Butanoic acid,3-methyl-2-oxo- supplier

Name
3-METHYL-2-OXOBUTYRIC ACIDDISCONTINUED
EINECS 212-065-4
CAS No. 759-05-7
Article Data103
CAS DataBase
Density 1.125 g/cm³
Solubility 400.6g/L(20 oC)
Melting Point 31.5℃
Formula C₅H₈O₃
Boiling Point 170.2 °C at 760 mmHg
Molecular Weight 116.117
Flash Point 71 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Butyricacid, 3-methyl-2-oxo- (8CI);2-Ketoisovaleric acid;2-Oxo-3-methylbutanoicacid;2-Oxo-3-methylbutyric acid;2-Oxoisovaleric acid;2-keto-3-Methylbutyricacid;3-Methyl-2-oxobutanoate;3-Methyl-2-oxobutanoic acid;3-Methyl-2-oxobutyrate;3-Methyl-2-oxobutyric acid;Dimethylpyruvic acid;Isopropylglyoxylic acid;Ketovaline;a-Ketoisovaleric acid;a-Oxo-b-methylbutyric acid;a-Oxoisovaleric acid;a-keto-Isovaleric acid;a-keto-b-Methylbutyric acid;
PSA 54.37000
LogP 0.29610

Synthetic route

: 20201-24-5
ethyl 3-methyl-2-oxobutanoate

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With water; lithium hydroxide at 0 - 25℃; for 1h; Inert atmosphere;	95%
With sodium hydroxide In water at 0 - 23℃; for 0.666667h;	62%
With potassium hydroxide

: 7682-64-6
4-isopropylidene-oxazolidine-2,5-dione

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran for 0.5h; Ambient temperature;	95%

: 152343-06-1
2,5-dihydro-4-(1-methylethyl)-2-(3-oxocyclohexyl)-oxazol-5-one

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: 69814-26-2
3-oxocyclohexanecarbaldehyde

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A n/a B 84%

: 152343-05-0
methyl 2,5-dihydro-4-(1-methylethyl)-γ,5-dioxo-2-oxazol-undecanoate

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: 50266-44-9
11-formyl-9-oxo-undecanoic acid methyl ester

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A n/a B 80%

: 152343-03-8
2,5-dihydro-4-(1-methylethyl)-5-oxo-2-(3-oxobutyl)-oxazol-5-one

A: 626-96-0
4-oxopentanal

B: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A 76% B n/a

: 152343-04-9
methyl 2,5-dihydro-4-(1-methylethyl)-5-oxo-2-oxazol-propionate

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: 13865-19-5
4-oxobutanoic acid methyl ester

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A n/a B 72%

: 152343-07-2
2,5-dihydro-4-(1-methylethyl)-2-(3-oxocyclopentyl)-oxazol-5-one

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: 77852-95-0, 65550-06-3
3-formylcyclopentanone

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A n/a B 70%

: 2357-39-3
2-trifluoromethyl-4-isopropyl-Δ3-oxazolin-5-one

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With water; sodium hydroxide at 20℃; for 12h; Inert atmosphere;	69%

: 152343-08-3
2,5-dihydro-4-(1-methylethyl)-2-(2-nitroethyl)-oxazol-5-one

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: 58657-26-4
3-nitropropanaldehyde

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A n/a B 64%

: 2-[((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-4-isopropyl-2H-oxazol-5-one

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: 583-50-6
D-erythrose

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A n/a B 59%

: 2,5-dihydro-4-(1-methylethyl)-5-oxo-2-(α-phenyl)-oxazolemethanol

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: (2-Oxo-1-phenyl-ethoxy)-phenyl-acetaldehyde

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A n/a B 51%

: 2-[Hydroxy-((S)-2-phenyl-[1,3]dioxan-4-yl)-methyl]-4-isopropyl-2H-oxazol-5-one

A: 18439-27-5
L-erythro-4-deoxy-pentose

B: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A 49% B n/a

: 2,5-dihydro-2-(1-hydroxyethyl)-4-(1-methylethyl)-oxazol-5-one

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: 2-(1-Methyl-2-oxo-ethoxy)-propionaldehyde

