Product Name

  • Name

    3-isobutylglutaric acid

  • EINECS 1592732-453-0
  • CAS No. 75143-89-4
  • Article Data26
  • CAS DataBase
  • Density 1.126 g/cm3
  • Solubility
  • Melting Point 47 °C
  • Formula C9H16O4
  • Boiling Point 326.197 °C at 760 mmHg
  • Molecular Weight 188.224
  • Flash Point 165.289 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 75143-89-4 (3-isobutylglutaric acid)
  • Hazard Symbols
  • Synonyms 3-(2-methylpropyl)pentanedioic acid;
  • PSA 74.60000
  • LogP 1.59810

Synthetic route

2,4-dicyano-3-isobutylglutaramide

2,4-dicyano-3-isobutylglutaramide

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With sulfuric acid for 12h; Reflux;99.4%
With hydrogenchloride; water at 140℃; for 30h; pH=1 - 2; Temperature; Reagent/catalyst;85%
1,5-diethy 3-isobutylpentanedioate

1,5-diethy 3-isobutylpentanedioate

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water for 4h; Time; Reflux;91%
(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
Stage #1: (3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid With water; sodium hydroxide for 5h; Reflux;
Stage #2: With hydrogenchloride In water pH=7; Reflux;		85%
2‑cyano‑5‑methylhex‑2‑enoic acid methyl ester
868-52-0

2‑cyano‑5‑methylhex‑2‑enoic acid methyl ester

diethyl malonate
105-53-3

diethyl malonate

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
Stage #1: 2‑cyano‑5‑methylhex‑2‑enoic acid methyl ester; diethyl malonate With piperidine at 55℃; for 2h;
Stage #2: With hydrogenchloride In water at 100 - 120℃; for 72h;		85%
2,4-dicyano-3-isobutylglutaramide

2,4-dicyano-3-isobutylglutaramide

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With sulfuric acid Heating;42%
malonic acid
141-82-2

malonic acid

isovaleraldehyde
590-86-3

isovaleraldehyde

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With piperidine auf dem Wasserbade unter Rueckfluss und Erhitzen dann im Vakuum zur Abspaltung von Kohlendioxyd;
2-isobutyl-propane-1,1,3,3-tetracarboxylic acid tetraethyl ester
102710-09-8

2-isobutyl-propane-1,1,3,3-tetracarboxylic acid tetraethyl ester

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride for 24h; Heating; Yield given;
With hydrogenchloride; water at 100 - 125℃; for 20 - 24h; Product distribution / selectivity;
Stage #1: 2-isobutyl-propane-1,1,3,3-tetracarboxylic acid tetraethyl ester With hydrogenchloride; sodium hydroxide; ethanol; water at -10 - -5℃; for 2 - 3h;
Stage #2: With hydrogenchloride; water; acetic acid In ethanol pH=5 - 6;
Stage #3: With hydrogenchloride; water at 100 - 125℃; for 20 - 24h; Product distribution / selectivity;
With hydrogenchloride; water at 100 - 105℃; for 72h; Heating / reflux;
With hydrogen bromide In water at 100℃; for 72h; Product distribution / selectivity;
2-oxo-6-imino-4-isobutyl-3-cyano-piperidine-carboxylic acid-(5)-amide

2-oxo-6-imino-4-isobutyl-3-cyano-piperidine-carboxylic acid-(5)-amide

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride
isopentylidene-bis-malonic acid ester

isopentylidene-bis-malonic acid ester

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride
1,1,3-triethyl 3-cyano-2-(2-methylpropyl)propane-1,1,3-tricarboxylate

1,1,3-triethyl 3-cyano-2-(2-methylpropyl)propane-1,1,3-tricarboxylate

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With water; hydrogen bromide at 100 - 125℃; for 6 - 10h; Product distribution / selectivity;
With hydrogenchloride; water at 100 - 125℃; for 50 - 125h; Product distribution / selectivity;
With hydrogenchloride; water for 72h; Reflux;
With hydrogenchloride Reflux;
C16H23NO6

C16H23NO6

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 100 - 125℃; for 15 - 20h; Product distribution / selectivity;
C17H24O8
392669-46-4

C17H24O8

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 100 - 125℃; for 12 - 15h; Product distribution / selectivity;
C18H28O8

C18H28O8

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 100 - 125℃; for 12 - 15h; Product distribution / selectivity;
C15H23NO6

C15H23NO6

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 110 - 115℃; for 10 - 12h; Product distribution / selectivity;
isovaleraldehyde
590-86-3

isovaleraldehyde

3-methyl-ξ-pentenedioic acid dimethyl ester

3-methyl-ξ-pentenedioic acid dimethyl ester

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KF
2: HCl conc. / 24 h / Heating
View Scheme
(3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid
930585-94-7

