10147-68-9

Basic information

• Product Name: 2-HYDROXY CHLOROACETOANILIDE
• Synonyms: 2-HYDROXY CHLOROACETOANILIDE;2-chloro-N-(2-hydroxyphenyl)acetaMide;2-CHLORO-2'-HYDROXYACETANILIDE
• CAS NO: 10147-68-9
• Molecular Formula: C₈H₈ClNO₂
• Molecular Weight: 185.61
• Mol File: 10147-68-9.mol

Chemical Properties

• Boiling Point: 376.7°C at 760 mmHg
• Flash Point: 181.6°C
• Appearance: /
• Density: 1.402g/cm³
• Vapor Pressure: 3.28E-06mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: 2-HYDROXY CHLOROACETOANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY CHLOROACETOANILIDE(10147-68-9)
• EPA Substance Registry System: 2-HYDROXY CHLOROACETOANILIDE(10147-68-9)

Safety Data

• Hazardous Substances Data: 10147-68-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy chloroacetoanilide is used as an intermediate in the synthesis of pharmaceuticals for its analgesic and antipyretic properties. It plays a crucial role in the development of pain relief medications, contributing to the management of pain and fever.
Used in Pesticide Industry:
In the pesticide industry, 2-Hydroxy chloroacetoanilide is utilized as a chemical intermediate, facilitating the production of various pesticides. Its involvement in this sector highlights its versatility in chemical synthesis and its contribution to agricultural chemical development.
Used in Dye Industry:
2-Hydroxy chloroacetoanilide is also used as an intermediate in the synthesis of dyes. Its chemical structure allows for the creation of a range of dye products, demonstrating its application in the colorants market and the textile industry.

InChI:InChI=1/C8H8ClNO2/c9-5-8(12)10-6-3-1-2-4-7(6)11/h1-4,11H,5H2,(H,10,12)

Upstream product

• 24265-34-7 2-nitrophenyl 2-chloroacetate 
• 79-04-9 chloroacetyl chloride 
• 95-55-6 2-amino-phenol 

Downstream Products

• 5428-96-6 carbamoylsulfanyl-acetic acid-(2-hydroxy-anilide) 
• 5466-88-6 3,4-dihydro-3-oxo-2H-1,4-benzoxazine 
• 106477-59-2 phenylsulfanyl-acetic acid-(2-hydroxy-anilide) 
• 102880-97-7 2-[(4-chloro-phenylsulfanyl)-methyl]-benzoxazole 
• 41014-43-1 2-(chloromethyl)benzoxazole 
• 916337-57-0 C₁₀H₁₂ClNO₃ 
• 73037-92-0 1-acetoxy-2-(2-chloro-acetylamino)-benzene 

Relevant articles and documents

The syntheses of nonnucleoside, HIV-1 reverse transcriptase inhibitors containing a CF2 group: The SRN1 reactions of 2-(bromodifluoromethyl)benzoxazole with the anions derived from heterocyclic thiols and phenolic compounds

In an effort to prepare new fluorine-containing compounds which are active against HIV, the SRN1 reactions of 2-(bromodifluoromethyl)benzoxazole (5) with the anions of heterocyclic thiols and phenolic compounds were carried out. The products (6

Carbamylmethyl Mercaptoacetate Thioether: A Novel Scaffold for the Development of L1 Metallo-β-lactamase Inhibitors

Given the clinical importance of metallo-β-lactamases (MβLs), a new scaffold, N-substituted carbamylmethyl mercaptoacetate thioether, was constructed. The obtained molecules 1-16 inhibited MβLs from all three subclasses, but preferentially L1 from subclass B3. Compound 9 with a p-carboxyphenyl substituent exhibited the broadest spectrum with at least 70% inhibition of enzymes from all subclasses at 100 μM, while compound 5 with a p-methylphenyl substituent was the most potent inhibitor of any individual enzyme, with 97% inhibition at 100 μM and an IC50 value of 0.41 μM against L1. Isothermal titration calorimetry assays corroborate findings from UV-vis spectrophotometric assays that the inhibition of L1 by 5 is dose-dependent. Docking studies suggest that the carboxyl group, the sulfide atom, and the carbonyl group of the carbamyl coordinate Zn2 in a chelating fashion. Using E. coli cells expressing L1, 6 and 8 were able to decrease cefazolin minimum inhibitory concentration 8-fold.

