134134-76-2

Basic information

• Product Name: (4,4-Difluoro-3-buten-1-yl)benzene
• Synonyms: (4,4-Difluoro-3-buten-1-yl)benzene
• CAS NO: 134134-76-2
• Molecular Formula: C₁₀H₁₀F₂
• Molecular Weight: 168.1832064
• Mol File: 134134-76-2.mol

Chemical Properties

• Boiling Point: 178.858 °C at 760 mmHg
• Flash Point: 48.758 °C
• Appearance: /
• Density: 1.054 g/cm³
• CAS DataBase Reference: (4,4-Difluoro-3-buten-1-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (4,4-Difluoro-3-buten-1-yl)benzene(134134-76-2)
• EPA Substance Registry System: (4,4-Difluoro-3-buten-1-yl)benzene(134134-76-2)

Safety Data

• Hazardous Substances Data: 134134-76-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(4,4-Difluoro-3-buten-1-yl)benzene is utilized as a key intermediate in organic synthesis for the creation of complex organic molecules. Its unique structure, with fluorinated side chains, allows for versatile chemical reactions, making it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (4,4-Difluoro-3-buten-1-yl)benzene is employed as a starting material for the development of new drugs. Its chemical properties enable the production of medicinal compounds with specific therapeutic effects, contributing to the advancement of pharmaceutical research and development.
Used in Agrochemicals:
(4,4-Difluoro-3-buten-1-yl)benzene also serves as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its application in this field is crucial for the development of effective and environmentally friendly agricultural products.
Used in Electronics Industry Materials:
(4,4-Difluoro-3-buten-1-yl)benzene is further utilized in the electronics industry, where it is a starting material for the production of materials with specific electronic properties. Its use in this sector highlights its versatility and importance in the development of innovative electronic components and devices.
Used in Material and Technology Development:
(4,4-Difluoro-3-buten-1-yl)benzene is an important reagent in the research and development of new materials and technologies. Its unique chemical structure allows for the exploration of novel applications and properties, driving innovation in various scientific and industrial fields.

Upstream product

• 178100-74-8 methyl 4-phenyl-1,1-difluoro-1-butyl sulfoxide 
• 895164-11-1 methanesulfonic acid 1-(benzenesulfonyl-difluoro-methyl)-3-phenyl-propyl ester 
• 100-42-5 styrene 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 
• 104-53-0 3-phenyl-propionaldehyde 
• 4119-41-9 1-iodo-3-phenylpropan 
• 1821-12-1 4-Phenylbutyric acid 
• 300-57-2 allylbenzene 
• 1219454-89-3 2-((difluoromethyl)sulfonyl)pyridine 
• 151-67-7 1,1,1-trifluoro-2-bromo-2-chloroethane 
• 120801-75-4 trimethylsilyl-2,2-difluoro-2-(fluorosulphonyl)acetate 
• 75-45-6 Chlorodifluoromethane 
• 1600503-70-5 potassium 2-pyridinyl sulfonyl-difluoroacetate 
• 115262-00-5 [chloro(difluoro)methyl]trimethylsilane 

Downstream Products

• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 104315-86-8 1-trifluoromethyl-3-phenylpropane 
• 52376-48-4 1-cyclohexylidene-3-phenylpropane 

Relevant articles and documents

Direct Difluoromethylenation of Carbonyl Compounds by Using TMSCF3: The Right Conditions

A deoxygenative difluoromethylenation of carbonyl compounds has been developed by using readily available, inexpensive trifluoromethyltrimethylsilane, LiI, and PPh3. The presence of the Li+ion prevents the unproductive exhaustion of trifluoromethyltrimethylsilane (TMSCF3) by keeping the soluble free fluoride concentration in the reaction medium under control. The strategy of combining solvents to increase the reactivity and thereby reduce the reaction temperature and time is disclosed.

High-selectivity silane-based olefin and preparation method thereof

The invention provides high-selectivity silane-based olefin and a preparation method thereof. The preparation method comprises the following steps that an iron catalyst, a ligand and sodium tert-butoxide are subjected to nitrogen extraction and gas exchange twice under the sealed condition, so that a mixed raw material is obtained; then, aliphatic gem-difluoroolefin, triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaboridine-2-yl)silane and an organic solvent are added to form a reactant; and after quenching, extraction, drying, filtration, vacuum concentration and purification are successively carriedout to obtain the high-selectivity silyl olefin. The invention also provides the high-selectivity silane-based olefin prepared by the method. According to the invention, iron catalysis is used for selective silanization of non-activated aliphatic gem-difluoroolefin, gem-disilyl olefin with controllable regioselectivity and stereoselectivity and silylated fluoroolefin with controllable Z/E selectivity are efficiently synthesized, and the problems of low regioselectivity and stereoselectivity and difficult conversion are effectively solved.

Design and Synthesis of TY-Phos and Application in Palladium-Catalyzed Enantioselective Fluoroarylation of gem-Difluoroalkenes

The first example of highly enantioselective fluoroarylation of gem-difluoroalkenes with aryl halides is presented by using a new chiral sulfinamide phosphine (Sadphos) type ligand TY-Phos. N-Me-TY-Phos can be easily synthesized on a gram scale from readily available starting materials in three steps. Salient features of this work including readily available starting materials, good yields, high enantioselectivities as well as broad substrate scope make this approach very practical and attractive. Notably, the asymmetric synthesis of an analogue of a biologically active molecule is also reported.

