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Quality Control of Sodium 3-methyl-2-oxobutanoate Purity: 95% SDS Specification

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Product Details of Sodium 3-methyl-2-oxobutanoate

CAS No. :	3715-29-5
Formula :	C₅H₇NaO₃
M.W :	138.10
SMILES Code :	CC(C)C(C([O-])=O)=O.[Na+]
MDL No. :	MFCD00002581
InChI Key :	WIQBZDCJCRFGKA-UHFFFAOYSA-M
Pubchem ID :	2724059

Safety of Sodium 3-methyl-2-oxobutanoate

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of Sodium 3-methyl-2-oxobutanoate

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 3715-29-5 ]

[ 3715-29-5 ] Synthesis Path-Downstream 1~35

1
[ 50-00-0 ]
[ 3715-29-5 ]
[ 13031-04-4 ]
[ 79-50-5 ]

References: [1]Helvetica Chimica Acta,1982,vol. 65,p. 2024 - 2028.

2
[ 64-67-5 ]
[ 3715-29-5 ]
[ 151561-32-9 ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 6920 - 6921.

3
[ 51308-35-1 ]
[ 3715-29-5 ]
[ 57304-91-3 ]

References: [1]Tetrahedron,1991,vol. 47,p. 1411 - 1416.

4
[ 3715-29-5 ]
[ 135967-46-3 ]
[ 135967-48-5 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 3623 - 3626.

5
[ 3715-29-5 ]
[ 72-18-4 ]

References: [1]Chemistry Letters,1982,p. 1765 - 1768.

6
[ 3715-29-5 ]
[ 17407-56-6 ]

References: [1]Agricultural and Biological Chemistry,1986,vol. 50,p. 2621 - 2632.

7
[ 3715-29-5 ]
[ 59935-29-4 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2008,vol. 51,p. 171 - 174.
[2]Tetrahedron Letters,1994,vol. 35,p. 6533 - 6536.

8
[ 3715-29-5 ]
[ 77257-02-4 ]
[ 77257-03-5 ]

References: [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 3652 - 3656.

9
[ 3715-29-5 ]
sodium α-keto-β-deuteroisovalerate [ No CAS ]

References: [1]Tetrahedron,1981,vol. 37,p. 1589 - 1595.

10
[ 3715-29-5 ]
C₅H₆⁽³⁾HO₃^(1-)*Na⁽¹⁺⁾ [ No CAS ]

References: [1]Tetrahedron,1981,vol. 37,p. 1589 - 1595.

11
[ 1068-55-9 ]
[ 95-92-1 ]
[ 3715-29-5 ]

References: [1]Helvetica Chimica Acta,1982,vol. 65,p. 2024 - 2028.

12
[ 3715-29-5 ]
[ 77-78-1 ]
[ 58973-18-5 ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 6920 - 6921.

13
[ 67-56-1 ]
[ 3715-29-5 ]
[ 3952-67-8 ]

References: [1]Australian Journal of Chemistry,1995,vol. 48,p. 1747 - 1756.

14
[ 550-44-7 ]
[ 3715-29-5 ]
[ 32360-86-4 ]

References: [1]Synlett,1999,p. 492 - 494.
[2]Synlett,2000,p. 1455 - 1457.

15
[ 3715-29-5 ]
[ 100-51-6 ]
[ 76585-78-9 ]

References: [1]Helvetica Chimica Acta,2001,vol. 84,p. 3766 - 3772.

16
[ 3715-29-5 ]
(2S,5Z)-2-(1-methylethyl)-4-oxo-5-(phenylmethylene)-1,3-dioxolane-2-carboxylic acid [ No CAS ]

References: [1]Helvetica Chimica Acta,2001,vol. 84,p. 3766 - 3772.

17
[ 3715-29-5 ]
[ 408516-42-7 ]

References: [1]Helvetica Chimica Acta,2001,vol. 84,p. 3766 - 3772.

