608534-39-0

Usage

Uses

Used in Organic Synthesis:
(E)-3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propen-1-ol is used as a reagent in organic synthesis for its unique structure and reactivity, making it a valuable building block in the creation of complex organic molecules.
Used in Pharmaceutical Synthesis:
(E)-3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propen-1-ol is used as a building block in the synthesis of various pharmaceuticals due to its unique structure and reactivity.
Used in Agrochemical Synthesis:
(E)-3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propen-1-ol is used as a building block in the synthesis of agrochemicals, contributing to the development of new chemical entities for agricultural applications.
Used in Medicinal Chemistry Research:
(E)-3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-propen-1-ol is used as a subject of interest in medicinal chemistry research due to its anti-inflammatory and anti-oxidant properties, which have potential applications in the development of new therapeutic agents.

InChI:InChI=1/C9H17BO3/c1-8(2)9(3,4)13-10(12-8)6-5-7-11/h5-6,11H,7H2,1-4H3/b6-5+

Upstream product

• 180516-86-3 C₁₂H₂₅BO₃Si 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 107-19-7 propargyl alcohol 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 870777-31-4 2-(3-bromo-1-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Stereocomplementary syntheses of 1,ω-distannylated E,Z-isomeric conjugated trienes, tetraenes, and pentaenes

Stereoselective syntheses of 1,6-bis(tributylstannyl)hexa-1,3,5-trienes, 1,8-bis(tributylstannyl)octa-1,3,5,7-tetraenes, and 1,10-bis(tributylstannyl) deca-1,3,5,7,9-pentaenes with various methylation patterns were achieved based on stereocomplementary C=C bond-forming reactions. All-E isomers resulted from Ramberg-Baecklund rearrangements of distannylated diallyl-, allylpentadienyl-, or bis- (pentadienyl)sulfones. Mono-Z-configured 1,ω-bis(tributylstannyl)-1,3,5-polyenes emerged from (Sylvestre-)Julia olefinations of Bu3Sn-substituted enals or dienals with Bu 3Sn-substituted allyl or pentadienyl benzothiazolylsulfones. Related Ramberg-Baecklund approaches provided all-E-1-bromo-6-(tributylstannyl)hexa- 1,3,5-triene but not all-E-1-(tetramethyldioxaborolanyl)-6-(tributylstannyl) hexa-1,3,5-triene. Copyright

Copper-catalyzed hydroboration of propargyl-functionalized alkynes in water

The Cu-catalyzed hydroboration of alkynes in operationally simple and environmentally friendly conditions is reported. The reactions are performed in water, at room temperature, under micellar catalysis. Conditions to form the α or β borylated products se

Metal free catalytic hydroboration of multiple bonds in methanol using N-heterocyclic carbenes under open atmosphere

An easy to operate method of catalytic hydroboration of unsaturated compounds has been developed with wide substrate scope. Reactions of various aldimines, ketimines, α,β-unsaturated carbonyl compounds, and alkynes were successfully executed with bis(pinacolato)diboron and N-heterocyclic carbenes in methanol without requiring a transition metal or inert atmosphere.

Rewriting the bacterial glycocalyx via Suzuki-Miyaura cross-coupling

Suzuki-Miyaura cross-coupling has been used to couple novel carbohydrate-based boronic acids, site-selectively, to the surface of E. coli at an unnatural amino acid. In this way, benign metal-catalyzed cellular switching allowed modulation of interactions with biomolecular partners via prokaryotic O-glycosylation mimics. The Royal Society of Chemistry 2013.

Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC-Cu-catalyzed hydroboration of terminal alkynes. Utility in chemical synthesis and mechanistic basis for selectivity

Cu-catalyzed methods for site-selective hydroboration of terminal alkynes, where the internal or α-vinylboronate is generated predominantly (up to >98%) are presented. Reactions are catalyzed by 1-5 mol % of N-heterocyclic carbene (NHC) complexes of copper, easily prepared from N-aryl-substituted commercially available imidazolinium salts, and proceed in the presence of commercially available bis(pinacolato)diboron [B2(pin)2] and 1.1 equiv of MeOH at -50 to -15 °C in 3-24 h. Propargyl alcohol and amine and the derived benzyl, tert-butyl, or silyl ethers as well as various amides are particularly effective substrates; also suitable are a wide range of aryl-substituted terminal alkynes, where higher α-selectivity is achieved with substrates that bear an electron-withdrawing substituent. α-Selective Cu-catalyzed hydroborations are amenable to gram-scale procedures (1 mol % catalyst loading). Mechanistic studies are presented, indicating that α selectivity arises from the structural and electronic attributes of the NHC ligands and the alkyne substrates. Consistent with suggested hypotheses, catalytic reactions with a Cu complex, derived from an N-adamantyl-substituted imidazolinium salt, afford high β selectivity with the same class of substrates and under similar conditions.