6065-63-0

Basic information

• Product Name: Diethyl dipropylmalonate
• Synonyms: Diethyldi-n-propylmalonate,97%;Dipropylpropanedioic acid diethyl ester;DIETHYL DIPROPYL MALONATE - REVERSE;2,2-Dipropylmalonic acid diethyl ester;diethyl 2,2-dipropylpropanedioate;Diethyl dipropyl;NSC 163902;DEDNPM
• CAS NO: 6065-63-0
• Molecular Formula: C₁₃H₂₄O₄
• Molecular Weight: 244.33
• EINECS: 227-998-2
• Product Categories: Pharmaceutical Intermediates;TheMalonateRamificationProducts;Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 6065-63-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 129-131°C 12mm
• Flash Point: STABILITY
• Appearance: Clear liquid
• Density: 0.96
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: 1.4270-1.4290
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Diethyl dipropylmalonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl dipropylmalonate(6065-63-0)
• EPA Substance Registry System: Diethyl dipropylmalonate(6065-63-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 6065-63-0(Hazardous Substances Data)

Usage

Description

Diethyl dipropylmalonate is an organic compound with the chemical formula C13H24O4. It is a light yellow oil at room temperature and is known for its unique chemical properties that make it suitable for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
Diethyl dipropylmalonate is used as an intermediate in the synthesis of various pharmaceutical compounds. One of its primary applications is in the preparation of Valproic Acid (V094750), a medication used to treat epilepsy and bipolar disorder. Its chemical properties allow it to serve as a crucial building block in the development of these medications, contributing to their effectiveness in treating the targeted conditions.

InChI:InChI=1/C13H24O4/c1-5-9-13(10-6-2,11(14)16-7-3)12(15)17-8-4/h5-10H2,1-4H3

Synthetic route

diallylmalonic acid diethyl ester (3195-24-2) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0)

Conditions	Yield
With 6C53H32O8(4-)*13Zr(4+)*18O(2-)*8Co(2+)*8H(1-); hydrogen In tetrahydrofuran at 23℃; under 30003 Torr; for 36h; Catalytic behavior; Mechanism; Reagent/catalyst;	100%
With sodium tetrahydroborate; ruthenium trichloride In tetrahydrofuran; water at 20℃; for 1h;	93%
With 6C53H32O8(4-)*13Zr(4+)*18O(2-)*8Co(2+)*8Cl(1-); hydrogen; sodium triethylborohydride In tetrahydrofuran at 23℃; under 30402 Torr; for 36h; Catalytic behavior; Time; Glovebox; Inert atmosphere;	100 %Spectr.
With fac-[Mn(1,2-bis(di-isopropylphosphino)ethane)(CO)3(CH2CH2CH3)]; hydrogen In diethyl ether at 25℃; under 37503.8 Torr; for 18h;	75 %Chromat.
With hydrogen In water at 60℃; under 22502.3 Torr; for 18h; Autoclave; Green chemistry;

diethyl 2-(3-iodopropyl)-2-propylmalonate (1439866-82-6) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0)

Conditions	Yield
With [Ir(2-phenylpyridine)-2-(4,4’-di-tert-butyl-2,2’-bipyridine)]PF6; N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 5h; Irradiation;	88%

propyl bromide (106-94-5) + diethyl propylmalonate (2163-48-6) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0)

Conditions	Yield
With sodium ethanolate In ethanol for 10h; Heating;	83%

1-iodo-propane (107-08-4) + diethyl propylmalonate (2163-48-6) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0)

Conditions	Yield
With caesium carbonate In butanone at 70℃; for 15h;	70%

propyl bromide (106-94-5) + diethyl malonate (105-53-3) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + n-propylmalonic acid (616-62-6)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 16h;	A 48% B 41%

1-iodo-propane (107-08-4) + diethyl malonate (105-53-3) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0)

Conditions	Yield
With zinc

1-iodo-propane (107-08-4) + diethyl malonate (105-53-3) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + diethyl propylmalonate (2163-48-6)

Conditions	Yield
With zinc

1-iodo-propane (107-08-4) + diethyl malonate (105-53-3) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + diethyl propylmalonate (2163-48-6)

diethyl malonate (105-53-3) + 6-ethoxy-4-cyano-5-methyl-hex-2ξ-enoic acid ethyl ester → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / NaOEt / ethanol / 7 h / Heating 2: 83 percent / NaOEt / ethanol / 10 h / Heating View Scheme

4,4-bis(ethoxycarbonyl)-1-hepten-6-yne (101268-55-7) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + diethyl cis-3,4-dimethylcyclopentane-1,1-dicarboxylate (1114376-78-1) + diethyl (3R,4R)-3,4-dimethylcyclopentane-1,1-dicarboxylate

Conditions	Yield
With (IPr2,6-(2,6-iPr2C6H3N=CMe)2C5H3N)Fe(N2)2; hydrogen In benzene at 23℃; under 3040.2 Torr; for 3h; Inert atmosphere; optical yield given as %de;	A 25.9 %Chromat. B n/a C n/a

diethyl propylmalonate (2163-48-6) → 2,2-dipropyl-malonic acid diethyl ester (6065-63-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride; hydrogen / mineral oil; tetrahydrofuran / 12 h / 0 - 20 °C 2: [Ir(2-phenylpyridine)-2-(4,4’-di-tert-butyl-2,2’-bipyridine)]PF6; N-ethyl-N,N-diisopropylamine / acetonitrile / 5 h / 25 °C / Irradiation View Scheme

