18069-17-5

Basic information

• Product Name: 2-METHYLGLUTARIC ACID
• Synonyms: Pentanedioic acid, 2-methyl-, (.+/-.)-;RARECHEM AL BO 0092;2-METHYLPENTANEDIOIC ACID;2-METHYLGLUTARIC ACID;AKOS 237-134;A-METHYLGLUTARIC ACID;ALPHA-METHYLGLUTARIC ACID;2-MethylglutaricAcid98%
• CAS NO: 18069-17-5
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.14
• EINECS: 210-521-7
• Product Categories: Miscellaneous Biochemicals;C6;Carbonyl Compounds;Carboxylic Acids
• Mol File: 18069-17-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 80-82 °C(lit.)
• Boiling Point: 214-215 °C22 mm Hg(lit.)
• Flash Point: 214-215°C/22mm
• Appearance: white to almost white fine crystalline powder
• Density: 1.4528 (rough estimate)
• Vapor Pressure: 2.76E-05mmHg at 25°C
• Refractive Index: 1.4336 (estimate)
• BRN: 1723219
• CAS DataBase Reference: 2-METHYLGLUTARIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLGLUTARIC ACID(18069-17-5)
• EPA Substance Registry System: 2-METHYLGLUTARIC ACID(18069-17-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 18069-17-5(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white fine crystalline powder

Uses

2-Methylglutaric acid was used in the preparation of acetic acid.

Purification Methods

Crystallise the acid from distilled water, then dry it under vacuum over conc H2SO4. [Beilstein 2 IV 1989.]

InChI:InChI=1/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)/p-2/t4-/m1/s1

Synthetic route

carbon monoxide (201230-82-2) + 5-methyl-dihydro-furan-2-one (108-29-2) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With hexafluoroantimonic acid at 30℃; for 1h;	100%

2-methylglutaronitrile (4553-62-2) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With sulfuric acid; nitric acid at 90℃; for 16h; Reagent/catalyst; Temperature; Inert atmosphere;	96%
With hydrogenchloride
acid hydrolysis;
With sulfuric acid; water at 105 - 125℃; for 8.42h; Inert atmosphere;

3-methyltetrahydropyran (26093-63-0) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With sodium bromate; potassium hydrogensulfate In water at 25 - 30℃; for 120h; Oxidation;	87%

2H-pyran-2-one-5-carboxylic acid (500-05-0) → 6-oxo-tetrahydro-pyran-3-carboxylic acid (5807-38-5) + 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With methanol; palladium on activated charcoal Hydrogenation;

methyl coumalate (6018-41-3) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With methanol; platinum(IV) oxide Hydrogenation.Verseifung der NaHCO3-loeslichen Anteile des Reaktionsprodukts mit konz. HCl;

2,6-dimethyl-5-oxo-heptanoic acid (74457-59-3) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
bei weiterer Oxidation; α-methyl-isobutyryl-butyric acid from dihydrocamphorphorone;

2,6-dimethyl-5-oxo-heptanoic acid (74457-59-3) → 2-methylglutaric acid (18069-17-5) + acetone (67-64-1)

Conditions	Yield
durch Oxidation; substance from carvenone;

chloroform (67-66-3) + 5-methyl-2-isopropylidenecyclopentanone (6784-16-3) → 2-methylglutaric acid (18069-17-5) + acetone (67-64-1)

Conditions	Yield
bei der Ozonspaltung;

rac-2,6-dimethylhept-5-enenitrile (54088-65-2) → 2-methylbutanedioic acid (498-21-5, 636-60-2) + 2-methylglutaric acid (18069-17-5) + acetone (67-64-1)

Conditions	Yield
bei der Oxydation und nachfolgender Verseifung des Reaktionsproduktes;

methyl α-methyl-γ-carboethoxy-γ-acetylbutyrate (74650-83-2) → 2-methylglutaric acid (18069-17-5) + 4-methyl-cyclohexane-1,3-dione (14203-46-4)

Conditions	Yield
With sodium methylate anschliessend Erwaermen mit wss. KOH;

methyl α-methyl-γ-carboethoxy-γ-acetylbutyrate (74650-83-2) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With methanol; sodium methylate anschliessendes Erhitzen mit wss.Kalilauge;

cyano-2 methyl-4 glutarate de diethyle (35299-16-2) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
mit verd. Mineralsaeuren;

