76-72-2

Basic information

• Product Name: Diethyl ethyl(1-methylbutyl)malonate
• Synonyms: ETHYL(1-METHYLBUTYL)-MALONIC ACID DIETHYL ESTER;ETHYL 2-ETHYL-2-(1-METHYLBUTYL)MALONATE;DIETHYL ETHYL (1-METHYLBUTYL) MALONATE;2-Ethyl-2-(1-methylbutyl)-malonic acid diethyl ester;Ethyl(1-methylbutyl)propanedioic acid diethyl ester;diethyl 2-ethyl-2-pentan-2-ylpropanedioate;diethyl 2-ethyl-2-pentan-2-yl-propanedioate;Propanedioic acid,2-ethyl-2-(1-Methylbutyl)-, 1,3-diethyl ester
• CAS NO: 76-72-2
• Molecular Formula: C₁₄H₂₆O₄
• Molecular Weight: 258.35
• EINECS: 200-981-7
• Mol File: 76-72-2.mol

Chemical Properties

• Boiling Point: 267.6 °C at 760 mmHg
• Flash Point: 114.2 °C
• Appearance: /
• Density: 0.967 g/cm³
• Vapor Pressure: 0.00808mmHg at 25°C
• Refractive Index: 1.44
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Diethyl ethyl(1-methylbutyl)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl ethyl(1-methylbutyl)malonate(76-72-2)
• EPA Substance Registry System: Diethyl ethyl(1-methylbutyl)malonate(76-72-2)

Safety Data

• Hazardous Substances Data: 76-72-2(Hazardous Substances Data)

Usage

Uses

Used in Electrochemistry:
Diethyl ethyl(1-methylbutyl)malonate is used as a reagent in electrochemistry for the synthesis of ureides from esters. Its ability to participate in electrochemical reactions involving urea allows for the formation of ureide compounds, which are important in various chemical processes and applications.

InChI:InChI=1/C14H26O4/c1-6-10-11(5)14(7-2,12(15)17-8-3)13(16)18-9-4/h11H,6-10H2,1-5H3

Synthetic route

diethyl (1-methylbutyl)malonate (117-47-5) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
With sodium t-butanolate; tert-butyl alcohol anschliessend Erwaermen mit Aethylbromid;

2-iodopentane (637-97-8) + ethyl diethyl malonate (133-13-1) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
With sodium; toluene

1-(1-Methylbutyl)-2,4,6-triphenylpyridinium tetrafluoroborate + ethyl diethyl malonate (133-13-1) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
With sodium hydride 1.) toluene, reflux; 2.) 110 deg C, 2.5 h; Yield given. Multistep reaction;

1-(1-Methylbutyl)-2,4-diphenyl-5,6-dihydrobenzoquinolinium tetrafluoroborate + ethyl diethyl malonate (133-13-1) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
With sodium hydride 1.) toluene, reflux; 2.) 25 deg C, 36 h; Yield given. Multistep reaction;

ethyl bromide (74-96-4) + sodium compound of <1-methyl-butyl>-malonic acid diethyl ester → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
With ethanol inactive form;

sodium compound of ethylmalonic acid diethyl ester + active 2-bromo-pentane → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
With ethanol dextrorotatory form;

sodium compound of ethylmalonic acid diethyl ester + inactive 2-bromo-pentane → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
With ethanol inactive form;
With ethanol inactive form;

2-pentylamine (625-30-9) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) acetic acid / 1.) CH2Cl2, room temp., 40 min; 2.) room temp., 14 h 2: 1.) NaH / 1.) toluene, reflux; 2.) 110 deg C, 2.5 h View Scheme
Multi-step reaction with 2 steps 1: 2.) acetic acid / 1.) CH2Cl2, room temp., 40 min; 2.) room temp., 14 h 2: 1.) NaH / 1.) toluene, reflux; 2.) 25 deg C, 36 h View Scheme

(S)-2-pentanol (26184-62-3) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus; iodine 2: sodium; toluene View Scheme

pentan-2-yl methanesulfonate (4551-09-1) + ethyl diethyl malonate (133-13-1) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
Stage #1: ethyl diethyl malonate With sodium ethanolate In ethanol; ethyl acetate at 125℃; for 2h; Stage #2: pentan-2-yl methanesulfonate In ethyl acetate; toluene at 40 - 135℃; for 5h;	236.5 g

(+/-)-2-pentanol (6032-29-7) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate; phosphorus tribromide / 5 h / -15 - 150 °C 2: sodium ethanolate / ethanol; ethyl acetate / 5 h / 75 - 125 °C View Scheme

2-bromopentane (107-81-3) + ethyl diethyl malonate (133-13-1) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
With sodium ethanolate In ethanol; ethyl acetate at 75 - 125℃; for 5h;	217.3 g

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) + urea (57-13-6) → pentobarbital (76-74-4)

Conditions	Yield
With tetraethylammonium perchlorate In N,N-dimethyl-formamide Ambient temperature; electrolysis;	27%
With sodium methylate In methanol; ethanol; ethyl acetate at 135 - 140℃;	99.3 g
With sodium methylate In methanol; ethyl acetate at 60 - 140℃;	99.6 g

