69611-02-5

Basic information

• Product Name: E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;trans-Crotylboronic acid pinacol ester;E-crotylboron pinacolate;trans-Crotylboronic acid pinacol ester 95%
• CAS NO: 69611-02-5
• Molecular Formula: C₁₀H₁₉BO₂
• Molecular Weight: 182.07
• Mol File: 69611-02-5.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 68-76 °C(Press: 7 Torr)
• Flash Point: 63 °C
• Appearance: /
• Density: 0.888 g/mL at 25 °C
• Refractive Index: n20/D 1.434
• Storage Temp.: 2-8°C
• CAS DataBase Reference: E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(69611-02-5)
• EPA Substance Registry System: E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(69611-02-5)

Safety Data

• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 69611-02-5(Hazardous Substances Data)

Usage

General Description

E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a chemical compound used in organic synthesis. It is a boronic acid pinacol ester, which is a reagent commonly used in organic chemistry for C-C bond forming reactions. The trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane portion of the compound contains boron, a key element in the synthesis of pharmaceuticals and agrochemicals. E-Crotylboronic acid pinacol ester, trans-2-(2-Buten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a valuable tool in the creation of complex organic molecules and plays a crucial role in the development of new drugs and materials.

Upstream product

• 563-52-0 2-chloro-3-butene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 591-97-9 1-chloro-2-butene 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 624-64-6 trans-2-Butene 
• 367-46-4 fluorodimethoxyborane 
• 6386-72-7 (E)-propenyl lithium 
• 83622-42-8 2-(chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 504-61-0 (E)-but-2-enol 
• 73183-34-3 bis(pinacol)diborane 
• 1301680-12-5 2-[(1E)-but-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1352747-95-5 C₁₀H₁₉BO₂ 
• 4894-61-5 trans-but-2-enyl chloride 
• 7204-29-7 trans-2-butenyl acetate 

Downstream Products

• 159248-93-8 (2S,1'R,2'R)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine 
• 159173-40-7 (2S,1'R,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine 
• 159248-94-9 (2S,1'S,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine 
• 116376-33-1 (6R^*,5R^*,3S^*,4S^*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-4-ol 
• 52922-10-8 (1SR,2SR)-2-methyl-1-phenylbut-3-en-1-ol 
• 63553-62-8 (1S*,2R*)-2-methyl-1-phenylbut-3-en-1-ol 
• 304459-85-6 4-methyl-1-phenyl-hex-5-en-3-ol 
• 25201-44-9 2-methyl-1-phenyl-3-butene-1-ol 
• 83173-74-4 (anti)-4-hydroxy-3-methyl-6-phenyl-1-hexene 
• 745813-62-1 (-)-(2S,3S)-3-methyl-2-phenyl-4-penten-2-ol 
• 75851-77-3 (E)-1-phenyl-3-penten-1-ol 
• 94453-46-0 1-cyclohexylpent-3-en-1-ol 
• 3107-04-8 DL-alloisoleucine 
• 73-32-5 DL-isoleucine 

Relevant articles and documents

Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines

The Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral α-alkoxy N-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon-carbon bond, resulting in stereochemical control of C1, C2, and C3 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexene products. A computational analysis to elucidate the high selectivity is also presented. This methodology was employed in the synthesis of two naturally occurring isomers of clausenamide.

Nickel-Catalysed Allylboration of Aldehydes

A nickel catalyst for the allylboration of aldehydes is reported, facilitating the preparation of homoallylic alcohols in high diastereoselectivity. The observed diastereoselectivities and NMR experiments suggest that allylation occurs through a well-defined six-membered transition state, with nickel acting as a Lewis acid.

Selective Isomerization of Terminal Alkenes to (Z)-2-Alkenes Catalyzed by an Air-Stable Molybdenum(0) Complex

Positional and stereochemical selectivity in the isomerization of terminal alkenes to internal alkenes is observed using the cis-Mo(CO)4(PPh3)2 precatalyst. A p-toluenesulfonic acid (TsOH) cocatalyst is essential for catalyst activity. Various functionalized terminal alkenes have been converted to the corresponding 2-alkenes, generally favoring the Z isomer with selectivity as high as 8:1 Z:E at high conversion. Interrogation of the catalyst initiation mechanism by 31P NMR reveals that cis-Mo(CO)4(PPh3)2 reacts with TsOH at elevated temperatures to yield a phosphine-ligated Mo hydride (MoH) species. Catalysis may proceed via 2,1-insertion of a terminal alkene into a MoH group and stereoselective β-hydride elimination to yield the (Z)-2-alkene.