59239-44-0

Basic information

• Product Name: 1-PENTENYLBORONIC ACID
• Synonyms: 1-PENTENYLBORONIC ACID;(E)-1-PENTENYLBORONIC ACID;E-PENTEN-1-YLBORONIC ACID;RARECHEM AH PB 0245;(1E)-(Pent-1-en-1-yl)boronic acid;(E)-pent-1-en-1-ylboronic acid
• CAS NO: 59239-44-0
• Molecular Formula: C₅H₁₁BO₂
• Molecular Weight: 113.95
• Mol File: 59239-44-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 100-105 °C(lit.)
• Boiling Point: 209.9 °C at 760 mmHg
• Flash Point: 80.7 °C
• Appearance: /
• Density: 0.936 g/cm³
• CAS DataBase Reference: 1-PENTENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PENTENYLBORONIC ACID(59239-44-0)
• EPA Substance Registry System: 1-PENTENYLBORONIC ACID(59239-44-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 59239-44-0(Hazardous Substances Data)

Usage

General Description

1-Pentenylboronic acid is a chemical compound with the formula C5H9BO2. It is a boronic acid derivative that is used in organic synthesis as a reagent for the Suzuki-Miyaura cross-coupling reaction, which is a method for creating carbon-carbon bonds. 1-PENTENYLBORONIC ACID is a colorless liquid at room temperature and has a characteristic boronic acid functional group, which contains a boron atom bonded to a carbon atom and two oxygen atoms. 1-Pentenylboronic acid is a versatile and important tool in organic chemistry, allowing for the formation of complex molecules through carbon-carbon bond formation.

Upstream product

• 59278-44-3 tris(ethylenedioxyboryl)methane 
• 123-72-8 butyraldehyde 
• 37494-02-3 (E)-pent-1-en-1-yl-1,3,2-benzodioxaborole 
• 627-19-0 1-Pentyne 
• 55671-55-1 dibromoborane dimethylsulfide 
• 7732-18-5 water 
• 121-43-7 Trimethyl borate 
• 38203-74-6 C₅H₉BrMg 

Downstream Products

• 16002-93-0 (E)-1-phenyl-1-pentene 
• 805325-71-7 (1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-(1-pentenyl)-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 4-methoxybenzyl ester 
• 649552-11-4 methyl 2-(E)-1-pentenyl-6-benzyloxybenzoate 
• 1483-36-9 (E)-N-phenylhex-2-enamide 
• 1020106-50-6 1-(2,4-dichlorophenyl)-4-methyl-5-[((E)-pent-1-enyl)thiophen-2-yl]-1H-pyrazole-3-carboxylic acid ethyl ester 
• 1092446-63-3 2-[3-methyl-2-((E)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester 
• 1072123-37-5 C₂₀H₁₉NO 
• 1215120-06-1 (3E,5E)-1-(2-methoxyphenyl)non-3,5-dien-1-yne 
• 201996-70-5 (E)-N-methoxy-N-methyl hex-2-enamide 
• 1155870-67-9 tert-Butyl (6R)-6-({5-[(1E)-pent-1-en-1-yl]-6-phenylfuro[2,3-d]pyrimidin-4-yl}oxy)heptanoate 
• 1268249-88-2 methyl (6S)-1-benzyl-6-[(1E)-pent-1-en-1yl]-1,6-dihydropyridine-3-carboxylate 

Relevant articles and documents

Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.

Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides

Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydrobora

Lithium bis(ethylenedioxyboryl)methide and its reactions with carbonyl compounds and with the chlorotriphenyl derivatives of germanium, tin and lead

Transesterification of tris(dimethoxyboryl)methane, HC[B(OCH3)2]3, with ethylene glycol yielded tris(ethylenedioxyboryl)methane (I), HC(BO2C2H4)3 which with methyllithium in THF at -70°C precipitated lithium bis(ethylenedioxyboryl)methide (II), Li+ HC(BO2C2H4)2-. Reaction of II with Ph3MCl, where M = Ge, Sn, or Pb, gave Ph3MCH(BO2C2H4)2. The analogous 1,3-propanediol ester, Li+HC(BO2C3H6)2-, yielded Ph3MCH(BO2C3H6)2. Treatment of Ph3SnCH(BO2C2H4)2 with MeLi followed by Ph3SnCl gave (Ph3Sn)2CHBO2C2H4, showing that one B and one Sn atom are sufficient to stabilize a carbanion. Reaction of II with aldehydes gave high yields of 1-alkene-1-boronic esters, RCHCHBO2C2H4, with unexpectedly high stereoselectivity, 90-100% trans by NMR analysis. Aqueous work-up of these boronic esters yielded the boronic acids, RCHCHB (OH)2, which crystallized as the pure trans isomers. Ketones react with II in an analogous manner. The reaction with acetophenone was not stereospecific. Functional group compatibility has been demonstrated in condensations of II with 1,3-dichloroacetone, cinnamaldehyde, p-nitrobenzaldehyde, and p-dimethylaminobenzaldehyde. The trans geometry of the major isomer of CH3CHCHBO2C2H4 was proved by B-butylation with butyllithium followed by rearrangement with iodine and base to form cis-2-heptene, a sequence of known stereochemistry, and analogous structure proofs were carried out with cis-CH3CHCHBO2C2H4 and trans-C6H5CHCHBO2C2H4.