3288-99-1

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C12H15N/c1-12(2,3)11-6-4-10(5-7-11)8-9-13/h4-7H,8H2,1-3H3

Upstream product

• 151-50-8 potassium cyanide 
• 19692-45-6 4-tert-butylbenzyl chloride 
• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 140874-33-5 1-(tert-butyl)-4-(iodomethyl)benzene 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 253185-03-4 tert-butylbenzene 
• 98-51-1 4-tert-butyltoluene 
• 108-88-3 toluene 
• 143-33-9 sodium cyanide 
• 13361-30-3 isopropyl cyanoacetate 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 105-34-0 methyl 2-cyanoacetate 

Downstream Products

• 32857-63-9 4-t-butylphenylacetic acid 
• 91552-82-8 N-[2-[4-(t-butyl)phenyl]ethyl]amine 
• 139512-41-7 dimethyl 2-methyl-2-(4-tert-butylphenyl)malonate 
• 73312-12-6 4-(4-tert-Butyl-phenyl)-4-cyano-heptanedioic acid dimethyl ester 
• 154777-56-7 2-(4-t-butylphenyl)-2-(cyclohex-2-enyl)acetonitrile 
• 3549-23-3 methyl 2-(4-tert-butylphenyl)acetate 
• 1026394-03-5 2-(4-tert-butyl-phenyl)-3-oxo-pentanenitrile 
• 64321-35-3 4-(1,1-Dimethylethyl)phenylmethyl ketone 
• 855389-83-2 4-(4-tert-butyl-phenyl)-pyrrolidine-2,3,5-trione 
• 100368-57-8 2-(4-(tert-butyl)phenyl)acetamide 
• 14062-22-7 ethyl 2-(4-(tert-butyl)phenyl)acetate 
• 865722-29-8 2,3-bis(4-(tert-butyl)phenyl)propanenitrile 
• 1016534-37-4 2-(4-(tert-butyl)phenyl)ethanethioamide 
• 1334320-21-6 C₂₃H₂₁N₅ 

Relevant academic research and scientific papers

Synthesis method of acaricide cyflumetofen intermediate p-tert-butyl phenylacetonitrile

The invention discloses a synthesis method of an acaricide cyflumetofen intermediate p-tert-butyl phenylacetonitrile, and belongs to the field of pesticide preparation. The synthesis method is characterized in that a reaction is performed on 4-tert-butyl

A method of preparing P-tert-butyl benzyl cyanide

The invention discloses a method for preparing butylphenylacetonitrile, and the method is capable of preparing butylphenylacetonitrile by using p-tert-butylphenol as a raw material through catalyzing, hydrogenating, and condensation with Knoevenagel of cyanoacetic acid, and catalyzing dehydro-aromatization, wherein a small amount of ethylbenzene is added into the reaction mixture in the dehydro-aromatization catalyzing step, and meanwhile, as the technical means of introducing inert gas with a certain flow rate is adopted, the preparation method provided by the invention has industrial application value. Compared with the existing preparation method, the method provided by the invention has the advantages that the raw material is easy to get, the yield is high, the cost is low, isomers which are difficult to separate are not contained, highly toxic sodium cyanide and other highly toxic irritating ingredients are not used, the three wastes are less, the security is high and the like, so that the method provided by the invention is suitable for industrial production.

Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers

A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles

A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.

Ionic liquid-induced conversion of methoxymethyl-protected alcohols into nitriles and iodides using [Hmim][NO3]

This Letter reports a one-pot efficient conversion of methoxymethyl-ethers into their corresponding nitriles and iodides using the ionic liquid, 1-methyl-3H-imidazolium nitrate ([Hmim][NO3]) under microwave irradiation. A variety of products were prepared in high yields using this method.

Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.

Calixarene ionic liquids: Excellent phase transfer catalysts for nucleophilic substitution reaction in water

The first examples of calixarene ionic liquids 3 and 6 with 3D-shaped cavities were obtained in high yields by reacting calix[4]arene or thiacalix[4]arene with 1,6-dibromohexane and then refluxing in 1-methylimidazole. The experiments of phase transfer catalysis in water suggested that they possessed excellent catalytic properties of aromatic nucleophilic substitution reaction and benzyl nucleophilic substitution. The optimized yields of product in catalytic reaction were as high as approximate 97% under mild reaction conditions. The cavities of calixarene skeleton played the crucial roles in catalysis and the stable cone conformation was favorable for catalysis.

Copper-catalyzed cyanation of benzyl chlorides with non-toxic K 4[Fe(CN)6]

Copper-based catalysts were firstly introduced into the cyanation of benzyl chlorides with non-toxic K4[Fe(CN)6]. The presented method avoids the use of extremely poisonous alkali cyanides and precious palladium catalysts. No other reagent apart from CuI, K4[Fe(CN) 6] and toluene was used in the cyanation, showing that the presented protocol is simple and practical. A series of benzyl chlorides were smoothly cyanated in up to 85% yield under the optimal conditions.

A new phenylalanine derivative acts as an antagonist at the AMPA Receptor GluA2 and introduces partial domain closure: Synthesis, resolution, pharmacology, and crystal structure

In order to map out molecular determinants for competitive blockade of AMPA receptor subtypes, a series of 2-carboxyethylphenylalanine derivatives has been synthesized and pharmacologically characterized in vitro. One compound in this series, (RS)-3h, showed micromolar affinity for GluA1o and GluA2(R)o receptors with an approximately 4-fold preference for GluA1/2 vs GluA3/4. In TEVC electrophysiological experiments (RS)-3h competitively antagonized GluA2(Q)i receptors. The X-ray structure of the active enantiomer (S)-3h in complex with GluA2-S1S2J showed a domain closure around 8°. Even though the nitro and the carboxyethyl groups of (S)-3h were both anchored to Tyr702 through a water H-bond network, these interactions only induced weak subtype selectivity. In spite of the fact that (S)-3h induced a domain closure close to that observed for partial agonists, it did not produce agonist responses at GluA2 receptors under nondesensitizing conditions. 2-Carboxyethylphenylalanine derivatives provide a new synthetic scaffold for the introduction of substituents that could lead to AMPA receptor subtype-selective ligands.