597-43-3

Basic information

• Product Name: 2,2-Dimethylsuccinic acid
• Synonyms: ALPHA,ALPHA-DIMETHYLSUCCINIC ACID;2,2-DIMETHYL-1,4-BUTANEDIOIC ACID;2,2-DIMETHYLSUCCINIC ACID;Butanedioic acid, 2,2-dimethyl-;Succinic acid, 2,2-dimethyl-;2,2-Dimethlsuccinic acid;2,2-dimethylbutanedioic acid;3,3-Dimethylsuccinic acid
• CAS NO: 597-43-3
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.14
• EINECS: 209-899-6
• Product Categories: C6;Carbonyl Compounds;Carboxylic Acids
• Mol File: 597-43-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 138-142 °C(lit.)
• Boiling Point: 311.39°C (rough estimate)
• Flash Point: 114.359 °C
• Appearance: white crystalline powder
• Density: 1.4528 (rough estimate)
• Vapor Pressure: 0.0116mmHg at 25°C
• Refractive Index: 1.4328 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.80±0.10(Predicted)
• Water Solubility: 70g/L(14 oC)
• BRN: 1764476
• CAS DataBase Reference: 2,2-Dimethylsuccinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethylsuccinic acid(597-43-3)
• EPA Substance Registry System: 2,2-Dimethylsuccinic acid(597-43-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 597-43-3(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Definition

ChEBI: An alpha,omega-dicarboxylic acid that is succinic acid substituted by two methyl groups at positions 2 and 2 respectively.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3418, 1949 DOI: 10.1021/ja01178a044Synthesis, p. 710, 1980 DOI: 10.1055/s-1980-29181

Purification Methods

Crystallise the acid from EtOH/ether or EtOH/chloroform. [Beilstein 2 IV 1996.]

InChI:InChI=1/C6H10O4/c1-6(2,5(9)10)3-4(7)8/h3H2,1-2H3,(H,7,8)(H,9,10)/p-2

Synthetic route

3,3-dimethyl-1-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)pyrrolidine-2,5-dione (1257521-45-1) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With hydrogenchloride; water; trifluoroacetic acid for 24h; Reflux; regioselective reaction;	92.5%

3,3-dimethyl-1-(quinolin-8-yl)pyrrolidine-2,5-dione (1360590-32-4) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With hydrogenchloride; trifluoroacetic acid for 36h; Reflux;	91%

2,2,6-trimethyl-cyclohexanol (10130-91-3) → 2,2-dimethylsuccinic acid (597-43-3) + 2,2-dimethylglutaric acid (681-57-2) + 2,2-dimethyladipic acid (763-06-4)

Conditions	Yield
With ammonium vanadate; nitric acid; copper(II) nitrate at 73℃; Product distribution; Mechanism; other α-substituted cyclohexanols and 2-methyl-6-oxoheptanoic acid;	A 1.8% B 65.5% C 25.6%

ethyl 2-bromoisobutyrate (600-00-0) + sodium diethylmalonate (996-82-7, 34727-00-9, 73177-21-6) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With xylene at 180 - 190℃; Man verseift das Reaktionsprodukt nach der Fraktionierung mit Schwefelsaeure und treibt die Saeure mit Wasserdampf ueber;

ethyl 2-bromoisobutyrate (600-00-0) + sodium cyanoacetic acid ethyl ester (18852-51-2) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With ethanol at 100℃; Man erhitzt unter Druck und kocht den α.α-Dimethyl-α'-cyan-bernsteinsaeurediaethylester mit konz. Salzsaeure;

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With potassium permanganate
With sodium hypobromide

pulegone (89-82-7, 3285-04-9, 3391-90-0, 15932-80-6) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With potassium permanganate
With chromium(VI) oxide; sulfuric acid

chloroform (67-66-3) + prenyl bromide (870-63-3) → succinic acid (110-15-6) + 2,2-dimethylsuccinic acid (597-43-3) + acetone (67-64-1)

Conditions	Yield
beim Ozonisieren und nachfolgenden Oxydieren mit Permanganat;

