167678-46-8

Basic information

• Product Name: 3-ACETOXY-2-METHYLBENZOYL CHLORIDE
• Synonyms: Benzoyl chloride, 3-(acetyloxy)-2-methyl- (9CI);3-Acetoxy-2-methylbenzoylchloride (AMBC);2-METHYL-3-ACETOXYBENZOYLCHLORIDE;2-methyl-3-acetoxybenzoic chloride(3-acetoxy-2-methylbenzoic chloride);(1-[6-(Dimethylamino)-2-naphthalenyl]);2-Methyl-3-Acetoxybenzoic Chloride(3-Acetoxy-2-Methylbenzoic Ch;3-(Chlorocarbonyl)-2-Methylphenyl Acetate;Acetic Acid 3-Chlorocarbonyl-2-Methylphenyl Ester
• CAS NO: 167678-46-8
• Molecular Formula: C₁₀H₉ClO₃
• Molecular Weight: 212.63
• EINECS: 433-690-0
• Product Categories: ACIDHALIDE;Aromatics Compounds;Aromatics;Inhibitors
• Mol File: 167678-46-8.mol

Chemical Properties

• Melting Point: 31-35°C
• Boiling Point: 148°C/11mmHg(lit.)
• Flash Point: 123.6 °C
• Appearance: light yellow oil
• Density: 1,25 g/cm3
• Vapor Pressure: 0.00151mmHg at 25°C
• Refractive Index: 1.532
• Solubility: Chloroform, Dichloromethane
• Sensitive: Moisture Sensitive
• BRN: 8054543
• CAS DataBase Reference: 3-ACETOXY-2-METHYLBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETOXY-2-METHYLBENZOYL CHLORIDE(167678-46-8)
• EPA Substance Registry System: 3-ACETOXY-2-METHYLBENZOYL CHLORIDE(167678-46-8)

Safety Data

• Statements: 34-43-35
• Safety Statements: 26-36/37/39-45-7/8
• RIDADR: 3261
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 167678-46-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-ACETOXY-2-METHYLBENZOYL CHLORIDE is used as an intermediate for the preparation of small-sized HIV protease inhibitors. Its chemical properties make it a suitable candidate for the development of antiretroviral drugs, which are crucial in the treatment of HIV and AIDS.
As an intermediate, 3-ACETOXY-2-METHYLBENZOYL CHLORIDE plays a vital role in the synthesis of HIV protease inhibitors, which are designed to block the activity of the HIV protease enzyme. This enzyme is essential for the replication of the virus, and by inhibiting its function, the spread of the virus can be significantly reduced, thus helping to manage the progression of the disease in patients.

