54810-63-8

Basic information

• Product Name: Methyl 2-Chloro-5-methoxybenzoate
• Synonyms: Methyl 2-Chloro-5-methoxybenzoate
• CAS NO: 54810-63-8
• Molecular Formula: C₉H₉ClO₃
• Molecular Weight: 200.61896
• Mol File: 54810-63-8.mol

Chemical Properties

• Boiling Point: 108-110 °C(Press: 0.2 Torr)
• Appearance: /
• Density: 1.228±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Methyl 2-Chloro-5-methoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-Chloro-5-methoxybenzoate(54810-63-8)
• EPA Substance Registry System: Methyl 2-Chloro-5-methoxybenzoate(54810-63-8)

Safety Data

• Hazardous Substances Data: 54810-63-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-Chloro-5-methoxybenzoate is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl 2-Chloro-5-methoxybenzoate serves as an intermediate in the production of agrochemicals, playing a crucial role in the formulation of effective pesticides and other agricultural chemicals.
Used in Fragrance and Flavor Industry:
Methyl 2-Chloro-5-methoxybenzoate is utilized as a component in the creation of fragrances and flavors, capitalizing on its distinctive aromatic properties to enhance the sensory characteristics of various consumer products.
Used in Chemical Industry:
Beyond its applications in specific sectors, Methyl 2-Chloro-5-methoxybenzoate is broadly employed in the chemical industry for the manufacturing of a wide array of products, highlighting its versatility and importance in chemical synthesis.

InChI:InChI=1/C9H9ClO3/c1-12-6-3-4-8(10)7(5-6)9(11)13-2/h3-5H,1-2H3

Upstream product

• 67-56-1 methanol 
• 586-38-9 3-Methoxybenzoic acid 
• 56961-30-9 2-chloro-5-hydroxybenzoic acid 
• 74-88-4 methyl iodide 
• 5368-81-0 methyl 3-methoxybenzoate 
• 89-54-3 2-chloro-5-aminobenzoic acid 
• 6280-89-3 2-chloro-5-methoxybenzoic acid 

Downstream Products

• 96826-30-1 2-(2-Chloro-5-methoxy-phenyl)-propan-2-ol 
• 101252-66-8 (2-chloro-5-methoxyphenyl)methanol 
• 6280-89-3 2-chloro-5-methoxybenzoic acid 
• 56961-30-9 2-chloro-5-hydroxybenzoic acid 
• 882674-30-8 2-(2-chloro-5-methoxyphenyl)ethan-1-amine 
• 13719-61-4 2-chloro-5-methoxybenzaldehyde 
• 1417409-64-3 8-bromo-1-(2-chloro-5-methoxyphenyl)-4-methyl[1,2,4]triazolo[4,3-a]quinoxaline 
• 1417409-83-6 1-(2-chloro-5-methoxyphenyl)-4-methyl-8-(morpholin-4-ylmethyl)[1,2,4]triazolo[4,3-a]quinoxaline 
• 92492-22-3 4-(2-Chlor-5-methoxy-phenyl)-buttersaeure 
• 90919-41-8 (2-chloro-5-methoxy-phenyl)-acetic acid methyl ester 
• 90562-49-5 C-(2-Chlor-5-methoxy-phenyl)-acetamid 
• 93089-30-6 2-<β-(2-Chlor-5-methoxy-phenyl)-ethyl>-malonsaeure-diethylester 
• 91393-84-9 2-<β-(2-Chlor-5-methoxy-phenyl)-ethyl>-malonsaeure 
• 91367-10-1 2-(2-chloro-5-methoxy-phenyl)acetic acid 

Relevant articles and documents

ADAMANTANYL-SUBSTITUTED BENZAMIDE COMPOUNDS AND THEIR USE AS P2X7 RECEPTOR ANTAGONISTS

The present invention relates to adamantanyl-substituted benzamide compounds and their use as antagonists of the P2X7 purinoreceptor. The invention further relates to methods for the treatment of disease and conditions associated with the P2X7 purinoreceptor.

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe3 or PhSSPh

We developed a mild aromatic halogenation reaction using a combination of N-halosuccinimide and PhSSiMe3 or PhSSPh. Less reactive aromatic compounds, such as methyl 4-methoxybenzoate, were brominated with PhSSiMe3 or PhSSPh and N-bromosuccinimide in high yields. No reaction was observed in the absence of PhSSiMe3 or PhSSPh. This method is also applicable to chlorination reactions using N-chlorosuccinimide and PhSSPh.

