17738-71-5

Basic information

• Product Name: (4-CHLOROPHENYL)AMINO](OXO)ACETIC ACID
• Synonyms: Aceticacid, [(4-chlorophenyl)amino]oxo- (9CI); Oxanilic acid, 4'-chloro- (8CI);4'-Chlorooxanilic acid; N-(4-Chlorophenyl)oxamic acid; p-Chlorooxanilic acid
• CAS NO: 17738-71-5
• Molecular Formula: C₈H₆ClNO₃
• Molecular Weight: 199.59114
• Mol File: 17738-71-5.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.546g/cm³
• CAS DataBase Reference: (4-CHLOROPHENYL)AMINO](OXO)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (4-CHLOROPHENYL)AMINO](OXO)ACETIC ACID(17738-71-5)
• EPA Substance Registry System: (4-CHLOROPHENYL)AMINO](OXO)ACETIC ACID(17738-71-5)

Safety Data

• Hazardous Substances Data: 17738-71-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(4-CHLOROPHENYL)AMINO](OXO)ACETIC ACID is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical structure allows it to serve as a building block in the development of new medications, potentially contributing to advancements in healthcare.
Used in Dye and Pigment Production:
In the chemical industry, (4-CHLOROPHENYL)AMINO](OXO)ACETIC ACID is utilized in the production of dyes and pigments. Its chemical properties make it a valuable component in the creation of a wide range of colorants used in various applications, from textiles to plastics.
Used in Environmental Research:
Given its suspected environmental toxicity, (4-CHLOROPHENYL)AMINO](OXO)ACETIC ACID is also used in environmental research to study its potential impact on aquatic life and ecosystems. This research can help in the development of strategies to mitigate its harmful effects and ensure the safety of water systems.

InChI:InChI=1/C8H6ClNO3/c9-5-1-3-6(4-2-5)10-7(11)8(12)13/h1-4H,(H,10,11)(H,12,13)/p-1

Upstream product

• 17722-17-7 N-(4-chlorophenyl)-2-cyanoacetamide 
• 41374-66-7 methyl 2-[(4-chlorophenyl)amino]-2-oxoacetate 
• 106-47-8 4-chloro-aniline 
• 5397-14-8 ethyl 2-[(4-chlorophenyl)amino]-2-oxoacetate 
• 4755-77-5 Ethyl oxalyl chloride 
• 17118-74-0 ethyl oxalylchloride 

Downstream Products

• 104-12-1 p-chlorphenylisocyanate 
• 1040763-02-7 C₂₁H₁₁BrCl₂F₃N₃O₃ 
• 1253393-98-4 C₁₄H₁₈ClN₃O₂ 
• 1211293-87-6 C₂₀H₂₂ClN₃O₂ 
• 20406-14-8 4-Chlor-oxanilsaeurechlorid 
• 331264-58-5 C₁₄H₁₇ClN₂O₂ 
• 1354933-57-5 C₁₆H₁₁ClN₂O₄ 
• 333353-44-9 NBD-556 
• 1375736-72-3 N¹-(4-chlorophenyl)-N²-((5-(hydroxymethyl)-4-methylthiazol-2-yl)(pyrrolidin-2-yl)methyl)oxalamide formate 
• 1375736-74-5 N¹-(4-chlorophenyl)-N²-((5-(2-hydroxyethyl)-4-methylthiazol-2-yl)(pyrrolidin-2-yl)methyl)oxalamide formate 
• 1375736-76-7 N¹-(4-chlorophenyl)-N²-(1-ethyl-1H-pyrazol-4-yl)oxalamide 
• 1376434-46-6 N₁-(4-chlorophenyl)-N₂-((5-(2-hydroxyethyl)-4-methylthiazol-2-yl)(piperidin-3-yl)methyl)oxalamide dihydrochloride 
• 1375736-69-8 N¹-(4-chlorophenyl)-N²-((5-(2-hydroxyethyl)-4-methylthiazol-2-yl)(1-methylpiperidin-2-yl)methyl)oxalamide 

Relevant articles and documents

Exploratory studies on soluble small molecule CD4 mimics as HIV entry inhibitors

Several small molecule CD4 mimics, which inhibit the interaction of gp120 with CD4, have been developed. Original CD4 mimics such as NBD-556, which has an aromatic ring, an oxalamide linker and a piperidine moiety, possess significant anti-HIV activity bu

Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates

We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, and phosgene-free route includes the generation of an isocyanate intermediate in situ via anodic decarboxylation of an oxamic acid in the presence of an organic base, followed by the one-pot addition of suitable nucleophiles to afford the corresponding ureas, carbamates, and thiocarbamates. This procedure is applicable to different amines, alcohols, and thiols. Furthermore, when single-pass continuous electrochemical flow conditions were used and this reaction was run in a carbon graphite Cgr/Cgr flow cell, urea compounds could be obtained in high yields within a residence time of 6 min, unlocking access to substrates that were inaccessible under batch conditions while being easily scalable.

