Di-tert-butyl 2-methylenemalonate

Base Information

• Chemical Name: Di-tert-butyl 2-methylenemalonate
• CAS No.: 86633-09-2
• Molecular Formula: C12H20O4
• Molecular Weight: 228.28
• DSSTox Substance ID: DTXSID30455089
• Nikkaji Number: J688.637J
• Wikidata: Q82276950
• Mol file: 86633-09-2.mol

Synonyms:86633-09-2;Di-tert-butyl 2-methylenemalonate;Ditert-butyl 2-methylidenepropanedioate;Propanedioic acid, methylene-, bis(1,1-dimethylethyl) ester;di-t-butyl methylenemalonate;SCHEMBL2712242;Di-tert-butyl2-methylenemalonate;DTXSID30455089;LPEDZARVHHELPJ-UHFFFAOYSA-N;di(tert-butyl) 2-methylenemalonate;tert-butyl 2-tert-butoxycarbonylacrylate;Methylenemalonic acid di-tert-butyl ester;2-Methylene-malonic acid di-tert-butyl ester;2-methylene-propanedioic acid ditert-butyl ester;1,3-DI-TERT-BUTYL 2-METHYLIDENEPROPANEDIOATE;Propanedioic acid, 2-methylene-, 1,3-bis(1,1-dimethylethyl) ester

Chemical Property of Di-tert-butyl 2-methylenemalonate

Chemical Property:

• PSA: 52.60000
• LogP: 2.22600
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 228.13615911
• Heavy Atom Count: 16
• Complexity: 272

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(=C)C(=O)OC(C)(C)C

Technology Process of Di-tert-butyl 2-methylenemalonate

There total 3 articles about Di-tert-butyl 2-methylenemalonate 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: 81.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + t-butyl malonate (541-16-2) → di-tert-butyl methylenemalonate (86633-09-2)

Guidance literature:

With trifluoroacetic acid; diisopropylamine 2,2,2-trifluoroacetic acid salt; In tetrahydrofuran; Reflux; Portion-wise addition of paraformaldehyde;

DOI:10.1039/b924577d

Reference yield: 53.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + t-butyl malonate (541-16-2) → di-tert-butyl methylenemalonate (86633-09-2) + 2,2-Bis-hydroxymethyl-malonic acid di-tert-butyl ester

Guidance literature:

With potassium acetate; copper diacetate; In acetic acid; at 95 - 100 ℃; for 2h;

DOI:10.1021/jo00168a061

Reference yield: 41.0%

→ di-tert-butyl methylenemalonate (86633-09-2)

Guidance literature:

upstream raw materials:

formaldehyd

t-butyl malonate

Downstream raw materials:

2-((3S,5S,6R)-4-Benzyloxycarbonyl-2-oxo-5,6-diphenyl-morpholin-3-ylmethyl)-malonic acid di-tert-butyl ester

Refernces

• 1、 Zhang, Kaining,Chang, Liang,An, Qing,Wang, Xin,Zuo, Zhiwei. "Dehydroxymethylation of alcohols enabled by cerium photocatalysis". supporting information. p. 10556 - 10564. Retrieved 2019/08/20.
• 2、 -. "SYNTHESIS OF METHYLENE MALONATES USING RAPID RECOVERY IN THE PRESENCE OF A HEAT TRANSFER AGENT". Page/Page column 81-83. . Retrieved 2012/05/05.