3715-29-5

Basic information

• Product Name: Sodium 3-methyl-2-oxobutanoate
• Synonyms: Sodium 3-methyl-2-oxobutanoate;SODIUM 3-METHYL-2-OXOBUTYRATE;SODIUM ALPHA-KETOISOVALERATE;2-KETOISOVALERIC ACID SODIUM SALT;3-METHYL-2-OXOBUTANOIC ACID, NA SALT;3-METHYL-2-OXOBUTANOIC ACID SODIUM SALT;3-METHYL-2-OXOBUTYRIC ACID SODIUM SALT;ALPHA-KETOISOVALERIC ACID SODIUM SALT
• CAS NO: 3715-29-5
• Molecular Formula: C₅H₇O₃*Na
• Molecular Weight: 138.1
• EINECS: 223-062-2
• Product Categories: Aliphatics;Intermediates
• Mol File: 3715-29-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 220-230 °C (dec.)(lit.)
• Boiling Point: 170.2 °C at 760 mmHg
• Flash Point: 71 °C
• Appearance: White or slightly yellow to beige/Crystalline Powder or Crystals
• Vapor Pressure: 0.732mmHg at 25°C
• Storage Temp.: Store at 0-5°C
• Solubility: water: soluble100mg/mL, clear, colorless
• BRN: 4334552
• CAS DataBase Reference: Sodium 3-methyl-2-oxobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium 3-methyl-2-oxobutanoate(3715-29-5)
• EPA Substance Registry System: Sodium 3-methyl-2-oxobutanoate(3715-29-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 3715-29-5(Hazardous Substances Data)

Usage

Description

Sodium 3-methyl-2-oxobutanoate, also known as 3-Methyl-2-oxobutanoic acid sodium salt, is an organic compound that is found naturally in various food items such as banana, bread, blue and provolone cheeses, asparagus, beer, and cocoa. It is an α-keto ester derivative and exhibits a fruity aroma. This white or slightly yellow to beige crystalline substance is utilized in the synthesis of (S)-2-hydroxy-3-methylbutanoic acid, which is a significant intermediate in the production of various pharmaceuticals and specialty chemicals.

Uses

Used in Pharmaceutical Synthesis:
Sodium 3-methyl-2-oxobutanoate is used as a key intermediate in the pharmaceutical industry for the synthesis of (S)-2-hydroxy-3-methylbutanoic acid. Sodium 3-methyl-2-oxobutanoate serves as a building block for the development of various drugs, highlighting its importance in the medicinal field.
Used in Flavor and Fragrance Industry:
Due to its fruity aroma, Sodium 3-methyl-2-oxobutanoate is used as a flavoring agent in the food and beverage industry. It adds a pleasant and distinct taste to various products, enhancing their overall flavor profile.
Used in the Synthesis of Specialty Chemicals:
Sodium 3-methyl-2-oxobutanoate is also utilized as a starting material in the synthesis of specialty chemicals, which have applications in various industries such as cosmetics, agriculture, and materials science. Its versatility as a chemical intermediate makes it a valuable component in the development of novel products.

InChI:InChI=1/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)/p-1

Synthetic route

isopropylmagnesium chloride (1068-55-9) + oxalic acid diethyl ester (95-92-1) → sodium 3-methyl-2-oxobutyrate (3715-29-5)

Conditions	Yield
With sodium hydroxide 1.) ether/CH2Cl2, -10 to 5 deg C, 2.) H2O, 5 deg C; Yield given. Multistep reaction;

ethyl 3-methyl-2-oxobutanoate (20201-24-5) → sodium 3-methyl-2-oxobutyrate (3715-29-5)

Conditions	Yield
With lithium hydroxide; water In tetrahydrofuran at 20℃;

sodium 3-methyl-2-oxobutyrate (3715-29-5) → (S)-(15)N-2-amino-3-methyl butanoic acid (59935-29-4, 71261-62-6, 96817-46-8)

Conditions	Yield
With ammonium-15N hydrochloride; NAD; recombinant glucose dehydrogenase from Bacillus subtilis; recombinant galactomutarotase from Escherichia coli In sodium hydroxide at 30℃; pH=8.0 - 8.2;	90%
With formate dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide; 15N-ammonium formate; leucine dehydrogenase; diothiothreitol Ambient temperature; TRIS, pH=6.5-7.0, 0.1M HCl;	84%

