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105-07-7

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105-07-7 Usage

Chemical Description

4-cyanobenzaldehyde is an organic compound with a cyanide group and an aldehyde group attached to a benzene ring.

Chemical Properties

WHITE TO SLIGHTLY BEIGE CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 105-07-7 differently. You can refer to the following data:
1. 4-Cyanobenzaldehyde, is used as an intermediate for organic synthesis.It is also used as an intermediate in the pharmaceutical and research department.
2. 4-Formylbenzonitrile can be used in the synthesis of various boron-dipyrromethenes (BODIPY), porphyrins, corroles and other related macrocycles.
3. 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.

Synthesis Reference(s)

Synthesis, p. 747, 1984 DOI: 10.1055/s-1984-30956Tetrahedron Letters, 34, p. 8037, 1993 DOI: 10.1016/S0040-4039(00)61444-2

Check Digit Verification of cas no

The CAS Registry Mumber 105-07-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 5 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 105-07:
(5*1)+(4*0)+(3*5)+(2*0)+(1*7)=27
27 % 10 = 7
So 105-07-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H5NO/c1-9-8-4-2-7(6-10)3-5-8/h2-6H

105-07-7 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (C0443)  4-Formylbenzonitrile  >98.0%(GC)

  • 105-07-7

  • 5g

  • 350.00CNY

  • Detail
  • TCI America

  • (C0443)  4-Formylbenzonitrile  >98.0%(GC)

  • 105-07-7

  • 25g

  • 990.00CNY

  • Detail
  • Alfa Aesar

  • (A14914)  4-Cyanobenzaldehyde, 98+%   

  • 105-07-7

  • 5g

  • 333.0CNY

  • Detail
  • Alfa Aesar

  • (A14914)  4-Cyanobenzaldehyde, 98+%   

  • 105-07-7

  • 25g

  • 1328.0CNY

  • Detail
  • Alfa Aesar

  • (A14914)  4-Cyanobenzaldehyde, 98+%   

  • 105-07-7

  • 100g

  • 4598.0CNY

  • Detail

105-07-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Cyanobenzaldehyde

1.2 Other means of identification

Product number -
Other names 4-cyano-benzaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:105-07-7 SDS

105-07-7Relevant articles and documents

Selectivity Modulation of the Ley–Griffith TPAP Oxidation with N-Oxide Salts

Moore, Peter W.,Jiao, Yanxiao,Mirzayans, Paul M.,Sheng, Lexter Ng Qi,Hooker, Jordan P.,Williams, Craig M.

, p. 3401 - 3407 (2016)

A wide variety of novel non-hygroscopic N-oxide tetraphenylborate salts were synthesized and evaluated as co-oxidants in the Ley–Griffith (TPAP) oxidation of benzylic and allylic alcohols under non-anhydrous conditions. The novel DABCOO·TPB (2:1) salt was herein unearthed as a viable competitor to the first-generation NMO·TPB (2:1) salt, but more importantly gave increased performance under oxidative competition. X-ray crystal structure analysis and NMR spectroscopy revealed that depending on the crystallization conditions 1:1, 2:1 or 3:2 N-oxide–tetraphenylborate salts could be formed.

Copper-catalyzed cyanation of arylboronic acids using DDQ as cyanide source

Zhang, Guangyou,Chen, Shuyou,Fei, Haiyang,Cheng, Jiang,Chen, Fan

, p. 2247 - 2250 (2012)

In this paper, a copper-catalyzed cyanation of arylboronic acids is achieved with DDQ, providing nitriles with good yields. This new approach represents a safe method for the synthesis of aryl nitriles. Georg Thieme Verlag Stuttgart ? New York.

