114897-92-6

Basic information

• Product Name: 4-Bromo-2-fluorophenylacetic acid
• Synonyms: 4-Bromo-2-fluorophenylacetic acid
• CAS NO: 114897-92-6
• Molecular Formula: C₈H₆BrFO₂
• Molecular Weight: 233.0344432
• Mol File: 114897-92-6.mol

Chemical Properties

• Boiling Point: 320.432 °C at 760 mmHg
• Flash Point: 147.592 °C
• Appearance: /Solid
• Density: 1.698 g/cm³
• Vapor Pressure: 0.000132mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.89±0.10(Predicted)
• CAS DataBase Reference: 4-Bromo-2-fluorophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-fluorophenylacetic acid(114897-92-6)
• EPA Substance Registry System: 4-Bromo-2-fluorophenylacetic acid(114897-92-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 114897-92-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-fluorophenylacetic acid is used as a pharmaceutical intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its unique structure allows it to serve as a building block in the development of new medications, particularly those targeting specific biological pathways or receptors.
Used in Scientific Research:
In addition to its applications in the pharmaceutical industry, 4-Bromo-2-fluorophenylacetic acid is also utilized in scientific research. Researchers use this compound to study its chemical properties, reactivity, and potential interactions with other molecules. This can lead to a better understanding of its potential applications and the development of new methodologies or techniques in organic chemistry.

Synthesis

4-Bromo-2-fluorophenylacetic acid can be prepared by reacting 2-(4-bromo-2-fluorophenyl)acetonitrile with MeOH in NaOH solution.

InChI:InChI=1/C8H6BrFO2/c9-6-2-1-5(3-8(11)12)7(10)4-6/h1-2,4H,3H2,(H,11,12)

Upstream product

• 114897-91-5 (4-bromo-2-fluorophenyl)acetonitrile 
• 924312-09-4 ethyl 2-(4-bromo-2-fluorophenyl)acetate 
• 76283-09-5 4-bromo-2-fluorobenzyl bromide 
• 151982-51-3 4-bromo-2-fluorobenzoyl chloride 
• 112704-79-7 2-fluoro-4-bromobenzoic acid 
• 1000668-71-2 2-(4-bromo-2-fluorophenyl)acetamide 

Downstream Products

• 193290-20-9 2-(4-bromo-2-fluorophenyl)ethan-1-ol 
• 5366-51-8 2-(2-fluorobiphenyl-4-yl)acetic acid 
• 1008779-97-2 (4-bromo-2-ethoxy-5-methylphenyl)acetic acid 
• 193290-19-6 methyl 2-(4-bromo-2-fluoro-phenyl)acetate 
• 1370447-94-1 2-(4-bromo-2-fluorophenyl)ethyl methanesulfonate 
• 1370447-97-4 4-[2-(4-bromo-2-fluorophenyl)ethyl]morpholine 
• 1370446-23-3 2-[3-(3-chlorophenyl)-1-{3-fluoro-4-[2-(morpholin-4-yl)ethyl]phenyl}-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]-N-(propan-2-yl)acetamide 

Relevant articles and documents

Discovery of a First-in-Class Gut-Restricted RET Kinase Inhibitor as a Clinical Candidate for the Treatment of IBS

Abdominal pain and abnormal bowel habits represent major symptoms for irritable bowel syndrome (IBS) patients that are not adequately managed. Although the etiology of IBS is not completely understood, many of the functions of the gastrointestinal (GI) tract are regulated by the enteric nervous system (ENS). Inflammation or stress-induced expression of growth factors or cytokines may lead to hyperinnervation of visceral afferent neurons in GI tract and contribute to the pathophysiology of IBS. Rearranged during transfection (RET) is a neuronal growth factor receptor tyrosine kinase critical for the development of the ENS as exemplified by Hirschsprung patients who carry RET loss-of-function mutations and lack normal colonic innervation leading to colonic obstruction. Similarly, RET signaling in the adult ENS maintains neuronal function by contributing to synaptic formation, signal transmission, and neuronal plasticity. Inhibition of RET in the ENS represents a novel therapeutic strategy for the normalization of neuronal function and the symptoms of IBS patients. Herein, we describe our screening effort and subsequent structure-activity relationships (SARs) in optimizing potency, selectivity, and mutagenicity of the series, which led to the discovery of a first-in-class, gut-restricted RET kinase inhibitor, 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)acetamide (15, GSK3179106), as a clinical candidate for the treatment of IBS. GSK3179106 is a potent, selective, and gut-restricted pyridone hinge binder small molecule RET kinase inhibitor with a RET IC50 of 0.3 nM and is efficacious in vivo.