N-methylphthalimide (550-44-7) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → 3-hydroxy-3-isopropyl-2-methyl-2,3-dihydroisoindol-1-one (32360-86-4)

Conditions	Yield
In water; acetone at 15℃; Irradiation;	86%
In water; acetone at 15℃; Alkylation; UV-irradiation;	86%

sodium 3-methyl-2-oxobutyrate (3715-29-5) → (R)-2-Hydroxy-3-methylbutyric acid (17407-56-6)

Conditions	Yield
With phosphate buffer; D-glucose; 2-hydroxyethanethiol; sodium chloride; formate dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide; benzoylformate reductase; bovine serum albumin; yeast alcohol dehydrogenase In ethanol; water; toluene at 30℃; for 48h;	84%

sodium 3-methyl-2-oxobutyrate (3715-29-5) + benzyl alcohol (100-51-6) → phenylmethyl 3-methyl-2-oxobutanoate (76585-78-9)

Conditions	Yield
With thionyl chloride at 0℃; for 0.5h;	82%

dichloromethane (75-09-2) + CuCl(hydrotris(3,5-diisopropyl-1-pyrazolyl)borate)*CH2Cl2 + sodium 3-methyl-2-oxobutyrate (3715-29-5) → Cu(3-methyl-2-oxobutyrate)(hydrotris(3,5-diisopropyl-1-pyrazolyl)borate)*0.5CH2Cl2

Conditions	Yield
In methanol for 1h; Cooling with ice;	75%

2-chloro-3-aminopyridine (6298-19-7) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → C10H11ClN2O2 (1360432-80-9)

Conditions	Yield
Stage #1: sodium 3-methyl-2-oxobutyrate With hydrogenchloride In 1,4-dioxane; chloroform at 20℃; for 0.5h; Stage #2: 2-chloro-3-aminopyridine With dicyclohexyl-carbodiimide In 1,4-dioxane; chloroform at -5℃; for 2h; Inert atmosphere;	68%

sodium 3-methyl-2-oxobutyrate (3715-29-5) → L-valine (72-18-4)

Conditions	Yield
With zinc(II) perchlorate; (R)-15-amino-methyl-14-hydroxy-5,5-dimethyl-2,8-dithia<9>(2,5)pyridinophane In methanol for 24h; Ambient temperature;	57%
With ammonium sulfate; NADP+-specific glutamate dehydrogenase from Pseudomonas putida, I406F mutant; NADPH In aq. phosphate buffer at 35℃; pH=7.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; enantioselective reaction;

C12H19N3O6 + sodium 3-methyl-2-oxobutyrate (3715-29-5) → C17H27NO8

Conditions	Yield
Stage #1: C12H19N3O6 With sodium hydroxide; trimethylphosphane In methanol; water at 20℃; Stage #2: sodium 3-methyl-2-oxobutyrate With 4-methyl-morpholine; 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate In dimethyl sulfoxide at 20℃;	53%

potassium hydridotris(3,5-diphenylpyrazol-1-yl)borate + Fe(perchlorate)2*8water + water (7732-18-5) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → 3-methyl-2-oxobutanoato(hydrotris(3,5-diphenylpyrazol-1-yl)borate)iron(II) monohydrate

Conditions	Yield
In methanol under inert atmosphere; NaO2CCO-i-Pr added to slurry of Fe salt and B compd. (molar ratio 1:1:1) in MeOH; stirred at room temp. for 30 min; modified from R. Y. N. Ho et al., J. Am. Chem. Soc., 2001, 123, 5022-5029; filtered; ppt. dissolved in min. amt. of CH2Cl2; filtered; Et2O vapor diffused into soln.; crystals collected; elem. anal.;	52%

sodium tetrachloropalladate(II) + hydroxylamine hydrochloride (5470-11-1) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → [Pd(O2CC(C3H7)NOH)(HO2CC(C3H7)NO)]*2H2O