SYNTHESIS OF 2-(4-ARYL-1E,3E-BUTADIENYL)BENZOXAZOLES BY THE HORNER-WADSWORTH-EMMONS REACTION

2-(4-Aryl-1E,3E-butadienyl)benzoxazole derivatives were synthesized by the Horner-Wadsworth-Emmons reaction of 2-phosphorylmethylbenzoxazoles with cinnamaldehydes in fair to good yield.

Synthesis and reactivity of halogeno-difluoromethyl aromatics and heterocycles: Application to the synthesis of gem-difluorinated bioactive compounds

In an effort to prepare new fluorine-containing compounds which are active against HIV, and based on the electrochemical reduction of a series of bromodifluoromethyl compounds, the tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reduct

Synthesis, Molecular Docking and Biological Evaluation of 2-Aryloxy-N-Phenylacetamide and N′-(2-Aryloxyoxyacetyl) Benzohydrazide Derivatives as Potential Antibacterial Agents

A new class of 2-aryloxy-N-phenylacetamide and N′-(2-aryloxyoxyacetyl) benzohydrazide derivatives with different active moieties were synthesized and screened for their antibacterial activity. Structural characterization of synthesized compounds was perfo

Biosensitivity and Theoretical Electronic Structure Investigations on 3-(2-Hydroxyphenyl)-2-iminothiazolidin-4-one and Its Zn2+and Cd2+ Metal Complexes

A two-step cyclocondensation reaction has been carried out using 2-aminophenol with 2-chloroacetyl chloride to produce o-hydroxyphenyl chloroacetamide followed by treatment with KSCN in CH3COCH3 to produce the heterocyclic ligand 3-(2-hydroxyphenyl)-2-imi

Antidiabetic compounds

Compounds for the treatment of hyperglycemia and/or diabetes are provided. The compounds, which inhibit the enzyme dipeptidyl peptidase (DPP-4), are based on the structure where X may be present or absent an may be OH, Ar is an aryl group; and n ranges from 0 to 5.

Synthesis, antimicrobial, antioxidant and docking study of novel 2H-1,4-Benzoxazin-3(4H)-One derivatives

A NOVEL series of 1,4-benzoxazinone derivatives were synthesized and characterized using FT-IR , 1H-NMR, 13C-NMR and Mass spectroscopy. These compounds were in vitro screened against several bacterial species gram positive and gram negative as well as Candida albicans and found exhibiting moderate to potent activity. The antioxidant study was confirmed for the synthesized derivatives against 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical. Docking study for the potent compound 8 against glucosamine-6-phosphate synthase , the target enzyme for the antimicrobial agents was explored to explain the interactions of the discovered hits with in the amino acid residues of the enzyme active side. The docking parameters enhanced the activity of new compound as promising antimicrobial agents.

Discovery and characterization of novel imidazopyridine derivative CHEQ-2 as a potent CDC25 inhibitor and promising anticancer drug candidate

Cell division cycle (CDC) 25 proteins are key phosphatases regulating cell cycle transition and proliferation via the interactions with CDK/Cyclin complexes. Overexpression of CDC25 proteins is frequently observed in cancer and is related to aggressiveness, high-grade tumors and poor prognosis. Thus, inhibiting CDC25 activity in cancer treatment appears a good therapeutic strategy. In this article, refinement of the initial hit XDW-1 by synthesis and screening of a focused compound library led to the identification of a novel set of imidazopyridine derivatives as potent CDC25 inhibitors. Among them, the most potent molecule was CHEQ-2, which could efficiently inhibit the activities of CDC25A/B enzymes as well as the proliferation of various different types of cancer cell lines in vitro assay. Moreover, CHEQ-2 triggered S-phase cell cycle arrest in MCF-7, HepG2 and HT-29 cell lines, accompanied by generation of ROS, mitochondrial dysfunction and apoptosis. Besides, oral administration of CHEQ-2 (10 mg/kg) significantly inhibited xenografted human liver tumor growth in nude mice, while demonstrated extremely low toxicity (LD50 > 2000 mg/kg). These findings make CHEQ-2 a good starting point for further investigation and structure modification.

A concise and efficient synthesis of substituted morpholines

A simple and efficient method has been developed for the synthesis of substituted morpholines by a sequence of coupling, cyclization, and reduction reactions of easily available amino alcohols and α-halo acid chlorides. Various mono-, di-, and trisubstituted morpholines, spiro morpholines, and ring-fused morpholines, as well as morpholine homologues, were synthesized in good to excellent yields by a single methodology under similar reaction conditions. The method was also used in a multigram synthesis of (3S)-3-methylmorpholine.