4068-78-4

Basic information

• Product Name: Methyl 5-chloro-2-hydroxybenzoate
• Synonyms: 5-chloro-2-hydroxy-benzoicacimethylester;RARECHEM AL BF 0041;BUTTPARK 34\07-98;LABOTEST-BB LT00033611;METHYL 5-CHLOROSALICYLATE;METHYL 5-CHLORO-2-HYDROXYBENZOATE;5-CHLORO-2-HYDROXYBENZOIC ACID METHYL ESTER;5-CHLORO METHYLSALICYLATE
• CAS NO: 4068-78-4
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.59
• EINECS: 223-778-5
• Product Categories: Aromatic Esters;Esters;Phenyls & Phenyl-Het;Intermediate of azasetron hcl;Phenyls & Phenyl-Het;C8 to C9;Carbonyl Compounds;alcohol| alkyl chloride|carboxylic ester
• Mol File: 4068-78-4.mol

Chemical Properties

• Melting Point: 46-50 °C(lit.)
• Boiling Point: 266.91°C (rough estimate)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.3245 (rough estimate)
• Vapor Pressure: 0.00751mmHg at 25°C
• Refractive Index: 1.5250 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.31±0.18(Predicted)
• CAS DataBase Reference: Methyl 5-chloro-2-hydroxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 5-chloro-2-hydroxybenzoate(4068-78-4)
• EPA Substance Registry System: Methyl 5-chloro-2-hydroxybenzoate(4068-78-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 4068-78-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 5-chloro-2-hydroxybenzoate is used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to undergo further chemical reactions makes it a valuable building block for the development of new drugs.
Used in Chemical Synthesis:
Methyl 5-chloro-2-hydroxybenzoate is used as a key component in the synthesis of N-p-methoxyphenylbenzimino-p-chloro-o-carbomethoxyphenyl ether, a compound with potential applications in the chemical industry.
Used in Iodination Process:
Methyl 5-chlorosalicylate can be iodinated to yield 3-iodo-5-chlorosalicylate, which may have further applications in the synthesis of other organic compounds or materials.

InChI:InChI=1/C8H7ClO3/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4,10H,1H3

Upstream product

• 67-56-1 methanol 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 16487-46-0 methyl N,N-dichlorocarbamate 
• 119-36-8 methyl salicylate 
• 13698-16-3 ethyl N,N-dichlorocarbamate 
• 76-06-2 chloropicrin 
• 117369-90-1 6-Chloro-3-oxo-hept-6-enoic acid methyl ester 
• 74-88-4 methyl iodide 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 124-41-4 sodium methylate 
• 75-36-5 acetyl chloride 
• 69-72-7 salicylic acid 

Downstream Products

• 66498-15-5 5-Chloro-2-{2-[4-(4-trifluoromethyl-phenoxy)-phenoxy]-propionyloxy}-benzoic acid methyl ester 
• 2643-11-0 N,N'-<1,5-Naphthylen>-bis-benzimidsaeure-bis<4-chlor-2-methoxycarbonyl-phenylester> 
• 52803-90-4 Methyl-5-chlor-2-(4-chlorbenzyloxy)benzoat 
• 85174-97-6 3-(5-Chlor-2-hydroxybenzoyl)-1-methyl-2-pyrrolidinon 
• 73050-77-8 chloro-5 α,α-diethyl hydroxy-2 benzene methanol 
• 88599-37-5 2-Carbamoyloxy-5-chloro-benzoic acid methyl ester 
• 85174-93-2 3-(5-Chlor-2-hydroxybenzoyl)-1-phenyl-2-pyrrolidinon 
• 115149-47-8 methyl-5-chloro-2-<3-(N-phthalimido)propoxy>benzoate 
• 75230-18-1 N-(5-Chloro-2-hydroxy-benzoyl)-N'-cyclooctyl-guanidine; hydrochloride 
• 5043-79-8 5-chloro-2-hydroxy-3-nitrobenzoic acid methyl ester 
• 103620-87-7 methyl 5-chloro-2-(phenylmethoxy)benzoate 
• 31456-94-7 methyl 2-allyloxy-5-chlorobenzoic acid 
• 125341-28-8 methyl 5-chloro-2-(3'-cyclohexenyl)salicylate 
• 6626-89-7 5-chloro-2-hydroxy-benzoic acid-(2-hydroxy-ethylamide) 

