123989-31-1

Usage

Main properties

1. Chemical name: Benzenemethanol, 4-chloro-a-(1-methyl-2-propenyl)-
2. Common name: 4-chloro-alpha-methylstyrene
3. Molecular formula: C10H11ClO
4. Appearance: Colorless to pale yellow liquid
5. Odor: Pungent

Specific content

Used in the production of resins, polymers, and other chemicals
Used as a solvent
Used as an intermediate in the synthesis of pharmaceuticals
Classified as a hazardous substance
Proper safety precautions should be followed when handling and storing Benzenemethanol, 4-chloro-a-(1-methyl-2-propenyl)-

Upstream product

• 4784-77-4 (E/Z)-crotyl bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 4894-61-5 trans-but-2-enyl chloride 
• 504-61-0 (E)-but-2-enol 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 35998-93-7 tri-n-butylcrotyltin 
• 35998-94-8 (Z)-crotyltri-n-butylstannane 
• 106-99-0 buta-1,3-diene 
• 107-01-7 butene-2 
• 167773-12-8 2-<(2E/Z)-2-butenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 69611-01-4 (Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 693-03-8 n-butyl magnesium bromide 
• 122-01-0 4-chloro-benzoyl chloride 
• 598-32-3 2-hydroxy-3-butene 

Downstream Products

• 123989-28-6 1-(4-chlorophenyl)-2-cyclopropyl-1-propanol 

Relevant academic research and scientific papers

Preparation method of 1-(4-chlorphenyl)-2-methylbutyl-3-ene-1-ol

The invention discloses a preparation method of 1-(4-chlorphenyl)-2-methylbutyl-3-ene-1-ol, which comprises the following steps of: reacting p-chlorobenzaldehyde and 1-chloro-2-butene serving as raw materials under the action of zinc powder, ammonium chloride saturated aqueous solution and silica gel to generate a compound represented by a formula (III): 1-(4-chlorphenyl)-2-methylbutyl-3-ene-1-ol. The invention provides a brand new preparation method of a cyproconazole intermediate 1-(4-chlorphenyl)-2-methylbutyl-3-ene-1-ol, the purity of 1-(4-chlorphenyl)-2-methylbutyl-3-ene-1-ol prepared by the method can reach 98.9%, the yield reaches 93.8%, the quality is extremely high, and the purity of cyproconazole is greatly improved when the intermediate is used for preparing cyproconazole.

An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate.

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.

Catalytic Allylation of Aldehydes Using Unactivated Alkenes

Simple feedstock organic molecules, especially alkenes, are attractive starting materials in organic synthesis because of their wide availability. Direct utilization of such bulk, inert organic molecules for practical and selective chemical reactions, however, remains limited. Herein, we developed a ternary hybrid catalyst system comprising a photoredox catalyst, a hydrogen-atom-transfer catalyst, and a chromium complex catalyst, enabling catalytic allylation of aldehydes with simple alkenes, including feedstock lower alkenes. The reaction proceeded under visible-light irradiation at room temperature and with high functional group tolerance. The reaction was extended to an asymmetric variant by employing a chiral chromium complex catalyst.

Photoredox Ni-Catalyzed Branch-Selective Reductive Coupling of Aldehydes with 1,3-Dienes

We report here a Ni-catalyzed reductive coupling of aldehydes with widely available 1,3-dienes under visible-light photoredox dual catalysis. The homoallyic alcohols are obtained in broad scope with complete branched regioselectivity. Hantzsch ester is used as the hydrogen radical source to oxidize low-valent nickel salt affording Ni-H species. Preliminary mechanistic studies indicate a successive single-electron transfer (SET) pathway and the generation of a key π-allylnickel intermediate via Ni-H insertion of 1,3-diene in this synergistic catalytic process.

Lead-Mediated Highly Diastereoselective Allylation of Aldehydes with Cyclic Allylic Halides

Lead was found to efficiently mediate the allylation reactions of carbonyl compounds with cyclic allylic halides in the presence of stoichiometric amounts of lithium chloride and a catalytic amount of GaCl3 (20 mol %), leading to the desired homoallylic alcohols in modest to high yields with excellent diastereocontrol (>99:1 syn/anti) and good functional group tolerance. In contrast, the use of either 2-pyridinecarboxaldehyde as the carbonyl substrate or (E)-cinnamyl bromide as the allylating agent produced the corresponding product with reversed diastereoselectivity (>99:1 anti/syn).

Active bismuth mediated allylation of carbonyls/N-tosyl aldimines and propargylation of aldehydes in water

Abstract: Active bismuth is synthesized by the chemical reduction of bismuth trichloride using freshly prepared sodium stannite solution as the reducing agent at room temperature. The as-synthesized active bismuth is applied as a reagent for the synthesis of homoallyl alcohol/homopropargyl alcohol from allyl bromide/propargyl bromide and carbonyl compounds in water at 50°C. The homoallyl amines are also synthesized from N-tosyl aldimines and allyl bromide using active bismuth reagent in good yields. No assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere is required for this reaction. The waste bismuth material obtained after the completion of the organic reaction can be reduced to active bismuth by sodium stannite solution and successfully reused for mediating the allylation of aldehydes. Graphical Abstract:: Synopsis Active bismuth mediated allylation/crotylation of aldehydes is developed in water to get homoallyl alcohols. The method is also applied for the allylation of N-tosyl aldimines and propargylation of aldehydes in water to achieve the homoallyl amines and homopropargyl alcohols, respectively. The reactions do not require the assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere.[Figure not available: see fulltext.].

Syn -Selective crotylation of aldehydes using bismuth-crotyl bromide-(1-butyl-3-methylimidazolium bromide) combination: Some synthetic applications

The Bi-[bmim][Br] combination has been found to offer high syn-selectivity in the crotylation of aldehydes with crotyl bromide using practically stoichiometric amounts of the reagents. The room temperature ionic liquid (RTIL), [bmim][Br], activated Bi metal in the presence of oxygen to produce crotylbismuthdibromide, which reacted with the aldehydes at room temperature. The major anti-syn diastereomeric product obtained from the crotylation of (R)-cyclohexylideneglyceraldehyde was utilized for the synthesis of dictyostatin and cryptophycin segments, and (+)-cis-aerangis lactone, using standard synthetic protocols.

Nickel-catalyzed double bond transposition of alkenyl boronates for in situ syn-selective allylboration reactions

The transposition of a homoallyl pinacol boronic ester was realized by a highly reactive nickel-catalyst system comprising NiCl2(dppp), zinc powder, ZnI2, and Ph2PH. The in situ generated Z-crotyl pinacol boronic esters were reacted with various aldehydes to form syn-homoallylic alcohols in high diastereoselectivities. The present nickel-catalyzed reaction is complementary to the iridium-catalyzed transposition reported by Murakami leading to the corresponding anti-homoallylic alcohols. Also, the multiple transposition of pentenyl pinacol boronic ester was realized.

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