1,1,2-triethyl 2-methylpropane-1,1,2-tricarboxylate (132467-55-1) + sodium ethanolate (141-52-6) → 2-methylglutaric acid (18069-17-5) + 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
at 100℃; im Rohr und, Kochen des Reaktionsprodukts mit 20 prozentiger Salzsaeure;

p-menth-3-en-2-one (23733-68-8) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With potassium permanganate

4-methyl-cyclohexane-1,3-dione (14203-46-4) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With air

(+/-)-1-methyl-2-oxo-1-cyclopentanecarbonitrile (66984-18-7) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With nitric acid

5-methyl-2-isopropylidenecyclopentanone (6784-16-3) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With potassium permanganate

p-menth-4(8)-ene-2,3-dione-2-oxime → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide

sodium diethylmalonate (996-82-7) + methacrylic acid methyl ester (80-62-6) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
anschliessende Hydrolyse und Decarboxylierung;

sodium ethanolate (141-52-6) + diethyl malonate (105-53-3) + 3-bromo-2-methyl-propionic acid methyl ester (20609-71-6) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
Verseifen des entstandenen Esters mit HCl;

sodium cyanoacetic acid ethyl ester (18852-51-2) + ethyl 2-hydroxy-2,2-dimethylethanoate (80-55-7) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With ethanol man behandelt das saure Reaktionsprodukt mit kalter konzentrierter Schwefelsaeure, verduennt mit Wasser und kocht;

4-cyanopentanoic acid (23886-52-4) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With sodium hydroxide

dimethyl 2-methylglutarate (14035-94-0) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
(hydrolysis);

butane-1,3,3-tricarboxylic acid (89898-62-4) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
at 150℃;

diethyl 2-ethoxycarbonyl-2-methylglutarate (39555-01-6) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With hydrogenchloride

2-methyl-4-cyanobutyric acid (37810-29-0) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
With sulfuric acid

acrylic acid methyl ester (292638-85-8) + Diethyl methylmalonate (609-08-5) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
(i) , (ii) (decarboxylation); Multistep reaction;

methyl methacrylate (97-63-2) + diethyl malonate (105-53-3) → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
Yield given. Multistep reaction;

3-methyltetrahydro-2-furanone (1679-47-6) + powdered potassium cyanide → 2-methylglutaric acid (18069-17-5)

Conditions	Yield
at 270℃; im geschlossenen Rohr anschliessend Behandeln mit Kalilauge;

2-methylglutaric acid (18069-17-5) → 2-methylglutaric anhydride (31468-33-4)

Conditions	Yield
With acetic anhydride for 24h; Heating;	100%
With acetyl chloride Heating;	98.4%
With acetic anhydride at 140℃; for 7h;	92.2%

2-methylglutaric acid (18069-17-5) + 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (88150-42-9) → amlodipine hemi-2-methyl glutarate salt

Conditions	Yield
In diethyl ether; tert-butyl alcohol at 5 - 20℃; for 4h;	95%

furan (110-00-9) + 2-methylglutaric acid (18069-17-5) + dichloroacetic anhydride (4124-30-5) → methyl 4-furoylbutyrate (91061-95-9)

Conditions	Yield
In toluene	94.5%

2-methylglutaric acid (18069-17-5) → 2-methyl-1,5-pentanediol (42856-62-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 16h; Reflux;	93%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 16h; Inert atmosphere; Reflux;	93%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 25℃; for 16.15h; Inert atmosphere;	91%

2-methylglutaric acid (18069-17-5) + propionyl chloride (79-03-8) → 2,4-dimethyl-1,3-cyclohexanedione (20990-14-1)

Conditions	Yield
Stage #1: 2-methylglutaric acid With aluminum (III) chloride; nitromethane at 20℃; for 1h; Inert atmosphere; Stage #2: propionyl chloride at 80℃; for 3h; Inert atmosphere;	89%

methanol (67-56-1) + 2-methylglutaric acid (18069-17-5) + C6H11NO3 → dimethyl 2-methylglutarate (14035-94-0)