Relevant articles and documents

Design, modification of phyllanthone derivatives as anti-diabetic and cytotoxic agents

Twelve benzylidene derivatives, one Baeyer-Villiger oxidative, six imine derivatives were successfully designed and synthesised from phyllanthone. In the search for potential new anti-diabetic agents, phyllanthone along with its benzylidene and oxidation analogues were evaluated for enzyme inhibition against α-glucosidase. In the benzylidene series, most analogues displayed stronger activity than the mother compound. Compound 1c revealed the strongest activity, outperforming the acarbose positive control with an IC50 value of 19.59 μM. Phyllanthone and its derivatives were then tested for cytotoxic activity against the K562 cell line. The imine analogues displayed the most powerful cytotoxic activity with 3cand 3d having IC50 values of 57.55 and 68.02 μM, respectively.

Rhodium(III)-Catalyzed Oxidative Intramolecular 1,1-Oxyamination of Alkenes with Protected Amino Acids to Produce Oxazoloisoindole-2,5-diones

It has been established that an electron-deficient bis(ethoxycarbonyl)-substituted cyclopentadienyl (CpE) rhodium(III) complex catalyzes the oxidative intramolecular 1,1-oxyamination of alkenes with N-benzoyl amino acids to produce oxazoloisoindole-2,5-diones. Experimental and theoretical mechanistic studies revealed that this oxidative 1,1-oxyamination proceeds via not the aza-Wacker reaction but the formation of a rhoda(III)oxazolidine initiated by the carboxylic acid-directed N?H bond cleavage.

Synthesis and biological evaluation of novel 5,6,7-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents

5,6,7-Trimethoxy flavonoid salicylate derivatives were designed by the joining of three important pharmacophores (TMP, flavonoid, and SA) according to the combination principle. A series of novel trimethoxy flavonoid salicylate derivatives were synthesized and their in vitro anti-tumor activities were evaluated. Among these derivatives, compound 7f exhibited excellent antiproliferative activity against HGC-27 cells and MGC-803 cells with IC50 values of 10.26 ± 6.94 μM and 17.17 ± 3.03 μM, respectively. Subsequently, the effects on cell colony formation (clonogenic survival assay), cell migration (wound healing assay), cell cycle distribution (PI staining assay), cell apoptosis (Hoechst 33258 staining assay and annexin V-FITC/PI dual staining assay), lactate level (lactate measurement), microtubules disarrangement (immunofluorescence staining analysis) and docking posture (molecular docking simulation) were determined. Further western blot analysis confirmed that compound 7f could effectively down-regulate the expression of glycolysis-related proteins HIF-1α, PFKM and PKM2 and tumor angiogenesis-related proteins VEGF. Overall, these studies suggested that compound 7f, as the representative compound of those, might be a promising candidate for the treatment of gastric cancer and deserved the further studies.

Synthesis, α-glucosidase inhibition, and molecular docking studies of novel N-substituted hydrazide derivatives of atranorin as antidiabetic agents

A series of novel N-substituted hydrazide derivatives were synthesized by reacting atranorin, a compound with a natural depside structure (1), with a range of hydrazines. The natural product and 12 new analogues (2–13) were investigated for inhibition of α-glucosidase. The N-substituted hydrazide derivatives showed more potent inhibition than the original. The experimental results were confirmed by docking analysis. This study suggests that these compounds are promising molecules for diabetes therapy. Molecular dynamics simulations were carried out with compound 2 demonstrating the best docking model using Gromac during simulation up to 20 ns to explore the stability of the complex ligand-protein. Furthermore, the activity of all synthetic compounds 2–13 against a normal cell line HEK293, used for assessing their cytotoxicity, was evaluated.

