22418-65-1

Basic information

• Product Name: 2-methylenedecan-1-al
• Synonyms: 2-methylenedecan-1-al;2-Methylenedecanal;Decanal, 2-methylene-;Einecs 244-979-4
• CAS NO: 22418-65-1
• Molecular Formula: C₁₁H₂₀O
• Molecular Weight: 168.2759
• EINECS: 244-979-4
• Mol File: 22418-65-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 241.6°Cat760mmHg
• Flash Point: 91.1°C
• Appearance: /
• Density: 0.831g/cm³
• Vapor Pressure: 0.0356mmHg at 25°C
• Refractive Index: 1.434
• CAS DataBase Reference: 2-methylenedecan-1-al(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylenedecan-1-al(22418-65-1)
• EPA Substance Registry System: 2-methylenedecan-1-al(22418-65-1)

Safety Data

• Hazardous Substances Data: 22418-65-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H20O/c1-3-4-5-6-7-8-9-11(2)10-12/h10H,2-9H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 112-31-2 caprinaldehyde 
• 64-18-6 formic acid 

Downstream Products

• 808137-55-5 2-[(phenylsulfanyl)methyl]decanal 
• 19009-56-4 2-methyldecanal 

Relevant articles and documents

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Diastereoselective addition of organozinc reagents to 2-alkyl-3- (arylsulfanyl)propanals

The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-alkyl moiety of high diastereomeric purity is described. Such compounds can serve as potential building blocks for the preparation of several kinds of natural products. Diastereoselective synthesis of two potential pine sawfly pheromone components, one the pure racemic threo-isomer of 3-methylpentadecan-2-ol and the other the racemic erythro-isomer of 3-methyltridecan-2-ol are described. The diastereoselective addition of R2Zn (R=Me, Et and n-Bu) to several 2-alkyl-3-(arylsulfanyl)propanals in the presence of a Lewis acid and CH 2Cl2 as solvent was studied. An excellent diastereomeric ratio (95/5 anti-Cram/Cram) was obtained with 2-[(phenylsulfanyl)methyl] pentanal, 2-[(phenylsulfanyl)methyl]decanal and 2-[(phenylsulfanyl)methyl] dodecanal and Me2Zn in the presence of TiCl4. (a) Lewis acid catalysed dimethylzinc addition; (b) 1. Prot. and oxidation to sulfone, 2. Alkylation; (c) Deprot. and desulfonation; (d) Desulfurisation.