3,3,6-trimethylhepta-1,5-diene (35387-63-4) → formaldehyd (50-00-0) + 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
bei der Ozonisierung;

ethanol (64-17-5) + ethyl 3-methylbut-2-enoate (638-10-8) + potassium cyanide (151-50-8) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
und Verseifen des entstandenen Esters mit siedender Natronlauge;

1,1,3-trimethyl glutaric acid (19265-05-5) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With nitric acid

chloroform (67-66-3) + 1-methylene-2-isopropylidene-4,4-dimethylcyclobutane (24648-34-8) → Tetramethyl-[1,2,4,5]tetroxan (1073-91-2) + 2,2-dimethylsuccinic acid (597-43-3) + 3,3-dimethyl-2-methylene-cyclobutanon (861575-36-2) + acetone (67-64-1)

Conditions	Yield
at -40℃; bei der Ozonisation; Behandeln mit Wasser;

1,2-dibromo-2-methyl-propane (594-34-3) + potassium cyanide (151-50-8) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With ethanol Man erhitzt das erhaltene Dinitril mit starker Salzsaeure im geschlossenen Rohr auf 150grad;

3,3-dimethyl-1,5-hexadiene (24253-25-6) → formaldehyd (50-00-0) + 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
bei der Ozonspaltung;

ethyl 3-methylbut-2-enoate (638-10-8) + potassium cyanide (151-50-8) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With ethanol beim Verseifen des Reaktionsprodukts mit siedender Natronlauge;

3,3-dimethyl-hexane-2,5-dione (866-71-7) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With sodium hypochlorite

β-chloro-isovaleric acid ethyl ester (6414-70-6) + potassium cyanide (151-50-8) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With ethanol at 150 - 160℃; Man verseift das Reaktionsprodukt durch verduennte Salzsaeure;

3-cyano-3,3-dimethylpropanoic acid (99839-17-5) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With hydrogenchloride

2,2-dimethylglutaric acid (681-57-2) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With sulfuric acid; nitric acid

2,3,3-trimethyl-glutaric acid (30168-03-7) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With sulfuric acid; dichromate anion

ethyl 2,3-dicyano-3-methylbutanoate (52119-01-4) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With hydrogenchloride
With hydrogenchloride
bei der Verseifung;

2-methyl-propane-1,1,2-tricarboxylic acid (408535-92-2) → 2,2-dimethylsuccinic acid (597-43-3) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

Conditions	Yield
at 170℃;

3,3,7,7-tetramethyl-5-oxo-nonanedioic acid (101171-41-9) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With alkaline potassium permanganate

2,2,6,6-tetramethyl-4-oxo-heptanedioic acid (14206-15-6) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With nitric acid at 90℃;

2,2,6,6-tetramethyl-4-oxo-heptanedioic acid (14206-15-6) → 2,2-dimethylsuccinic acid (597-43-3) + 2,2-dimethylmalonic acid (595-46-0)

Conditions	Yield
With nitric acid at 90℃;

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;

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

Conditions	Yield
at 78℃; Kochen des Reaktionsprodukts mit 20 prozentiger Salzsaeure;

2,4,4-trimethylcyclopentan-1-one (4694-12-6) → 1,1,3-trimethyl glutaric acid (19265-05-5) + 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With nitric acid racemic 2.2.4-trimethyl-glutaric acid;

2,4,4-trimethylcyclopentan-1-one (4694-12-6) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With potassium permanganate

eucarvone (503-93-5) → 2,2-dimethylsuccinic acid (597-43-3)

Conditions	Yield
With potassium permanganate

methanol (67-56-1) + 2,2-dimethylsuccinic acid (597-43-3) → dimethyl 2,2-dimethylsuccinate (49827-44-3)

Conditions	Yield
With sulfuric acid for 5h; Heating;	100%
With sulfuric acid
With sulfuric acid

2,2-dimethylsuccinic acid (597-43-3) → 2,2-dimethylbutane-1,4-diol (32812-23-0)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 5h;	99%
With lithium aluminium tetrahydride In diethyl ether at -78 - 20℃; for 1h; Inert atmosphere;	96%
With lithium aluminium tetrahydride In diethyl ether at 0 - 22℃; for 2h; Inert atmosphere;	86%

2,2-dimethylsuccinic acid (597-43-3) → 3,3-dimethylpyrrolidine-2,5-dione (3437-29-4)