Conditions	Yield
With sulfuric acid In water at 60℃; for 3h; Temperature; Inert atmosphere;	86.1%

2-methylglutaric acid (18069-17-5) + amlodipine (103129-82-4) → (S)-(-)-amlodipine hemi-2-methylglutarate salt

Conditions	Yield
In ethanol at 20℃; for 1h;	84%

2-methylglutaric acid (18069-17-5) → 3-methyl-piperidine-2,6-dione (29553-51-3)

Conditions	Yield
Stage #1: 2-methylglutaric acid With acetic anhydride at 20 - 60℃; for 8h; Stage #2: With ammonia In tetrahydrofuran; water at 0 - 20℃; for 8h; Stage #3: With acetic anhydride at 60℃; for 8h;	78%
With acetyl chloride Behandeln des erhaltenen Saeureanhydrids mit Ammoniak bei 120grad und Erhitzen des Reaktionsprodukts auf 200grad;
With ammonia 1.) 150 deg C, 1.5 h, 2.) 200 deg C, 0.5 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: Ac2O 2: NH4OH View Scheme

2-methylglutaric acid (18069-17-5) + butyryl chloride (141-75-3) → 2-ethyl-4-methylcyclohexane-1,3-dione

Conditions	Yield
Stage #1: 2-methylglutaric acid With aluminum (III) chloride; nitromethane In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; Stage #2: butyryl chloride In 1,2-dichloro-ethane at 80℃; for 3h; Inert atmosphere;	73%

2-methylglutaric acid (18069-17-5) + dimethyl amine (124-40-3) → N,N,N',N'-tetramethyl-2-methylglutaramide (1033820-68-6)

Conditions	Yield
Stage #1: 2-methylglutaric acid With thionyl chloride at 60℃; for 5h; Stage #2: dimethyl amine With triethylamine In toluene at 0 - 20℃;	67%

2-methylglutaric acid (18069-17-5) + diethylamine (109-89-7) → N,N,N',N'-tetraethyl-2-methylglutaramide (100071-13-4)

Conditions	Yield
Stage #1: 2-methylglutaric acid With thionyl chloride at 60℃; for 5h; Stage #2: diethylamine With triethylamine In toluene at 0 - 20℃;	66%

1,3-di(4-pyridyl)propane (17252-51-6) + cadmium(II) nitrate tetrhydrate + 2-methylglutaric acid (18069-17-5) + water (7732-18-5) → {[Cd(1,3-bis(4-pyridyl)propane)(2-methylglutarate)(OH2)]·2H2O}n

Conditions	Yield
In dimethyl sulfoxide at 20℃;	65%

2-methylglutaric acid (18069-17-5) + acetyl chloride (75-36-5) → 2-acetyl-4-methylcyclohexane-1,3-dione (134746-37-5)

Conditions	Yield
Stage #1: 2-methylglutaric acid With aluminum (III) chloride In nitromethane at 20℃; for 1h; Inert atmosphere; Stage #2: acetyl chloride In nitromethane at 80℃; for 2h; Inert atmosphere;	65%

copper(II) bis(tetrafluoroborate) + 2-methylglutaric acid (18069-17-5) + water (7732-18-5) + 4-pyridinealdazine (6957-22-8) → {[Cu2(μ4-2-methylglutarate)2(μ-1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene)]*5H2O}n

Conditions	Yield
With urea In ethanol at 20℃; for 168h;	60%

2-methylglutaric acid (18069-17-5) + Heptanoic acid chloride (2528-61-2) → 2-pentyl-4-methylcyclohexane-1,3-dione

Conditions	Yield
Stage #1: 2-methylglutaric acid With aluminum (III) chloride; nitromethane at 20℃; for 1h; Inert atmosphere; Stage #2: Heptanoic acid chloride at 80℃; for 3h; Inert atmosphere;	57%

2-methylglutaric acid (18069-17-5) + N,N'-diphenyl-1,4-phenylenediamine (74-31-7) → C24H18N2

Conditions	Yield
With zinc(II) chloride for 0.0833333h; microwave irradiation;	34%

ethanol (64-17-5) + 2-methylglutaric acid (18069-17-5) → diethyl 2-methylglutarate (18545-83-0)

