114095-75-9

Usage

Primary Uses

Pharmaceutical and agrochemical industries

Functional Groups

Benzene ring, hydroxyl group (-OH), allyl group (2-propenyl), trifluoromethyl group (-CF3)

Physical State

Colorless liquid

Odor

Characteristic odor

Hazards

Requires careful handling due to potential hazards

Applications

Drug Discovery and Development: Potential applications due to unique structural properties
Organic Synthesis: Used as a reagent in organic synthesis

Building Block

Used in the synthesis of various compounds in pharmaceutical and agrochemical industries.

Upstream product

• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 106-95-6 allyl bromide 
• 2622-05-1 allylmagnesium bromide 
• 13911-49-4 allyltriethyllead 
• 1730-25-2 allylmagnesium bromide 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 1027665-16-2 C₁₆H₂₁F₃OSi 
• 939025-13-5 C₁₆H₂₃F₃O₃SSi 
• 939025-14-6 C₁₆H₂₃F₃O₃SSi 
• 939024-93-8 C₁₇H₂₀F₆O₂Si 
• 1027271-06-2 C₁₄H₁₇F₃OSi 
• 71104-87-5 4--4-methoxy-1-butene 
• 71104-83-1 4-acetoxy-4--1-butene 

Relevant academic research and scientific papers

SUBSTITUENT EFFECTS FOR THE BF3-MEDIATED REACTIONS OF ALLYLTRIBUTYLTIN AND ALLYLTRIETHYLLEAD WITH BENZALDEHYDE

Substituent effects were measured for the reactions of substituted benzaldehydes with allyltributyltin (1) and allyltriethyllead (2) reagents in the presence of BF3*OEt2 in CH2Cl2.The Hammet ρ values were small and positive at 25 deg C and negative at -78

Enantioselective Synthesis of Isoxazolines Enabled by Palladium-Catalyzed Carboetherification of Alkenyl Oximes

Reported here is a highly efficient Pd/Xiang-Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines in good yields with u

Copper-Catalyzed Aerobic Cyclization of β,γ-Unsaturated Hydrazones with Concomitant CC Bond Cleavage

A Cu-catalyzed aerobic oxidative cyclization of β,γ-unsaturated hydrazones for the preparation of pyrazole derivatives has been developed. The hydrazonyl radical promoted the cyclization, along with a concomitant CC bond cleavage of β,γ-unsaturated hydrazones. This process has been verified via several control experiments, including a radical-trapping study, an 18O-labeling method, and the identification of the possible byproducts. The advantages of this reaction include operational simplicity, a broad reaction scope, and a mild selective reaction process.

Copper-Promoted 6- endo-trig Cyclization of β,γ-Unsaturated Hydrazones for the Synthesis of 1,6-Dihydropyridazines

A novel and efficient strategy for the synthesis of 1,6-dihydropyridazines via copper-promoted 6-endo-trig cyclization of readily available β,γ-unsaturated hydrazones have been developed. A series of 1,6-dihydropyridazines have been synthesized by this method with good yields, high functional group tolerance, and remarkable regioselectivity under mild conditions. Importantly, the 1,6-dihydropyridazines can be efficiently converted to biologically important pyridazines in the presence of NaOH.

Oxime-mediated oxychlorination and oxybromination of unactivated olefins

An oxime-mediated oxychlorination and oxybromination of unactivated olefins relying on palladium catalysis has been developed. A wide range of chlorinated and brominated isoxazolines has been synthesized in moderate to good yields. To demonstrate the value of the method, the brominated isoxazoline has been further converted to other useful synthetic feedstock.

Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin

A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).

Homoallyl-cyclopropylcarbinyl cation manifold. Trimethylsilyl versus aryl stabilization

(Chemical Equation Presented) A series of E- and Z-1-aryl-5-trimethylsilyl- 3-buten-1-yl trifluoroacetates were solvolyzed in CD3CO2D, and rates of reaction as well as products derived from these reactions were determined. Hammett pl

Gadolinium(III) chloride: a novel and an efficient reagent for the synthesis of homoallylic alcohols

Carbonyl compounds efficiently undergo nucleophilic addition reactions with allylstannanes in the presence of GdCl3·6H2O in acetonitrile under extremely mild reaction conditions to give the corresponding homoallylic alcohols in excellent yields and with high chemoselectivity.

SnCl2-mediated carbonyl allylation of aldehydes and ketones in ionic liquid

In ionic liquid [bmim]BF4, SnCl2·2H 2O acts as an inexpensive and efficient metal salt for carbonyl allylation. By applying ionic liquid, some previously reported serious operational problems associated with the SnCl2-mediated allylation reaction are avoided. Furthermore, ketones, which are less reactive than aldehydes, can also be allylated in high yields with this system.

On the Reaction Pathway and Stereochemistry of Allylic Tin Reagents-Benzaldehyde Condensation. A Substituent Effect Study

A substituent effect study on the reactivity and stereoselectivity of the Lewis acid mediated addition of allyl- and crotylstannanes to arylaldehydes indicates that the reaction proceeds via a polar antiperiplanar transition state with the exception of 2,