63125-05-3

Basic information

• Product Name: methyl 2-hexadecynoate
• Synonyms: methyl 2-hexadecynoate
• CAS NO: 63125-05-3
• Molecular Formula: C₁₇H₃₀O₂
• Molecular Weight: 266.42
• Mol File: 63125-05-3.mol

Chemical Properties

• Boiling Point: 362.7°C at 760 mmHg
• Flash Point: 156.1°C
• Appearance: /
• Density: 0.9g/cm³
• Vapor Pressure: 1.9E-05mmHg at 25°C
• Refractive Index: 1.456
• CAS DataBase Reference: methyl 2-hexadecynoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-hexadecynoate(63125-05-3)
• EPA Substance Registry System: methyl 2-hexadecynoate(63125-05-3)

Safety Data

• Hazardous Substances Data: 63125-05-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H30O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19-2/h3-14H2,1-2H3

Upstream product

• 63125-03-1 Methyl 3-oxo-2-(triphenylphosphoranylidene)hexadecanoate 
• 112-64-1 tetradecanoyl chloride 

Downstream Products

• 100485-96-9 methyl 2-methoxy-6-tridecyl benzoate 
• 20261-38-5 2-hydroxy-6-tridecylbenzoic acid 
• 75808-38-7 Methyl 2-hydroxy-6-tridecylbenzoate 

Relevant articles and documents

Synthesis of Anacardic Acids

The anacardic acids 1-11, isolated from various plants, were synthesized by a new general method.Reaction of the methyl alkynoates 12-18 with 1-methoxy-1,4-cyclohexadiene at 200 deg C afforded directly the methyl 2-methoxybenzoates 19-25 with long chain substituents in 6-position in 74-85percent yield.The dienophiles 12-16 were prepared by pyrolysis of the corresponding acylphosphoranes 26-30, the dienophiles 17 and 18 by methoxycarbonylation of the corresponding alkynes 31 and 32 via the hydroxy esters 33 and 34.Demethylation of 19-23 with AlI3 gave the methyl salicylates 35-39 which could be hydrolized to the anacardic acids 1-4 and 7.Hydrolysis of 24 and 25 provided the hydroxy acids 40 and 41, which were converted by treatment with CBr4/PPh3 into the acids 42 and 43 bearing bromoalkyl side chains.These were transformed into 44-47 by reaction with 1-hexynyllithium and 1-octynyllithium.Stereoselective hydrogenation of 44-47 gave 48-51 with (Z)-alkene side chains.In a similar approach 42 was converted into 52 and then into 53, which gave upon treatment with 1-pentynylmagnesium bromide or 1-heptynylmagnesium bromide the acids 54 and 55 with alkadiyne side chains.Stereoselective hydrogenation provided 56 and 57 with (Z,Z)-alkadiene side chains.The 2-methoxy group in 48-51, 56, 57 was demethylated by treatment with AlI3 to give the anacardic acids 5, 6, 8-11. - Keywords: Anacardic acids; Benzoates, methyl 6-alkyl-2-methoxy-; 2-Alkynoates, methyl; Aluminium triiodide, demethylation by treatment with

Method for the preparation of an alkynyl compound

A novel and efficient method is proposed for the synthetic preparation of a long-chain alkynyl compound in a one-pot reaction without isolating the intermediate from the reaction mixture. The inventive method comprises the steps of: (a) a Grignard coupling reaction of an ω-halogeno-1-alkynyl magnesium halide compound of the general formula X1 MgC C(CH2)n X2, in which X1 is a halogen atom, X2 is an atom of Br or I and n is 3 to 10, and a Grignard reagent of the general formula RMgX1, in which R is a group selected from the class consisting of alkyl groups, alkenyl groups, alkynyl groups, alkapolyenyl groups, aryl groups and hydrocarbon groups having protected hydroxy group to give an intermediate compound of the general formula X1 MgC C(CH2)n R; (b) subjecting the intermediate compound to a reaction with a reactant selected from the class consisting of C2 -synthons, C1 -synthons and chlorosilane compounds having reactivity with the intermediate compound at the X1 Mg-terminal; and (c) hydrolyzing the reaction product obtained in step (b).