18
[ 3715-29-5 ]
phenylmethyl (2R,5R)-2-(1-methylethyl)-4-oxo-5-(phenylmethyl)-1,3-dioxolane-2-carboxylate [ No CAS ]

References: [1]Helvetica Chimica Acta,2001,vol. 84,p. 3766 - 3772.

19
[ 3715-29-5 ]
[ 408516-36-9 ]

References: [1]Helvetica Chimica Acta,2001,vol. 84,p. 3766 - 3772.

20
[ 3715-29-5 ]
[ 408516-40-5 ]

References: [1]Helvetica Chimica Acta,2001,vol. 84,p. 3766 - 3772.

21
[ 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 [ No CAS ]

References: [1]Australian Journal of Chemistry,1995,vol. 48,p. 1747 - 1756.

22
[ 3715-29-5 ]
N-acetyl-DL-<3-(2)H>-valine [ No CAS ]

References: [1]Tetrahedron,1981,vol. 37,p. 1589 - 1595.

23
[ 3715-29-5 ]
N-acetyl-DL-<3-(3)H>-valine [ No CAS ]

References: [1]Tetrahedron,1981,vol. 37,p. 1589 - 1595.

24
[ 3715-29-5 ]
[ 79168-24-4 ]

References: [1]Tetrahedron,1981,vol. 37,p. 1589 - 1595.

25
[ 3715-29-5 ]
[ 79168-22-2 ]

References: [1]Tetrahedron,1981,vol. 37,p. 1589 - 1595.

26
[ 3715-29-5 ]
[ 79168-23-3 ]

References: [1]Tetrahedron,1981,vol. 37,p. 1589 - 1595.

27
[ 3715-29-5 ]
[ 79168-21-1 ]

References: [1]Tetrahedron,1981,vol. 37,p. 1589 - 1595.

28
[ 3715-29-5 ]
[ 125816-10-6 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 3623 - 3626.

29
[ 3715-29-5 ]
[ 135967-50-9 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 3623 - 3626.

30
[ 3715-29-5 ]
[ 142687-80-7 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 3623 - 3626.

31
[ 3715-29-5 ]
[ 135967-45-2 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 3623 - 3626.

32
[ 3715-29-5 ]
[ 135967-49-6 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 3623 - 3626.

33
[ 20201-24-5 ]
[ 3715-29-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; water; In tetrahydrofuran; at 20℃;	Example 8 25. N-toluenesulfonyl-alpha-dehydrovaline.; To Ethyl 3-methyl-2-oxobutanoate, (15.0 g, 104.0 mmol) in THF (150 mL) was added LiOHNo.H2O(5.30 g, 125.0 mmol). This stirred at rt overnight, then the solvent was stripped. The resulting white solid was slurried in MTBE (150 mL) and cooled to 0 C, then HCI (12.1 N, 11.0 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (50 mL). The combined organics were stripped to give a light yellow oil. This oil was dissolved in toluene (84 mL) and diethyleneglycol diethyl ether (12 mL) and p-toluenesulfonamide (14.2 g, 83.2 mmol) then methanesulfonic acid (0.54 mL, 8.3 mmol) were added. The resulting mixture was heated at reflux with Dean-Stark removal of water for 24h, then cooled to rt. The resulting mixture was mixed with EtOAc (45 mL) and NaHC03 (14.1 g) in water (150 mL). Upon complete C02 evolution and dissolution, the aqueous layer was separated, then the organics were washed with NaHC03 (1.6 g) in water (45 mL). The combined aqueous layers were washed with EtOAc (2 x 45 mL), then cooled to 0 C, and treated with HCl (12. IN, 15.4 mL), to give a white solid precipitate, which upon filtration and drying gave 15.0 g of crude material. This material was dissolved in MeOH (45 mL), then toluene (100 mL) was added. This was heated to 90 C, and the MeOH was removed. Then n-heptane (100 mL) was added slowly over 2h at 80 C, then cooled slowly to 0 C. Filtration gave 12.0 g of pure white material (54% yield). mp 188.5-189.5 C. IH-NMR (400 MHz, CD30D) d 7.67 (d, 2H, 20.1 Hz), 7.32 (d, 2H, 20.1 Hz), 2.42 (s, 3H), 2.09 (s, 3H), 1.79 (s, 3H); ¹3C NMR (100 MHz, DMSO-d6) 166.8,146.9,142.8,138.6,129.6, 126.9, 122.1, 22.1, 21.4, 21.3 ppm. HRMS calcd for C12H14N04S (M-H) : 268.0644, Found: 268.0638.