CRYSTALLINE FORMS OF 2-(4-(4-ETHOXY-6-OXO-1,6-DIHYDROPYRIDIN-3-YL)-2-FLUOROPHENYL)-N-(5-(1,1,1-TRIFLUORO-2-METHYLPROPAN-2-YL)ISOXAZOL-3-YL)ACETAMIDE

Disclosed are novel crystalline forms of 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin- 3-yl)-2-fluorophenyl)-N-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)acetamide and pharmaceutical compositions containing the same. Also disclosed are processes for the preparation thereof and methods for use thereof.

PYRIDONE DERIVATIVES AS REARRANGED DURING TRANSFECTION (RET) KINASE INHIBITORS

This invention relates to novel compounds which are inhibitors of the Rearranged during Transfection (RET) kinase, to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy, alone or in combination, for the normalization of gastrointestinal sensitivity, motility and/or secretion and/or abdominal disorders or diseases and/or treatment related to diseases related to RET dysfunction or where modulation of RET activity may have therapeutic benefit including but not limited to all classifications of irritable bowel syndrome (IBS) including diarrhea-predominant, constipation-predominant or alternating stool pattern, functional bloating, functional constipation, functional diarrhea, unspecified functional bowel disorder, functional abdominal pain syndrome, chronic idiopathic constipation, functional esophageal disorders, functional gastroduodenal disorders, functional anorectal pain, inflammatory bowel disease, proliferative diseases such as non-small cell lung cancer, hepatocellular carcinoma, colorectal cancer, medullary thyroid cancer, follicular thyroid cancer, anaplastic thyroid cancer, papillary thyroid cancer, brain tumors, peritoneal cavity cancer, solid tumors, other lung cancer, head and neck cancer, gliomas, neuroblastomas, Von Hippel-Lindau Syndrome and kidney tumors, breast cancer, fallopian tube cancer, ovarian cancer, transitional cell cancer, prostate cancer, cancer of the esophagus and gastroesophageal junction, biliary cancer, adenocarcinoma, and any malignancy with increased RET kinase activity.

NOVEL COMPOUNDS AS REARRANGED DURING TRANSFECTION (RET) INHIBITORS

This invention relates to novel compounds which are inhibitors of the Rearranged during Transfection (RET) kinase, to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy, alone or in combination, for the normalization of gastrointestinal sensitivity, motility and/or secretion and/or abdominal disorders or diseases and/or treatment related to diseases related to RET dysfunction or where modulation of RET activity may have therapeutic benefit including but not limited to all classifications of irritable bowel syndrome (IBS) including diarrhea-predominant, constipation-predominant or alternating stool pattern, functional bloating, functional constipation, functional diarrhea, unspecified functional bowel disorder, functional abdominal pain syndrome, chronic idiopathic constipation, functional esophageal disorders, functional gastroduodenal disorders, functional anorectal pain, inflammatory bowel disease, proliferative diseases such as non-small cell lung cancer, hepatocellular carcinoma, colorectal cancer, medullary thyroid cancer, follicular thyroid cancer, anaplastic thyroid cancer, papillary thyroid cancer, brain tumors, peritoneal cavity cancer, solid tumors, other lung cancer, head and neck cancer, gliomas, neuroblastomas, Von Hippel-Lindau Syndrome and kidney tumors, breast cancer, fallopian tube cancer, ovarian cancer, transitional cell cancer, prostate cancer, cancer of the esophagus and gastroesophageal junction, biliary cancer, adenocarcinoma, and any malignancy with increased RET kinase activity.

