52313-87-8

Basic information

• Product Name: DIMETHYL 3-METHYLGLUTACONATE
• Synonyms: DIMETHYL 3-METHYLGLUTACONATE;2-Pentenedioic acid, 3-methyl-, dimethyl ester;Dimethyl (2E)-2-methyl-2-pentenedioate;dimethyl 3-methylglutaconate, mixture of ci;Dimethyl 3-methylglutaconate,mixture of cis and trans;dimethyl 3-methylpent-2-enedioate;DIMETHYL 3-METHYLGLUTACONATE, 95%, MIXTU RE OF CIS AND TRANS;3-Methyl-2-pentenedioic acid dimethyl ester
• CAS NO: 52313-87-8
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• EINECS: 257-839-2
• Product Categories: C8 to C9;Carbonyl Compounds;Esters
• Mol File: 52313-87-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 109-110 °C12 mm Hg(lit.)
• Flash Point: 208 °F
• Appearance: /
• Density: 1.095 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0579mmHg at 25°C
• Refractive Index: n20/D 1.456(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: DIMETHYL 3-METHYLGLUTACONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 3-METHYLGLUTACONATE(52313-87-8)
• EPA Substance Registry System: DIMETHYL 3-METHYLGLUTACONATE(52313-87-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 52313-87-8(Hazardous Substances Data)

Usage

Uses

Dimethyl 3-Methylglutaconate are shown to induce oxidative damage on striatum and the liver in rats. Also used in the preparation of insect growth regulators with juvenile hormone activity.

InChI:InChI=1/C8H12O4/c1-6(4-7(9)11-2)5-8(10)12-3/h4H,5H2,1-3H3/b6-4-

Synthetic route

methyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (41264-06-6) + sodium methylate (124-41-4) → 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8)

Conditions	Yield
In methanol

3-Hydroxy-3-methyl-5,5-bis-methylsulfanyl-pent-4-enoic acid ethyl ester → 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8)

Conditions	Yield
With boron trifluoride diethyl etherate In methanol for 20h; Heating; Yield given;

methanol (67-56-1) + 3-methylpent-2-enedioic acid (372-42-9, 15649-56-6, 5746-90-7) → 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8)

Conditions	Yield
With sulfuric acid
Stage #1: 3-methylpent-2-enedioic acid at 72℃; for 8h; Stage #2: methanol at 90 - 120℃; for 0.5h;	485 g

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → dimethyl 3-methylglutarate (19013-37-7)

Conditions	Yield
With hydrogen; palladium on activated charcoal at 65℃; under 3040 Torr;	91%

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + pivalaldehyde (630-19-3) → anti-6-tert-butyl-5-methoxycarbonyl-4-methyl-5,6-dihydro-2H-pyran-2-one

Conditions	Yield
With zinc(II) chloride; lithium hexamethyldisilazane In tetrahydrofuran 1.) -35 deg C, 0.5 h, 2.) -65 deg C, 15 min, 3.) -30 deg C to -10 deg C, 7 h;	90%

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + phenylacetaldehyde (122-78-1) → (Z)-3-Methyl-2-((E)-styryl)-pent-2-enedioic acid 1-methyl ester (135628-90-9)

Conditions	Yield
With sodium methylate In diethyl ether at 20℃; for 2h;	85%

Diphenylacetaldehyde (947-91-1) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → (Z)-2-(2,2-Diphenyl-vinyl)-3-methyl-pent-2-enedioic acid 1-methyl ester (135628-95-4)

Conditions	Yield
With sodium methylate In diethyl ether at 20℃; for 2h;	65%

4-Methoxyphenylacetaldehyde (5703-26-4) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → (Z)-2-[(E)-2-(4-Methoxy-phenyl)-vinyl]-3-methyl-pent-2-enedioic acid 1-methyl ester (135628-92-1)

Conditions	Yield
With sodium methylate In diethyl ether at 20℃; for 2h;	65%

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 2-Phenylpropanal (34713-70-7) → (Z)-3-Methyl-2-((E)-2-phenyl-propenyl)-pent-2-enedioic acid 1-methyl ester (135628-94-3)

