6304-89-8

Basic information

• Product Name: 3-ACETOXYBENZOIC ACID
• Synonyms: m-acetoxybenzoicacid;RARECHEM AL BE 0249;3-(ACETYLOXY)BENZOIC ACID;3-ACETOXYBENZOIC ACID;3-Acetoxybenzoic acid 98%
• CAS NO: 6304-89-8
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.16
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;C9;Carbonyl Compounds;Carboxylic Acids;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 6304-89-8.mol
• Article Data: 40

Chemical Properties

• Melting Point: 131-134 °C(lit.)
• Boiling Point: 338.1°C at 760 mmHg
• Flash Point: 139°C
• Appearance: White/Powder
• Density: 1.29g/cm³
• Vapor Pressure: 3.93E-05mmHg at 25°C
• Refractive Index: 1.55
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: pK1: 4.00 (25°C)
• CAS DataBase Reference: 3-ACETOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETOXYBENZOIC ACID(6304-89-8)
• EPA Substance Registry System: 3-ACETOXYBENZOIC ACID(6304-89-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 6304-89-8(Hazardous Substances Data)

Usage

Description

3-Acetoxybenzoic acid, also known as 3-aBH, is an organic compound with the chemical formula C9H8O4. It is a derivative of benzoic acid, where a hydroxyl group is replaced by an acetoxy group. This modification gives 3-acetoxybenzoic acid unique chemical properties and makes it a versatile building block for various applications.

Uses

Used in Coordination Chemistry:
3-Acetoxybenzoic acid is used as a ligand in the preparation of coordination compounds. It forms complexes with metal ions, such as antimony and bismuth, resulting in bis-(3-acetoxybenzoato)triphenylantimony(V) and bis-(3-acetoxybenzoato)triphenylbismuth(V). These complexes have potential applications in various fields, including catalysis, medicine, and materials science.
Used in Lanthanide Complexes:
3-Acetoxybenzoic acid is also used as a ligand in the synthesis of lanthanide complexes, such as [Ln(3-ab)3(N2H4)2]·xH2O, where Ln represents lanthanide elements like La, Ce, Pr, Nd, Sm, and Gd, and N2H4 stands for hydrazine. These complexes have potential applications in areas such as luminescent materials, magnetic materials, and catalysts.
Used in Organic Synthesis:
3-Acetoxybenzoic acid serves as a starting material for the synthesis of 3-acetoxybenzoyl chloride, which is an important intermediate in the production of various pharmaceuticals, agrochemicals, and other organic compounds. The conversion of 3-acetoxybenzoic acid to 3-acetoxybenzoyl chloride allows for further functionalization and modification of the molecule, expanding its potential applications in the chemical industry.

InChI:InChI=1/C9H8O4/c1-6(10)13-8-4-2-3-7(5-8)9(11)12/h2-5H,1H3,(H,11,12)

Upstream product

• 99-06-9 3-Carboxyphenol 
• 75-36-5 acetyl chloride 
• 6548-96-5 2,4-dinitronaphthyl acetate 
• 830-03-5 4-nitrophenol acetate 
• 122-46-3 3-acetoxytoluene 
• 34241-39-9 azobisisobutyronitrile 
• 143435-52-3 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione 
• 24781-23-5 3-acetoxybenzoic acid methyl ester 
• 108-39-4 3-methyl-phenol 
• 20375-42-2 3-(3-acetoxyphenyl)-2-acrylic acid 
• 14755-02-3 3-hydroxycinnamic acid 
• 124-38-9 carbon dioxide 
• 13031-39-5 3-chlorophenyl acetate 
• 108-24-7 acetic anhydride 

Downstream Products

• 98-89-5 Cyclohexanecarboxylic acid 
• 905584-18-1 4-(3-acetoxybenzoyloxy)benzaldehyde 
• 258862-89-4 3-(3-acetoxybenzamido)-4-chloro-N-(3-fluoro-5-morpholinophenyl)benzamide 
• 1048025-57-5 3-acetoxy-2,6-diiodobenzoic acid 
• 1391926-53-6 C₁₁H₁₃NO₃ 
• 1477503-50-6 C₁₆H₁₂ClF₃N₂O₃ 
• 1477503-51-7 3-(8-chloro-6-(trifluoromethyl)imidazo[1,5-a]pyridin-3-yl)phenyl acetate 
• 1477503-66-4 3-(8-chloro-6-(trifluoromethyl)imidazo[1,5-a]pyridin-3-yl)phenyl cyclohexane carboxylate 
• 1477503-67-5 1-(3-(8-chloro-6-(trifluoromethyl)imidazo[1,5-a]pyridin-3-yl)phenoxy)propan-2-one 
• 1477503-52-8 C₁₄H₈ClF₃N₂O 
• 591-27-5 m-Hydroxyaniline 
• 108-46-3 recorcinol 

