4-Isocyanobutyric acid methyl ester

Base Information

• Chemical Name: 4-Isocyanobutyric acid methyl ester
• CAS No.: 51642-06-9
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.143
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID10374784
• Wikidata: Q82163346
• Mol file: 51642-06-9.mol

Synonyms:4-Isocyanobutyric acid methyl ester;Methyl 4-isocyanobutanoate;51642-06-9;SCHEMBL2588508;DTXSID10374784;AKOS006293443

Chemical Property of 4-Isocyanobutyric acid methyl ester

Chemical Property:

• PSA: 26.30000
• LogP: 0.08960
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 127.063328530
• Heavy Atom Count: 9
• Complexity: 133

Purity/Quality:

97% ^*data from raw suppliers

PN100367:Methyl-4-isocyanobutyrate 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC[N+]#[C-]

Technology Process of 4-Isocyanobutyric acid methyl ester

There total 3 articles about 4-Isocyanobutyric acid methyl ester 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: 93.0%

methyl 4-(N-formyl)aminobutyrate (1345855-50-6) → methyl 4-isocyanobutanoate (51642-06-9)

Guidance literature:

With triethylamine; trichlorophosphate; In dichloromethane; for 0.0666667h; Cooling with ice; Green chemistry;

DOI:10.1039/d0gc02722g

Reference yield:

methyl γ-aminobutyrate hydrochloride (13031-60-2) → methyl 4-isocyanobutanoate (51642-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 6 h / Reflux

2: diisopropylamine; trichlorophosphate / dichloromethane / 2 h / 0 - 20 °C / Cooling with ice

With diisopropylamine; trichlorophosphate; In dichloromethane;

DOI:10.1002/chem.201103341

Reference yield:

methyl 4-aminobutyrate (3251-07-8) → methyl 4-isocyanobutanoate (51642-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic anhydride / 1 h / 20 °C

1.2: 0 - 20 °C

2.1: triethylamine; trichlorophosphate / dichloromethane / 0.42 h / 0 - 20 °C

With acetic anhydride; triethylamine; trichlorophosphate; In dichloromethane;

DOI:10.1002/cmdc.201500318

upstream raw materials:

methyl 4-(N-formyl)aminobutyrate

methyl γ-aminobutyrate hydrochloride

methyl 4-aminobutyrate

Downstream raw materials:

methyl 4-(2-(N-(2-nitrobenzyl)undec-10-enamido)dodec-11-enamido)butanoate

Refernces

• 1、 Ahmadian-Moghaddam, Maryam,D?mling, Alexander,Patil, Pravin. "Isocyanide 2.0". supporting information. p. 6902 - 6911. Retrieved 2020/11/09.
• 2、 Kreye, Oliver,Tueruenc, Oguz,Sehlinger, Ansgar,Rackwitz, Jenny,Meier, Michael A. R.. "Structurally diverse polyamides obtained from monomers derived via the Ugi multicomponent reaction". supporting information; experimental part. p. 5767 - 5776. Retrieved 2012/06/01.