188187-03-3

Basic information

• Product Name: METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE
• Synonyms: METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE;Benzoic acid, 2-(bromomethyl)-3-chloro-, methyl ester;2-(BroMoMethyl)-3-chloro-benzoic acid Methyl ester
• CAS NO: 188187-03-3
• Molecular Formula: C₉H₈BrClO₂
• Molecular Weight: 263.52
• Mol File: 188187-03-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 330.979 °C at 760 mmHg
• Flash Point: 153.971 °C
• Appearance: /
• Density: 1.561 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE(188187-03-3)
• EPA Substance Registry System: METHYL 2-BROMOMETHYL-3-CHLORO-BENZOATE(188187-03-3)

Safety Data

• RIDADR: 3261
• HazardClass: 8
• PackingGroup: Ⅱ
• Hazardous Substances Data: 188187-03-3(Hazardous Substances Data)

Usage

General Description

Methyl 2-bromomethyl-3-chloro-benzoate is a chemical compound that falls into the category of organic compounds known as benzoic acids and derivatives. These are compounds containing a benzene ring which bears at least one carboxyl group. The chemical is used in research and industrial settings. The bromine and chlorine substituents on the benzene ring are halogens, which often indicate that the molecule can participate in electrophilic aromatic substitution reactions. The ester group (benzoate) suggests that it could possibly be metabolized in organisms through ester hydrolysis reactions. However, specific information about its toxicity, reactivity, and environmental impact vary and should be evaluated in the context of its specific use.

InChI:InChI=1/C9H8BrClO2/c1-13-9(12)6-3-2-4-8(11)7(6)5-10/h2-4H,5H2,1H3

Upstream product

• 7499-08-3 3-chloro-2-methylbenzoic acid 
• 99586-84-2 methyl 2-methyl-3-chlorobenzoate 

Downstream Products

• 1449754-12-4 C₂₁H₂₈ClF₂N₃O₃ 
• 1427309-44-1 tert-butyl 4-[(3S,4R)-3-[2-(tert-butoxy)-2-oxoethyl]-1-{[2-chloro-6-(difluoromethyl)phenyl]methyl}-4-methylpyrrolidin-3-amido]piperidine-1-carboxylate 
• 1427058-40-9 2-[(3S,4R)-1-{[2-chloro-6-(difluoromethyl)phenyl]methyl}-3-{[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetic acid 

Relevant articles and documents

HPK1 ANTAGONISTS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of HPK1, and the treatment of HPK1-mediated disorders.

Rapid generation of novel benzoic acid–based xanthine derivatives as highly potent, selective and long acting DPP-4 inhibitors: Scaffold-hopping and prodrug study

A series of novel xanthine derivatives 2a-l incorporating benzoic acid moieties were rapidly generated by using strategy of scaffold-hopping from our previously reported scaffold uracil to xanthine, a scaffold of approved drug linagliptin. After systematic structure-activity relationship (SAR) study around benzoic acid moieties, 5 novel DPP-4 inhibitors with low picomolar potency range (IC50 50 value of 0.1 nM for DPP-4, showed 22-fold improvement in inhibitory activity compared to lead compound uracil 1, its activity was 45-fold more potent than alogliptin. 2e, 2f, 2i and 2k were selected for pharmacokinetic evaluation, and 2f and 2i showed the better pharmacokinetic profiles after iv administration, but poor oral bioavailability. To improve the oral pharmacokinetic profile, prodrug design approach was performed around 2f and 2i. Esters of 2f and 2i were synthesized and evaluated for stability, toxicity and pharmacokinetics. Compound 3e, the methyl ester of compound 2f, was identified to demonstrate good stability, low toxicity and improved oral bioavailability, with 3-fold higher blood concentration compared to 2f in rats. The following in vivo evaluations revealed 3e provided a sustained pharmacodynamics effect for 48h, and robustly improved glucose tolerance in normal ICR and db/db mice in dose-dependent manner. Chronic treatments investigations demonstrated that 3e achieved more beneficial effects on fasting blood glucose levels and glucose tolerance than alogliptin in type 2 diabetic db/db mice. The overall results have shown that compound 3e has the potential to efficacious, safety and long-acting treatment for T2DM.

Isosteric analogs of lenalidomide and pomalidomide: Synthesis and biological activity

A series of analogs of the immunomodulary drugs lenalidomide (1) and pomalidomide (2), in which the amino group is replaced with various isosteres, was prepared and assayed for immunomodulatory activity and activity against cancer cell lines. The 4-methyl and 4-chloro analogs 4 and 15, respectively, displayed potent inhibition of tumor necrosis factor-α (TNF-α) in LPS-stimulated hPBMC, potent stimulation of IL-2 in a human T cell co-stimulation assay, and anti-proliferative activity against the Namalwa lymphoma cell line. Both of these analogs displayed oral bioavailability in rat.