Diethyl malonate-d2

Base Information

• Chemical Name: Diethyl malonate-d2
• CAS No.: 4303-49-5
• Molecular Formula: CD2(COOCH2CH3)2
• Molecular Weight: 162.154
• European Community (EC) Number: 689-507-1
• DSSTox Substance ID: DTXSID60480026
• Nikkaji Number: J1.050.730H
• Wikidata: Q82314495
• Mol file: 4303-49-5.mol

Synonyms:Diethyl malonate-d2;4303-49-5;diethyl 2,2-dideuteriopropanedioate;dideuterodiethyl malonate;SCHEMBL1332048;DTXSID60480026;Diethyl malonate-d2 98 atom % D;1,3-Diethyl propanedioate-2,2-d2;Diethyl malonate-d2, 98 atom % D;AKOS015916129;D98476;A935561

Chemical Property of Diethyl malonate-d2

Chemical Property:

• Melting Point: -51--50oC(lit.)
• Refractive Index: n20/D 1.4134(lit.)
• Boiling Point: 199oC(lit.)
• Flash Point: 212 °F
• PSA: 52.60000
• Density: 1.068 g/mL at 25oC
• LogP: 0.50270
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 162.08611235
• Heavy Atom Count: 11
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

Diethyl Malonate-d2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)OCC
• Isomeric SMILES: [2H]C([2H])(C(=O)OCC)C(=O)OCC
• Uses: Diethyl Malonate-d2 is the isotope labelled analog of Diethyl Malonate (D444420). Diethyl Malonate occurs naturally in grapes and strawberries. It is used in the preparation of barbiturates, artificial flavourings, vitamin B1, and vitamin B6 as well as in perfumes.

Technology Process of Diethyl malonate-d2

There total 4 articles about Diethyl malonate-d2 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%

diethyl malonate (105-53-3) → diethyl [2H2]malonate (4303-49-5)

Guidance literature:

With water-d2; cetyltrimethylammonim bromide; potassium carbonate;

DOI:10.1002/(SICI)1099-1344(199901)42:1<55::AID-JLCR166>3.0.CO;2-V

Reference yield: 61.0%

10-phenyl-10H-phenothiazine (7152-42-3) + diethyl malonate (105-53-3) → diethyl [2H2]malonate (4303-49-5) + diethyl 2-(10-phenyl-10H-5λ4-phenothiazin-5-ylidene)malonate

Guidance literature:

With potassium dihydrogenphosphate; tetrabutylammonium acetate; trifluoroethanol-d₃; In dimethyl sulfoxide; at 20 ℃; for 0.05h; Electrochemical reaction; Flow reactor;

DOI:10.1039/d1gc00226k

Reference yield:

diethyl malonate (105-53-3) → diethyl [2H2]malonate (4303-49-5) + d1-diethyl malonate (126581-85-9)

Guidance literature:

With water-d2; tetra-(n-butyl)ammonium iodide; potassium carbonate; Title compound not separated from byproducts;

DOI:10.1021/ol052456x

upstream raw materials:

diethyl malonate

10-phenyl-10H-phenothiazine

Downstream raw materials:

diethyl 2-phenylaminomalonate

[1,1,2,2,3,3‐D₆]‐propanediol

1-Chlorohexane

6-chlorohexene

Refernces

• 1、 Kadish, Dora,Kokel, Anne,T?r?k, Béla. "Preparation of Deuterium Labeled Compounds by Pd/C-Al-D2O Facilitated Selective H-D Exchange Reactions". supporting information. . Retrieved 2022/01/24.
• 2、 Rappenglück, Sebastian,Sichler, Sonja,H?fner, Georg,Wein, Thomas,Niessen, Karin V.,Seeger, Thomas,Paintner, Franz F.,Worek, Franz,Thiermann, Horst,Wanner, Klaus T.. "Synthesis of a Series of Structurally Diverse MB327 Derivatives and Their Affinity Characterization at the Nicotinic Acetylcholine Receptor". supporting information. p. 1806 - 1816. Retrieved 2018/09/11.