Optimization of a Benzoylpiperidine Class Identifies a Highly Potent and Selective Reversible Monoacylglycerol Lipase (MAGL) Inhibitor

Monoacylglycerol lipase (MAGL) is the enzyme degrading the endocannabinoid 2-arachidonoylglycerol, and it is involved in several physiological and pathological processes. The therapeutic potential of MAGL is linked to several diseases, including cancer. The development of MAGL inhibitors has been greatly limited by the side effects associated with the prolonged MAGL inactivation. Importantly, it could be preferable to use reversible MAGL inhibitors in vivo, but nowadays only few reversible compounds have been developed. In the present study, structural optimization of a previously developed class of MAGL inhibitors led to the identification of compound 23, which proved to be a very potent reversible MAGL inhibitor (IC50 = 80 nM), selective for MAGL over the other main components of the endocannabinoid system, endowed of a promising antiproliferative activity in a series of cancer cell lines and able to block MAGL both in cell-based as well as in vivo assays.

The role of polycyclic frameworks in modulating P2X7 receptor function

Herein we describe our recent attempts to target the P2X7 receptor for potential treatment of neurological disorders. This work focusses on different polycycles including carborane, adamantane or cubane, joined by either a cyanoguanidine or an amide linker to phenyl or isoquinoline moieties. We have demonstrated the superiority of the adamantyl moiety over other polycycles in terms of synthetic accessibility and biological (cellular) activity. We have also shown that an amide or cyanoguanidine linker can greatly alter the biological activity of compounds. This SAR study provides important insights into the types of functionality required to target the P2X7 receptor.

Mathematical and Structural Characterization of Strong Nonadditive Structure-Activity Relationship Caused by Protein Conformational Changes

In medicinal chemistry, accurate prediction of additivity-based structure-activity relationship (SAR) analysis rests on three assumptions: (1) a consistent binding pose of the central scaffold, (2) no interaction between the R group substituents, and (3) a relatively rigid binding pocket in which the R group substituents act independently. Previously, examples of nonadditive SAR have been documented in systems that deviate from the first two assumptions. Local protein structural change upon ligand binding, through induced fit or conformational selection, although a well-known phenomenon that invalidates the third assumption, has not been linked to nonadditive SAR conclusively. Here, for the first time, we present clear structural evidence that the formation of a hydrophobic pocket upon ligand binding in PDE2 catalytic site reduces the size of another distinct subpocket and contributes to strong nonadditive SAR between two otherwise distant R groups.

Room temperature C(sp2)-H oxidative chlorination: Via photoredox catalysis

Photoredox catalysis has been developed to achieve oxidative C-H chlorination of aromatic compounds using NaCl as the chlorine source and Na2S2O8 as the oxidant. The reactions occur at room temperature and exhibit exclusive selectivity for C(sp2)-H bonds over C(sp3)-H bonds. The method has been used for the chlorination of a diverse set of substrates, including the expedited synthesis of key intermediates to bioactive compounds and a drug.

POLYCYCLIC MOLECULAR COMPOUNDS

This invention relates to compounds of Formula (I), wherein A is a carboaromatic or heteroaromatic ring having one or more substituents; R6 Formula (A) is optionally substituted with one or more substituents; and n is 0, 1 or an integer greater than 1 and when n is 1 or greater the bond or bonds between the carbon atoms may be saturated or unsaturated, which bind the P2X7 receptor with high affinity. This invention also relates to methods for the diagnosis, treatment or monitoring of disorders in which the P2X7 receptor is implicated, in particular the diagnosis, treatment or monitoring of (the progression of) neuroinflammatory and neurodegenerative disorders in a subject.

Cubyl amides: Novel P2X7 receptor antagonists

Polycyclic amides 2 and 5-9 were successfully synthesised and their lipophilicity profiles were evaluated using reverse-phase HPLC. All synthesised compounds possessed P2X7R antagonistic properties when tested on rat spinal cord microglia cells. Extensive screening for binding to other neuroreceptor subtypes demonstrated their P2X7 selectivity.