InChI:InChI=1/C10H9ClO3/c1-6-8(10(11)13)4-3-5-9(6)14-7(2)12/h3-5H,1-2H3

Upstream product

• 168899-58-9 3-acetoxy-2-methylbenzoic acid 

Downstream Products

• 188936-02-9 Acetic acid 3-((5S,6R)-6-hydroxy-2,2-dimethyl-[1,3]dioxepan-5-ylcarbamoyl)-2-methyl-phenyl ester 
• 245414-50-0 Acetic acid 3-[(1S,2S)-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-1-phenylsulfanylmethyl-propylcarbamoyl]-2-methyl-phenyl ester 
• 245414-50-0 Acetic acid 3-[(1R,2S)-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-1-phenylsulfanylmethyl-propylcarbamoyl]-2-methyl-phenyl ester 
• 245414-50-0 Acetic acid 3-[(1S,2R)-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-1-phenylsulfanylmethyl-propylcarbamoyl]-2-methyl-phenyl ester 
• 188936-06-3 (2R)-1-acetoxy-2-((4S)-2-(3-acetoxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)-2-methanesulfonyloxyethane 
• 201402-95-1 Acetic acid 3-{(S)-4-[(S)-1-hydroxy-2-(toluene-4-sulfonyloxy)-ethyl]-4,5-dihydro-oxazol-2-yl}-2-methyl-phenyl ester 
• 159989-64-7 nelfinavir 
• 755012-12-5 RG-100749 
• 188936-07-4 (3S,4aS,8aS)-N-tert-butyl-2-((R)-2-hydroxy-2-((S)-2-(3-hydroxy-2-methylphenyl)-4,5-dihydrooxazol-4-yl)ethyl)-decahydroisoquinoline-3-carboxamide 
• 188936-03-0 Acetic acid 3-((5S,6R)-6-methanesulfonyloxy-2,2-dimethyl-[1,3]dioxepan-5-ylcarbamoyl)-2-methyl-phenyl ester 
• 478411-22-2 (2S,3S)-3-(3-Acetoxy-2-methyl-benzoylamino)-2-hydroxy-4-phenyl-butyric acid 
• 775329-77-6 3-benzoyl-2-methylphenyl acetate 
• 245414-50-0 (3S,4AS,8AS)-2-[(2R,3R)-3-(3-acetoxy-2-methylbenzoylamino)-2-hydroxy-4-phenylthiobutyl]decahydroisoquinoline-3-carboxylic acid t-butylamide 
• 854052-94-1 acetic acid 2-methyl-3-(methylphenylcarbamoyl)phenyl ester 

Relevant articles and documents

Two new benzamides: Synthesis, spectroscopic characterization, X-ray diffraction, and electronic structure analyses

This work includes the syntheses, molecular and electronic structure analyses of two novel secondary amide compounds 3-acetoxy-2-methyl-N-(2-methoxyphenyl)benzamide, 1 and 3-acetoxy-2-methyl-N-(3-methylphenyl)benzamide, 2. The title compounds were charact

Synthesis and characterization of 3-acetoxy-2-methyl-N-(phenyl)benzamide and 3-acetoxy-2-methyl-N-(4- methylphenyl)benzamide

This study treats about two successfully synthesized secondary amide compounds 3-Acetoxy-2-methyl-N-(phenyl)benzamide, I and 3-Acetoxy-2-methyl-N-(4-methylphenyl)benzamide, II. Compounds were characterized by FTIR, 1H NMR, 13C NMR and X-ray single crystal diffraction analysis techniques. Single crystal X-ray diffraction analyses show that while I crystallized in the orthorhombic system with space group Pbca, II crystallized in the triclinic system with space group P-1 and the asymmetric unit of II consists of two crystallographically independent molecules. Lattice constants are a = 7.9713 (3) ?, b = 9.5059 (3) ?, c = 37.1762 (2) ?, Z = 8 for I and a = 7.5579 (8) ?, b = 8.8601 (8) ?, c = 23.363 (3) ?, α = 97.011 (9) °, β = 96.932 (9)°, γ = 90.051 (8)°, Z = 4 for II. Crystallographic studies also show that the supramolecular structures were stabilized by intramolecular, intermolecular hydrogen bonds and C[sbnd]H … π interactions for both compounds. Characteristic amide bonds were observed in IR and NMR spectra.

Synthesis, characterization, antioxidant, and antibacterial activities of new 2,3-dimethoxy and 3-acetoxy-2-methyl benzamides

Abstract: We performed a series of novel benzamide compounds which were synthesized starting from 2,3-dimethoxybenzoic acid or 3-acetoxy-2-methylbenzoic acid and amine derivatives. All the obtained products were purified, and the analysis of these product

Rhodium-Catalyzed Alkylation of C?H Bonds in Aromatic Amides with Non-activated 1-Alkenes: The Possible Generation of Carbene Intermediates from Alkenes

The alkylation of C?H bonds (hydroarylation) in aromatic amides with non-activated 1-alkenes using a rhodium catalyst and assisted by an 8-aminoquinoline directing group is reported. The addition of a carboxylic acid is crucial for the success of this reaction. The results of deuterium-labeling experiments indicate that one of deuterium atoms in the alkene is missing, suggesting that the reaction does not proceed through the commonly accepted mechanism for C?H alkylation reactions. Instead the reaction is proposed to proceed through a carbene mechanism. The carbene mechanism is also supported by preliminary DFT calculations.

Rhodium-Catalyzed Alkenylation of C-H Bonds in Aromatic Amides with Alkynes

The rhodium-catalyzed alkenylation of C-H bonds of aromatic amides with alkynes is reported. A variety of functional groups, including OMe, OAc, Br, Cl, and even NO2, are applicable to this reaction to give the corresponding hydroarylation prod

BORON-CONTAINING DIACYLHYDRAZINES

The present disclosure provides boron-containing diacylhydrazines having Formula I: and the pharmaceutically acceptable salts and solvates thereof, wherein R1, R2, R3, R4, and R5 are defined as set forth in the specification. The present disclosure also provides the use of boron-containing diacylhydrazines is ecdysone receptor-based inducible gene expression systems. Thus, the present disclosure is useful for applications such as gene therapy, treatment of disease, large scale production of proteins and antibodies, cell-based screening assays, functional genomics, proteomics, metabolomics, and regulation of traits in transgenic organisms, where control of gene expression levels is desirable.

Ni(II)-catalyzed oxidative coupling between C(sp2)-H in benzamides and C(sp3)-H in toluene derivatives

Oxidative coupling between C(sp2)-H bonds and C(sp3)-H bonds is achieved by the Ni(II)-catalyzed reaction of benzamides containing an 8-aminoquinoline moiety as the directing group with toluene derivatives in the presence of heptafluoroisopropyl iodide as the oxidant. The method has a broad scope and shows high functional group compatibility. Toluene derivatives can be used as the coupling partner in an unreactive solvent.

Nickel-catalyzed direct alkylation of C-H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance

The alkylation of the ortho C-H bonds in benzamides and acrylamides containing an 8-aminoquinoline moiety as a bidentate directing group with unactivated alkyl halides using nickel complexes as catalysts is described. The reaction shows high functional group compatibility. In reactions of meta-substituted aromatic amides, the reaction proceeds in a highly selective manner at the less hindered C-H bond.

Palladium-catalyzed direct ortho -alkynylation of aromatic carboxylic acid derivatives

The palladium-catalyzed direct alkynylation of C-H bonds in aromatic carboxylic acid derivatives is described. The use of 8-aminoquinoline as a directing group facilitates the alkynylation of an electronically diverse range of C(sp2)-H bonds.

Classical and three-dimensional QSAR for the inhibition of [ 3H]ponasterone a binding by diacylhydrazine-type ecdysone agonists to insect Sf-9 cells

The activity of 52 diacylhydrazine congeners was evaluated by measuring the inhibition of the incorporation of [3H]ponasterone A into intact Sf-9 cells. Eleven compounds were newly synthesized in this study. Results showed that the substitution of the 2-CH3 or 3-OCH3 moiety of methoxyfenozide with other groups or the removal of either group was unfavorable to the activity. The activity was quantitatively analyzed using both classical QSAR (Hansch-Fujita) and three-dimensional QSAR methods (comparative molecular field analysis, CoMFA). Sterically favorable fields were observed at the 3- and 4-positions of the benzene ring opposite from the t-butyl group (B-ring), and a sterically unfavorable field was evidenced at the 2-position. Another sterically unfavorable field developed surrounding the favorable field observed at the 4-position of the B-ring. Electrostatically negative fields were observed near the CO moiety, above the benzene ring, and at the 4-position of the B-ring. The optimum hydrophobicity of compounds in terms of their log P values was calculated to be ≈4.1. Results of the three dimensional structure-activity relationship analyses were consistent with those obtained from the previously reported classical QSAR for 2-chlorobenzoyl analogs containing various para-substituents. The high activity of potent insecticides such as tebufenozide and chromafenozide were rationalized by CoMFA. Thus, this CoMFA result will be useful in the design of new compounds and in understanding the molecular mechanism of the ligand-receptor interactions.