-dioxolane 
• 1332490-87-5 (3′R,9′S)-9′-(tert-butyldimethylsilyloxy)-4′-isopropyl-7′,7′-dimethyl-3′-(4-(trifluoromethyl)phenyl)-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]5′-oxide 
• 1332490-85-3 (3′R,6′R,9′S)-9′-(tert-butyldimethylsilyloxy)-4′-isopropyl-7′,7′-dimethyl-3′-(4-(trifluoromethyl)phenyl)-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]-6′-yl acetate 
• 1332490-86-4 (3′R,6′S,9′S)-9′-(tert-butyldimethylsilyloxy)-4′-isopropyl-7′,7′-dimethyl-3′-(4-(trifluoromethyl)phenyl)-6′,7′,8′,9′-tetrahydro-3′H-spiro[cyclopentane-1,1′-furo[3,4-c]quinoline]-6′-yl acetate 
• 1332490-10-4 (R)-((S)-5-(tert-butyldimethylsilyloxy)-4-cyclopentenyl-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl)(4-isopropylphenyl)methanol 
• 1373840-33-5 5-(cyclopent-1-en-1-yl)-6-[ethyl(methylsulfonyl)amino]-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide 
• 1373840-35-7 5-cyclopentyl-6-[ethyl(methylsulfonyl)amino]-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide 
• 1421186-63-1 1-((2-cyclopentenylphenyl)ethynyl)-2-methoxynaphthalene 
• 1415899-17-0 6-(3-chloro-phenyl)-5-cyclopentyl-pyridine-2-carboxylic acid 
• 1445790-44-2 methyl 3-(cyclopent-1-en-1-yl)-5-nitrobenzoate 
• 1445789-14-9 methyl 3-(3-carbamoyl-7-chloro-6-isopropoxyquinolin-4-ylamino)-5-cyclopentylbenzoate 
• 1445790-46-4 methyl 3-amino-5-cyclopentylbenzoate 
• 1445789-16-1 methyl 3-(3-carbamoyl-7-(2,4-dimethoxypyrimidin-5-yl)-6-isopropoxyquinolin-4-ylamino)-5-cyclopentylbenzoate 

Relevant articles and documents

Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation

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Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.

Copper-catalyzed cross-coupling of vinyliodonium salts and diboron reagents to generate alkenyl boronic esters

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