401514-50-9

Basic information

• Product Name: Benzaldehyde, 2-fluoro-, hydrazone
• CAS NO: 401514-50-9
• Molecular Formula: C7H7FN2
• Molecular Weight: 138.144
• Mol File: 401514-50-9.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 2-fluoro-, hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 2-fluoro-, hydrazone(401514-50-9)
• EPA Substance Registry System: Benzaldehyde, 2-fluoro-, hydrazone(401514-50-9)

Safety Data

• Hazardous Substances Data: 401514-50-9(Hazardous Substances Data)

Upstream product

• 446-52-6 2-Fluorobenzaldehyde 
• 394-47-8 2-fluorobenzonitrile 

Downstream Products

• 15332-09-9 2-fluorobenzaldehyde N-[-(2-fluorophenyl)methylidene]hydrazone 
• 271-44-3 benzimidazole 
• 95-52-3 2-Fluorotoluene 
• 93524-64-2 1,1,1-trifluoro-2-(2'-fluorophenyl)ethane 
• 71813-51-9 1-(but-3-en-1-yl)-2-fluorobenzene 
• 3794-15-8 1-benzyl-2-fluorobenzene 
• 187463-12-3 (Z)-1-[2-bromovinyl]-2-fluorobenzene 
• 401514-42-9 1-(2,2-dibromovinyl)-2-fluorobenzene 
• 911825-55-3 methyl 4-(2-fluorophenyl)butanoate 

Relevant articles and documents

Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketonesviaN2H4mediated deoxygenative couplings

Umpolung (polarity reversal) tactics of aldehydes/ketones have greatly broadened carbonyl chemistry by enabling transformations with electrophilic reagents and deoxygenative functionalizations. Herein, we report the first ruthenium-catalyzed β-selective alkylation of vinylpyridines with both naturally abundant aromatic and aliphatic aldehyde/ketonesviaN2H4mediated deoxygenative couplings. Compared with one-electron umpolung of carbonyls to alcohols, this two-electron umpolung strategy realized reductive deoxygenation targets, which were not only applicable to the regioselective alkylation of a broad range of 2/4-alkene substituted pyridines, but also amenable to challenging 3-vinyl and steric-embedded internal pyridines as well as their analogous heterocyclic structures.

Copper-Catalyzed Conjugate Addition of Carbonyls as Carbanion Equivalent via Hydrazones

Copper-catalyzed conjugate addition is a classic method for forming new carbon-carbon bonds. However, copper has never showed catalytic activity for umpolung carbanions in hydrazone chemistry. Herein, we report a facile conjugate addition of hydrazone catalyzed by readily available copper complexes at room temperature. The employment of mesitylcopper(I) and electron-rich phosphine bidentate ligand is a key factor affecting reactivity. The reaction allows various aromatic hydrazones to react with diverse conjugated compounds to produce 1,4-adducts in yields of about 20 to 99%.

Switch in Selectivity for Formal Hydroalkylation of 1,3-Dienes and Enynes with Simple Hydrazones

Controlling reaction selectivity is a permanent pursuit for chemists. Regioselective catalysis, which exploits and/or overcomes innate steric and electronic bias to deliver diverse regio-enriched products from the same starting materials, represents a powerful tool for divergent synthesis. Recently, the 1,2-Markovnikov hydroalkylation of 1,3-dienes with simple hydrazones was reported to generate branched allylic compounds when a nickel catalyst was used. As part of the effort, shown here is that a complete switch of Markovnikov to anti-Markovnikov addition is obtained by changing to a ruthenium catalyst, thus providing direct and efficient access to homoallylic products exclusively. Isotopic substitution experiments indicate that no reversible hydro-metallation across the metal-π-allyl system occurred under ruthenium catalysis. Moreover, this protocol is applicable to the regiospecific hydroalkylation of the distal C=C bond of 1,3-enynes.