Products Categories
CAS No.: | 609-08-5 |
---|---|
Name: | Diethyl methylmalonate |
Article Data: | 95 |
Molecular Structure: | |
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 |
Boiling Point: | 204.4 °C at 760 mmHg |
Flash Point: | 76.7 °C |
Solubility: | Immiscible with water |
Appearance: | Clear liquid |
Safety: | 23-24/25 |
PSA: | 52.60000 |
LogP: | 0.74870 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sulfuric acid In tetrahydrofuran at 60 - 70℃; | 97.51% |
Conditions | Yield |
---|---|
With sulfuric acid at 20 - 80℃; for 4h; Temperature; | 91.2% |
at 20 - 65℃; for 3h; Temperature; Large scale; |
diethyl malonate
methyl iodide
A
2,2-dimethylmalonic acid diethyl ester
B
Diethyl methylmalonate
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
In acetoacetic acid methyl ester | 82.6% |
diethyl allylmethylmalonate
Diethyl methylmalonate
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -50 - -40℃; for 1h; deallylation; | 81% |
diethyl α-(chloro)-methylmalonate
Diethyl methylmalonate
Conditions | Yield |
---|---|
With zinc In water; acetic acid for 4h; Heating; | 80% |
Diethyl methylmalonate
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -50 - -40℃; for 1h; dealkynylation; | 80% |
What can I do for you?
Get Best Price
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.