6068-72-0

Basic information

• Product Name: 4-Cyanobenzoyl chloride
• Synonyms: 4-CYANOBENZOYL CHLORIDE;LABOTEST-BB LTBB000677;P-CYANOBENZOYL CHLORIDE;4-(Chlorocarbonyl)benzonitrile;4-Cyanbenzoesαurechlorid;4-Cyanobenzoicacidchloride;Benzoylchloride,4-cyano-;Benzoylchloride,p-cyano-
• CAS NO: 6068-72-0
• Molecular Formula: C₈H₄ClNO
• Molecular Weight: 165.58
• EINECS: 228-005-5
• Product Categories: Aromatic Halides (substituted);Absolute Configuration Determination (Exciton Chirality CD Method);Analytical Chemistry;Benzonitriles (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Enantiomer Excess & Absolute Configuration Determination;Exciton Chirality CD Method (for Hydroxyl Groups);Functional Materials;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 6068-72-0.mol
• Article Data: 116

Chemical Properties

• Melting Point: 68-70 °C(lit.)
• Boiling Point: 110 °C / 2mmHg
• Flash Point: 128.9 °C
• Appearance: Almost white to beige/Crystalline Powder
• Density: 1.2744 (rough estimate)
• Vapor Pressure: 0.00219mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 386729
• CAS DataBase Reference: 4-Cyanobenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyanobenzoyl chloride(6068-72-0)
• EPA Substance Registry System: 4-Cyanobenzoyl chloride(6068-72-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-24/25
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 6068-72-0(Hazardous Substances Data)

Usage

Chemical Properties

almost white to beige crystalline powder

Uses

4-Cyanobenzoyl chloride has been used in the synthesis of new liquid crystalline heteroaromatic compounds containing the five-membered isoxazole, tetrazole and 1,2,4-oxadiazole rings. It has been used in the synthesis of substituted benzoate esters and to study their excited-state behavior.

General Description

4-Cyanobenzoyl chloride participates in the benzylamine acylation of Argopore MB-CHO resin in the presence of pyridine and catalyst. It reacts with 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinoxyl (4-hydroxy-TEMPO) in pyridine under nitrogen atmosphere to form 4-cyanobenzoyl-TEMPO.

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

• 874-89-5 4-Cyanobenzyl alcohol 
• 1877-72-1 3-Cyanobenzoic acid 
• 75-44-5 phosgene 
• 619-65-8 4-cyanobenzoic Acid 
• 34241-39-9 azobisisobutyronitrile 
• 105-07-7 4-cyanobenzaldehyde 
• 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 
• 79-37-8 oxalyl dichloride 
• 874-86-2 4-cyanobenzyl chloride 
• 201230-82-2 carbon monoxide 

Downstream Products

• 145098-44-8 4-cyano-benzoic acid furfuryl ester 
• 80239-67-4 4-Cyano-benzoic acid 1-methyl-piperidin-4-yl ester; hydrochloride 
• 99325-91-4 4-(p-cyanobenzoyl)-cis-2,6-dimethylmorpholine 
• 126921-78-6 3-(4-cyano-benzoylamino)-2-chloropyridine 
• 144412-45-3 1-(p-cyanobenzoyl)-L-proline 
• 151475-03-5 1,3,4,6-Tetra-O-acetyl-2-O-(4-cyanobenzoyl)-α-D-glucopyranose 
• 226882-49-1 4-cyano-N’-(4-cyanobenzoyl)benzohydrazide 
• 182162-12-5 1-(4-cyanophenyl)-3-(phenyl)propan-1,3-dione 
• 153489-21-5 <γ-(trimethylsilyl)butyryl>p-cyanophenone 
• 171725-11-4 2-[N-(N'-Cbz-glycyl)amino]-4'-cyanobenzophenone 
• 202600-59-7 3-cyanophenyl 4-cyanobenzoate 
• 93135-68-3 7,8-dihydro-2',3'-O-isopropylidene-N⁶,N⁶,7-tris(p-cyanobenzoyl)-8,5'-O-cycloadenosine 

Relevant articles and documents

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

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.

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.