69316-08-1

Usage

Chemical Properties

BEIGE FLAKY CRYSTALS

Uses

Methyl 4-(cyanoacetyl)benzoate may be used in chemical synthesis.

General Description

Methyl 4-(cyanoacetyl)benzoate (Methyl 4-(2-cyanoacetyl)benzoate) is an ester. Its various physical properties such as density, refractive index, melting point and boiling point have been reported.

InChI:InChI=1/C11H9NO3/c1-15-11(14)9-4-2-8(3-5-9)10(13)6-7-12/h2-5H,6H2,1H3

Upstream product

• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 75-05-8 acetonitrile 
• 22163-52-6 methyl ethyl benzene-1,4-dicarboxylate 
• 7377-26-6 4-Methoxycarbonylbenzoyl chloride 
• 372-09-8 cyanoacetic acid 
• 7677-24-9 trimethylsilyl cyanide 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 619-44-3 methyl 4-iodobenzoate 
• 13939-06-5 molybdenum hexacarbonyl 
• 586-89-0 4-acetyl-benzoic acid 
• 3609-53-8 methyl 4-acetylbenzoate 
• 56893-25-5 methyl 4-(2-bromoacetyl)benzoate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 122545-30-6 4-(2-cyanoacetyl)benzoic acid 
• 69347-25-7 3-(4-Methoxycarbonyl-phenyl)-2-oximino-3-oxo-propionitril 
• 247206-91-3 LUF₅₄₉₂ 
• 681843-64-1 C₁₆H₁₅NO₄S 
• 333737-29-4 4-(5-amino-2H-pyrazol-3-yl)-benzoic acid methyl ester 
• 877791-58-7 C₁₈H₁₃N₃O₅ 
• 1079038-93-9 C₁₈H₁₀F₃N₃O₄ 
• 1079038-86-0 C₁₇H₁₀FN₃O₄ 
• 1361229-81-3 methyl 4-[5-(4-methoxybenzamido)-1H-pyrazol-3-yl]benzoate 
• 1361229-82-4 4-[5-(4-methoxybenzamido)-1H-pyrazol-3-yl]benzoic acid 

Relevant academic research and scientific papers

Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole with B(C6F5)3 Enabling the Electrophilic Cyanation of Silyl Enol Ethers

The Lewis acidic activation of a hypervalent iodine reagent containing a transferable cyano group, 1-cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole (CDBX), with B(C6F5)3, to achieve the catalytic electrophilic cyanation of silyl enol ethers is presented. Mechanistic studies indicate that CDBX is activated through coordination of its cyano group to B(C6F5)3, thus enabling the electrophilic cyanation reaction to occur.

Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers

An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

Palladium-catalyzed carbonylation with Mo(CO)for the synthesis of benzoylacetonitriles

Benzoylacetonitriles were synthesized by the palladium-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile using Mo(CO)as a carbon monoxide source. Pd(PPhCland CuFwere employed as the catalyst and activator, respectively. A variety of aryl iodides bearing alkyl, alkoxy, fluoro, chloro, bromo, nitrile, ester, and ketone groups afforded the corresponding benzoylacetonitriles in moderate to good yields. Georg Thieme Verlag Stuttgart ? New York.

Structure-based design of novel potent protein kinase CK2 (CK2) inhibitors with phenyl-azole scaffolds

Protein kinase CK2 (CK2) is a ubiquitous serine/threonine protein kinase for hundreds of endogenous substrates. CK2 has been considered to be involved in many diseases, including cancers. Herein we report the discovery of a novel ATP-competitive CK2 inhibitor. Virtual screening of a compound library led to the identification of a hit 2-phenyl-1,3,4-thiadiazole compound. Subsequent structural optimization resulted in the identification of a promising 4-(thiazol-5-yl)benzoic acid derivative.

Synthesis of benzoylacetonitriles from Pd-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile

Palladium-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile to produce benzoylacetonitrile derivatives through a one-pot, three-component reaction is described. This preparation method provides good yields of the carbonylated products without any additional ligands. It has a broad substrate scope with a high tolerance for a variety of functional groups.

Biocatalytic strategy toward asymmetric β-hydroxy nitriles and γ-amino alcohols

A library of 20 bakers' yeast reductases, that are overexpressed in Escherichia coli, were screened against a variety of β-keto nitriles. Enzymes from the aldose reductase and the short chain dehydrogenase family displayed activity toward these substrates. All of the seven substrates were reduced with high enantioselectivities and in some cases both antipodes could be synthesized in high ees. These whole-cell reactions afforded gram quantities of asymmetric compounds that could ultimately lead to scaleable and simple synthesis to new drug analogs of serotonin reuptake inhibitors and β-adrenergic blocking agents.

Synthesis of mono- and disubstituted 1H-imidazo[1,2-b]pyrazoles

The improved synthesis of 1H-imidazo[1,2-b]pyrazole 1 and of mono- and disubstituted derivatives is described and representative experimental procedures are given. Namely, 2-, 3-, 7- and 6-monosubstituted (2-15k), 2,3- and 6,7-disubstituted (16,17) compounds are prepared and characterized.