Conditions	Yield
With sodium methylate In methanol; water (N2); dissoln. of the Na salt and NH2OH*HCl in MeOH/H2O, addn. of methanolic NaOMe, stirring (48 h), evapn. to dryness, dissoln. (H2O), addn. ofaq. Na2PdCl4; centrifugation, washing (cold H2O), drying (vac., 70°C); elem. anal.;	51%

3-(2-fluoro-4-(2,3,5,6-tetrafluorophenoxy)phenyl)-1-((R)-pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine + sodium 3-methyl-2-oxobutyrate (3715-29-5) → 1-((R)-3-(4-amino-3-(2-fluoro-4-(2,3,5,6-tetrafluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-pyrrolidin-1-yl)-3-methylbutane-1,2-dione

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 1h;	42%

1-methyl-1-phenylethyl alcohol (617-94-7) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → C14H18O3

Conditions	Yield
With pyridine; methanesulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 0.416667h;	40%

(chloro)(hydrotris(3,5-diisopropyl-1-pyrazolyl)borate)nickel(II) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → Ni(3-methyl-2-oxobutyrate)(hydrotris(3,5-diisopropyl-1-pyrazolyl)borate)(H2O)

Conditions	Yield
In methanol for 2h; Cooling with ice;	18%

formaldehyd (50-00-0) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → ketopantolactone (13031-04-4) + pantolactone (79-50-5)

Conditions	Yield
With hydrogenchloride; potassium carbonate 1.) H2O, 38-40 deg C, (well controlled addition of formaldehyde); Yield given. Multistep reaction. Yields of byproduct given;

diethyl sulfate (64-67-5) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → 3-Methyl-2-ethoxy-2-butenoic acid (151561-32-9)

Conditions	Yield
With n-butyllithium; potassium tert-butylate In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane 1.) -70 deg C, 1 h, 2.) 25 deg C, 1 d;	12 % Spectr.

methyl 7-chloro-5-oxoheptanoate (51308-35-1) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → 3-(1-carboxy-6,6-dimethyl-3-oxo-cyclohex-2-enyl)-propanoic acid (57304-91-3)

Conditions	Yield
With potassium hydroxide at 100℃; for 3h; Yield given;

sodium 3-methyl-2-oxobutyrate (3715-29-5) + Dimethyl 3(S)-4-Cyclohexyl-3-(N-triphenylmethyl)amino-2-oxobutylphosphonate (135967-46-3) → (6S)-7-Cyclohexyl-2-methyl-6-(N-triphenylmethyl)-amino-5-oxohept-2-ene-3-oic acid (135967-48-5)

Conditions	Yield
1) THF, 0 deg C, 2) DME, reflux; Yield given. Multistep reaction;

sodium 3-methyl-2-oxobutyrate (3715-29-5) → D-<2-2H>valine (77257-02-4) + α-2H-(S)-valine (77257-03-5)

Conditions	Yield
With zinc(II) perchlorate; (R)-15-aminomethyl-14-hydroxy-5,5-dimethyl-2,8-dithia<9>(2,5)pyridinophane In deuteromethanol for 96h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

sodium 3-methyl-2-oxobutyrate (3715-29-5) → sodium α-keto-β-deuteroisovalerate

Conditions	Yield
With sodium hydroxide; water for 2h; Ambient temperature;

sodium 3-methyl-2-oxobutyrate (3715-29-5) → C5H6(3)HO3(1-)*Na(1+)

Conditions	Yield
With sodium hydroxide; water for 96h; Ambient temperature;

sodium 3-methyl-2-oxobutyrate (3715-29-5) + dimethyl sulfate (77-78-1) → 3-Methyl-2-methoxy-2-butenoic acid (58973-18-5)

Conditions	Yield
With n-butyllithium; potassium tert-butylate In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane 1.) -70 deg C, 1 h, 2.) 25 deg C, 0.5 d;	30 % Spectr.

methanol (67-56-1) + sodium 3-methyl-2-oxobutyrate (3715-29-5) → methyl 3-methyl-2-ketobutanoate (3952-67-8)

Conditions	Yield
With thionyl chloride for 0.5h;

sodium 3-methyl-2-oxobutyrate (3715-29-5) → (2S,5Z)-2-(1-methylethyl)-4-oxo-5-(phenylmethylene)-1,3-dioxolane-2-carboxylic acid

