764651-68-5

Basic information

• Product Name: 5-BROMO-N,N,4-TRIMETHYLPYRIDIN-2-AMINE
• Synonyms: 5-BROMO-N,N,4-TRIMETHYLPYRIDIN-2-AMINE;5-BroMo-2-diMethylaMino-4-Methylpyridine
• CAS NO: 764651-68-5
• Molecular Formula: C₈H₁₁BrN₂
• Molecular Weight: 215.09
• Mol File: 764651-68-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 286℃
• Flash Point: 127℃
• Appearance: /
• Density: 1.404
• Vapor Pressure: 0.00257mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: 2-8°C
• PKA: 5.89±0.10(Predicted)
• CAS DataBase Reference: 5-BROMO-N,N,4-TRIMETHYLPYRIDIN-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-N,N,4-TRIMETHYLPYRIDIN-2-AMINE(764651-68-5)
• EPA Substance Registry System: 5-BROMO-N,N,4-TRIMETHYLPYRIDIN-2-AMINE(764651-68-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 764651-68-5(Hazardous Substances Data)

Usage

General Description

5-BROMO-N,N,4-TRIMETHYLPYRIDIN-2-AMINE is a chemical compound with the molecular formula C8H11BrN2. It is a derivative of pyridine and contains a bromo and trimethyl substituent at the 5 and 4 positions, respectively. 5-BROMO-N,N,4-TRIMETHYLPYRIDIN-2-AMINE is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used in organic synthesis and as a reagent in chemical reactions. 5-BROMO-N,N,4-TRIMETHYLPYRIDIN-2-AMINE may have potential applications in various fields including medicine, agriculture, and research. However, it is important to handle this chemical with care and follow proper safety protocols due to its potential hazards.

InChI:InChI=1/C8H11BrN2/c1-6-4-8(11(2)3)10-5-7(6)9/h4-5H,1-3H3

Upstream product

• 20173-72-2 2-(N,N-dimethylamino)-4-methylpyridine 
• 506-59-2 N,N-dimethylammonium chloride 
• 778611-64-6 5-bromo-2-chloro-4-methylpyridine 
• 98198-48-2 2-amino-5-bromo-4-methylpyridine 
• 50-00-0 formaldehyd 

Downstream Products

• 764651-70-9 2-dimethylamino-4-methyl-5-(cyanomethyl)pyridine 
• 195055-03-9 3-[6-(dimethylamino)-4-methyl-3-pyridinyl]-2,5-dimethyl-N,N-dipropylpyrazolo[2,3-a]pyrimidine-7-amine 
• 764651-69-6 2-dimethylamino-4-methyl-5-formylpyridine 

Relevant articles and documents

CRF RECEPTOR ANTAGONISTS AND METHODS OF USE

Compounds are provided herein that antagonize corticotropin-releasing factor (CRF) receptors, in particular CRF receptor 1 (CRF1), as well as related preparations, compositions and methods for treating diseases and/or disorders that would benefit from the same such as congenital adrenal hyperplasia (CAH).

Synthesis and structure-activity relationships of 8-(pyrid-3-yl)pyrazolo[1, 5-a]-1,3,5-triazines: Potent, orally bioavailable corticotropin releasing factor receptor-1 (CRF1) antagonists

This report describes the syntheses and structure-activity relationships of 8-(substituted pyridyl)pyrazolo[1,5-a]-1,3,5-triazine corticotropin releasing factor receptor-1 (CRF1) receptor antagonists. These CRF1 receptor antagonists may be potential anxiolytic or antidepressant drugs. This research resulted in the discovery of compound 13-15, which is a potent, selective CRF1 antagonist (hCRF1 IC50 = 6.1 ± 0.6 nM) with weak affinity for the CRF-binding protein and biogenic amine receptors. This compound also has a good pharmacokinetic profile in dogs. Analogue 13-15 is orally effective in two rat models of anxiety: the defensive withdrawal (situational anxiety) model and the elevated plus maze test. Analogue 13-15 has been advanced to clinical trials.

Design of 2,5-dimethyl-3-(6-dimethyl-4-methylpyridin-3-yl)-7-dipropylamino- pyrazolo[1,5-a]pyrimidine (NBI 30775/R121919) and structure-activity relationships of a series of potent and orally active corticotropin-releasing factor receptor antagonists

We previously shown that 3-phenylpyrazolo[1,5-a]pyrimidines exemplified by 8 were potent antagonists of the human corticotropin-releasing factor-1 receptor. A series of 3-pyridylpyrazolo-[1,5-a]pyrimidines 15, 25-30, 34, and 35 containing a weakly basic pyridine ring at the 3-position of the bicyclic nucleus was designed to reduce lipophilicity from the initial leads such as 7. Here, we showed that these 3-pyridyl compounds exhibited potent antagonists at the human CRF1 receptor. Moreover, the hydrophilic and weakly basic pyridine moiety increased the water solubility of some analogues. Compound 26h exhibited good binding affinity at the human CRF1 receptor with a Ki value of 3.5 nM. As a functional antagonist, it dose-dependently inhibited CRF-stimulated cAMP production in cells expressing the CRF1 receptor (IC50 = 50 nM), and CRF-stimulated ACTH release from cultured rat pituitary cells (IC50 = 20 nM). 26h had a log P value of 4.9 and water solubility of greater than 10 mg/mL. Pharmacokinetic studies in rats showed that 26h was orally bioavailable and able to penetrate into the brain. 26h has been demonstrated in vivo efficacy in animal behavioral models that measure anxiolytic activity. These results suggest that analogues from this series were potent CRF1 receptor antagonists with proper physicochemical properties and good pharmacokinetic profiles. 26h was developed into a clinical compound and exhibited efficacy in patients with major depression.