Direct C-H Functionalization of Phenanthrolines: Metal- And Light-Free Dicarbamoylations

A direct method for C-H dicarbamoylations of phenanthrolines has been developed, which is capable of directly installing primary, secondary as well as tertiary amides. This is a significant improvement on the previous direct method, which was limited to primary amides. The metal-, light-, and catalyst-free Minisci-type reaction is cheap, operationally simple, and scalable. We demonstrate that the step efficiency toward dicarbamoylated phenanthroline targets can now be significantly improved.

Direct C3 Carbamoylation of 2H-Indazoles

We developed a novel method for direct C3 carbamoylation of 2H-indazoles using oxamic acids as carbamoyl radical sources. In the presence of ammonium persulfate, carbamoyl radicals were generated from oxamic acids, then used for further reactions with 2H-indazoles to afford the desired products. The reaction proceeds under metal- and catalyst-free conditions. This simple process allows for the efficient synthesis of C3 carbamoylated 2H-indazoles, which are important scaffolds in organic synthesis.

POLYCYCLIC COMPOUND ACTING AS IDO INHIBITOR AND/OR IDO-HDAC DUAL INHIBITOR

The present invention provides polycyclic compounds as IDO inhibitors and/or dual inhibitors of IDO-HDAC. Specifically, the present invention provides compounds represented by the following formula (I), wherein each group is defined as described in the specification. The compounds have IDO inhibitory activity or IDO-HDAC dual inhibitory activity and can be used for preventing or treating diseases associated with IDO and/or IDO-HDAC activity or expression levels. At the same time, the compounds of the present invention can be combined with an antitumor antibody such as PD-1 and PD-L1, and such a combination can greatly increase the antitumor response rate of the antibody and broaden the types of tumors to be treated.

Design, synthesis, and antiviral activity of entry inhibitors that target the CD4-binding site of HIV-1

The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next- generation therapeutics and microbicides against HIV-1.

Synthesis and biological evaluation of novel oxalamido derivatives as caspase-3 inhibitors

A new series of 5-fluoro-3-[(4-substituted-phenylaminooxalyl)-amino]-4-oxo- pentanoic acid, 7a-c, 3-[(4-substitutedphenylaminooxalyl)- amino]-4-oxo-5-(2,3, 5,6-tetrafluoro-phenoxy)-pentanoic acid, 7d-h and 5-(2,6-difluoro-phenoxy)-3- [(substituted-phenylaminooxalyl)-amino]-4-oxo-pentanoic acid, 7i-p have been synthesized from N-(substituted-phenyl)- oxalamic acid, 1 and their activities have been evaluated in vitro. Compounds 7b,c and k show low micromolar inhibitory activity against caspase-3.

CD4 mimics targeting the HIV entry mechanism and their hybrid molecules with a CXCR4 antagonist

Small molecules behaving as CD4 mimics were previously reported as HIV-1 entry inhibitors that block the gp120-CD4 interaction and induce a conformational change in gp120, exposing its co-receptor-binding site. A structure-activity relationship (SAR) study of a series of CD4 mimic analogs was conducted to investigate the contribution from the piperidine moiety of CD4 mimic 1 to anti-HIV activity, cytotoxicity, and CD4 mimicry effects on conformational changes of gp120. In addition, several hybrid molecules based on conjugation of a CD4 mimic analog with a selective CXCR4 antagonist were also synthesized and their utility evaluated.

Synthesis, crystal structure, and insecticidal activity of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole

Two series of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole were synthesized, and their structures were characterized by 1H NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities, and their insecticidal activities against oriental armyworm, mosquito, and spider mite are comparable to those of the commercialized Chlorfenapyr.

Diamine derivatives

A compound represented by the general formula (1): Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4??(1) wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.