Diethyl malonate-2-13C

Base Information

• Chemical Name: Diethyl malonate-2-13C
• CAS No.: 67035-94-3
• Molecular Formula: C6¹³CH12O4
• Molecular Weight: 161.159
• DSSTox Substance ID: DTXSID20480027
• Nikkaji Number: J410.687C
• Wikidata: Q82314499
• Mol file: 67035-94-3.mol

Synonyms:Diethyl malonate-2-13C;67035-94-3;diethyl (213C)propanedioate;starbld0016583;SCHEMBL1330550;DTXSID20480027;AKOS015913060;Propanedioic-2-13cacid,1,3-diethyl ester;Diethyl malonate-2-13C, 99 atom % 13C

Chemical Property of Diethyl malonate-2-13C

Chemical Property:

• Vapor Pressure: 1 mm Hg ( 40 °C)
• Melting Point: 51--50 °C(lit.)
• Boiling Point: 199 °C(lit.)
• Flash Point: 212 °F
• PSA: 52.60000
• Density: 1.06 g/cm³
• LogP: 0.50270
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 161.07691370
• Heavy Atom Count: 11
• Complexity: 125

Purity/Quality:

99% ^*data from raw suppliers

Diethyl malonate-2-13C 99 atom % ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)OCC
• Isomeric SMILES: CCOC(=O)[13CH2]C(=O)OCC
• Uses: Diethyl Malonate-2-13C is the labelled form of Diethyl Malonate(D444420) which 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-2-13C

There total 1 articles about Diethyl malonate-2-13C 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: 92.0%

ethyl <2-13C>acetate (58735-82-3) + chloroformic acid ethyl ester (541-41-3) → diethyl [2-13C]malonate (67035-94-3)

Guidance literature:

ethyl <2-13C>acetate; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h; Schlenk technique; Inert atmosphere;

chloroformic acid ethyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.15227/orgsyn.078.0113

Reference yield: 85.0%

4-pyrone (108-97-4) + diethyl [2-13C]malonate (67035-94-3) → ethyl 4-hydroxy[1-13C]benzoate (211519-29-8)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; for 20h; Heating;

DOI:10.1055/s-1998-2109

Reference yield: 74.0%

[3,5-(13)C2]4H-pyran-4-one (1134383-98-4) + diethyl [2-13C]malonate (67035-94-3) → ethyl 4-hydroxy-[1,3,5-(13)C3]benzoate (1134384-02-3)

Guidance literature:

[3,5-⁽¹³⁾C₂]4H-pyran-4-one; diethyl [2-¹³C]malonate; With potassium tert-butylate; In tert-butyl alcohol; Reflux; Inert atmosphere;

With hydrogenchloride; water; In tert-butyl alcohol; for 1h; Reflux;

DOI:10.1039/b813991a

upstream raw materials:

ethyl <2-13C>acetate

chloroformic acid ethyl ester

Downstream raw materials:

ethyl 4-hydroxy[1-¹³C]benzoate

ethyl 4-hydroxy-[1,3,5-⁽¹³⁾C₃]benzoate

diethyl 2,4,6-trihydroxy-[1,3,5-⁽¹³⁾C]isophthalate

Refernces

• 1、 Lang, Martin,Lang-Fugmann, Susanne,Steglich, Wolfgang. "4-Hydroxy[1-13C]benzoic acid [ Benzoic-1-13C acid, 4-hydroxy- ]". . p. 113 - 113. Retrieved 2017/09/14.