3378-82-3

Basic information

• Product Name: 1-BROMO-2-NAPHTHALDEHYDE
• Synonyms: 1-BROMO-2-NAPHTHALDEHYDE;1-BROMONAPHTHALENE-2-CARBALDEHYDE;1-bromo-2-naphthaldehyde crystalline;1-BROMO-2-NAPHTHALDEHYDE 96+%;1-Bromo-2-naphthalenecarbaldehyde;1-Bromo-2-naphthalenecarboxaldehyde;1-broMo-2-phthaldehyde;1-Bromo-2-naphthaldehyde >=96.0% (HPLC)
• CAS NO: 3378-82-3
• Molecular Formula: C₁₁H₇BrO
• Molecular Weight: 235.08
• EINECS: 222-180-1
• Mol File: 3378-82-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 118°C
• Boiling Point: 347℃
• Flash Point: 120℃
• Appearance: /
• Density: 1.552
• Vapor Pressure: 5.45E-05mmHg at 25°C
• Refractive Index: 1.7
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• BRN: 2613639
• CAS DataBase Reference: 1-BROMO-2-NAPHTHALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2-NAPHTHALDEHYDE(3378-82-3)
• EPA Substance Registry System: 1-BROMO-2-NAPHTHALDEHYDE(3378-82-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 3378-82-3(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow solid

Uses

1-Bromo-2-naphthaldehyde is used as a reagent in the synthesis of Hoveyda-Grubbs type metathesis catalysts which are used in cross olefin metathesis. 1-Bromo-2-naphthaldehyde is also used in the preparation of novel (-)-cercosporamide derivatives as potent selective PPARγ modulators.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4617, 1981 DOI: 10.1021/jo00335a076

InChI:InChI=1/C11H7BrO/c12-11-9(7-13)6-5-8-3-1-2-4-10(8)11/h1-7H

Upstream product

• 37763-43-2 1-bromo-2-(bromomethyl)naphthalene 
• 35810-04-9 benzenesulfinic acid cyclohexylamide 
• 117582-62-4 1-bromo-2-formyl-3,4-dihydronaphthalene 
• 68-12-2 N,N-dimethyl-formamide 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 91-57-6 2-Methylnaphthalene 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 127349-02-4 1-bromo-2-(dibromomethyl)naphthalene 
• 76635-70-6 (1-bromo-2-naphthyl)methanol 
• 64689-70-9 1-bromo-2-(methoxymethyl)naphthalene 

Downstream Products

• 712278-61-0 1-(phenylethynyl)naphthalene-2-carbaldehyde 
• 895532-23-7 2-ethynyl-1-(phenylethynyl)naphthalene 
• 895532-25-9 2-(4,4-dimethyl-3-phenyl-pent-1-ynyl)-1-phenylethynyl-naphthalene 
• 895532-24-8 4,4-dimethyl-3-phenyl-1-(1-phenylethynyl-naphthalen-2-yl)-pent-1-yn-3-ol 
• 59632-40-5 2-(1-Bromo-2-naphthylmethylamino)-1-phenyl-1-propanol hydrochloride 
• 1243026-97-2 1-(1-bromo-naphthalene-2-yl)-2-phenyl-ethanol 
• 1243026-99-4 1-(1-bromo-naphthalene-2-yl)-2-p-tolyl-ethanol 
• 1350966-06-1 C₃₅H₂₂ 
• 1001911-66-5 ethyl 1-biphenyl-4-ylnaphthalene-2-carboxylate 
• 1350967-38-2 9-phenyl-7H-benzo[c]fluoren-7-one 
• 773134-84-2 1-bromonaphthalene-2-carboxylic acid ethyl ester 
• 1374192-92-3 N-(1-(1-(3,5-difluorophenyl)naphthalen-2-yl)ethyl)-2-methylpropane-2-sulfinamide 
• 1374193-03-9 1-(1-(3,5-difluorophenyl)naphthalen-2-yl)ethanamine 
• 1374193-12-0 4-amino-6-((1-(1-(3,5-difluorophenyl)-2-naphthalenyl)ethyl)amino)-5-pyrimidinecarbonitrile 

Relevant articles and documents

A New Strategy for the Synthesis of Axially Chiral Biaryl Compounds

Axially chiral compounds can be synthesized in high atropisomeric purity by aryl coupling of a conformationally locked dihydroxy-stilbenoids, which are readily available via Sharpless asymmetric dihydroxylation of olefin precursors.

Rh-Catalyzed Formal [3+2] Cyclization for the Synthesis of 5-Aryl-2-(quinolin-2-yl)oxazoles and Its Applications in Metal Ions Probes

A facile and efficient strategy for the synthesis of 5-aryl-2-(quinolin-2-yl)oxazoles via rhodium-catalyzed formal [3+2] cyclization of 4-aryl-1-tosyl-1H-1,2,3-triazoles with quinoline-2-carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5-aryloxazole derivatives with a broad reaction scope. It is amenable to gram-scale synthesis and easily transformation. Moreover, this 5-aryl-2-(quinolin-2-yl)oxazole skeleton is indeed a new fluorophore and its applications in metal ions probes are also investigated and showed fluorescent responses to mercury ion.

Ruthenium-Catalyzed Atropoenantioselective Synthesis of Axial Biaryls via Reductive Amination and Dynamic Kinetic Resolution

The unprecedented ruthenium-catalyzed atropoenantioselective reductive amination of aldehydes with alkylamines via a cascade transfer hydrogenation and dynamic kinetic resolution strategy is described. This protocol features broad substrate scope and good functional group tolerance and allows the rapid assembly of axially chiral biaryls in good to high yields with high to excellent enantioselectivities. In addition, such structural motifs may have potential applications in enantioselective catalysis as chiral ligands or catalysts.