Methyl 11-cyanoundecanoate

Base Information

• Chemical Name: Methyl 11-cyanoundecanoate
• CAS No.: 22915-49-7
• Molecular Formula: C13H23NO2
• Molecular Weight: 225.331
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID40450500
• Nikkaji Number: J446.491E
• Wikidata: Q82270257
• Mol file: 22915-49-7.mol

Synonyms:Methyl 11-cyanoundecanoate;22915-49-7;Undecanoic acid,11-cyano-, methyl ester;Methyl=11-cyanoundecanoate;SCHEMBL5978990;DTXSID40450500;Undecanoic acid,11-cyano-,methyl ester;SY296015;FT-0607214

Chemical Property of Methyl 11-cyanoundecanoate

Chemical Property:

• Boiling Point: 328.482 °C at 760 mmHg
• Flash Point: 154.672 °C
• PSA: 50.09000
• Density: 0.939 g/cm³
• LogP: 3.58398
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 225.172878976
• Heavy Atom Count: 16
• Complexity: 217

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCCCCCCCCC#N
• Uses: Methyl 11-cyanoundecanoate is a precursor for many reactions.

Technology Process of Methyl 11-cyanoundecanoate

There total 24 articles about Methyl 11-cyanoundecanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl 12-hydroxydodecanoate (71655-36-2) → 11-cyanoundecanoic acid methyl ester (22915-49-7)

Guidance literature:

With [2,2]bipyridinyl; ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In acetonitrile; at 50 ℃; for 24h; under 5688.78 Torr; Reagent/catalyst; Temperature; Sealed tube;

Reference yield: 100.0%

methyl 11-cyanoundec-10-enoate → 11-cyanoundecanoic acid methyl ester (22915-49-7)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; hydrogen; In toluene; under 7500.75 Torr; Autoclave;

DOI:10.1039/b816917a

Reference yield: 90.0%

Methyl 10-undecenoate (111-81-9) + acrylonitrile (107-13-1,25014-41-9) → 11-cyanoundecanoic acid methyl ester (22915-49-7)

Guidance literature:

Methyl 10-undecenoate; acrylonitrile; With Hoveyda-Grubbs catalyst second generation; In toluene; at 100 ℃; for 1h;

With hydrogen; In toluene; at 80 ℃; for 48h; under 22502.3 Torr;

DOI:10.1002/cssc.201200086

upstream raw materials:

methanol

(Z)-2-hydroxyiminocyclododecanone

2,2-dimethoxycyclododecanone oxime

methyl 11-hydroxyundecanoate

Downstream raw materials:

1,12-dodecanedioic acid

12-aminolauric acid hydrogen chloride salt

Refernces

• 1、 Miao,Fischmeister,Dixneuf,Bruneau,Dubois,Couturier. "Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis". . p. 2179 - 2183. Retrieved 2012.
• 2、 -. "PREPARATION OF AMINO ACIDS AND AMINO ACID DERIVATIVES". . . Retrieved 2018/04/20.
• 3、 Koh, Moo-Hyun,Kim, Hyeonjeong,Shin, Nara,Kim, Hyun Su,Yoo, Dongwon,Kim, Young Gyu. "Divergent process for C10, C11 and C12 ω-amino acid and α,ω-dicarboxylic acid monomers of polyamides from castor oil as a renewable resource". . p. 1873 - 1878. Retrieved 2012/08/07.