31076-84-3

Basic information

• Product Name: Benzoyl chloride, 4-acetyl- (9CI)
• Synonyms: Benzoyl chloride, 4-acetyl- (9CI);BENZOYL CHLORIDE,4-ACETYL-;4-Acetylbenzoyl chloride
• CAS NO: 31076-84-3
• Molecular Formula: C₉H₇ClO₂
• Molecular Weight: 182.60368
• Product Categories: ACIDHALIDE
• Mol File: 31076-84-3.mol

Chemical Properties

• Melting Point: 67.4-68 °C
• Boiling Point: 296.3±23.0 °C(Predicted)
• Appearance: /
• Density: 1.239±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzoyl chloride, 4-acetyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoyl chloride, 4-acetyl- (9CI)(31076-84-3)
• EPA Substance Registry System: Benzoyl chloride, 4-acetyl- (9CI)(31076-84-3)

Safety Data

• Hazardous Substances Data: 31076-84-3(Hazardous Substances Data)

Usage

Uses

Used in Pesticide Industry:
Benzoyl chloride, 4-acetyl(9CI) is used as an intermediate in the synthesis of RH 1788 (R315765), which is a pesticide derivative of Tebufenozide (T013200). Tebufenozide is a synthetic nonsteroidal ecdysone agonist used in pesticide formulations that causes premature molting in insects, acting as a novel insect growth regulator specific to lepidopteran species.
Used in Environmental Contaminant Management:
Benzoyl chloride, 4-acetyl(9CI) is listed as a Drinking Water Contaminant Candidate List 3 (CCL3) by the United States Environmental Protection Agency (EPA). This indicates its potential role as an environmental contaminant, and its presence in drinking water sources may require monitoring and management to ensure public health and safety.
Used in Food Contamination Control:
As a potential food contaminant, Benzoyl chloride, 4-acetyl(9CI) may be used in the development of methods and technologies to detect and control its presence in the food supply. This is important for maintaining food safety and quality, as well as protecting consumers from potential health risks associated with contamination.

Upstream product

• 13329-40-3 4-Iodoacetophenone 
• 99-90-1 para-bromoacetophenone 
• 141-75-3 butyryl chloride 
• 105580-41-4 4-acetylbenzoic acid tert-butyl ester 
• 3457-45-2 p-formylacetophenone 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 586-89-0 4-acetyl-benzoic acid 

Downstream Products

• 3457-45-2 p-formylacetophenone 
• 128015-91-8 4-nitrophenyl 4-acetylbenzoate 
• 84369-69-7 1-[4-(2,4,6-Triisopropyl-benzoyl)-phenyl]-ethanone 
• 1053213-23-2 ketotaxol 
• 220461-59-6 1-[4-(4H,10H-pyrazolo[5,1-c][1,4]benzodiazepine-5-carbonyl) phenyl]-ethanone 
• 1008119-09-2 4-acetyl-N,N-dimethylbenzamide 
• 1005460-24-1 p-acetyl-N-benzyl-N-methylbenzamide 
• 1158949-01-9 4-acetyl-N-(pyridin-2-ylmethyl)benzamide 
• 1123884-08-1 4-acetyl-N-(tert-butyl)benzamide 
• 25944-71-2 diethyl (4-acetylphenyl)phosphonate 

Relevant articles and documents

Efficient Synthesis of Phthalimides via Cobalt-Catalyzed C(sp2)?H Carbonylation of Benzoyl Hydrazides with Carbon Monoxide

A cobalt-catalyzed C?H carbonylation of benzoyl hydrazides has been developed by using 2-(1-methylhydrazinyl)pyridine as the bidentate directing group. This transformation is mild, efficient, operationally simple, and highly functional-group-tolerant. The protocol has generated a broad range of phthalimide derivatives in good to excellent yields. The ligand moiety can be readily removed through hydrogenolysis. (Figure presented.).

Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones

Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.

Cobalt-Catalyzed 2-(1-Methylhydrazinyl)pyridine-Assisted C-H Alkylation/Annulation: Mechanistic Insights and Rapid Access to Cyclopenta[ c]isoquinolinone Derivatives

We have developed cobalt-catalyzed, bidentate 2-(1-methylhydrazinyl)pyridine (MHP)-directed C(sp2)-H alkylation/annulation of benzoic hydrazides with various alkenes. Notably, diverse cyclopenta[c]isoquinolinones and dihydroisoquinolinones were obtained v

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

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).

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.

DELIVERY SYSTEMS FOR CONTROLLED DRUG RELEASE

The present invention provides a compound having the structure of Formula (I) or a pharmaceutically acceptable salt, hydrate, solvate, or isomer thereof, for the controlled delivery and release of Agent.

Ligand-Promoted RhIII-Catalyzed Thiolation of Benzamides with a Broad Disulfide Scope

A ligand-promoted RhIII-catalyzed C(sp2)?H activation/thiolation of benzamides has been developed. Using bidentate mono-N-protected amino acid ligands led to the first example of RhIII-catalyzed aryl thiolation reactions directed by weakly coordinating directing amide groups. The reaction tolerates a broad range of amides and disulfide reagents.

Cu-Mediated C-H Thioetherification of Arenes at Room Temperature

Cu-mediated C-H thioetherification of arenes with ethylene sulfide has been developed using a readily removable directing group. The reaction proceeded at room temperature, and a variety of sensitive functional groups including chloro, bromo, and vinyl were well tolerated. The thiolated products could be converted to the seven-membered benzoxathiepinones derivatives by a sequence of hydrolysis-lactonization reactions.