Pd-Catalyzed Selective Carbonylation of gem-Difluoroalkenes: A Practical Synthesis of Difluoromethylated Esters

The first catalyst for the alkoxycarbonylation of gem-difluoroalkenes is described. This novel catalytic transformation proceeds in the presence of Pd(acac)2/1,2-bis((di-tert-butylphosphan-yl)methyl)benzene (btbpx) (L4) and allows for an efficient and straightforward access to a range of difluoromethylated esters in high yields and regioselectivities. The synthetic utility of the protocol is showcased in the practical synthesis of a Cyclandelate analogue using this methodology as the key step.

Coupling of Trifluoroacetaldehyde N-Triftosylhydrazone with Organoboronic Acids for the Synthesis of gem-Difluoroalkenes

The synthesis of alkyl gem-difluoroalkenes remains a difficult task in organic synthesis. Here, we report a general and efficient approach for tackling this problem by gem-difluoroolefination of trifluoroacetaldehyde N-triftosylhydrazone with organoboronic acids. This protocol is operationally simple, free of transition metals, and suitable for a broad range of organoboronic acids. Moreover, the utility of the products was demonstrated by further conversion of the gem-difluorovinyl group.

Copper(I)-catalyzed stereoselective defluoroborylation of aliphatic gem-difluoroalkenes

This study reports a method for the stereoselective copper(I)catalyzed defluoroborylation of aliphatic gem-difluoroalkenes to afford (Z)-monofluoro-substituted borylalkenes. Gem-difluoro-alkenes bearing a variety of functional groups were efficiently borylated with high stereoselectivity. A theoretical study of the reaction mechanism is also described.

Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of gem-Difluoroalkenes with Water

A copper catalytic system was established for the stereoselective hydrodefluorination of gem-difluoroalkenes through C?F activation to synthesize various Z fluoroalkenes. H2O is used as the hydrogen source for the fluorine acceptor moiety. This mild catalytic system shows good-functional group compatibility, accepting a range of carbonyls as precursors to the gem-difluoroalkenes, including aliphatic, aromatic, and α,β-unsaturated aldehydes and even ketones. It serves as a powerful synthetic method for the late-stage modification of complex compounds.

Palladium-Catalyzed Fluoroarylation of gem-Difluoroalkenes

A Pd-catalyzed fluoroarylation of gem-difluoroalkenes with aryl halides is reported. By taking advantage of the in situ generated α-CF3-benzylsilver intermediates derived from the nucleophilic addition of silver fluoride to gem-difluoroalkenes, this strategy bypasses the use of a strong base, thus enabling a mild and general synthetic method for ready access to non-symmetric α,α-disubstituted trifluoroethane derivatives.

Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources

The trifluoromethylation of carbonyl compounds is accomplished by the stable (trifluoromethyl)zinc reagent generated and then isolated from CF3I and ZnEt2, which can be utilized as a trifluoromethyl anion source (CF3-). The reaction proceeds smoothly with diamine as a ligand and ammonium salt as an initiator, providing the corresponding trifluoromethylated alcohol products. Moreover, the (trifluoromethyl)zinc reagent can also be employed as a difluorocarbene source (:CF2) not only for gem-difluoroolefination of carbonyl compounds with phosphine but also for gem-difluorocyclization of alkenes or alkynes via the thermal decomposition, respectively.

Gem-difluoroolefination of diaryl ketones and enolizable aldehydes with difluoromethyl 2-pyridyl sulfone: New insights into the Julia-Kocienski reaction

The direct conversion of diaryl ketones and enolizable aliphatic aldehydes into gem-difluoroalkenes has been a long-standing challenge in organofluorine chemistry. Herein, we report efficient strategies to tackle this problem by using difluoromethyl 2-pyridyl sulfone as a general gem-difluoroolefination reagent. The gem-difluoroolefination of diaryl ketones proceeds by acid-promoted Smiles rearrangement of the carbinol intermediate; the gem-difluoroolefination is otherwise difficult to achieve through a conventional Julia-Kocienski olefination protocol under basic conditions due to the retro-aldol type decomposition of the key intermediate. Efficient gem-difluoroolefination of aliphatic aldehydes was achieved by the use of an amide base generated in situ (from CsF and tris(trimethylsilyl)amine), which diminishes the undesired enolization of aliphatic aldehydes and provides a powerful synthetic method for chemoselective gem-difluoroolefination of multi-carbonyl compounds. Our results provide new insights into the mechanistic understanding of the classical Julia-Kocienski reaction. What a gem! The gem-difluoroolefination of diaryl ketones was realized by an acid-promoted Julia-Kocienski olefination reaction at elevated temperatures. The gem-difluoroolefination of aliphatic aldehydes and chemoselective gem-difluoroolefination of dicarbonyl compounds was achieved with the use of an amide base generated in situ (see scheme).