Conditions	Yield
With ammonium hydroxide	94%
With formamide In 1-methyl-pyrrolidin-2-one at 170 - 180℃;	65.8%
With urea In neat (no solvent) at 160℃; for 12h; Inert atmosphere;	51%
Stage #1: 2,2-dimethylsuccinic acid With urea at 160℃; for 8h; Stage #2: With water at 20 - 100℃;

2,2-dimethylsuccinic acid (597-43-3) → 2,2-dimethylsuccinic anhydride (17347-61-4)

Conditions	Yield
With acetic anhydride In toluene at 130℃; for 3h;	93%
With acetic anhydride at 160℃; for 2h;	90%
bei der Destillation;

2,2-dimethylsuccinic acid (597-43-3) + benzylamine (100-46-9) → 1-benzyl-3,3-dimethylpyrrolidine-2,5-dione (42856-53-1)

Conditions	Yield
for 1.5h; Reflux;	93%

di-n-butyltin(IV) oxide + 2,2-dimethylsuccinic acid (597-43-3) → Bu2Sn(1,1-dimethylsuccinato)2

Conditions	Yield
In toluene byproducts: water; mixt. refluxed until soln. become homogeneous (0.5 h); evapn. of H2O by azeotropic distn., evapn. in vac. addn. of pentane for crystn., filtered, washed with pentane, dried in vac.; elem. anal.;	85%

erbium(III) nitrate pentahydrate + 2,2-dimethylsuccinic acid (597-43-3) → [Er2(2,2-dimethylsuccinate)3(H2O)4]

Conditions	Yield
With C5H5N In water High Pressure; Er(NO3)3*5H2O and 2,2-dimethylsuccinic acid were mixed in water, pH was adjusted to 4.5 with pyridine, heated in bomb at 170°C for 24 h, cooled to room temp.; crystals were washed with water and acetone;	83.7%

2,2-dimethylsuccinic acid (597-43-3) + N-4-chlorophenylhydrazine (1073-69-4) → 1-(4-chlorophenylamino)-3,3-dimethylpyrrolidine-2,5-dione (1034317-01-5)

Conditions	Yield
In water at 180℃; for 1h;	81%

2,2-dimethylsuccinic acid (597-43-3) + rac-Ala-OH (302-72-7) → 2-(3,3-dimethyl-2,5-dioxopyrrolidin-1-yl)propanoic acid

Conditions	Yield
at 180℃; for 1h;	81%

2,2-dimethylsuccinic acid (597-43-3) + (2-chlorophenyl)hydrazine (10449-07-7) → 1-(2-chlorophenylamino)-3,3-dimethylpyrrolidine-2,5-dione (1034316-99-8)

Conditions	Yield
In water at 180℃; for 1h;	79%

2,2-dimethylsuccinic acid (597-43-3) + (4-bromophenyl)hydrazine (589-21-9) → C12H13BrN2O2 (1034317-03-7)

Conditions	Yield
In water at 180℃; for 1h;	78%

2,2-dimethylsuccinic acid (597-43-3) + phenylhydrazine (100-63-0) → 1-anilino-3,3-dimethyl-pyrrolidine-2,5-dione

Conditions	Yield
In water at 180℃; for 1h;	76%
In water at 25 - 180℃; for 1h; Inert atmosphere;	33%
In water at 180℃;

2,2-dimethylsuccinic acid (597-43-3) + (2,4-dichlorophenyl)hydrazine (13123-92-7) → 1-(2,4-dichlorophenylamino)-3,3-dimethylpyrrolidine-2,5-dione (1034317-02-6)

Conditions	Yield
In water at 180℃; for 1h;	76%

2,2-dimethylsuccinic acid (597-43-3) + 2-aminobutanoic acid (2835-81-6) → 2-(3,3-dimethyl-2,5-dioxopyrrolidin-1-yl)butanoic acid

Conditions	Yield
at 180℃; for 1h;	74%

erbium(III) nitrate pentahydrate + 2,2-dimethylsuccinic acid (597-43-3) → [Er2(2,2-dimethylsuccinate)3(H2O)]