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + thiourea (17356-08-0) → 5,5-di-n-propyl-2-thiobarbituric acid (99167-62-1)

Conditions	Yield
With sodium ethanolate In ethanol at 50℃; for 12h;	96%
With sodium ethanolate
With ethanol; sodium ethanolate at 100℃;

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) → 2,2-di-n-propyl-1,3-propanediol (24765-54-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;	92%
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride In diethyl ether

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + urea (57-13-6) → 5,5-dipropylbarbituric acid (2217-08-5)

Conditions	Yield
With sodium ethanolate In ethanol for 12h; Heating;	23%
With sodium ethanolate at 100℃; im geschlossenen Gefaess;
With sodium ethanolate at 100℃; im geschlossenen Gefaess;

methyl magnesium iodide (917-64-6) + 2,2-dipropyl-malonic acid diethyl ester (6065-63-0) → valproic acid (99-66-1)

Conditions	Yield
und durch Behandeln des Reaktionprodukts mit Barytwasser, neben Aceton;

methyl magnesium iodide (917-64-6) + 2,2-dipropyl-malonic acid diethyl ester (6065-63-0) → valproic acid (99-66-1) + acetone (67-64-1)

Conditions	Yield
Verseifung des Reaktionsproduktes;

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + benzamidine monohydrochloride (1670-14-0) → 2-phenyl-5,5-dipropyl-1H-pyrimidine-4,6-dione

Conditions	Yield
With sodium ethanolate at 70℃;

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + methylmagnesium iodide → valproic acid (99-66-1) + acetone (67-64-1)

Conditions	Yield
Verseifung des Reaktionsprodukts;

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + phenylhydrazine hydrochloride (59-88-1) → 1-phenyl-4,4-dipropyl-pyrazolidine-3,5-dione

Conditions	Yield
With ethanol; sodium ethanolate at 160℃;

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) → 4,4-dipropyl-pyrazolidine-3,5-dione (342618-11-5)

Conditions	Yield
With hydrazine hydrochloride; sodium ethanolate
With sodium ethanolate; hydrazine hydrate

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) → monoethyl α,α-dipropylmalonate (258264-00-5)

Conditions	Yield
With potassium hydroxide Kaliumsalz entsteht;
With ethanol; sodium hydroxide at 20℃; for 12h;

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + 1,2-diamino-benzene (95-54-5) → 3,3-dipropyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione

Conditions	Yield
With sodium ethanolate

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) → valproic acid (99-66-1)

Conditions	Yield
(i) aq. KOH, (ii) (decarboxylation); Multistep reaction;

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) → dimethyl 2,2-propylmalonamide (90728-92-0)

Conditions	Yield
With sodium methylate; formamide In methanol Heating;

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + sodium ethanolate (141-52-6) + hydrazine hydrochloride → 4,4-dipropyl-pyrazolidine-3,5-dione (342618-11-5)

Conditions	Yield
at 100 - 110℃;

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + ZnCl2 → ethene (74-85-1) + ethyl 2-propylpentanoate (17022-31-0)

diethyl ether (60-29-7) + 2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + potassium → ethyl 2-propylpentanoate (17022-31-0) + monoethyl α,α-dipropylmalonate (258264-00-5) + CO

diethyl ether (60-29-7) + 2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + sodium → ethyl 2-propylpentanoate (17022-31-0) + monoethyl α,α-dipropylmalonate (258264-00-5) + CO

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) + phenylhydrazine (100-63-0) → dipropyl-malonic acid mono-(N'-phenyl-hydrazide) + 1-phenyl-3.5-dioxo-4.4-dipropyl-pyrazolidine

Conditions	Yield
With sodium ethanolate

2,2-dipropyl-malonic acid diethyl ester (6065-63-0) → 1-<2-Diaethylamino-aethoxy>-2,2-dipropyl-propanol-(3) (101082-35-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: (i) Na, benzene, (ii) /BRN= 605300/ View Scheme

Upstream product

• 107-08-4 1-iodo-propane 
• 105-53-3 diethyl malonate 
• 2163-48-6 diethyl propylmalonate 
• 1439866-82-6 diethyl 2-(3-iodopropyl)-2-propylmalonate 
• 101268-55-7 4,4-bis(ethoxycarbonyl)-1-hepten-6-yne 
• 3195-24-2 diallylmalonic acid diethyl ester 
• 106-94-5 propyl bromide 

Downstream Products

• 74-85-1 ethene 
• 17022-31-0 ethyl 2-propylpentanoate 
• 24765-54-6 2,2-di-n-propyl-1,3-propanediol 
• 99-66-1 valproic acid 
• 67-64-1 acetone 
• 2217-08-5 5,5-dipropylbarbituric acid 
• 258264-00-5 monoethyl α,α-dipropylmalonate 

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