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) + sodium ethanolate (141-52-6) → 2-ethyl-3-methyl-hexanoic acid ethyl ester (106593-73-1)

Conditions	Yield
at 220 - 230℃; inactive form;

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → 2-ethyl-2-(1-methyl-butyl)-propane-1,3-diol (99868-16-3)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → 2-ethyl-3-methyl-hexanoic acid ethyl ester (106593-73-1)

Conditions	Yield
With sodium ethanolate at 220 - 230℃;

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → ethyl-(1-methyl-butyl)-malonic acid (408536-20-9)

Conditions	Yield
With potassium hydroxide

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → 2-ethyl-3-methyl-hexan-1-ol (66794-04-5)

Conditions	Yield
With copper-chromium barium oxide at 250℃; under 128714 Torr; Hydrogenation;
With i-Amyl alcohol; sodium; xylene

<(35)S>-Thiourea (5022-67-3) + diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → <35S>-thiopental

Conditions	Yield
With sodium ethanolate

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) + copper-chromium barium oxide → 2-ethyl-3-methyl-hexan-1-ol (66794-04-5)

Conditions	Yield
at 250℃; under 128714 Torr; Hydrogenation; inactive form;

tetrachloromethane (56-23-5) + i-Amyl alcohol (123-51-3) + diethyl ethyl(1-methyl-butyl)malonate (76-72-2) + sodium → 2-ethyl-3-methyl-hexan-1-ol (66794-04-5)

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → 3-(2-ethyl-3-methyl-hexyloxy)-propane-1,2-diol

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium; xylene; isopentyl alcohol 2: sodium ethylate; ethanol View Scheme

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → 2-ethyl-3-methylhexanoic acid (74581-94-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethylate / 220 - 230 °C 2: durch Verseifen View Scheme

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → 2-ethyl-2-(1-methylbutyl)propanediamide (74581-91-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq.-ethanolic KOH-solution 2: thionyl chloride / Behandeln des Reaktionsprodukts mit Ammoniak in Aether View Scheme

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → Ethyl(1-methylbutyl)malonuric Acid (106686-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq.-ethanolic KOH-solution 2: aqueous sulfuric acid View Scheme

diethyl ethyl(1-methyl-butyl)malonate (76-72-2) → ethyl-(1-methyl-butyl)-malonic acid methyl ester ureide

Conditions	Yield
Multi-step reaction with 3 steps 1: aq.-ethanolic KOH-solution 2: aqueous sulfuric acid 3: diethyl ether View Scheme

Upstream product

• 117-47-5 diethyl (1-methylbutyl)malonate 
• 637-97-8 2-iodopentane 
• 133-13-1 ethyl diethyl malonate 
• 74-96-4 ethyl bromide 
• 625-30-9 2-pentylamine 
• 26184-62-3 (S)-2-pentanol 
• 4551-09-1 pentan-2-yl methanesulfonate 
• 6032-29-7 (+/-)-2-pentanol 
• 107-81-3 2-bromopentane 

Downstream Products

• 76-74-4 pentobarbital 
• 74581-94-5 2-ethyl-3-methylhexanoic acid 

Relevant articles and documents

High-purity 5-ethyl-5-(1-methylbutyl)barbituric acid preparation method

The present invention relates to a preparation method of a drug pentobarbital (1) for sedation, hypnosis, pre-anesthesia administration and anti-convulsion, and provides a new preparation process for preparing high-purity pentobarbital (I) from diethyl ethylmalonate, wherein the process comprises three steps: A, bromination; B, alkylation; and C, cyclization, acidification, and purification. According to the present invention, the method has advantages of simple operation, short production cycle, low energy consumption, mother liquor circulation, less three-waste, stable process, good product quality, high product purity, isomer impurity content of less than 0.1%, high yield and low production cost, and is suitable for industrial production.

5-ethyl-5 - (1-methyl butyl) method for preparing malonyl urea (by machine translation)

The invention belongs to the technical field of drug synthesis, in particular relates to a 5-ethyl-5 - (1-methyl butyl) method for preparing malonyl urea. Ethyl malonic acid diethyl ester (III) with ethanol after the reaction ethanol solution of sodium in toluene in the presence of a mixture of the methanesulfonic acid (2-pentyl) should be ester instead, rectification to get ethyl-(1-methyl butyl) malonic acid diethyl ester compound (II); compound (II) in the presence of a methanol solution of sodium methoxide reaction with urea, acidified by hydrochloric acid, is recrystallized to get 5-ethyl-5 - (1-methyl butyl) malonyl urea fine (I). The process of the invention is stable, mild reaction conditions, is easy to control, the resulting product has high purity, high yield, the conversion is almost 100%, after treatment is simple and convenient, low energy consumption, little three waste, the mother liquor can be used continuously, low production cost, is suitable for industrial production. (by machine translation)

Alkylation of Monosubstituted Malonate Anions With Pyridinium and Quinolinium Salts

Monosubstituted malonate anions are alkylated at room temperature with 1-(sec-alkyl)quinolinium salts.Hindered disubstituted malonate esters can thus be prepared under very mild conditions.