4-Cyanobenzaldehyde

Base Information

• Chemical Name: 4-Cyanobenzaldehyde
• CAS No.: 105-07-7
• Molecular Formula: C8H5NO
• Molecular Weight: 131.134
• Hs Code.: 29269095
• European Community (EC) Number: 203-267-3
• NSC Number: 5091
• UNII: DWH62Y9TCA
• DSSTox Substance ID: DTXSID6059312
• Nikkaji Number: J22.132E
• Wikidata: Q72457875
• ChEMBL ID: CHEMBL1922276
• Mol file: 105-07-7.mol

Synonyms:4-cyanobenzaldehyde

Chemical Property of 4-Cyanobenzaldehyde

Chemical Property:

• Appearance/Colour: white to slightly beige crystalline powder
• Melting Point: 100 - 102°C
• Refractive Index: 1.4700 (estimate)
• Boiling Point: 262.3 °C at 760 mmHg
• Flash Point: 124.2 °C
• PSA: 40.86000
• Density: 1.15 g/cm³
• LogP: 1.37078
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: It is soluble in water, ethanol, ether and chloroform.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 131.037113783
• Heavy Atom Count: 10
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

4-Cyanobenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=O)C#N
• Uses: 4-Cyanobenzaldehyde, is used as an intermediate for organic synthesis.It is also used as an intermediate in the pharmaceutical and research department. 4-Formylbenzonitrile can be used in the synthesis of various boron-dipyrromethenes (BODIPY), porphyrins, corroles and other related macrocycles. 4-Cyanobenzaldehyde is used as a reagent in the synthesis of hydrazone based inhibitors of adipose-triglyceride lipase (ATGL). 4-Cyanobenzaldehyde is also used as a reagent in the synthesis of BAZ2-ICR which is a chemical probe targeting the bromo domains of BAZ2A and BAZ2B.

Technology Process of 4-Cyanobenzaldehyde

There total 226 articles about 4-Cyanobenzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

4-((1R*,2R*)-1,2-dihydroxy-2-phenylethyl)benzonitrile → benzaldehyde (100-52-7) + 4-cyanobenzaldehyde (105-07-7)

Guidance literature:

With C₂₁H₁₂Cl₆NO₄V; In toluene; at 80 ℃; under 760.051 Torr; chemoselective reaction;

DOI:10.1002/adsc.201800050

Reference yield: 75.0%

para-methylbenzonitrile (104-85-8) → 4-cyanobenzoic Acid (619-65-8,333406-09-0) + 4-cyanobenzaldehyde (105-07-7)

Guidance literature:

With sodium ortho-iodobenzenesulfonate; Oxone; tetra(n-butyl)ammonium hydrogensulfate; In acetonitrile; at 60 ℃; for 36h;

DOI:10.1039/c0ob00722f

Reference yield: 53.0%

4-(bis(phenylthio)methyl)benzonitrile → bis(benzenethio)tellurium(II) (75264-81-2) + 4-cyanobenzaldehyde (105-07-7) + diphenyldisulfane (882-33-7)

Guidance literature:

With tellurium tetrachloride; In dichloromethane; Ambient temperature;

upstream raw materials:

hexamethylenetetramine

4-cyanobenzyl bromide

4-Cyanobenzyl alcohol

4-cyanobenzylidene diacetate

Downstream raw materials:

(E)-4-[2-(pyridin-2-yl)vinyl]benzonitrile

(E)-4-[2-(4-pyridyl)ethenyl]benzenecarbonitrile

(E)-4-[2-(6-methylpyridin-2-yl)vinyl]benzonitrile

E,E-2,6-bis(4-cyanostyryl)pyridine

Refernces

A simple and efficient synthesis of new mono- and bis([1,2,4]-oxadiazol)- benzaldehyde building blocks

10.1055/s-2007-990834

The research focuses on the development of a simple and efficient method for synthesizing new mono- and bis([1,2,4]-oxadiazol)benzaldehyde building blocks, which are valuable in organic chemistry for a variety of applications. The purpose of this study was to create a high-yielding, five-step procedure with minimal and straightforward purifications, starting from readily available benzamidoxime, derived from 4-cyanobenzaldehyde. The conclusion of the research is that the team successfully developed a general method for synthesizing these compounds with aromatic and aliphatic linkers, yielding overall yields between 66% and 80%. Key chemicals used in the process include 4-cyanobenzaldehyde, ethylene glycol, p-toluenesulfonic acid, hydroxylamine hydrochloride, sodium carbonate, pyridine, phenylacetyl chloride, and various dicarboxylic acids or acid dichlorides to introduce different linkers. The final products, the mono- and bis([1,2,4]-oxadiazol)benzaldehydes, were obtained through a series of reactions involving O-acylation, acetal deprotection, and cyclization steps.

Organocatalytic tandem three-component reaction of aldehyde, alkyl vinyl ketone, and amide: One-pot syntheses of highly functional alkenes

10.1039/c0ob00644k

The study presents an efficient one-pot synthesis method for highly functional alkenes through a phosphine-catalyzed tandem three-component reaction involving aldehydes, alkyl vinyl ketones, and amides. The process utilizes either EtPPh2 or PPh3 as catalysts and achieves high yields (68–99%) with excellent stereoselectivity (E/Z ratios up to 98:2) within a total reaction time of 3 to 29.5 hours. The study also explores the scope of the reaction with various aryl- and heteroaryl-substituted aldehydes, amides, and alkyl vinyl ketones, demonstrating the versatility and practicality of the method. The reaction mechanism is proposed to involve a Morita–Baylis–Hillman reaction followed by a Michael addition, leading to the formation of the desired alkenes. The mild reaction conditions and the high atom economy of the process make it a valuable addition to organic synthesis.

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