Conditions	Yield
With C5H5N In water High Pressure; Er(NO3)3*5H2O and 2,2-dimethylsuccinic acid were mixed in water, pH was adjusted to 4.5 with pyridine, heated in bomb at 190°C for 4 d, cooled to room temp.; crystals were washed with water and acetone;	72.2%
With C5H5N In water High Pressure; Er(NO3)3*5H2O and 2,2-dimethylsuccinic acid were mixed in water, pH was adjusted to 4.5 with pyridine, heated in bomb at 180°C for 10 d, cooled to room temp.; crystals were washed with water and acetone;	26.8%

cadmium(II) nitrate tetrhydrate + N-(pyridin-3-ylmethyl)nicotinamide (25297-38-5) + 2,2-dimethylsuccinic acid (597-43-3) → {[Cd(2,2-dimethylsuccinate)(3-pyridylmethylnicotinamide)(H2O)]·4.5H2O}

Conditions	Yield
With sodium hydroxide In water at 100℃; for 24h; Sealed tube;	71%

2,2-dimethylsuccinic acid (597-43-3) + N-4-methylphenylhydrazine (539-44-6) → 1-(4-methylphenylamino)-3,3-dimethylpyrrolidine-2,5-dione (1034316-98-7)

Conditions	Yield
In water at 180℃; for 1h;	70%

2,2-dimethylsuccinic acid (597-43-3) + 3-chlorophenyl hydrazine (14763-20-3) → C12H13ClN2O2 (1034317-00-4)

Conditions	Yield
In water at 180℃; for 1h;	70%

2,2-dimethylsuccinic acid (597-43-3) + 3-O-(3',3'-dimethylsuccinyl)betulin benzhydryl ester (1252258-40-4) → 3-O-(4'-benzhydryloxy-3',3'-dimethylsuccinyl)-28-O-(3'',3''-dimethylsuccinyl)betulin (1252258-46-0) + 3-O-(4'-benzhydryloxy-3',3'-dimethylsuccinyl)-28-O-(2'',2''-dimethylsuccinyl)betulin (1252258-47-1)

Conditions	Yield
Stage #1: 2,2-dimethylsuccinic acid; 3-O-(3',3'-dimethylsuccinyl)betulin benzhydryl ester With pyridine; dmap Reflux; Stage #2: With water Cooling with ice;	A 68.4% B 31.6%

2-Amino-4-methylpyridine (695-34-1) + 2,2-dimethylsuccinic acid (597-43-3) → C12H14N2O2 (1169866-77-6)

Conditions	Yield
In water Heating;	67%

2,2-dimethylsuccinic acid (597-43-3) + betulinic aldehyde (13159-28-9, 92594-07-5) → (3β)-3-hydroxylup-20(29)-en-28-al 3-(1-hydrogen 2,2-dimethylbutanedioate) (911140-87-9)

Conditions	Yield
With pyridine; dmap at 20℃; for 30h; Product distribution / selectivity; Heating / reflux;	66%
With dmap In pyridine

3-methylpyridin-2-ylamine (1603-40-3) + 2,2-dimethylsuccinic acid (597-43-3) → C12H14N2O2 (1169866-76-5)

Conditions	Yield
In water Heating;	66%

2,2-dimethylsuccinic acid (597-43-3) + betulin (473-98-3) → 2,2-Dimethyl-succinic acid 1-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-3a-ylmethyl) ester (332346-39-1) + 2,2-Dimethyl-succinic acid 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-3a-ylmethyl) ester (332346-38-0)

Conditions	Yield
With pyridine Heating;	A 15% B 63%

(S)-Alaninol (2749-11-3) + 2,2-dimethylsuccinic acid (597-43-3) + acetic anhydride (108-24-7) → (S)-2-(3,3-dimethyl-2,5-dioxopyrrolidin-1-yl)propyl acetate (1352306-19-4)

Conditions	Yield
Stage #1: 2,2-dimethylsuccinic acid With acetic anhydride at 85℃; for 0.5h; Stage #2: (S)-Alaninol In toluene for 1h; Reflux; Inert atmosphere; Stage #3: acetic anhydride at 80℃; Inert atmosphere;	62.3%

methanol (67-56-1) + 2,2-dimethylsuccinic acid (597-43-3) → 4-methoxy-2,2-dimethyl-4-oxobutanoic acid (54043-71-9)