An effective synthesis of N,N-dimethylamides from carboxylic acids and a new route from N,N-dimethylamides to 1,2-diaryl-1,2-diketones

Kumagai, Takashi,Anki, Tomohiro,Ebi, Takahiro,Konishi, Akihito,Matsumoto, Kouzou,Kurata, Hiroyuki,Kubo, Takashi,Katsumoto, Kenta,Kitamura, Chitoshi,Kawase, Takeshi

, p. 8968 - 8973 (2010)

Carboxylic acids were heated at 150 °C in DMF in the presence of 1.25 equiv of thionyl chloride to give corresponding N,N-dimethylamides in good yields. Tandem chlorination and amidation reactions occurred in the one-pot procedure. Dicarboxylic acids needed prolonged reaction time to produce bisamides in good yields. Some benzamides were efficiently converted into corresponding 1,2-diaryl-1,2-diketones (benzils) under acyloin condensation conditions in the presence of 4,4′-di-tert-butylbiphenyl (DBB) in THF. Ultrasonic irradiation effectively accelerates the reaction, but it is not critical. However, the presence of DBB is fatal to the reaction. Although a few synthetic methods for benzils from benzoic acids have been reported so far, this method is one of the most convenient and highly reproducible procedures.

New selective metal-free oxidations of primary alcohols by HNO3 or HNO3 and O2, catalyzed by Br2

Minisci, Francesco,Porta, Ombretta,Recupero, Francesco,Punta, Carlo,Gambarotti, Cristian,Pierini, Monica,Galimberti, Laura

, p. 2203 - 2205 (2004)

Primary benzylic alcohols are selectively oxidized to the corresponding aromatic aldehydes by molecular oxygen at atmospheric pressure, under Br 2-HNO3 catalysis in a biphasic medium (1,2-dichloroethane- water, 5:1) at 60 °C. Under paragonable experimental conditions the aliphatic alcohols are oxidized to esters.

4CzIPN catalyzed photochemical oxidation of benzylic alcohols

Zhang, Heng,Guo, Tianyun,Wu, Mingzhong,Huo, Xing,Tang, Shouchu,Wang, Xiaolei,Liu, Jian

, (2021)

A green photoredox oxidation of benzylic primary and secondary alcohols to aldehydes and ketones with air as an oxidant was reported. The oxidation shows broad substrate scope and excellent selectivity over benzylic alcohols to the aliphatic alcohols. Further mechanistic studies revealed a quinuclidine mediated HAT process, and blue LEDs promoted 4CzlPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) photoredox cycle were involved in our oxidation.

Efficient and Highly Selective Solvent-Free Oxidation of Primary Alcohols to Aldehydes Using Bucky Nanodiamond

Lin, Yangming,Wu, Kuang-Hsu Tim,Yu, Linhui,Heumann, Saskia,Su, Dang Sheng

, p. 3497 - 3505 (2017)

Selective oxidation of alcohols to aldehydes is widely applicable to the synthesis of various green chemicals. The poor chemoselectivity for complicated primary aldehydes over state-of-the-art metal-free or metal-based catalysts represents a major obstacle for industrial application. Bucky nanodiamond is a potential green catalyst that exhibits excellent chemoselectivity and cycling stability for the selective oxidation of primary alcohols in diverse structures (22 examples, including aromatic, substituted aromatic, unsaturated, heterocyclic, and linear chain alcohols) to their corresponding aldehydes. The results are comparable to reported transition-metal catalysts including conventional Pt/C and Ru/C catalysts for certain substrates under solvent-free conditions. The possible activation process of the oxidant and substrates by the surface oxygen groups and defect species are revealed with model catalysts, ex situ electrochemical measurements, and ex situ attenuated total reflectance. The zigzag edges of sp2 carbon planes are shown to play a key role in these reactions.

