1129-35-7

Usage

Uses

Used in Organic Synthesis:
Methyl 4-cyanobenzoate is used as a key intermediate for the synthesis of various organic compounds. Its unique structure and reactivity make it a versatile building block in the creation of a range of molecules with different applications across various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 4-cyanobenzoate is used as a starting material for the development of new drugs. Its chemical properties allow for the creation of novel drug candidates with potential therapeutic benefits.
Used in Chemical Research:
Methyl 4-cyanobenzoate is also utilized in academic and industrial research settings as a model compound for studying various chemical reactions and mechanisms. This helps researchers gain a deeper understanding of organic chemistry and develop new synthetic strategies.
Used in Material Science:
In the field of material science, Methyl 4-cyanobenzoate can be used as a component in the development of new materials with specific properties, such as improved stability or enhanced reactivity. Its incorporation into these materials can lead to advancements in various applications, including coatings, adhesives, and polymers.
Used in Agrochemical Industry:
Methyl 4-cyanobenzoate is employed in the agrochemical industry as a precursor for the synthesis of various pesticides and other agricultural chemicals. Its use in this industry contributes to the development of more effective and environmentally friendly products for crop protection and management.

Synthesis Reference(s)

Synthesis, p. 750, 1991 DOI: 10.1055/s-1991-26566

InChI:InChI=1/C9H7NO2/c1-12-9(11)8-4-2-7(6-10)3-5-8/h2-5H,1H3

Upstream product

• 151-50-8 potassium cyanide 
• 619-45-4 4-methoxycarbonyl aniline 
• 623-26-7 terephthalonitrile 
• 67-56-1 methanol 
• 57031-51-3 Methyl-tert.-butylperoxyoxalat 
• 100-47-0 benzonitrile 
• 544-92-3 copper(I) cyanide 
• 186581-53-3 diazomethane 
• 619-65-8 4-cyanobenzoic Acid 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 201230-82-2 carbon monoxide 
• 3058-39-7 4-iodobenzonitrile 
• 1067-21-6 triethylmethoxystannane 

Downstream Products

• 94254-60-1 N,N'-methanediyl-bis-terephthalamic acid dimethyl ester 
• 99855-50-2 methyl 4-[ethoxy(imino)methyl]benzoate hydrochloride 
• 5874-11-3 methyl 4-[(methylthio)thiocarbonyl]benzoate 
• 103560-24-3 4-[(Trimethylsilanyl-amino)-methyl]-benzoic acid methyl ester 
• 103560-23-2 4-(1,1,1,3,3,3-Hexamethyl-disilazan-2-ylmethyl)-benzoic acid methyl ester 
• 49744-93-6 ethyl 4-cyanobenzoylacetate 
• 131786-61-3 2-(4-carbomethoxyphenyl)-4-hydroxy-5-methylthiazole 
• 62585-03-9 1-(4-cyanophenyl)-1,3-butanedione 
• 1679-64-7 Monomethyl terephthalate 
• 184778-33-4 methyl (Z)-4-(N’-hydroxycarbamimidoyl)benzoate 
• 6520-87-2 methyl 4-cyano-3-hydroxybenzoate 
• 80393-38-0 methyl 4-(aminothioxomethyl)benzoate 
• 105-07-7 4-cyanobenzaldehyde 

Relevant academic research and scientific papers

Copper-catalyzed cyanation of aryl iodides with α-cyanoacetates via C-CN bond activation

A Cu(i)-catalyzed cyanation reaction of aryl iodides with α-cyanoacetates is reported herein, which uses α-cyanoacetates as the nontoxic and easy-handling CN source through copper-mediated C-CN bond cleavage. This reaction enables access to aryl nitriles with an array of functional groups on the aromatic ring in good to excellent yields.

Open air palladium catalyzed cyanation-the use of PMHS to protect from oxygen

PMHS (polymethylhydrosiloxane) used in catalytic amounts has a remarkable ability to prevent catalyst poisoning by oxygen contamination during palladium catalyzed cyanation reactions. The procedure is applicable to a wide range of substrates and is so effective that it allows the reactions to be run fully open to the atmosphere.