Relevant articles and documents

Structure-Activity Study of Nitazoxanide Derivatives as Novel STAT3 Pathway Inhibitors

We identified nitazoxanide (NTZ) as a moderate STAT3 pathway inhibitor through immunoblot analysis and a cell-based IL-6/JAK/STAT3 pathway activation assay. A series of thiazolide derivatives were designed and synthesized to further validate the thiazolide scaffold as STAT3 inhibitors. Eight out of 25 derivatives displayed potencies greater than that of NTZ, and their STAT3 pathway inhibitory activities were found to be significantly correlated with their antiproliferative activities in HeLa cells. Derivatives 15 and 24 were observed to be more potent than the positive control WP1066, which is under phase I clinical trials. Compared with NTZ, 15 also exhibited much improved in vivo pharmacokinetic parameters in rats and efficacies against proliferations in multiple cancer cell lines, indicating a broad-spectrum effect of these thiazolides as antitumor agents targeted on STAT3.

Discovery of 4-methyl-N-(4-((4-methylpiperazin- 1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((6-(pyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-oxy)benzamide as a potent inhibitor of RET and its gatekeeper mutant

The receptor tyrosine kinase rearranged during transfection (RET) plays pivotal roles in several cancers, including thyroid carcinoma and non-small cell lung cancer (NSCLC). Currently, there are several FDA-approved RET inhibitors, but their indication is limited to thyroid cancer, and none can overcome their gatekeeper mutants (V804L and V804M). Here, we report the discovery of 9x representing a new chemotype of potent and selective RET inhibitors, using a rational design strategy of type II kinase inhibitors. 9x exhibited both superior antiproliferative activities against NSCLC-related carcinogenic fusions KIF5B-RET and CCDC6-RET and gatekeeper mutant-transformed Ba/F3 cells, with the lowest GI50 of 9 nM, and substantial inhibitory activities against wild-type RET and RET mutant proteins, with the best IC50 of 4 nM. More importantly, 9x also showed nanomole potency against RET-positive NSCLC cells LC-2/ad, but not against a panel of RET-negative cancer cells, such as A549, H3122, A375 or parental Ba/F3 cells, demonstrating its selective ‘on-target’ effect. In mouse xenograft models, 9x repressed tumor growth driven by both wild type KIF5B-RET-Ba/F3 and gatekeeper mutant KIF5B-RET(V804M)-Ba/F3 cells in a dose-dependent manner. Together, these data establish that 9x provides a good starting point for the development of targeted therapeutics against RET-positive cancers, especially NSCLC.

Technological method for preparing m-aminophenol

The invention relates to a technological method for preparing m-aminophenol, belongs to the technical field of chemical material preparation and solves the technical problem of limit caused by utilizing phenyl acetate as a preparation raw material. The technological method disclosed by the invention has the advantages of simpleness in operation, high product yield, reaction easy to control and thelike. The technological method is characterized by comprising the steps: preparing 3-carboxyphenyl phenyl acetate after preparing m-cresyl acetate and utilizing the prepared 3-carboxyphenyl phenyl acetate to prepare the m-aminophenol. The technological method comprises the steps: a, taking a C9H8O4 solvent, adding into an ethyl acetate solution, fully stirring until complete dissolution, dropwiseadding thionyl chloride into a system under the ice water bath condition, thermally insulating 1+/-0.5 hours, warming to 60 DEG C and refluxing; b, under the ice water bath condition, adding triethylamine and hydroxylamine hydrochloride into the system, thermally insulating for 2 hours and warming to a room temperature; c, spin drying the solvent on a rotary evaporator, then adding water and potassium carbonate, warming to 60 to 70 DEG C and hydrolyzing; d, utilizing ethyl acetate to extract the solution, utilizing a thin-layer chromatography to determine whether extraction is complete and obtaining the finished product of the m-aminophenol after the extraction is finished.