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A n/a B 44%

: 2,5-dihydro-4-(1-methylethyl)-5-oxo-2-oxazol-propionic aldehyde

A: 638-37-9
butanedial

B: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A 38% B n/a

: 2,5-dihydro-4-(1-methylethyl)-5-oxo-2-<α-(2-nitrophenyl)>-oxazolemethanol

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: (2-Nitro-phenyl)-[1-(2-nitro-phenyl)-2-oxo-ethoxy]-acetaldehyde

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran Ambient temperature;	A n/a B 37%

: 110-86-1
pyridine

: 56-23-5
tetrachloromethane

: 128-08-5
N-Bromosuccinimide

: 15344-34-0
2-hydroxy-3-methylbutanenitrile

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: 78-84-2
isobutyraldehyde

...Expand

: 56-23-5
tetrachloromethane

: 1578-14-9
2-bromo-3-methyl-crotonic acid

A: 44647-19-0
(E)-4-hydroxy-3-methylbut-2-enoic acid

B: 759-05-7
3-methyl-2-ketobutanoic acid

C: 91496-47-8
2-hydroxy-3-methylbut-3-enoic acid

Conditions

Conditions	Yield
at 100℃;

...Expand

: 56-23-5
tetrachloromethane

: 91496-47-8
2-hydroxy-3-methylbut-3-enoic acid

: 759-05-7
3-methyl-2-ketobutanoic acid

: 5166-53-0
5-methyl-3-hexene-2-one

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With potassium permanganate
With permanganate(VII) ion Oxydation;

: 72-18-4
L-valine

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III) In water at 55℃; Rate constant; Kinetics; Mechanism; var. reagents conc.;
With potassium nitrososulfonate In various solvent(s) at 26.9℃; Thermodynamic data; Rate constant; ΔH (activ.), ΔS (activ.);
With kidneys-extracts

: 516-06-3
D,L-valine

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With kidneys-extracts
With perchloric acid; hexachloroiridate(IV) at 34.9℃; Rate constant; Kinetics; Thermodynamic data; var. temp.; ΔH(excit.), ΔG(excit.), ΔS(excit.);
With pyridine-4-carbaldehyde; hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) DMF, r.t., 5 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: (heating) 2: aq. NaOH View Scheme
With ω-transaminase

: 4026-18-0, 17407-55-5, 17407-56-6, 600-37-3
2-hydroxy-3-methylbutanoic acid

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With Fructose 1,6-bisphosphate; Bacillus stearothermophilus; triethanolamine hydrochloride; NADH at 25℃; Rate constant; Equilibrium constant; also in presence of Gln102 or Asn enzyme;
With potassium hydroxide; potassium permanganate at 20℃;

: 42867-39-0
isobutyryl cyanide

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With hydrogenchloride

: 60703-31-3
2,5-Dimethyl-4-hexen-3-ol

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With potassium permanganate

: 15052-93-4
α-chloro β-dimethyl acrylic acid

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 1578-14-9
2-bromo-3-methyl-crotonic acid

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 35158-25-9
2-isopropyl-5-methyl-hex-2-enal

A: 503-74-2
3-methylbutyric acid

B: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With potassium permanganate

: 7346-12-5
dimethyl-oxalacetic acid

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With water; copper(II) ion Decarboxylation.pH 2-7;
With aluminium(III) ion; water Decarboxylation.pH 2-7;
With water; nickel(II) Decarboxylation.pH 2-7;
With water; manganese(II) Decarboxylation.pH 2-7;
at 25℃; Kinetics; Wss. Loesungen vom pH 0 bis pH 9, auch in Gegenwart verschiedener Metall-Ionen..Decarboxylation;

: 5447-64-3
diethyl 3,3-dimethyl-2-ketosuccinate

: 759-05-7
3-methyl-2-ketobutanoic acid

Conditions

Conditions	Yield
With sulfuric acid
With hydrogenchloride
With hydrogen bromide; acetic acid

: 57-50-1
Sucrose

A: 759-05-7
3-methyl-2-ketobutanoic acid

B: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ammonium salts; Aspergillus niger; sulfite(2-)

: 759-05-7
3-methyl-2-ketobutanoic acid

: 103-84-4
Acetanilid

: 1239986-59-4
N-(2-iso-butyrylphenyl)acetamide

Conditions

Conditions	Yield
With ammonium peroxydisulfate; palladium(II) trifluoroacetate In diethylene glycol dimethyl ether at 20℃;	93%

