6068-72-0

Usage

Uses

Used in Chemical Synthesis:
4-Cyanobenzoyl chloride is used as a key intermediate in the synthesis of new liquid crystalline heteroaromatic compounds. These compounds contain the five-membered isoxazole, tetrazole, and 1,2,4-oxadiazole rings, which are important for various applications in the chemical and materials science industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Cyanobenzoyl chloride is used in the synthesis of substituted benzoate esters. These esters are crucial for studying their excited-state behavior, which can provide valuable insights into their potential applications as drugs or drug candidates.
Used in Materials Science:
4-Cyanobenzoyl chloride is also used in the materials science field, particularly for the development of new liquid crystalline materials. These materials have potential applications in display technologies, sensors, and other advanced materials due to their unique properties.

Purification Methods

If the IR shows the presence of OH, then treat it with SOCl2 boil for 1hour, evaporate and distil it in a vacuum. The distillate solidifies and can be recrystallised from pet ether. It is moisture sensitive and an IRRITANT. [Ashley et al. J Chem Soc 103 1942, Fison et al. J Org Chem 16 648 1951,[Beilstein 9 III 4255, 14 IV 3327.]

InChI:InChI=1/C8H4ClNO/c9-8(11)7-3-1-6(5-10)2-4-7/h1-4H

Upstream product

• 619-65-8 4-cyanobenzoic Acid 
• 874-86-2 4-cyanobenzyl chloride 
• 1877-72-1 3-Cyanobenzoic acid 
• 34241-39-9 azobisisobutyronitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 79-37-8 oxalyl dichloride 
• 201230-82-2 carbon monoxide 
• 623-00-7 4-bromobenzenecarbonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 122-04-3 4-nitro-benzoyl chloride 
• 100-20-9 terephthaloyl chloride 
• 24167-50-8 4-cyano-N,N-dimethylbenzamide 
• 2179-45-5 p-cyanobenzo trichloride 
• 75-44-5 phosgene 

Downstream Products

• 3490-50-4 2-diazo-1-(4-cyanophenyl)ethanone 
• 145098-44-8 4-cyano-benzoic acid furfuryl ester 
• 5410-67-3 [4-(4-cyano-benzoylamino)-phenyl]-arsonic acid 
• 99851-98-6 4-cyano-benzoic acid-(2,3-dibromo-propyl ester) 
• 54210-46-7 pentyl 4-cyanobenzoate 
• 99851-97-5 4-cyano-benzoic acid-(β,β'-dibromo-isopropyl ester) 
• 76893-84-0 2,4,6-triisopropyl-4'-cyanobenzophenone 
• 54210-50-3 cyclopentyl 4-cyanobenzoate 
• 64545-27-3 4-(2,3,5,6-tetramethyl-benzoyl)-benzonitrile 
• 857542-38-2 4-(2-bromo-dibenz[b,f][1,4]oxazepin-11-yl)-benzonitrile 
• 125553-48-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-cyanobenzoate 
• 32792-59-9 4-cyano-benzoic acid-(4-chloro-phenyl ester) 
• 107676-58-4 N-(4-cyanophenyl)-N'-phenyl-urea 
• 36268-62-9 4‐cyano‐N‐methylbenzamide 

Relevant academic research and scientific papers

Synthesis and Liquid Crystalline Properties of Unsymmetrically Substituted Naphthalenediimides with a Polar Headgroup: Effect of Amide Hydrogen Bonding and Alkyl Chain Length

A series of new unsymmetrically substituted naphthalenediimide (NDI) moieties NDI-1 to NDI-6 were synthesized. The structures of these compounds were confirmed by means of FT-IR, 1H NMR, 13C NMR, ESI-mass and HRMS spectroscopic measu

Rh(iii)-Catalyzed three-component cascade annulation to produce theN-oxopropyl chain of isoquinolone derivatives

Developing powerful methods to introduce versatile functional groups at theN-substituents of isoquinolone scaffolds is still a great challenge. Herein, we report a novel three-component cascade annulation reaction to efficiently construct theN-oxopropyl chain of isoquinolone derivativesviarhodium(iii)-catalyzed C-H activation/cyclization/nucleophilic attack, with oxazoles used both as the directing group and potential functionalized reagents.

Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids

The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.

Preparation method of benzoyl chloride compound

The invention provides a preparation method of a benzoyl chloride compound. The preparation method comprises the following step: with a trichloromethyl benzene compound and a benzoic acid compound as raw materials and ferric oxide as a catalyst, carrying out a catalytic reaction to prepare the benzoyl chloride compound. According to the method disclosed by the invention, the benzoyl chloride compound can be obtained under the condition of not using a solvent, yield is up to 95% or above, atom economy is good, cost is lower, operation is simpler, more convenient and safer, the treatment amount of three wastes is smaller, the three wastes is easier to treat, and the method is more suitable for industrial production.

Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters

A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.

One-step Conversion of Amides and Esters to Acid Chlorides with PCl3

A general and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time. Various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple, scalable and wide in scope, which provides an approach to preparation of these acid chlorides.

Design, synthesis and biological evaluation of anthranilamide derivatives as potent SMO inhibitors

A series of anthranilamide derivatives were designed and synthesized as novel smoothened (SMO) inhibitors based on the SMO inhibitor taladegib (LY2940680), which can also inhibit the SMO-D473H mutant, via a ring-opening strategy. The phthalazine core in LY2940680 was replaced with anthranilamide, which retained the inhibitory activity towards the hedgehog (Hh) signaling pathway as evidenced by a dual luciferase reporter gene assay. Compound 12a displayed the best inhibitory activity against the Hh signaling pathway with IC50 value of 34.09 nM, and exhibited better proliferation inhibitory activity towards the Daoy cell line (IC50 = 0.48 μM) than LY2940680 (IC50 = 0.79 μM).

Copper-mediated C–H thiolation of (hetero)arenes using weakly coordinating directing group

We have developed a copper-mediated C–H thiolation of (hetero)arenes by using monodentate amide as weakly coordinating directing group. This protocol features excellent functional group tolerance and shows satisfactory compatibility with various heterocycles, such as indole, pyrrole, imidazole, pyridine, thiophene and quinoline. The robust nature of this protocol renders that it has potential value in the synthetic application.

Discovery of carboxyl-containing biaryl ureas as potent RORγt inverse agonists

GSK805 (1) is a potent RORγt inverse agonist, but a drawback of 1 is its low solubility, leading to a limited absorption in high doses. We have explored detailed structure-activity relationship on the amide linker, biaryl and arylsulfonyl moieties of 1 trying to improve solubility while maintaining RORγt activity. As a result, a novel series of carboxyl-containing biaryl urea derivatives was discovered as potent RORγt inverse agonists with improved drug-like properties. Compound 3i showed potent RORγt inhibitory activity and subtype selectivity with an IC50 of 63.8 nM in RORγ FRET assay and 85 nM in cell-based RORγ-GAL4 promotor reporter assay. Reasonable inhibitory activity of 3i was also achieved in mouse Th17 cell differentiation assay (76percent inhibition at 0.3 μM). Moreover, 3i had greatly improved aqueous solubility at pH 7.4 compared to 1, exhibited decent mouse PK profile and demonstrated some in vivo efficacy in an imiquimod-induced psoriasis mice model.

Isothiazole bisoxadiazole biphenyl amide derivatives and preparation method and application thereof

The invention provides isothiazole bisoxadiazole biphenyl amide derivatives and a preparation method and application thereof, and particularly relates to 3, 4-dichloroisothiazole bisoxadiazole biphenyl amide derivatives. The general formula of the chemical structure is shown in the formula IV. The invention discloses a structural general formula, a synthesis method and application of the compoundas an insecticide, a bactericide and an anti-plant virus agent, and application and preparation method of the compound in preventing and treating agricultural, forestry and horticultural plant insectpests, diseases and virus diseases in combination with agriculturally acceptable auxiliaries or synergists and commercial insecticides, bactericides, plant virus resisting agents and acaricides.