Conditions	Yield
With sodium methylate In diethyl ether at 20℃; for 2h;	65%

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + phenylacetaldehyde (122-78-1) → syn-6-benzyl-5-methoxycarbonyl-4-methyl-5,6-dihydro-2H-pyran-2-one

Conditions	Yield
With zinc(II) chloride; lithium hexamethyldisilazane In tetrahydrofuran 1.) -35 deg C, 0.5 h, 2.) -65 deg C, 15 min, 3.) -30 deg C to -10 deg C, 7 h;	65%

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 4-methylphenylacetaldehyde (104-09-6) → (Z)-3-Methyl-2-((E)-2-p-tolyl-vinyl)-pent-2-enedioic acid 1-methyl ester (135628-91-0)

Conditions	Yield
With sodium methylate In diethyl ether at 20℃; for 2h;	60%

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 4-fluorophenylacetaldehyde (1736-67-0) → (Z)-2-[(E)-2-(4-Fluoro-phenyl)-vinyl]-3-methyl-pent-2-enedioic acid 1-methyl ester (135628-93-2)

Conditions	Yield
With sodium methylate In diethyl ether at 20℃; for 2h;	60%

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + salicylaldehyde (90-02-8) → methyl (E)-3-(2-oxo-2H-1-benzopyran-3-yl)-2-butenoate

Conditions	Yield
With piperidine In benzene at 80℃; for 45h;	55%

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 3,4-Dimethyl-5-(2-nitroethyl)-pyrrol-2-carbonsaeure-tert-butylester (80053-00-5) → 3,4-Dimethyl-5-(3,3-bis-methoxycarbonylmethyl-2-nitrobutyl)-pyrrol-2-carbonsaeure-tert-butylester (90702-48-0)

Conditions	Yield
	46%

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + benzaldehyde (100-52-7) → 5-methoxycarbonyl-4-methyl-6-phenyl-5,6-dihydro-2H-pyran-2-one

Conditions	Yield
With zinc(II) chloride; lithium hexamethyldisilazane In tetrahydrofuran 1.) -35 deg C, 0.5 h, 2.) -65 deg C, 15 min, 3.) -30 deg C to -10 deg C, 7 h;	31%

methanol (67-56-1) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 4-chlorophenyldiazonium salt (17333-85-6) → 1-(4-chloro-phenyl)-4-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester (100375-28-8)

Conditions	Yield
With sodium methylate; sodium acetate

nonan-1-al (124-19-6) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → 4-methyl-2-octyl-6-oxo-3,6-dihydro-2H-pyran-3-carboxylic acid (131591-88-3)

Conditions	Yield
With potassium hydroxide

benzenediazonium (2684-02-8) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → 4-methyl-6-oxo-1-phenyl-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester (107516-97-2)

Conditions	Yield
With sodium methylate; sodium acetate

heptanal (111-71-7) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → 4-heptylidene-3-methyl-pentenedioic acid

Conditions	Yield
With potassium hydroxide beim Behandeln des danach isolierten Salzes in wss. Loesung mit konz. wss. Salzsaeure;

heptanal (111-71-7) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → 2-hexyl-4-methyl-6-oxo-3,6-dihydro-2H-pyran-3-carboxylic acid (108996-63-0)

Conditions	Yield
With potassium hydroxide

p-methoxybenzenediazonium (17333-79-8) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → 1-(4-methoxy-phenyl)-4-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester (100870-84-6)

Conditions	Yield
With sodium methylate; sodium acetate

4-methylbenzene diazonium (57573-52-1) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → 4-methyl-6-oxo-1-p-tolyl-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester (106378-47-6) + 3-methyl-4-p-tolylhydrazono-pentenedioic acid dimethyl ester (109506-29-8)

Conditions	Yield
With sodium methylate; sodium acetate

4-methylbenzene diazonium (57573-52-1) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → 3-methyl-4-p-tolylhydrazono-pentenedioic acid dimethyl ester (109506-29-8)

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 3-chlorobenzenediazonium (17333-84-5) → 4-(3-chloro-phenylhydrazono)-3-methyl-pentenedioic acid dimethyl ester (109104-33-8)