A three-methoxy flavone salicylic acid derivatives and its anti-tumor activity (by machine translation)

The invention discloses a three-methoxy flavone salicylic acid derivatives, can be used as a tumor blood vessel and tumor cell glycolysis double-target inhibitors, in order to block the tumor tissue has generated the blood vessel, in order to block tumor cell nutrient supply, at the same time inhibiting glycolysis process of tumor cells, tumor cells in the absence of nutrition, also cannot use their own glycolysis proliferate, thereby accelerating the death of tumor cells. The design of this invention is of tumor blood vessel with the glycolysis double-target inhibitor has the role of both, but than the combined medication safer and more convenient. (by machine translation)

Evaluation of novel N′-(3-hydroxybenzoyl)-2-oxo-2H-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors

In an attempt to identify potential new agents that are active against HIV-1 IN, a series of novel coumarin-3-carbohydrazide derivatives were designed and synthesised. The toxicity profiles of these compounds showed that they were non-toxic to human cells and they exhibited promising anti-HIV-1 IN activities with IC50 values in nM range. Also, an accompanying molecular modeling study showed that the compounds bind to the active pocket of the enzyme.

Design, synthesis, and preliminary biological evaluation of 3′,4′,5′-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents

According to the pharmacophore combination principle, a set of new 3′,4′,5′-trimethoxy flavonoid salicylate derivatives were designed, synthesized, and evaluated for biological activity. The cytotoxicity evaluation revealed that compound 10v exhibited higher potency than 5-Fu against HCT-116 cells. Preliminary biological activity studies showed that compound 10v could inhibit the colony formation and migration of HCT-116 cells. Besides, the Hoechst 33258 staining assay and flow cytometry revealed that treatment with compound 10v induced the apoptosis of HCT-116 cells in a concentration-dependent manner, while it had no effect on their cell cycle. The WB analysis suggested that HIF-1α, tubulin, HK-2, and PFK might be the potential pharmacophore targets of compound 10v. Tubulin was a potential drug target for compound 10v, which was explained by analyzing the crystal structure of compound 10v complexed with tubulin. These results indicated that compound 10v might be a promising anti-tumor agent candidate, deserving further optimization and evaluation.

Gold promoted arylative cyclization of alkynoic acids with arenediazonium salts

Alkynoic acids derived from salicylic acid and analogues undergo arylative cyclization with arenediazonium salts promoted by gold in the absence of external ligands. The reaction is thermally induced and proceeds even in the absence of light. A difference in regioselectivity has been found compared with that observed in the cycloisomerization process of the same type of compounds.

2-ALKYLOXY BENZENE FORMYL ARYLAMINE COMPOUND AND PHARMACEUTICAL USE THEREOF

The present invention relates to 2-alkoxy benzene formyl arylamine compounds as scheme I , in which the R, G, X, Y, Z are consistent with the detailed description in the patent claim. The compounds can act as sphingomyelin synthase (SMS) inhibitors to treat diseases caused by abnormal increasing of sphingomyelin(SM). This invention also includes compounds as scheme I , their pharmaceutically acceptable salts, pharmaceutical compositions as the active ingredients, and their application in drugs which can prevent and cure diseases caused by SM level abnormal increase. These diseases include atherosclerosis, fatty liver, obesity, type II diabetes, and other metabolic syndromes.

COMPOUND HAVING ZNF143 INHIBITORY ACTIVITY AND USE THEREOF

PROBLEM TO BE SOLVED: To provide a compound having a ZNF143 inhibitory activity as well as to provide a ZNF143 inhibitory agent and pharmaceutical composition containing the same. SOLUTION: Provided is a compound represented by formula (I) or a salt thereof as well as a ZNF143 inhibitory agent containing the same and a pharmaceutical composition having the same as an active ingredient. A-B-C-D (I)[A is H, a methyl group, a naphthyl group, a phenyl group or a nitrogen-containing heterocyclic ring; B is as shown below, and C is an amide bond or a heteroaromatic ring containing N and O; D is a substituted/unsubstituted phenyl group or a monocyclic heteroaromatic ring containing N or S; and C and D are both fused heterocyclic ring or the like optionally having a substituent group.]. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPOandINPIT