tert-Butyl methyl malonate

Base Information

• Chemical Name: tert-Butyl methyl malonate
• CAS No.: 42726-73-8
• Molecular Formula: C8H14O4
• Molecular Weight: 174.197
• Hs Code.: 29171900
• European Community (EC) Number: 255-919-1
• DSSTox Substance ID: DTXSID40195404
• Nikkaji Number: J267.319C
• Wikidata: Q72503698
• Mol file: 42726-73-8.mol

Synonyms:tert-Butyl methyl malonate;42726-73-8;3-O-tert-butyl 1-O-methyl propanedioate;t-butyl methyl malonate;MFCD00042856;EINECS 255-919-1;1-tert-butyl 3-methyl propanedioate;tert.-Butyl Methyl Malonate;tert-Butylmethylmalonate;SCHEMBL332199;AMY3658;DTXSID40195404;tert-Butyl methyl malonate, 95%;XPSYZCWYRWHVCC-UHFFFAOYSA-N;BCP21701;GEO-00623;AKOS015892872;CS-W008068;AS-19096;BP-12790;Malonic acid 1-methyl 3-tert-butyl ester;SY004969;malonic acid tert-butyl ester methyl ester;FT-0654034;EN300-194028;A825993;propanedioic acid, 1,1-dimethylethyl methyl ester;W-200369

Chemical Property of tert-Butyl methyl malonate

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Melting Point: -10 °C
• Refractive Index: n20/D 1.415(lit.)
• Boiling Point: 197.7 °C at 760 mmHg
• PKA: 11.83±0.46(Predicted)
• Flash Point: 79 °C
• PSA: 52.60000
• Density: 1.039 g/cm³
• LogP: 0.89120
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 174.08920892
• Heavy Atom Count: 12
• Complexity: 178

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl methyl malonate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of tert-Butyl methyl malonate

There total 10 articles about tert-Butyl methyl 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: 93.0%

mono-tert-butyl malonate (40052-13-9) + methyl chloroformate (79-22-1) → methyl t-butyl malonate (42726-73-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo1002906

Reference yield: 91.0%

methanol (67-56-1) + mono-tert-butyl malonate (40052-13-9) → methyl t-butyl malonate (42726-73-8)

Guidance literature:

With hafnium(IV) chloride tetrahydrofuran complex; at 20 ℃; for 48h;

DOI:10.1016/j.tetasy.2015.01.006

Reference yield:

acetic acid tert-butyl ester (540-88-5) → methyl t-butyl malonate (42726-73-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaNH₂; liquid NH₃; diethyl ether / Umsetzen des Reaktionsprodukts mit festem CO₂

2: diethyl ether

With diethyl ether; ammonia; sodium amide;

upstream raw materials:

diazomethane

mono-tert-butyl malonate

Malonic acid monomethyl ester

isobutene

Downstream raw materials:

N-benzyl-3-(tert-butoxycarbonyl)succinimide

N-(p-methoxybenzyl)-3-(tert-butoxycarbonyl)succinimide

(S)-2-Bromo-2-((S)-bromo-p-tolyl-methyl)-malonic acid tert-butyl ester methyl ester

(S)-2-Bromo-2-((R)-bromo-p-tolyl-methyl)-malonic acid tert-butyl ester methyl ester

Refernces

• 1、 Kanemitsu, Takuya,Furukoshi, Saeka,Miyazaki, Michiko,Nagata, Kazuhiro,Itoh, Takashi. "Application of asymmetric alkylation of malonic diester with phase-transfer catalysis: Synthesis of LFA-1 antagonist BIRT-377". . p. 214 - 218. Retrieved 2015/03/04.
• 2、 Smith, Alexander M. R.,Rzepa, Henry S.,White, Andrew J. P.,Billen, Denis,Hii, King Kuok. "Delineating origins of stereocontrol in asymmetric Pd-catalyzed α-hydroxylation of 1,3-ketoesters". supporting information; experimental part. p. 3085 - 3096. Retrieved 2010/07/17.