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

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

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

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

Downstream Products

• 57304-91-3 3-(1-carboxy-6,6-dimethyl-3-oxo-cyclohex-2-enyl)-propanoic acid 
• 125816-10-6 <3S-<3α,5β(R^*)>>-5-(2-Cyclohexyl-1-aminoethyl)dihydro-3-isopropyl-2(3H)-furanone 
• 135967-50-9 (5S,6S)-6-Cyclohexylmethyl-3-isopropylidene-5-hydroxypiperidine-2-one 
• 142687-80-7 (3S,5S,6S)-6-Cyclohexylmethyl-5-hydroxy-3-isopropylpiperidin-2-one 
• 135967-45-2 (S)-6-Cyclohexylmethyl-3-isopropylidene-piperidine-2,5-dione 
• 135967-49-6 (S)-6-Cyclohexyl-2-isopropylidene-4-oxo-5-(trityl-amino)-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester 

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