One-pot oxidant-free dehydrogenation-Knoevenagel tandem reaction catalyzed by a recyclable magnetic base-metal bifunctional catalyst

Yuan, Xiaofeng,Wan, Zijuan,Ning, Jinfeng,Zhang, Qiang,Luo, Jun

, (2020)

A new base-metal bifunctional catalyst NH-Pd(0)@MNP was prepared via a facile procedure and fully characterized. The as-prepared catalyst was used as an efficient relay catalyst for the one-pot oxidant-free dehydrogenation-Knoevenagel condensation tandem reaction from benzyl alcohol in H2O under mild conditions and generated benzalmalononitriles with yield up to 96%. Meanwhile, the catalyst could be easily recovered from the reaction system by an external magnetic field, and is reusable with little loss of activity up to 6 runs (5%).

Candida parapsilosis ATCC 7330 mediated oxidation of aromatic (activated) primary alcohols to aldehydes

Sivakumari, Thakkellapati,Chadha, Anju

, p. 91594 - 91600 (2015)

A green, simple and high yielding [up to 86% yield] procedure is developed for the oxidation of aromatic (activated) primary alcohols to aldehydes using whole cells of Candida parapsilosis ATCC 7330. The biotransformation is carried out under mild conditions at 25 °C, in hexane: water (48 : 2) (v/v).

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Mowry

, (1945)

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Highly Productive Oxidative Biocatalysis in Continuous Flow by Enhancing the Aqueous Equilibrium Solubility of Oxygen

Chapman, Michael R.,Cosgrove, Sebastian C.,Turner, Nicholas J.,Kapur, Nikil,Blacker, A. John

, p. 10535 - 10539 (2018)

We report a simple, mild, and synthetically clean approach to accelerate the rate of enzymatic oxidation reactions by a factor of up to 100 when compared to conventional batch gas/liquid systems. Biocatalytic decomposition of H2O2 is used to produce a soluble source of O2 directly in reaction media, thereby enabling the concentration of aqueous O2 to be increased beyond equilibrium solubility under safe and practical conditions. To best exploit this method, a novel flow reactor was developed to maximize productivity (g product L?1 h?1). This scalable benchtop method provides a distinct advantage over conventional bio-oxidation in that no pressurized gas or specialist equipment is employed. The method is general across different oxidase enzymes and compatible with a variety of functional groups. These results culminate in record space-time yields for bio-oxidation.

Selective oxidation of alcohols using ferrocene-labeled Merrifield resin-supported ionic liquid phase catalysts

Kurane, Rajanikant,Bansode, Prakash,Khanapure, Sharanabasappa,Salunkhe, Rajashri,Rashinkar, Gajanan

, p. 7807 - 7821 (2016)

Abstract: A novel ferrocene-labeled Merrifield resin-supported ionic liquid phase catalysts has been synthesized and successfully utilized for the selective oxidation of primary alcohols into corresponding aldehydes. The catalysts were recovered by simple filtration which greatly simplified the purification step and allowed successive reuse for multiple times without significant loss in activity. Graphical Abstract: [Figure not available: see fulltext.]

Mechanisms of the Aerobic Oxidation of Alcohols to Aldehydes and Ketones, Catalysed under Mild Conditions by Persistent and Non-Persistent Nitroxyl Radicals and Transition Metal Salts - Polar, Enthalpic, and Captodative Effects

Minisci, Francesco,Recupero, Francesco,Cecchetto, Andrea,Gambarotti, Cristian,Punta, Carlo,Faletti, Roberta,Paganelli, Roberto,Pedulli, Gian Franco

, p. 109 - 119 (2004)

The oxidation of alcohols to aldehydes and ketones by air or oxygen under mild conditions (room temperature and atmospheric pressure), catalysed by persistent and non-persistent nitroxyl radicals in combination with transition metal salts, appears to be the most convenient of the numerous processes developed for these purposes. The thermochemistry, the kinetics, and the Hammett correlations have allowed us to establish, on a quantitative basis, the fundamental difference between the oxidation catalysed by persistent and non-persistent nitroxyl catalysts. In the latter case, an interesting significant captodative effect is displayed for the first time for the oxidation of substituted benzyl alcohols; the importance of enthalpic and polar effects is emphasised.