: 759-05-7
3-methyl-2-ketobutanoic acid

: (R)-3-((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyryl)-thiazolidine-4-carboxylic acid tert-butylamide; hydrochloride

: (R)-3-[(2S,3S)-2-Hydroxy-3-(3-methyl-2-oxo-butyrylamino)-4-phenyl-butyryl]-thiazolidine-4-carboxylic acid tert-butylamide

Conditions

Conditions	Yield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine	89%

: 759-05-7
3-methyl-2-ketobutanoic acid

: calcium 3-methyl-2-oxobutanoate

Conditions

Conditions	Yield
Stage #1: 3-methyl-2-ketobutanoic acid With pyrographite; potassium hydroxide In water pH=7; Reflux; Large scale; Stage #2: With calcium chloride In water at 0.2℃; for 3h; Solvent; Reagent/catalyst; Reflux; Large scale;	87.5%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 17407-55-5
(S)-2-Hydroxy-3-methylbutanoic acid

Conditions

Conditions	Yield
With NAD; hydrogen In hydrogenchloride for 42h; Ambient temperature;	86%

: 186581-53-3, 908094-01-9
diazomethane

: 759-05-7
3-methyl-2-ketobutanoic acid

: 3952-67-8
methyl 3-methyl-2-ketobutanoate

Conditions

Conditions	Yield
In diethyl ether at 0℃;	84%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 3290-99-1
4-methoxybenzoic acid hydrazide

: 152332-37-1
2-(4-Methoxybenzoylhydrazono)-3-methylbuttersaeure

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water at 60℃; for 2h;	84%

: 759-05-7
3-methyl-2-ketobutanoic acid

: potassium phenyltrifluoborate

: 611-70-1
phenyl isopropyl ketone

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; palladium diacetate In water; dimethyl sulfoxide at 20℃; for 3h;	83%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 1124196-10-6
(S)-tert-butyl 2-(hydroxyamino)-3-methylbutanoate

: tert-butyl 2-(N-hydroxy-3-methyl-2-oxobutanamido)-3-methylbutanoate

Conditions

Conditions	Yield
Stage #1: 3-methyl-2-ketobutanoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 15h; Inert atmosphere; Stage #2: (S)-tert-butyl 2-(hydroxyamino)-3-methylbutanoate With sodium carbonate In dichloromethane; water at 20℃; for 30h; Inert atmosphere;	82%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 104-54-1
3-Phenylpropenol

: cinnamyl 3-methyl-2-oxobutanoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	80%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 93188-01-3
2-(aminocarbonyl)-1-pyrrolidinecarboxylic acid, phenylmethyl ester

: 113586-10-0
Z-Pro-Δ Val

Conditions

Conditions	Yield
toluene-4-sulfonic acid In benzene for 10h; Heating;	75%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 65864-22-4
(S)-2-amino-3-phenylpropionamide hydrochloride

: N-2-oxo-3-methylbutanoyl-L-phenylalanine amide

Conditions

Conditions	Yield
Stage #1: (S)-2-amino-3-phenylpropionamide hydrochloride With triethylamine In dichloromethane at 4℃; Stage #2: 3-methyl-2-ketobutanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 4 - 20℃; for 2.5h;	74%

: 107-37-9
allyltrichlorosilane

: 759-05-7
3-methyl-2-ketobutanoic acid

: 2-hydroxy-2-isopropyl-pent-4-enoic acid

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 15h; Addition;	73%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 613-94-5
benzoic acid hydrazide

: 173973-79-0
2-Benzoylhydrazono-3-methylbuttersaeure

Conditions

Conditions	Yield
In water at 65℃; for 2h;	70%

: 759-05-7
3-methyl-2-ketobutanoic acid

: methyl S-((3R,5R)-5-hydroxyoctan-3-yl)-L-cysteinate

: methyl S-((3R,5R)-5-hydroxyoctan-3-yl)-N-(3-methyl-2-oxobutanoyl)-L-cysteinate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 0 - 23℃; for 18h;	70%