Conditions	Yield
With sulfuric acid
With hydrogenchloride

2-methylglutaric acid (18069-17-5) + 3-methyladipic acid (3058-01-3, 81177-02-8) → acetone (67-64-1)

Conditions	Yield
With dihydrogen peroxide

2-methylglutaric acid (18069-17-5) → 3-methyl-1-phenyl-piperidine-2,6-dione

2-methylglutaric acid (18069-17-5) → 2-chloro-4-methyl-glutaric acid dimethyl ester

Conditions	Yield
With thionyl chloride; chlorine Eingiessen des Reaktionsprodukts in Methanol;

2-methylglutaric acid (18069-17-5) → 2-bromo-4-methyl-glutaric acid dimethyl ester (474327-99-6)

Conditions	Yield
With thionyl chloride man setzt bei 40grad Brom hinzu, erwaermt die Reaktions-Loesung dann auf 60grad und giesst das Reaktionsprodukt in Methanol;

2-methylglutaric acid (18069-17-5) → 2-chloro-4-methyl-glutaric acid diethyl ester

Conditions	Yield
/BRN= 1783854/;

2-methylglutaric acid (18069-17-5) → N,N'-diphenyl-2-methylpentane-1,5-dicarboxamide (10171-93-4)

2-methylglutaric acid (18069-17-5) → 2-methyl-glutaric acid bis-(4-phenyl-phenacyl ester)

Upstream product

• 74457-59-3 2,6-dimethyl-5-oxo-heptanoic acid 
• 54088-65-2 rac-2,6-dimethylhept-5-enenitrile 
• 74650-83-2 methyl α-methyl-γ-carboethoxy-γ-acetylbutyrate 
• 58997-95-8 2-acetyl-2-methyl-glutaric acid diethyl ester 
• 7647-01-0 hydrogenchloride 
• 600-00-0 ethyl 2-bromoisobutyrate 
• 996-82-7 sodium diethylmalonate 
• 109-99-9 tetrahydrofuran 
• 469-44-3 2,3,4-trihydroxy-2-methyl-glutaric acid 
• 10034-85-2 hydrogen iodide 
• 6784-16-3 5-methyl-2-isopropylidenecyclopentanone 
• 52188-29-1 1-methyl-4-oxo-cyclopentane-1,3-dicarboxylic acid diethyl ester 
• 451-56-9 2-methyl-6-(4-methyl-cyclohexa-1,4-dienyl)-hept-1-ene 
• 7664-93-9 sulfuric acid 

Downstream Products

• 18545-83-0 diethyl 2-methylglutarate 
• 67-64-1 acetone 
• 474327-99-6 2-bromo-4-methyl-glutaric acid dimethyl ester 
• 10171-93-4 N,N'-diphenyl-2-methylpentane-1,5-dicarboxamide 
• 31468-33-4 2-methylglutaric anhydride 
• 1115-81-7 (R)-2-methylglutaric acid 
• 1115-82-8 (S)-2-methylglutaric acid 
• 62115-18-8 4-methoxycarbonyl-2-R-methylbutyric acid 
• 64623-97-8 4-methoxycarbonyl-2-methyl butanoic acid dicyclohexylamine salt 
• 14035-94-0 dimethyl 2-methylglutarate 
• 111797-93-4 (S)-2-methylpentane-1,5-diyl dibenzoate 
• 134746-37-5 2-acetyl-4-methylcyclohexane-1,3-dione 

Relevant articles and documents

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The invention provides a method used for synthesis of 2-methylpentanedioic acid dimethyl ester. The method used for synthesis of 2-methylpentanedioic acid dimethyl ester comprises following steps: 2-methyl pentanedinitrile is mixed with an acid, hydrolysis reaction is carried out, an obtained product is allowed to stand so as to obtain an upper layer oil phase and a lower layer water phase; the oil phase and the water phase are separated; the oil phase is mixed with methanol for esterification reaction so as to obtain 2-methylpentanedioic acid dimethyl ester. Operation of the method is simple;technology route is short; raw material consumption is low; and no waste gas, waste water, or waste residue is generated.

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