Convenient oxidation of benzylic and allylic halides to aldehydes and ketones

Chen, David X.,Ho, Chi M.,Rudy Wu,Wu, Peter R.,Wong, Freeman M.,Wu, Weiming

, p. 4147 - 4148 (2008)

Benzylic and allylic halides were conveniently oxidized to aldehydes and ketones by pyridine N-oxide in the presence of silver oxide under mild conditions.

The Room-Temperature Palladium-Catalyzed Cyanation of Aryl Bromides and Iodides with Tri-t-butylphosphine as Ligand

Ramnauth, Jailall,Bhardwaj, Namrta,Renton, Paul,Rakhit, Suman,Maddaford, Shawn P.

, p. 2237 - 2239 (2003)

The palladium-catalyzed cyanation of aryl bromides and iodides to the corresponding nitriles occurs at room temperature when tri-t-butylphosphine is used as ligand, Zn(CN)2 as the cyanide source and Zn dust as a co-catalyst in DMF as solvent. A variety of aromatic halides, including electron-withdrawing and electron-donating, can be efficiently cyanated under these conditions. The reactions are completed in less than 1 hour and products are produced in good to excellent yield.

Oxidant free dehydrogenation of alcohols using chitosan/polyacrylamide entrapped Ag nanoparticles

Kurhe, Deepak K.,Fernandes, Thomson A.,Deore, Tushar S.,Jayaram, Radha V.

, p. 46443 - 46447 (2015)

Silver nanoparticles encaged in a nanoporous chitosan/polyacrylamide interpenetrating polymer network (Ag@IPN) were synthesized and characterized by various techniques such as Fourier Transform Infra Red (FTIR), X-ray Diffraction (XRD), Scanning Electron Microscopy-Energy Dispersive X-ray Spectroscopy (SEM-EDX), Transmission Electron Microscopy (TEM), Thermogravimetric Analysis (TGA) and ICP-AES. This material exhibits good catalytic activity for the oxidant free dehydrogenation of alcohols to the corresponding carbonyl compounds. The reusability of Ag@IPN for this reaction was compared with a chitosan-silver complex under the same reaction conditions. It was found that encaging silver nanoparticles in interpenetrating polymer networks (IPN) has improved their stability by avoiding leaching and aggregation.

C- vsN-Oxidations of Benzyltriazanes: Selective Access to Triazones, Azimines, and Triazenes

Glowacki, Aurore,Jeux, Victorien,Gasnier, Gwéna?l,Joucla, Lionel,Jacob, Guy,Lac?te, Emmanuel

, p. 566 - 570 (2018)

The oxidation of several benzyltriazanes has been studied. Routes to the selective formation of triazenes, azimines, and triazones via C- or N-oxidation (and rearrangement) were devised. The rich reactivity of triazanes shows that trinitrogen chains are interesting functions, whose reactivity has been overlooked despite their interest as 3-N building blocks.

Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis

De Jesus Silva, Jordan,Bartalucci, Niccolò,Jelier, Benson,Grosslight, Samantha,Gensch, Tobias,Schünemann, Claas,Müller, Bernd,Kamer, Paul C. J.,Copéret, Christophe,Sigman, Matthew S.,Togni, Antonio

, (2021/11/10)

A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand σ-donation, π-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong σ-donating, weak π-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts.

DIBALH: From known fundamental to an unusual reaction; Chemoselective partial reduction of tertiary amides in the presence of esters

An, Duk Keun,Heo, Yu Jin,Jaladi, Ashok Kumar,Kim, Hyun Tae

, p. 33809 - 33813 (2021/12/09)

This study presents a quick and reliable approach to the chemoselective partial reduction of tertiary amides to aldehydes in the presence of readily reducible ester groups using commercial DIBALH reagent. Moreover, the developed method was also extended to multi-functional molecules bearing ester moieties, which were successfully chemoselectively reduced to the corresponding aldehydes. This journal is

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