106650-98-0

Basic information

• Product Name: 1-(4-bromophenyl)but-3-en-1-ol
• CAS NO: 106650-98-0
• Molecular Weight: 227.101
• Mol File: 106650-98-0.mol
• Article Data: 120

Chemical Properties

• CAS DataBase Reference: 1-(4-bromophenyl)but-3-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-bromophenyl)but-3-en-1-ol(106650-98-0)
• EPA Substance Registry System: 1-(4-bromophenyl)but-3-en-1-ol(106650-98-0)

Safety Data

• Hazardous Substances Data: 106650-98-0(Hazardous Substances Data)

Upstream product

• 24856-58-4 1,1-dimethoxy-1-(4-bromophenyl)methane 
• 106-95-6 allyl bromide 
• 383-67-5 allyl trifluoroacetate 
• 28115-12-0 (E)-1-(4-bromophenyl)-N-(4-methoxyphenyl)methanimine 
• 2622-05-1 allylmagnesium bromide 
• 1122-91-4 4-bromo-benzaldehyde 
• 873-75-6 4-bromobenzenemethanol 
• 591-87-7 Allyl acetate 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 55605-27-1 (4-bromophenyl)methylenediacetate 
• 762-72-1 allyl-trimethyl-silane 
• 24850-33-7 allyltributylstanane 
• 1774-47-6 trimethylsulfoxonium iodide 
• 25062-46-8 4-bromobenzaldehyde oxime 

Downstream Products

• 1033605-65-0 C₂₀H₂₀Br₂O 
• 114095-76-0 1-bromo-4-(1-methoxy-but-3-enyl)benzene 
• 1210066-93-5 (E)-4-(4-bromophenyl)-4-hydroxybut-2-enyl propionate 
• 221898-37-9 (S)-1-(4-bromophenyl)but-3-en-1-ol 
• 915105-92-9 C₂₁H₃₂⁽²⁾H₂O₄Si 
• 915105-91-8 C₁₉H₂₈⁽²⁾H₂O₃Si 
• 915105-90-7 C₁₇H₂₆⁽²⁾H₂O₂Si 
• 915105-93-0 C₁₅H₁₇⁽²⁾HO₄ 
• 915105-89-4 C₁₁H₁₂⁽²⁾H₂O₂ 
• 184165-64-8 1-(4-bromophenyl)-3-buten-1-one 
• 71787-53-6 1-(p-cyanophenyl)-3-buten-1-ol 

Relevant articles and documents

A joint experimental and theoretical study of the palladium-catalyzed electrophilic allylation of aldehydes

(Chemical Equation Presented) Palladium-catalyzed electrophilic allylation of aldehydes with allylstannanes has been proposed in the literature as a model reaction illustrating the potential of nucleophilic η1-allyl palladium pincer complexes t

β-Cyclodextrin promoted allylation of aldehydes with allyltributyltin under supramolecular catalysis in water

A novel and highly efficient allylation of aldehydes using allyltributyltin has been developed in aqueous medium catalyzed by β-cyclodextrin in the presence of HCl without any metal catalysts to afford the corresponding homoallylic alcohols in good yields

A SeCSe-Pd(II) pincer complex as a highly efficient catalyst for allylation of aldehydes with allyltributyltin

An air- and moisture-stable SeCSe-Pd(II) pincer complex was synthesized and found to catalyze the nucleophilic allylation of aldehydes with allyltributyltin. The allylation of a variety of aromatic and aliphatic aldehydes to give the corresponding homoall

Catalytic asymmetric allylation of aldehydes using a chiral silver(I) complex

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Bi-mediated allylation of aldehydes in [bmim][Br]: A mechanistic investigation

The inexpensive room temperature ionic liquid (RTIL), [bmim][Br] has been found to be a superior medium for the Bi-mediated Barbier-type allylation of aldehydes compared to other conventional solvents. It plays the dual role of a solvent and a metal activ

Preparation of allyltin reagents grafted on solid support: Clean and easily recyclable reagents for allylation of aldehydes

The preparation of polymer-supported allyltin reagents was shown to be possible for both unfunctionalized and functionalized allyl units. These reagents were treated with aldehydes in the presence of cerium(III) or indium(III) salts to afford high yields

Metal free synthesis of homoallylic alcohols promoted by ultrasound

The use of ultrasound irradiation to promote the allylation of aldehydes containing different functionalities with potassium allyltrifluoroborates is described. The method features the use of a minimum amount of acetone as solvent, without any other catalyst or promoter. The products were obtained in high yields, short reaction times, at room temperature and without the need of further purification.

A practical procedure of low valent tin mediated Barbier allylation of aldehydes in wet solvent

Use of aluminium as the reducing metal in spontaneous bimetal redox reaction has been elegantly exploited for allylation/crotylation of aldehydes in wet solvent. Here, low valent tin was prepared in situ by reduction of SnCl2·2H2O wi

Nickel-Catalyzed Reductive Allylation of Aldehydes with Allyl Acetates

Carbonyl allylation reactions constitute an important step in the formation of carbon-carbon reactions, and involve various related reactions that chiefly use allylmetal reagents. This report presents a nickel-catalyzed carbonyl allylation reaction using allyl acetate, which produces homoallyl alcohols in moderate to good yields, as an efficient methodology under reductive coupling conditions.