(3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
Stage #1: (3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid With hydrogenchloride; water at 100 - 105℃; for 20 - 24h;
Stage #2: With sodium hydroxide In water pH=10 - 11;
Stage #3: With hydrogenchloride In water pH=1.5 - 2; Product distribution / selectivity;
Stage #1: (3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid With sulfuric acid; water at 120 - 125℃; for 1 - 2h;
Stage #2: With sodium hydroxide In water at 20 - 25℃; pH=10 - 11;
Stage #3: With hydrogenchloride In water pH=1.5 - 2; Product distribution / selectivity;
(S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid
181289-34-9

(S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride; water for 24h; Reflux;
isovaleraldehyde
590-86-3

isovaleraldehyde

diethyl malonate
105-53-3

diethyl malonate

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
Stage #1: isovaleraldehyde With di-n-propylamine; ethyl 2-cyanoacetate In cyclohexane at 25 - 30℃; for 2h; Reflux;
Stage #2: diethyl malonate With di-n-propylamine at 25 - 50℃; for 5.17h;
Stage #3: With hydrogenchloride; water for 48h; Product distribution / selectivity; Reflux;
diethyl 2-(3-methylbutylidene)malonate
51615-30-6

diethyl 2-(3-methylbutylidene)malonate

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: di-n-propylamine / 16 h / 15 - 55 °C
2: hydrogen bromide / water / 72 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium chloride / dimethyl sulfoxide; water / 3 h / 185 °C / Inert atmosphere
2.1: sodium methylate / 0.5 h / Reflux
2.2: 4 h / Reflux
3.1: hydrogenchloride / water / 4 h / Reflux
View Scheme
isovaleraldehyde
590-86-3

isovaleraldehyde

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: piperidine; pyridine; acetic acid / hexane / 48 h / Reflux; Inert atmosphere
2: di-n-propylamine / 16 h / 15 - 55 °C
3: hydrogen bromide / water / 72 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: tetramethyl ammoniumhydroxide; trimethyldodecylammonium chloride / ethanol / 6 h / 25 °C
2: water; hydrogenchloride / 30 h / 140 °C / pH 1 - 2
View Scheme
Multi-step reaction with 2 steps
1.1: piperidine / hexane / 100 °C / Dean-Stark
2.1: piperidine / 2 h / 55 °C
2.2: 72 h / 100 - 120 °C
View Scheme
Multi-step reaction with 4 steps
1.1: acetic acid; piperidine / cyclohexane / 3 h / Reflux
2.1: sodium chloride / dimethyl sulfoxide; water / 3 h / 185 °C / Inert atmosphere
3.1: sodium methylate / 0.5 h / Reflux
3.2: 4 h / Reflux
4.1: hydrogenchloride / water / 4 h / Reflux
View Scheme
C17H27NO6

C17H27NO6

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water; glycerol at 100℃; for 6h; Temperature;
C16H25NO6

C16H25NO6

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water; glycerol at 100℃; for 6h; Concentration; Temperature;
isovaleraldehyde
590-86-3

isovaleraldehyde

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
Stage #1: isovaleraldehyde; cyanoacetic acid amide With propylamine at 15 - 40℃; for 5h;
Stage #2: With sulfuric acid at 10 - 132℃; for 10h; pH=1;
Stage #1: isovaleraldehyde; cyanoacetic acid amide With morpholine In water at 6 - 12℃; for 20h;
Stage #2: With hydrogenchloride In water at 105 - 110℃; for 18h;		480 g
Stage #1: isovaleraldehyde; cyanoacetic acid amide With water; triethylamine at 20 - 30℃;
Stage #2: With hydrogenchloride at 70 - 100℃;
2-cyano-3-isobutyl-4-ethylformylglutaric acid diethyl ester

2-cyano-3-isobutyl-4-ethylformylglutaric acid diethyl ester

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride for 72h; Reflux;160.6 g
2,4-dicyano-3-isobutyl-glutaric acid

2,4-dicyano-3-isobutyl-glutaric acid

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 10 - 15℃; for 10h; Reflux;200 g
methanol
67-56-1

methanol

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

1,5-dimethy 3-isobutylpentanedioate
145328-03-6

1,5-dimethy 3-isobutylpentanedioate

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate at 20℃; for 12h;95%
With chloro-trimethyl-silane for 12h;90%
With potassium permanganate; sulfuric acid for 10h; Reagent/catalyst; Temperature; Reflux;83.1%
With sulfuric acid at 40 - 45℃; for 14h; Temperature; Reflux;100 g
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

