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% min ^*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

4-(trans-2-[4]quinolyl-vinyl)-benzonitrile

4-(1,3-dioxo-2,3-dihydro-1H-[4]isochinolyLiDenemethyl)-benzonitrile

Refernces

• 1、 Yeung, Pui Yee,Tsang, Chun Pui,Kwong, Fuk Yee. "Efficient cyanation of aryl bromides with K4[Fe(CN)6] catalyzed by a palladium-indolylphosphine complex". . p. 7038 - 7041. Retrieved 2011.
• 2、 Cohen, Daniel T.,Buchwald, Stephen L.. "Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media". . p. 202 - 205. Retrieved 2015.
• 3、 Fryszkowska, Anna,Klapars, Artis,Marshall, Nicholas,Ruccolo, Serge,Strotman, Neil A.,Zhang, Shaoguang. "Electrochemical Activation of Galactose Oxidase: Mechanistic Studies and Synthetic Applications". . p. 7270 - 7280. Retrieved 2021.
• 4、 Mowry. "-". . p. 992. Retrieved 1943.
• 5、 Zohreh, Nasrin,Tavakolizadeh, Maryam,Hosseini, Seyed Hassan,Pourjavadi, Ali,Bennett, Craig. "Tungstate-loaded triazine-based magnetic poly(Bis-imidazolium ionic liquid): An effective bi-functional catalyst for tandem selective oxidation/Knoevenagel condensation in water". . p. 342 - 350. Retrieved 2017.
• 6、 Ma, Xinyi,Li, Zhongfeng,Liu, Feijie,Cao, Shengli,Rao, Honghua. "Tetra-n-butylammonium bromide: A simple but efficient organocatalyst for alcohol oxidation under mild conditions". . p. 1741 - 1746. Retrieved 2014.
• 7、 Saha, Biswajit,Rahaman, S. M. Wahidur,Sinha, Arup,Bera, Jitendra K.. "Contrasting reactivity of 2-mesityl-1,8-naphthyridine (Mes-NP) with singly-bonded [RhIIRhII] and [RuIRu I] compounds". . p. 583 - 589. Retrieved 2011.
• 8、 Ahemed, Jakeer,Bhongiri, Yadagiri,Chetti, Prabhakar,Gade, Ramesh,Kore, Ranjith,Pasha, Jakeer,Pola, Someshwar,Rao D, Venkateshwar. "Synthesis of new Zn (II) complexes for photo decomposition of organic dye pollutants, industrial wastewater and photo-oxidation of methyl arenes under visible-light". . . Retrieved 2021.
• 9、 Wang, Bo,Bols, Mikael. "Artificial Metallooxidases from Cyclodextrin Diacids". . p. 13766 - 13775. Retrieved 2017.
• 10、 Zhang, Yichi,Wang, Zhan,Lang, Xianjun. "Merging visible light photocatalysis of dye-sensitized TiO2 with TEMPO: The selective aerobic oxidation of alcohols". . p. 4955 - 4963. Retrieved 2017.