Methyl lithiopropiolate

Base Information

• Chemical Name: Methyl lithiopropiolate
• CAS No.: 72036-29-4
• Molecular Formula: C4H3 Li O2
• Molecular Weight: 90.00642
• DSSTox Substance ID: DTXSID30453287
• Mol file: 72036-29-4.mol

Synonyms:72036-29-4;METHYL LITHIOPROPIOLATE;lithio methyl propiolate;METHYLLITHIOPROPIOLATE;DTXSID30453287;AKOS006332087;AG-G-83029

Chemical Property of Methyl lithiopropiolate

Chemical Property:

• PSA: 26.30000
• LogP: -0.33040
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 90.02930777
• Heavy Atom Count: 7
• Complexity: 99.5

Purity/Quality:

95% ^*data from raw suppliers

METHYL LITHIOPROPIOLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [Li+].COC(=O)C#[C-]

Technology Process of Methyl lithiopropiolate

There total 1 articles about Methyl lithiopropiolate 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:

propynoic acid methyl ester (922-67-8) → methyl propiolate lithium salt (72036-29-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -100 ℃;

Reference yield: 95.0%

methyl propiolate lithium salt (72036-29-4) + (Z)-N-{[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]methylidene}benzylamine N-oxide (243983-11-1,1050549-68-2) → (S)-2-[(S)-1-(Benzyl-hydroxy-amino)-3-methoxycarbonyl-prop-2-ynyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:

In tetrahydrofuran; at -80 ℃; for 0.5h;

DOI:10.1016/S0957-4166(99)00203-7

Reference yield: 90.0%

methyl propiolate lithium salt (72036-29-4) + C34H44N2O4Si → (2S,4R)-2-[(S)-1-(Benzyl-hydroxy-amino)-3-methoxycarbonyl-prop-2-ynyl]-4-(2,2-dimethyl-1,1-diphenyl-propylsilanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:

In tetrahydrofuran; at -80 ℃; for 0.5h;

DOI:10.1016/S0957-4166(99)00203-7

upstream raw materials:

propynoic acid methyl ester

Downstream raw materials:

methyl 3-(1-hydroxy-4-methyl-3-cyclohexen-1-yl)propynoate

methyl (R)-5-hydroxyhex-2-ynoate

(2α,3β)-1,1-ethylenedioxy-3-(5-benzylthio-2-furyl)-2-(3-hydroxy-5-methoxycarbonylpent-4-ynyl)cyclopentane