Di-tert-butyl malonate

Base Information

• Chemical Name: Di-tert-butyl malonate
• CAS No.: 541-16-2
• Molecular Formula: C11H20O4
• Molecular Weight: 216.277
• Hs Code.: 29171910
• European Community (EC) Number: 208-769-6
• UNII: 7E9XWT9380
• DSSTox Substance ID: DTXSID8060244
• Nikkaji Number: J6.391F
• Wikidata: Q27268154
• Mol file: 541-16-2.mol

Synonyms:Di-tert-butyl malonate;541-16-2;ditert-butyl propanedioate;Propanedioic acid, bis(1,1-dimethylethyl) ester;Malonic Acid Di-tert-butyl Ester;di-t-Butylmalonate;di-t-butyl malonate;1,3-di-tert-butyl propanedioate;Bis(1,1-dimethylethyl) malonate;di(tert-butyl) malonate;MFCD00008810;UNII-7E9XWT9380;7E9XWT9380;EINECS 208-769-6;Propanedioic acid 1,3-bis(1,1-dimethylethyl) ester;Ditert-butyl malonate;di-tert butyl malonate;Malonic acid di-tert-butyl;DI-TERT-BUTYL-MALONATE;SCHEMBL241533;Di-tert-butyl malonate, 98%;Di-tert-butyl malonate, stab. with potassium carbonate;DTXSID8060244;AMY3656;DI-TERT-BUTYL MALONATE [MI];bis(1,1-dimethylethyl) propanedioate;AKOS015920185;CS-W014843;AS-17308;MALONIC ACID, DI-TERT-BUTYL ESTER;SY013748;tert-butyl 2-(tert-butoxycarbonyl)acetate;1,3-Bis(1,1-dimethylethyl) propanedioate;CS-0198075;FT-0625357;M1522;EN300-84612;O11729;propanedioic acid bis(1,1-dimethylethyl) ester;A829971;W-105673;Q27268154;Di-tert-Butyl malonate stabilized with Potassium Carbonate;2,2-ditert-butylpropanedioate

Chemical Property of Di-tert-butyl malonate

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.132mmHg at 25°C
• Melting Point: -7 °C
• Refractive Index: n20/D 1.418(lit.)
• Boiling Point: 217.59 °C at 760 mmHg
• PKA: 11.87±0.46(Predicted)
• Flash Point: 84.282 °C
• PSA: 52.60000
• Density: 0.996 g/cm³
• LogP: 2.05990
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: It is hardly soluble in water.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 216.13615911
• Heavy Atom Count: 15
• Complexity: 216

Purity/Quality:

99.9% ^*data from raw suppliers

Di-tert-Butyl Malonate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38-24/25
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(=O)OC(C)(C)C
• General Description: Di-tert-Butyl malonate serves as a prochiral diester precursor in the enantioselective desymmetrization process, where it is alkylated with alkyl halides to form hydroxy diesters. These intermediates are subsequently transformed into enantiomerically enriched lactones using a chiral phosphoric acid catalyst, demonstrating its utility in asymmetric synthesis for constructing complex molecules with high stereocontrol. The compound's role highlights its importance in generating biologically relevant structures, such as all-carbon quaternary centers, with scalable efficiency and robust analytical validation.

Technology Process of Di-tert-butyl malonate

There total 11 articles about Di-tert-butyl malonate 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: 97.0%

malonic acid (141-82-2) + tert-butyl alcohol (75-65-0) → t-butyl malonate (541-16-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In diethyl ether; at 0 - 20 ℃; for 1h;

DOI:10.1002/anie.202108752

Reference yield: 94.3%

O-tert-butylmalonic acid ammonium salt → t-butyl malonate (541-16-2)

Guidance literature:

With hydrogenchloride; In diethyl ether; water; for 0.5h;

Reference yield: 85.0%

malonoyl dichloride (1663-67-8) + tert-butyl alcohol (75-65-0) → t-butyl malonate (541-16-2)

Guidance literature:

In diethyl ether; for 24h; Ambient temperature;

DOI:10.1021/ja00086a016

upstream raw materials:

malonic acid

isobutene

malonoyl dichloride

tert-butyl alcohol

Downstream raw materials:

trans-2-(3-methylphenyl)-3-oxo-1-cyclohexaneacetic acid

(+/-)-[2t-(3-methoxy-phenyl)-3-oxo-cyclohex-r-yl]-acetic acid

3t-(4-chloro-phenyl)-2-methyl-5-oxo-isoxazolidine-4r-carboxylic acid tert-butyl ester

Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester

Refernces

Enantioselective desymmetrization of diesters

10.1021/jo402853v

The research focuses on the enantioselective desymmetrization of prochiral diesters to produce lactones with high enantiomeric purity, utilizing a chiral phosphoric acid catalyst. The study is significant for its potential in asymmetric synthesis, particularly for creating biologically active molecules with all-carbon quaternary centers. The experiments involved the preparation of various prochiral diesters through alkylation of di-tert-butyl malonate with different alkyl halides and subsequent reactions to form hydroxy diesters. These diesters were then subjected to desymmetrization using the chiral catalyst in dichloromethane, yielding lactones with high yields and enantioselectivity. The scalability of the process was demonstrated, and the utility of the lactone products was showcased through their conversion into functionalized building blocks. Analyses included NMR for structural confirmation, IR for functional group identification, HRMS for molecular weight determination, and GC and HPLC for assessing enantiomeric excess, providing comprehensive characterization of the synthesized compounds.