Conditions	Yield
With sulfuric acid at 0 - 20℃;	62%
With sulfuric acid at 20℃; for 18h; Inert atmosphere;	55%
Stage #1: methanol; 2,2-dimethylsuccinic acid With sulfuric acid at 0 - 20℃; for 16h; Stage #2: With hydrogenchloride In water pH=2;	51%

2,2-dimethylsuccinic acid (597-43-3) + 1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine (40255-48-9) → 1-{2-[4-(3-methoxyphenyl)piperazin-1-yl]ethyl}-3,3-dimethylpyrrolidine-2,5-dione monohydrochloride

Conditions	Yield
Stage #1: 2,2-dimethylsuccinic acid; 1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine In water Heating; Stage #2: at 180℃; for 1.5h; Stage #3: With hydrogenchloride In ethanol	61%

2-Amino-6-methylpyridine (1824-81-3) + 2,2-dimethylsuccinic acid (597-43-3) → C12H14N2O2 (1169866-78-7)

Conditions	Yield
In water Heating;	60%

Upstream product

• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 64-17-5 ethanol 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 151-50-8 potassium cyanide 
• 19265-05-5 1,1,3-trimethyl glutaric acid 
• 67-66-3 chloroform 
• 24648-34-8 1-methylene-2-isopropylidene-4,4-dimethylcyclobutane 
• 52119-01-4 ethyl 2,3-dicyano-3-methylbutanoate 
• 1727-75-9 (2,3,3-trimethyl-cyclopent-1-enyl)-acetic acid 
• 564-24-9 (+/-)-α-cyclogeranic acid 
• 4683-51-6 5,5-dimethylcyclopentane-1,3-dione 
• 126-81-8 dimedone 
• 51145-96-1 5-Hydroxy-3,3-dimethyl-5-trifluoromethyl-dihydro-furan-2-one 
• 7732-18-5 water 

Downstream Products

• 54043-71-9 4-methoxy-2,2-dimethyl-4-oxobutanoic acid 
• 42856-53-1 1-benzyl-3,3-dimethylpyrrolidine-2,5-dione 
• 792915-20-9 3,3-dimethylpyrrolidine hydrochloride 
• 73434-00-1 1-Benzyl-3,3-dimethylpyrrolidine 
• 4239-25-2 2,2-dimethyl-1,4-butanediyl dimesylate 

Relevant articles and documents

Cobalt catalyzed carbonylation of unactivated C(sp3)-H bonds

A general efficient regioselective cobalt catalyzed carbonylation of unactivated C(sp3)-H bonds of aliphatic amides was demonstrated using atmospheric (1-2 atm) carbon monoxide as a C1 source. This straightforward approach provides access to α-spiral succinimide regioselectively in a good yield. Cobalt catalyzed sp3 C-H bond carbonylation is reported for the first time including the functionalization of (β)-C-H bonds of α-1°, 2°, 3° carbons and even internal (β)-C-H bonds. Our initial mechanistic investigation reveals that the C-H activation step is irreversible and will possibly be the rate determining step.

"ONE-POT" SYNTHESIS OF DISYMMETRICALLY α,α'-DISUBSTITUTED SUCCINIC ANHYDRIDES PRECURSORS

A "one-pot" synthesis for disymmetrically α,α'-disubstituted succinic anhydrides precursors isreported in the present paper.Substituents are aryl, primary or secondary alkyl groups.This reaction represents a simple and quick method with fair yields.

Oxidation of α-Substituted Cyclohexanols by Nitric Acid

The influence of α-substituents on the oxidative cleavage of cyclohexanol by nitric acid in the presence of copper(II) and vanadium(V) ions has been investigated.Following the initial oxidation to give the cyclohexanone, further reaction, leading to ring opening of the ketone, requires at least one α-hydrogen.Thus 2,2,6,6-tetramethylcyclohexanol is converted to the corresponding ketone whilst 2,2,6-trimethylcyclohexanol is oxidised to a mixture of dicarboxylic acids.The mechanisms of the oxidations are discussed and enolisation is shown to be the key to oxidative cleavage.For ketones that can give two alternative enols, reaction occurs predominantly via the more stable tautomer.