Simple, one-pot procedure for the generation of homoallylic alcohols from barbier-type allylation of gem-diacetates in the presence of β-cyclodextrin in water

A novel and highly efficient allylation of gem-diacetates using allylbromide has been developed in aqueous medium catalyzed by β-cyclodextrin in the presence of Zn-mediated Barbier-type allylation to afford the corresponding homoallylic alcohols in good y

Efficient allylation of aldehydes with allyltributylstannane catalyzed by CuI

Cuprous iodide has been found to be a very effective catalyst for allylation of aldehydes with allyltributylstannane. The catalytic system efficiently promotes the allylation reaction in DMF to produce homoallylic alcohols in high yield.

Allylation of functionalized aldehydes by potassium allyltrifluoroborate catalyzed by 18-Crown-6 in aqueous media

An efficient method for the allylation of aldehydes containing a broad range of functional groups using potassium allyltrifluoroborate is described. The reaction utilizes a catalytic amount of 18-C-6 in biphasic media under open atmosphere and room temperature to provide the corresponding homoallylic alcohols in high yields and without the necessity of any subsequent purification.

Palladacycles of unsymmetrical (N,C-,E) (E = S/Se) pincers based on indole: Their synthesis, structure and application in the catalysis of Heck coupling and allylation of aldehydes

Unsymmetrical (N,C,E)-type pincer ligand precursors [L1 and L2: E = S/Se] with an indole core were synthesized for the first time by the condensation of 1-(2-phenylsulfanyl/selenylethyl)-1H-indole-3-carbaldehyde with benzyl amine. The synthetic protocols

Rhenium complex-catalyzed allylation of aldehydes with allyltributylstannane

It was confirmed that the rhenium complex, ReBr(CO)5, catalyzed the allylation of aldehydes with allyltributylstannane to give the corresponding homoallylic alcohols in moderate to good yields. Similarly, the reaction of aldehydes with enol sil

Allylation of aldehydes with potassium allyltrifluoroborate catalyzed by Amberlyst A-15

The use of the commercially available resin Amberlyst-15 as catalyst for allylation of aldehydes by potassium allyltrifluoroborate is described. The method features the use of a commercially available catalyst, aqueous media, and the products were obtained in high yields, short reaction times, at room temperature and no further purification. The catalyst was recovered and reused up to six times in further allylation reactions without significant yield losses. 11B NMR experiments were conducted in order to evaluate the possible mechanism pathway. The formation of tricoordinate boron species was not observed.

An efficient electrochemical method for the paired synthesis of carbonyl compounds and homoallylic alcohols in a simple home-made cell

An efficient electrochemical synthesis of carbonyl compounds and homoallylic alcohols was developed in excellent yields using a simple home-made cell. The catalytic redox behavior of the electrode surface and the reaction mechanism was investigated by cyc

(ClO4)3: An efficient water-compatible Lewis acid catalyst for chemo-, regio-, and diastereo-selective allylation of various aldehydes

The use of [Cd2(tren)2(dl-alaninato)](ClO 4)3·H2O (I) (tren = tris(2-aminoethyl) amine) as an efficient water-compatible Lewis acid catalyst for the allylation of aldehydes in aqueous media was descri

Bulky aluminum Lewis acids as novel efficient and chemoselective catalysts for the allylation of aldehydes

Bulky aluminum Lewis acids such as MAD and MABR are introduced as new efficient catalysts in substoichiometric amounts for the allylation of aldehydes with allyltributylstannane. In addition, chemoselective allylation of a less hindered or aromatic aldehy

Palladacycles having normal and spiro chelate rings designed from bi- and tridentate ligands with an indole core: Structure, synthesis and applications as catalysts

1-Pyridin-2-ylmethyl-1H-indole-3-carbaldehyde and 1-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-1H-indole-3-carbaldehyde were synthesized. Their condensation with benzyl amine resulted in indole core containing Schiff bases benzyl-(1-pyridin-2-ylmethyl-1H-in

Ti-exchanged ZSM-5 as heterogeneous catalyst for allylation of aldehydes with allyltributylstannane

Titanium exchanged ZSM-5 catalyst has been prepared by treating an aqueous solution of titanium (IV) chloride with ZSM-5. The supported catalyst has been explored as effective and reusable catalyst for allylation reaction of aldehydes with allyltributylst

Palladium- and platinum-catalyzed addition of aldehydes and imines with allylstannanes. Chemoselective allylation of imines in the presence of aldehydes

The reaction of allylstannanes 1 with aldehydes 2 in THF was catalyzed by Pd(II) or Pt(II) complexes (10 mol%) either at room temperature or at reflux, giving the corresponding homoallylic alcohols 3 in high to good yields. Among the catalysts examined, P

Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton

An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).

Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes

The concept of "umpolung"reactivity of π-allylmetal complexes has been developed as a powerful method for the allylation of aldehydes. This paper describes the photocatalytic umpolung strategy for the synthesis of nucleophilic allylcobalt complexes through a single-electron-transfer (SET) process. This strategy enables the metallaphotoredox allylation of carbonyls with allyl acetate using organic N,N-diisopropylethylamine as the terminal reductant bypassing the use of a stoichiometric amount of metals. Ultraviolet-visible spectroscopy was used to monitor the redox changes of cobalt in the reaction.