405939-59-5

Basic information

• Product Name: (5-BROMO-6-CHLORO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: TERT-BUTYL (5-BROMO-6-CHLOROPYRIDIN-3-YL)CARBAMATE;(5-BROMO-6-CHLORO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER
• CAS NO: 405939-59-5
• Molecular Formula: C₁₀H₁₂BrClN₂O₂
• Molecular Weight: 307.57
• Mol File: 405939-59-5.mol

Chemical Properties

• Boiling Point: 319.2°C at 760 mmHg
• Flash Point: 146.9°C
• Appearance: /
• Density: 1.539g/cm³
• Vapor Pressure: 0.000343mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: 2-8°C
• PKA: 11.39±0.70(Predicted)
• CAS DataBase Reference: (5-BROMO-6-CHLORO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (5-BROMO-6-CHLORO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER(405939-59-5)
• EPA Substance Registry System: (5-BROMO-6-CHLORO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER(405939-59-5)

Safety Data

• Hazardous Substances Data: 405939-59-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5-BROMO-6-CHLORO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER is used as an intermediate in the synthesis of various pharmaceuticals for its potential to inhibit certain enzymes. This property makes it valuable in the development of drugs targeting specific biological pathways and diseases.
Used in Agrochemical Industry:
In the agrochemical industry, (5-BROMO-6-CHLORO-PYRIDIN-3-YL)-CARBAMIC ACID TERT-BUTYL ESTER is utilized as an intermediate in the production of agrochemicals. Its enzyme inhibitory properties can be harnessed to create compounds that protect crops from pests and diseases, thereby increasing agricultural productivity and crop yield.

InChI:InChI=1/C10H12BrClN2O2/c1-10(2,3)16-9(15)14-6-4-7(11)8(12)13-5-6/h4-5H,1-3H3,(H,14,15)

Upstream product

• 29241-62-1 5-bromo-6-chloronicotinic acid 
• 75-65-0 tert-butyl alcohol 
• 5006-66-6 6-hydroxy-3-pyridinecarboxylic acid 
• 41668-13-7 5-bromo-6-hydroxy-3-pyridinecarboxylic acid 

Downstream Products

• 882516-38-3 (6-{5-[tert-butoxycarbonyl-(3-hydroxy-propyl)-amino]-2-chloro-pyridin-3-yl}-pyrazin-2-yl)-(3-chloro-phenyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis and structure-activity relationships of pyrazine-pyridine biheteroaryls as novel, potent, and selective vascular endothelial growth factor receptor-2 inhibitors

There is much evidence that direct inhibition of the kinase activity of vascular endothelial growth factor receptor-2 (VEGFR-2) will result in the reduction of angiogenesis and the suppression of tumor growth. Palladium-catalyzed C-C bond, C-N bond formation reactions were used to assemble various pyrazine-pyridine biheteroaryls as potent VEGFR-2 inhibitors. Among them, 4-{5-[6-(3-chloro-phenylamino)-pyrazin-2-yl]-pyridin-3-ylamino}-butan-1-ol (39) and N-{5-[6-(3-chloro-phenylamino)-pyrazin-2-yl]-pyridin-3-yl}-N′, N′-dimethyl-ethane-1,2-diamine (41) exhibited the highest kinase selectivity against fibroblast growth factor receptor kinase, platelet-derived growth factor receptor kinase, and glycogen synthase kinase-3. All of these compounds showed good cellular potency to inhibit VEGF-stimulated proliferation of human umbilical vein endothelial cells (HUVEC) but with modest effects on the unstimulated growth of HUVEC. The low inhibition of these compounds to the growth of tumor cell lines, such as HeLa, HCT-116, and A375 further confirms that these VEGFR-2 inhibitors are not cytotoxic agents. The in vivo antitumor activity of 39 and 41 were demonstrated in the A375 human melanoma xenograft nude mice model. Molecular modeling (QSAR analysis) was conducted in an attempt to rationalize the observed structure-activity relationship.