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609-08-5

Basic Information
CAS No.: 609-08-5
Name: Propanedioicacid, 2-methyl-, 1,3-diethyl ester
Article Data: 95
Cas Database
Molecular Structure:
Molecular Structure of 609-08-5 (Propanedioicacid, 2-methyl-, 1,3-diethyl ester)
Formula: C8H14O4
Molecular Weight: 174.197
Synonyms: Malonicacid, methyl-, diethyl ester (6CI,7CI,8CI);Propanedioic acid, methyl-, diethylester (9CI);2-Methylmalonic acid diethyl ester;Diethyl 2-methylmalonate;Diethyl a-methylmalonate;Methylmalonic acid diethyl ester;NSC 8700;
EINECS: 210-175-7
Density: 1.037 g/cm3
Melting Point: N/A
Boiling Point: 204.4 °C at 760 mmHg
Flash Point: 76.7 °C
Solubility: Immiscible with water
Appearance: Clear liquid
Hazard Symbols: N/A
Risk Codes: N/A
Safety: 23-24/25
Transport Information: N/A
PSA: 52.60000
LogP: 0.74870
Synthetic route
105-53-3

diethyl malonate

74-88-4

methyl iodide

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With P(MeNCH2CH2)3N In hexane; acetonitrile at 25℃; for 0.5h;98%
With sodium In ethanol at 80℃; for 10h; Inert atmosphere;97%
With (3S,4S)-1-benzyl-3,4-pyrrolidin-diol-onium iodide; potassium carbonate In N,N-dimethyl-formamide for 2.5h; Ambient temperature;96%
64-17-5

ethanol

3696-36-4

2-methylmalononitrile

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 60 - 70℃;97.51%
632-07-5

2-cyanopropanoic acid

64-17-5

ethanol

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With sulfuric acid at 20 - 80℃; for 4h; Temperature;91.2%
at 20 - 65℃; for 3h; Temperature; Large scale;
105-53-3

diethyl malonate

74-88-4

methyl iodide

A

1619-62-1

2,2-dimethylmalonic acid diethyl ester

B

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 4h; Ambient temperature;A 5%
B 90%
With sodium hydride 1.) DMSO, cooling, 10 min, 2.) overnight; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
53651-72-2

diethyl allylmethylmalonate

naphthalen-2-ylzinc(II) bromide

A

2489-87-4

2-allylnaphthalene

B

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
Stage #1: diethyl allylmethylmalonate; naphthalen-2-ylzinc(II) bromide With dibromobis(triphenylphosphine)nickel(II); magnesium bromide In tetrahydrofuran; toluene at 20 - 60℃; Inert atmosphere;
Stage #2: With ammonium chloride In tetrahydrofuran; water; toluene
A 89%
B 95 %Spectr.
74-83-9

methyl bromide

105-53-3

diethyl malonate

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 3h; Heating;85%
With sodium ethanolate In ethanol
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: methyl bromide In tetrahydrofuran at 0℃; for 8h; Inert atmosphere;
105-53-3

diethyl malonate

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
In acetoacetic acid methyl ester82.6%
53651-72-2

diethyl allylmethylmalonate

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -50 - -40℃; for 1h; deallylation;81%
29263-82-9

diethyl α-(chloro)-methylmalonate

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With zinc In water; acetic acid for 4h; Heating;80%

2-methyl-2-trimethylsilanylethynyl-malonic acid diethyl ester

609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -50 - -40℃; for 1h; dealkynylation;80%
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Specification

The IUPAC name of Propanedioicacid, 2-methyl-, 1,3-diethyl ester is diethyl 2-methylpropanedioate. With the CAS registry number 609-08-5, it is also named as Methylmalonic acid diethyl ester; Ethyl methylmalonate (VAN). The product's categories are pharmaceutical intermediates, cyanoacetic acid esters and hydrocyanic acid derivatives. It is clear liquid which is immiscible with water. And people should not breathe the vapour of this chemical and must avoid contact with skin and eyes. 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.05; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.05; (4)ACD/LogD (pH 7.4): 1.05; (5)ACD/BCF (pH 5.5): 3.7; (6)ACD/BCF (pH 7.4): 3.7; (7)ACD/KOC (pH 5.5): 88.82; (8)ACD/KOC (pH 7.4): 88.82; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.421; (13)Molar Refractivity: 42.62 cm3; (14)Molar Volume: 167.9 cm3; (15)Polarizability: 16.89×10-24 cm3; (16)Surface Tension: 31.3 dyne/cm; (17)Enthalpy of Vaporization: 44.06 kJ/mol; (18)Vapour Pressure: 0.264 mmHg at 25°C; (19)Rotatable Bond Count: 6; (20)Exact Mass: 174.089209; (21)MonoIsotopic Mass: 174.089209; (22)Topological Polar Surface Area: 52.6; (23)Heavy Atom Count: 12.

Preparation of Propanedioicacid, 2-methyl-, 1,3-diethyl ester: It can be obtained by chloro-methyl-malonic acid diethyl ester. This reaction needs reagent Zn and solvent acetic acid and H2O by heating. The reaction time is 4.0 hours. The yield is 80%.

Uses of Propanedioicacid, 2-methyl-, 1,3-diethyl ester: It is used as pharmaceutical intermediates, e.g. non-steroidal anti-inflammatory agents with 2-acrylpropionic acid structures acrylpropionic acid structure. It is also used in the flavour and fragrance industries. It can react with iodoethane to get ethyl-methyl-malonic acid diethyl ester. This reaction needs reagent sodium ethylate. The yield is 82%.  

People can use the following data to convert to the molecule structure. 
1. SMILES: O=C(OCC)C(C(=O)OCC)C;
2. InChI: InChI=1/C8H14O4/c1-4-11-7(9)6(3)8(10)12-5-2/h6H,4-5H2,1-3H3.