PYRIDINE DERIVATIVES AS REARRANGED DURING TRANSFECTION (RET) KINASE INHIBITORS

This invention relates to novel compounds which are inhibitors of the Rearranged during Transfection (RET) kinase, to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy, alone or in combination, for the normalization of gastrointestinal sensitivity, motility and/or secretion and/or abdominal disorders or diseases and/or treatment related to diseases related to RET dysfunction or where modulation of RET activity may have therapeutic benefit including but not limited to all classifications of irritable bowel syndrome (IBS) including diarrhea-predominant, constipation-predominant or alternating stool pattern, functional bloating, functional constipation, functional diarrhea, unspecified functional bowel disorder, functional abdominal pain syndrome, chronic idiopathic constipation, functional esophageal disorders, functional gastroduodenal disorders, functional anorectal pain, inflammatory bowel disease, proliferative diseases such as non-small cell lung cancer, hepatocellular carcinoma, colorectal cancer, medullary thyroid cancer, follicular thyroid cancer, anaplastic thyroid cancer, papillary thyroid cancer, brain tumors, peritoneal cavity cancer, solid tumors, other lung cancer, head and neck cancer, gliomas, neuroblastomas, Von Hippel-Lindau Syndrome and kidney tumors, breast cancer, fallopian tube cancer, ovarian cancer, transitional cell cancer, prostate cancer, cancer of the esophagus and gastroesophageal junction, biliary cancer, adenocarcinoma, and any malignancy with increased RET kinase activity.

1, 2, 4-TRIAZOLONE DERIVATIVE

The present invention provides a 1,2,4-triazolone derivative represented by Formula (1A) having an antagonistic activity on the arginine-vasopressin 1b receptor or a pharmaceutically acceptable salt thereof and provides a pharmaceutical composition comprising the compound or the salt as an active ingredient, in particular, a therapeutic or preventive agent exhibiting favorable pharmacokinetics in a disease such as mood disorder, anxiety disorder, schizophrenia, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastrointestinal disease, drug addiction, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, head injury, inflammation, immune-related disease, or alopecia.

PYRIDINO-PYRIDINONE DERIVATIVES, PREPARATION AND THERAPEUTIC USE THEREOF

The present invention relates to derivatives of pyridino-pyridinones, and to their preparation and use thereof, having activity as inhibitors of kinase activity of receptors for PDGF (platelet derived growth factors) ligands and optionally of receptors for the FLT3 (fms-like tyrosine kinase receptor) ligand receptors, said derivatives comprising compounds of formula (I): wherein the various substituent groups are more specifically defined herein. The compounds are suitable as therapeutics for the treatment of various proliferative diseases.

C-LINKED HYDROXAMIC ACID DERIVATIVES USEFUL AS ANTIBACTERIAL AGENTS

The present invention is directed to a new class of hydroxamic acid derivatives, their use as LpxC inhibitors, and more specifically their use to treat bacterial infections.

COMPOUNDS WHICH POTENTIATE AMPA RECEPTOR AND USES THEREOF IN MEDICINE

Compounds of formula (I), and salts and solvates thereof are provided: Processes for preparation, pharmaceutical compositions, and uses thereof as a medicament, for example in the treatment of a disease or condition mediated by a reduction or imbalance in glutamate receptor function, such as schizophrenia or cognition impairment, are also disclosed.

COMPOUNDS WHICH POTENTIATE AMPA RECEPTOR AND USES THEREOF IN MEDICINE

A compound of formula (I) and salts thereof are provided: wherein A is defined in the specification. Processes for preparation, pharmaceutical compositions, and uses thereof as a medicament, for example in the treatment of a disease or condition mediated by a reduction or imbalance in glutamate receptor function, such as schizophrenia or cognition impairment, are also disclosed.