Conditions	Yield
Multi-step reaction with 5 steps 1: 82 percent / SOCl2 / 0.5 h / 0 °C 2: 48 percent / BF3*OEt2 / 2 h / 20 °C 3: 45 percent / NBS; AIBN / CCl4 / 0.17 h / Heating; irradiation 4: 100 percent / Et3N / acetone / 2 h / 20 °C 5: quinoline; H2 / Pd/C / toluene / 2 h / 20 °C View Scheme

sodium 3-methyl-2-oxobutyrate (3715-29-5) → phenylmethyl (2S,5Z)-2-(1-methylethyl)-4-oxo-5-(phenylmethylene)-1,3-dioxolane-2-carboxylate (408516-42-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 82 percent / SOCl2 / 0.5 h / 0 °C 2: 48 percent / BF3*OEt2 / 2 h / 20 °C 3: 45 percent / NBS; AIBN / CCl4 / 0.17 h / Heating; irradiation 4: 100 percent / Et3N / acetone / 2 h / 20 °C View Scheme

sodium 3-methyl-2-oxobutyrate (3715-29-5) → phenylmethyl (2R,5R)-2-(1-methylethyl)-4-oxo-5-(phenylmethyl)-1,3-dioxolane-2-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / SOCl2 / 0.5 h / 0 °C 2: BF3*OEt2 / 2 h / 20 °C View Scheme

sodium 3-methyl-2-oxobutyrate (3715-29-5) → phenylmethyl (2S,5R)-2-(1-methylethyl)-4-oxo-5-(phenylmethyl)-1,3-dioxolane-2-carboxylate (408516-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / SOCl2 / 0.5 h / 0 °C 2: 48 percent / BF3*OEt2 / 2 h / 20 °C View Scheme

sodium 3-methyl-2-oxobutyrate (3715-29-5) → phenylmethyl (2R,4S)-4-bromo-2-(1-methylethyl)-5-oxo-4-(phenylmethyl)-1,3-dioxolane-2-carboxylate (408516-40-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 82 percent / SOCl2 / 0.5 h / 0 °C 2: 48 percent / BF3*OEt2 / 2 h / 20 °C 3: 45 percent / NBS; AIBN / CCl4 / 0.17 h / Heating; irradiation View Scheme

sodium 3-methyl-2-oxobutyrate (3715-29-5) → (4aα,8aβ)-5,5,8a,9-Tetramethyl-3-(1'-methylethyl)-4a,5,6,7,8,8a-hexahydronaphtho<2,3-b>furan-2(4H)-one

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 0.5 h 2: 10 percent / LiI*2H2O / various solvent(s) / 21 h / Heating View Scheme

sodium 3-methyl-2-oxobutyrate (3715-29-5) → N-acetyl-DL-<3-(2)H>-valine

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOH, (2)H2O / 2 h / Ambient temperature 2: NH4Br, sodium cyanoborohydride / methanol / 96 h / Ambient temperature 3: 91 percent / acetic acid / 0.67 h / Heating View Scheme

Upstream product

• 20201-24-5 ethyl 3-methyl-2-oxobutanoate 
• 7526-77-4 5-iso-propylidenehydantoin 
• 1068-55-9 isopropylmagnesium chloride 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 759-05-7 3-methyl-2-ketobutanoic acid 
• 640-68-6 D-Val-OH 
• 72-18-4 L-valine 

Relevant articles and documents

Preparation method of alpha-ketovaline calcium and intermediate thereof

The invention relates to a preparation method of alpha-ketovaline calcium and an intermediate thereof, the alpha-ketovaline calcium intermediate isopropylidene hydantoin is obtained from hydantoin and acetone under the catalysis of ammonia water, and the high-yield and high-purity isopropylidene hydantoin can be obtained without a post-treatment step of impurity removal. The alpha-ketovaline calcium is prepared from isopropylidene hydantoin, the alpha-ketovaline calcium with high yield and high purity can also be obtained, and the method is suitable for industrial large-scale production.

Synthesis of 4,4-dimethyl-2,3-furanedione

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