175204-91-8

Basic information

• Product Name: METHYL 4,7-DIBROMO-3-METHOXY-2-NAPHTHOATE
• Synonyms: METHYL 4,7-DIBROMO-3-METHOXY-2-NAPHTHOATE;METHYL 1,6-DIBROMO-2-METHOXYNAPHTHALENE-3-CARBOXYLATE
• CAS NO: 175204-91-8
• Molecular Formula: C₁₃H₁₀Br₂O₃
• Molecular Weight: 374.02
• Mol File: 175204-91-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 438.7°C at 760 mmHg
• Flash Point: 219.1°C
• Appearance: /
• Density: 1.717g/cm³
• Vapor Pressure: 6.78E-08mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: METHYL 4,7-DIBROMO-3-METHOXY-2-NAPHTHOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4,7-DIBROMO-3-METHOXY-2-NAPHTHOATE(175204-91-8)
• EPA Substance Registry System: METHYL 4,7-DIBROMO-3-METHOXY-2-NAPHTHOATE(175204-91-8)

Safety Data

• Hazardous Substances Data: 175204-91-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H10Br2O3/c1-17-12-10(13(16)18-2)6-7-5-8(14)3-4-9(7)11(12)15/h3-6H,1-2H3

Upstream product

• 1779-10-8 1,6-dibromo-2-hydroxynaphthalene-3-carboxylic acid 
• 77-78-1 dimethyl sulfate 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 74-88-4 methyl iodide 
• 1160295-91-9 methyl 4,7-dibromo-3-hydroxynaphthalene-2-carboxylate 

Downstream Products

• 1346998-31-9 1,6-dibromo-2-methoxy-3-benzylnaphthalene 
• 1346998-33-1 3-benzyl-1,6-dibromonaphthalen-2-ol 

Relevant articles and documents

Design, synthesis and biological evaluation of novel triaryldimethylaminobutan-2-ol derivatives against Mycobacterium tuberculosis

Bedaquiline (TMC207), a typical diarylquinoline anti-tuberculosis drug, has been approved by FDA to specifically treat MDR-TB. Herein we describe design, synthesis, and in vitro biological evaluation against Mycobacterium tuberculosis of a series of triaryldimethylaminobutan-2-ol derivatives obtaining from the structural modification of TMC207. Compounds 23, 25, 28, 32, 39 and 43 provided superior anti-mycobacterial activity than positive control PC01 which shows the same configuration and contains TMC207. Compounds 16, 20, 29, 34, 37, 45 and 47 exhibited the similar activity to positive control PC01. Most importantly, the series of compounds showed excellent activity against XDR-Mtb. The result of acute toxicity suggested that this class of triaryldimethylaminobutan-2-ol derivatives should be graded as low. Further SAR analysis indicates that a large steric bulk of triaryl and 7-Br, 3-OCH3 on 1-naphthyl are critical.

Selective arylation, alkenylation, and cyclization of dibromonaphthols, using visible light, via carbene intermediates

(Chemical Equation Presented) The photoreactivity of several 3-substituted-1,6-dibromo-2-naphthols has been investigated in neat acetonitrile in the presence of diluted Et3N and in aqueous buffered acetonitrile (pH 8, phosphate buffered), using visible light (450 nm). Hydrobromic acid loss in the presence of the base, for the unsubstituted naphthol, or heterolytic C-Br cleavage directly from the naphtholates, for the more acid 3-substutited naphthols (R = COOCH3, CONH2, CONMe2), generates electrophilic carbene intermediates, which have been successfully trapped by molecular oxygen, pyrrole, acrylonitrile, ethyl vinyl ether, and allyltrimethylsilane. Product distribution analysis reveals three types of products arising from (i) arylation, (ii) alkenylation, and (iii) cyclization reactions. The generation and the reactivity of α-ketocarbene intermediates, as electrophilc diradicals, has been supported by laser flash photolysis, with the detection of both the carbene (λmax 510 nm) and 1,2-naphthoquinone-O-oxide (R = CONMe2, λ max 600 nm) in the presence of O2.