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 3-bromophenyldiazonium chloride (20893-74-7) → 4-(3-bromo-phenylhydrazono)-3-methyl-pentenedioic acid dimethyl ester (109286-51-3)

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 3-methyl-4-((E)-veratrylidene)-cis-pentenedioic acid (109311-73-1, 136454-20-1)

Conditions	Yield
With potassium hydroxide

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + hexanal (66-25-1) → 4-methyl-6-oxo-2-pentyl-3,6-dihydro-2H-pyran-3-carboxylic acid (108754-34-3)

Conditions	Yield
With potassium hydroxide

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + meta-hydroxybenzaldehyde (100-83-4) → 4-((E)-3-hydroxy-benzylidene)-3-methyl-ξ-pentenedioic acid

Conditions	Yield
With potassium hydroxide

3,7-dimethyl-1-octanal (60018-13-5, 81738-03-6, 124440-53-5, 25795-46-4, 5988-91-0) + 3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) → (Z)-4-[3,7-Dimethyl-oct-(E)-ylidene]-3-methyl-pent-2-enedioic acid

Conditions	Yield
With sodium hydroxide In methanol

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 7-methoxy-3,7-dimethyloctanal (3613-30-7) → (Z)-4-[7-Hydroxy-3,7-dimethyl-oct-(E)-ylidene]-3-methyl-pent-2-enedioic acid (95758-69-3)

Conditions	Yield
With sodium hydroxide In methanol

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + 7-methoxy-3,7-dimethyloctanal (3613-30-7) → (Z,E)-(+/-)-4-(7-methoxy-3,7-dimethyloctylidene)-3-methylpent-2-ene-1,5-dioic acid (53023-60-2)

Conditions	Yield
With sodium hydroxide In methanol

3-methyl-2-pentene-1,5-diacid dimethyl (52313-87-8) + (2Z,4E)-3-methyl-5-[2,6,6-trimethylcyclohex-1-enyl]penta-2,4-dienal (54226-17-4) → 11-cis,13-cis-12-carboxyretinoic acid (81176-73-0)

Conditions	Yield
With potassium hydroxide In methanol for 64h; Ambient temperature;

Upstream product

• 67-56-1 methanol 
• 372-42-9 3-methylpent-2-enedioic acid 
• 41264-06-6 methyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate 
• 124-41-4 sodium methylate 

Downstream Products

• 107516-97-2 4-methyl-6-oxo-1-phenyl-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester 
• 106378-47-6 4-methyl-6-oxo-1-p-tolyl-1,6-dihydro-pyridazine-3-carboxylic acid methyl ester 
• 109506-29-8 3-methyl-4-p-tolylhydrazono-pentenedioic acid dimethyl ester 
• 109311-73-1 3-methyl-4-((E)-veratrylidene)-cis-pentenedioic acid 
• 135628-94-3 (Z)-3-Methyl-2-((E)-2-phenyl-propenyl)-pent-2-enedioic acid 1-methyl ester 
• 81176-73-0 11-cis,13-cis-12-carboxyretinoic acid 
• 135628-91-0 (Z)-3-Methyl-2-((E)-2-p-tolyl-vinyl)-pent-2-enedioic acid 1-methyl ester 
• 135628-93-2 (Z)-2-[(E)-2-(4-Fluoro-phenyl)-vinyl]-3-methyl-pent-2-enedioic acid 1-methyl ester 
• 19013-37-7 dimethyl 3-methylglutarate 
• 39149-97-8 (Z)-3-methylpent-2-ene-1,5-diol 
• 16933-29-2 3-methyl-2-pentene-1,5-diol 

Relevant articles and documents

Method for preparing dimethyl 3-methylpentyl-2-enedionate

The invention provides a method for preparing dimethyl 3-methylpentyl-2-enedionate. The method has the advantages of easy availability of raw materials, high yield and less waste residues, and is suitable for industrial production.

Reformatsky Reaction on α-Oxoketene S,S-Acetals: Synthesis of Novel Polarized Vinylketene S,S-Acetals and Dimethyl 2-Aryl(methyl)-propene-1,3-dicarboxylates

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