Dependence of intramolecular dissociative electron transfer rates on driving force in Donor-Spacer-Acceptor systems

The voltammetric reduction of a series of phenyl-substituted 4- benzoyloxy-1-methylcyclohexyl bromides has been investigated in DMF. The reduction leads to the cleavage of the C-Br bond. On a thermodynamic ground, the direct reduction of the tertiary C-Br function is easier than that of the selected benzoates by at least 0.5 V. However, since the direct reduction of bromides is affected by a large activation overpotential, the electron is first located in the benzoate moiety. The rate constant for the following exergonic intramolecular dissociative electron transfer was determined by kinetic analysis of the cyclic voltammetry curves. The intermolecular rate constants for the reaction between the radical anions of methyl benzoates and 4-tert-butyl-1-methylcyclohexyl bromide were also determined and found to correlate very well with related literature data pertaining to tert-butyl bromide. The intramolecular rate constants were found to be more sensitive to variation of driving force than the corresponding intermolecular data. This result can be attributed to a shift of the center of the π* orbital of the radical anion donor away from the acceptor moiety, the shift being larger for the most easily reduced donors. The resulting distance increase is therefore envisaged as responsible for a more rapid rate drop, compared to the intermolecular pattern, when smaller driving forces are considered.

New method for the synthesis of nitriles from o-arylaldoximes with ZrCl4

Nitriles were readily synthesized from the corresponding O-phenyl- or O-(p-cyanophenyl)-aldoximes with ZrCl4 in nitromethane or in benzene.

A facile and efficient [bmim]N3 catalyzed direct oxidative esterification of arylaldehydes with alcohols

Task-specific ionic liquid, [bmim]N3 was used as an effective catalyst and reaction medium for the direct oxidative esterification of arylaldehydes with alcohols. The oxidative esterification reaction of a variety of arylaldehydes took place smoothly with some primary and secondary alcohols in [bmim]N3. Satisfactory results were obtained with arylaldehydes containing electron withdrawing groups. Tertiary alcohols did not react under these conditions.

Palladium-catalyzed cyanation of aryl and heteroaryl iodides with copper(i) cyanide

The palladium-catalyzed cyanation of aryl and heteroaryl iodides or bromides using copper(i) cyanide as a cyano group source afforded the corresponding aryl and heteroaryl cyanides in good yields.

Cyanation of aromatic/vinylic boronic acids with α-cyanoacetates

A friendly protocol is reported to achieve cyanation of aromatic and vinylic boronic acids using nontoxic and readily available α-cyanoacetates as a cyano source under aerobic conditions. Many aryl/vinyl boronic acids (as well as some iodides and bromides) are amenable substrates to give aryl nitriles and acrylonitriles. This cyanation method provides a safe and operationally convenient alternative to traditional ones requiring toxic cyanide salts.

Copper-mediated cyanation of aryl halides by activation of benzyl cyanide as the cyanide source

Aryl nitriles were efficiently synthesized through copper-mediated cyanation of aryl halides using benzyl cyanide as the cyanide source. Aryl halides with various substituents on the aromatic ring afforded the corresponding aryl nitriles in 32-97 % yields (25 examples). This reaction could also be carried on a gram scale by using commercially available reagents. Additionally, a C-H bond oxidation and a C-CN cleavage are proposed to be involved in this cascade process. An efficient, copper-mediated cascade synthesis of aryl nitriles from aryl halides using benzyl cyanide as the cyanide source is described. Compared with traditional copper-mediated cyanation reactions, this approach effectively avoided the use of toxic MCN and low soluble reagents. Furthermore, C-H oxidation and C-CN cleavage are proposed to be involved in this cascade process. Copyright

Copper-mediated cyanation of aryl boronic acids using benzyl cyanide

An efficient copper-mediated synthesis of aryl nitriles from aryl boronic acids has been achieved using benzyl cyanide as a user-friendly cyanide source. Various aryl boronic acids underwent the reaction smoothly, affording the corresponding aryl nitriles in moderate to good yields. tert-Butyl hydroperoxide (TBHP) was found to be a critical agent facilitating the cyanation reaction.

Palladium-catalyzed, copper(I)-mediated coupling of boronic acids and benzylthiocyanate. A cyanide-free cyanation of boronic acids

(Equation Presented) A new method for the synthesis of nitriles is described. As a complement to the classic cyanation of aryl halides using cyanide sources and a transition metal catalyst, the palladium-catalyzed cross-coupling of thiocyanates with boronic acids in the presence of copper(I) thiophene-2-carboxylate (CuTC) affords nitriles in good to excellent yields.