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
• Uses: In the preparation of ketones. Di-tert-butyl malonate, is used as a pharmaceutical intermediate. it can be used to produce Diazomalonsaeure-di-tert-butylester at the ambient temperature. It will need reagents cesium carbonate, p-toluenesulfonyl azide and solvent tetrahydrofuran with the reaction time of 1 hour. T Di-tert-butyl malonate was used in total synthesis of (+/?)-actinophyllic acid. It was also employed as precursor for metal-organic chemical vapor deposition of HfO2 and ZrO2 thin films.

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

di-tert-butyl methylenemalonate

O-benzyl carbamate

Refernces

• 1、 Bolt, Robert R. A.,Browne, Duncan L.,Howard, Joseph L.,Khan, Adam,Magri, Giuseppina,Morrill, Louis C.,Nicholson, William I.,Richards, Emma,Seastram, Alex C.. "Ball-Milling-Enabled Reactivity of Manganese Metal**". supporting information. p. 23128 - 23133. Retrieved 2021/09/20.
• 2、 Massa, Antonio,Scettri, Arrigo,Filosa, Rosanna,Capozzolo, Laura. "Synthesis of β-hydroxymalonates: the direct aldol addition of malonates to aldehydes in the presence of SiCl4 and i-Pr2EtN". scheme or table. p. 7318 - 7321. Retrieved 2010/02/28.