References: [1]Patent: WO2005/118529,2005,A2 .Location in patent: Page/Page column 26.

34
[ 3715-29-5 ]
[ 759-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; In tert-butyl methyl ether; at 0℃;Product distribution / selectivity;	Example 8 25. N-toluenesulfonyl-alpha-dehydrovaline.; To Ethyl 3-methyl-2-oxobutanoate, (15.0 g, 104.0 mmol) in THF (150 mL) was added LiOHNo.H2O(5.30 g, 125.0 mmol). This stirred at rt overnight, then the solvent was stripped. The resulting white solid was slurried in MTBE (150 mL) and cooled to 0 C, then HCI (12.1 N, 11.0 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (50 mL). The combined organics were stripped to give a light yellow oil. This oil was dissolved in toluene (84 mL) and diethyleneglycol diethyl ether (12 mL) and p-toluenesulfonamide (14.2 g, 83.2 mmol) then methanesulfonic acid (0.54 mL, 8.3 mmol) were added. The resulting mixture was heated at reflux with Dean-Stark removal of water for 24h, then cooled to rt. The resulting mixture was mixed with EtOAc (45 mL) and NaHC03 (14.1 g) in water (150 mL). Upon complete C02 evolution and dissolution, the aqueous layer was separated, then the organics were washed with NaHC03 (1.6 g) in water (45 mL). The combined aqueous layers were washed with EtOAc (2 x 45 mL), then cooled to 0 C, and treated with HCl (12. IN, 15.4 mL), to give a white solid precipitate, which upon filtration and drying gave 15.0 g of crude material. This material was dissolved in MeOH (45 mL), then toluene (100 mL) was added. This was heated to 90 C, and the MeOH was removed. Then n-heptane (100 mL) was added slowly over 2h at 80 C, then cooled slowly to 0 C. Filtration gave 12.0 g of pure white material (54% yield). mp 188.5-189.5 C. IH-NMR (400 MHz, CD30D) d 7.67 (d, 2H, 20.1 Hz), 7.32 (d, 2H, 20.1 Hz), 2.42 (s, 3H), 2.09 (s, 3H), 1.79 (s, 3H); ¹3C NMR (100 MHz, DMSO-d6) 166.8,146.9,142.8,138.6,129.6, 126.9, 122.1, 22.1, 21.4, 21.3 ppm. HRMS calcd for C12H14N04S (M-H) : 268.0644, Found: 268.0638.; Example 9 26. N-(4-methoxy)benzenesulfonyl-alpha-dehydrovaline. 3-methyl-2-oxobutyic acid, sodium salt (2.0 g, 14.2 mmol) was slurried in MTBE (10 mL) and cooled to 0 C, then HCl (12.1 N, 1.3 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (10 mL). The combined organics were stripped to give a light-yellow oil. This oil was dissolved in toluene (14 mL) and diethyleneglycol diethyl ether (2 mL) and p-methoxybenzenesulfonamide (2.2 g, 11.6 mmol) then methanesulfonic acid (0.08 mL, 1.2 mmol) were added. The resulting mixture was heated at reflux (65 C) at reduced pressure with Dean-Stark removal of water for 16 h. The resulting mixture was mixed with EtOAc (25 mL) and NaHC03 (2.0 g) in water (40 mL). Upon complete CO2 evolution and dissolution, the aqueous layer was separated, then the organics were washed with NaHC03 (0.2 g) in water (11 mL). The