Isobutyl bromide
78-77-3

Isobutyl bromide

1,5-diisobutyl 3-isobutylpentanedioate

1,5-diisobutyl 3-isobutylpentanedioate

Conditions
ConditionsYield
Stage #1: 5-methyl-3-carboxymethylhexanoic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 0.166667h;
Stage #2: Isobutyl bromide In acetonitrile at 0℃; for 12h;		95%
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid
181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
With urea In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 3h; Temperature; Solvent;93.5%
With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate In acetonitrile at 5 - 20℃; for 0.5h; Solvent;72.4%
With hydrogenchloride; ammonium hydroxide; acetic anhydride In tert-butyl methyl ether; water; ethyl acetate
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

ethanol
64-17-5

ethanol

1,5-diethy 3-isobutylpentanedioate

1,5-diethy 3-isobutylpentanedioate

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate at 20℃; for 24h;93%
With hydrogenchloride
With thionyl chloride In 1,2-dichloro-ethane at 55 - 65℃;
allyl iodid
556-56-9

allyl iodid

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

1,5-diallyl 3-isobutylpentanedioate
1403953-90-1

1,5-diallyl 3-isobutylpentanedioate

Conditions
ConditionsYield
Stage #1: 5-methyl-3-carboxymethylhexanoic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 0.166667h;
Stage #2: allyl iodid In acetonitrile at 0℃; for 12h;		93%
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

3-isobutylglutarimide

3-isobutylglutarimide

Conditions
ConditionsYield
Stage #1: 5-methyl-3-carboxymethylhexanoic acid With urea at 180℃; for 2h;
Stage #2: With pyrographite In ethanol; water at 80℃; for 0.5h; Reagent/catalyst; Temperature;		92%
Stage #1: 5-methyl-3-carboxymethylhexanoic acid With ammonium hydroxide at 100℃; for 2h;
Stage #2: With pyrographite In ethanol for 0.5h; Reagent/catalyst; Reflux;		88.5%
Multi-step reaction with 2 steps
1: phosphorus pentoxide / 3 h / 95 °C
2: urea / 1 h / 30 °C
View Scheme
With urea at 30℃; for 1h; Concentration; Temperature;
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

3-isobutylglutaric anhydride
185815-59-2

3-isobutylglutaric anhydride

Conditions
ConditionsYield
With propionic acid anhydride at 140 - 145℃; for 6h;91%
With acetyl chloride at 20 - 55℃; for 3.08333h; Inert atmosphere;85%
at 150℃; unter vermindertem Druck;
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

formamide
77287-34-4, 77287-35-5, 60100-09-6

formamide

C10H15NO4

C10H15NO4

Conditions
ConditionsYield
at 160℃; for 5h;87%
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

3-isobutylpentane-1,5-diol

3-isobutylpentane-1,5-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; Inert atmosphere; Schlenk technique;82%
propan-1-ol
71-23-8

propan-1-ol

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

1,5-dipropyl 3-isobutylpentanedioate

1,5-dipropyl 3-isobutylpentanedioate

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate at 20℃; for 24h;80%
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

3-isobutylpentane-1,1,5,5-d4-1,5-diol

3-isobutylpentane-1,1,5,5-d4-1,5-diol

Conditions
ConditionsYield
With sodium borodeuteride; iodine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;60%
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

1-([1,1'-biphenyl]-4-yl)pentan-1-ol
50673-89-7

1-([1,1'-biphenyl]-4-yl)pentan-1-ol

3-Isobutyl-pentanedioic acid mono-(1-biphenyl-4-yl-pentyl) ester

3-Isobutyl-pentanedioic acid mono-(1-biphenyl-4-yl-pentyl) ester

Conditions
ConditionsYield
32%
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

acetyl chloride
75-36-5

acetyl chloride

β-isobutyl-glutaric acid-anhydride

β-isobutyl-glutaric acid-anhydride

5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

2,6-dimethyl-4-isobutylheptane-2,6-diol

2,6-dimethyl-4-isobutylheptane-2,6-diol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / TMSCl / 12 h
2: 56 percent / tetrahydrofuran; diethyl ether / 10 h / Ambient temperature
View Scheme
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

3-isobutyl-N-phenyl-glutaramic acid

3-isobutyl-N-phenyl-glutaramic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 150 °C / unter vermindertem Druck
View Scheme

3-Isobutylglutaric acid Chemical Properties

Molecular Structure of 3-Isobutylglutaric acid (CAS NO.75143-89-4):

Systematic Name: 3-(2-Methylpropyl)pentanedioic acid 
Molecular Formula: C9H16O4
Molecular Weight: 188.22 
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 6
Index of Refraction: 1.472
Molar Refractivity: 46.791 cm3
Molar Volume: 167.101 cm3
Surface Tension: 43.27 dyne/cm
Density: 1.126 g/cm3
Flash Point: 165.289 °C
Enthalpy of Vaporization: 62.484 kJ/mol
Boiling Point: 326.197 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C
Product Categories: intermidiate of Pregablin 
SMILES: O=C(O)CC(CC(C)C)CC(=O)O
InChI: InChI=1/C9H16O4/c1-6(2)3-7(4-8(10)11)5-9(12)13/h6-7H,3-5H2,1-2H3,(H,10,11)(H,12,13)
InChIKey: UATSLDZQNXAKMA-UHFFFAOYAZ

3-Isobutylglutaric acid Specification

 3-Isobutylglutaric acid (CAS NO.75143-89-4), its Synonyms are Pentanedioic acid,3-(2-methylpropyl)- ; 3-(Aminomethyl)-5-methylhexanoic acid .

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