: 491-35-0
C6H4NCH2CHCCH2

: 759-05-7
3-methyl-2-ketobutanoic acid

: 91879-71-9
2-isopropyl-4-methylquinoline

Conditions

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; tetraethylammonium hexafluorophosphate; trifluoroacetic acid In acetonitrile at 50℃; Schlenk technique; Electrochemical reaction; Irradiation; Inert atmosphere;	68%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 621-84-1
O-benzyl carbamate

: 95863-98-2
2-(((benzyloxy)carbonyl)amino)-3-methylbut-2-enoic acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene at 99.85℃; for 8h;	67%
With toluene-4-sulfonic acid In benzene at 100℃; for 8h;	67%
With toluene-4-sulfonic acid In benzene at 100℃; for 8h;	67%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 100-63-0
phenylhydrazine

: 611-70-1
phenyl isopropyl ketone

Conditions

Conditions	Yield
With oxygen; silver(I) acetate; lithium carbonate In 1,2-dichloro-ethane at 100℃; under 760.051 Torr; for 16h; Schlenk technique; Green chemistry;	67%

: 290-37-9
1,4-pyrazine

: 759-05-7
3-methyl-2-ketobutanoic acid

: 86461-66-7
2-methyl-1-(pyrazin-2-yl)propan-1-one

Conditions

Conditions	Yield
With ferrous(II) sulfate heptahydrate; ammonium peroxydisulfate; formic acid; dimethyl sulfoxide In dichloromethane; water at 40℃; Minisci Aromatic Substitution;	65%

: 759-05-7
3-methyl-2-ketobutanoic acid

: 2643-92-7
2-Hydrazino-2-thiazolin-hydrobromid

: 90516-89-5
2,3-Dihydro-6-isopropyl-5H-thiazolo<2,3-c><1,2,4>-triazin-5-on

Conditions

Conditions	Yield
With sodium ethanolate In ethanol for 18h; Heating;	64%

: 1942-45-6
4-Octyne

: 759-05-7
3-methyl-2-ketobutanoic acid

: (Z)-3-isopropyl-4-propyl-5-propylidenefuran-2(5H)-one

Conditions

Conditions	Yield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate In toluene at 130℃; for 20h; Inert atmosphere; Sealed tube; diastereoselective reaction;	64%

: 759-05-7
3-methyl-2-ketobutanoic acid

: methyl S-((3R,5S)-5-hydroxyoctan-3-yl)-L-cysteinate

: methyl S-((3R,5S)-5-hydroxyoctan-3-yl)-N-(3-methyl-2-oxobutanoyl)-L-cysteinate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 0 - 23℃; for 18h;	62%

Butanoic acid,3-methyl-2-oxo- Specification

The Butanoic acid,3-methyl-2-oxo- is an organic compound with the formula C₅H₈O₃. The IUPAC name of this chemical is 3-methyl-2-oxobutanoic acid. With the CAS registry number 759-05-7, it is also named as 2-Ketoisovaleric acid.

Physical properties about Butanoic acid,3-methyl-2-oxo- are: (1)ACD/LogP: -0.36; (2)ACD/LogD (pH 5.5): -3.23; (3)ACD/LogD (pH 7.4): -4.08; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 43.37 Å²; (12)Index of Refraction: 1.432; (13)Molar Refractivity: 26.76 cm³; (14)Molar Volume: 103.1 cm³; (15)Polarizability: 10.61×10^-24cm³; (16)Surface Tension: 37.4 dyne/cm; (17)Density: 1.125 g/cm³; (18)Flash Point: 71 °C; (19)Enthalpy of Vaporization: 44.83 kJ/mol; (20)Boiling Point: 170.2 °C at 760 mmHg; (21)Vapour Pressure: 0.732 mmHg at 25°C.

Uses of Butanoic acid,3-methyl-2-oxo-: it can be used to produce valine at temperature of 20 °C. It will need reagent ammonium acetate, sodium cyanoborohydride and solvent methanol with reaction time of 46 hours. The yield is about 50%.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(C(=O)O)C(C)C
(2)InChI: InChI=1/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)
(3)InChIKey: QHKABHOOEWYVLI-UHFFFAOYAY
(4)Std. InChI: InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)
(5)Std. InChIKey: QHKABHOOEWYVLI-UHFFFAOYSA-N

Product Name

3-METHYL-2-OXOBUTYRIC ACIDDISCONTINUED

Synthetic route

Butanoic acid,3-methyl-2-oxo- Specification

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