combined aqueous layers were washed with EtOAc (11 mL), then cooled to 0 C, and treated with HCl (12.1N, 2.1mL), to give a white solid precipitate, which upon filtration and drying gave 0.45 g of crude material. This material was passed though silica-gel, eluting with EtOAc to give 0.44 g of pure white product (13% yield). mp 162.5-163.5 C. ¹H-NMR (400 MHz, CD3OD) d 7.72 (d, 2H, 22.2 Hz), 7.02 (d, 2H, 22.7 Hz), 3.86 (s, 3H), 2.09 (s, 3H), 1.81 (s, 3H); ¹3C NMR (100 MHz, CD30D) 167.0,163.2, 150.7,132.0, 129.2, 121.2, 113.7, 54.9,21.9, 20.5 ppm. HRMS calcd for C12H14N05S (M-H) : 284.0593, Found: 284.0591.; Example 10 27. N-(4-fluorobenzene)sulfonyl-alpha-dehydrovaline. 3-methyl-2-oxobutyic acid, sodium salt (5.0 g, 36.2 mmol) was slurried in MTBE (25 mL) and cooled to 0 C, then HCI (12.1 N, 3.1 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (25 mL). The combined organics were stripped to give a light-yellow oil. This oil was dissolved in toluene (35 mL) and diethyleneglycol diethyl ether (5 mL) and p-toluenesulfonamide (5.1 g, 29.0 mmol) then methanesulfonic acid (0.19 mL, 2.9 mmol) were added. The resulting mixture was heated at reflux with Dean-Stark removal of water for 24h, then cooled to 5 C. The resulting solid was filtered, and dried to give 5.4 g of crude material, which was recrystallized from MeOH/ water (16 mL/ 38 mL) to give 4.90 g of pure white solid (62% isolated yield). mp 172-173 C. IH-NMR (400 MHz, CD30D) d 7.83-7.86 (m, 2H), 7.22-7.27 (m, 2H), 2.12 (s, 3H), 1.87 (s, 3H); ¹3C NMR (100 MHz, CD30D) 166.6,166.3, 163.7, 151.6, 136.7 (2 peaks), 129.9,129.8, 120.8, 115.5, 115.3, 22.0, 20.4 ppm. HRMS calcd for C11H11FNO4S (M-H) : 272.0393, Found: 272.0398.; Example 11 28. N-(benzyl)sulfonyl-alpha-dehydrovaline. 3-methyl-2-oxobutyic acid, sodium salt (5.0 g, 36.2 mmol) was slurried in MTBE (25 mL) and cooled to 0 C, then HCl (12.1 N, 3.1 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (25 mL). The combined organics were stripped to give a light-yellow oil. This oil was diss...

References: [1]Patent: WO2005/118529,2005,A2 .Location in patent: Page/Page column 26-29.

35
[ 13485-59-1 ]
[ 3715-29-5 ]
N-(1-carboxy-2-methylpropyl)L-alanyl-L-proline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride;	EXAMPLE 7 N-(1-carboxy-2-methylpropyl)L-alanyl-L-proline A mixture of <strong>[3715-29-5]3-methyl-2-oxobutyric acid sodium salt</strong> (1.46 g) and L-alanyl-L-proline (0.40 g) was treated with sodium cyanoborohydride (0.41 g) as described above. Crude N-(1-carboxy-2-methylpropyl)L-alanyl-L-proline (0.45 g) was obtained by elution from ion-exchange resin. The product melted at 131-142. The nmr spectrum shows complex absorption in the 4.6 to 3.3 region, a broad multiplet centered at 2.2 and doublets at 1.65 and 1.1 ppm.

References: [1]Patent: US4374829,1983,A .

Historical Records

Technical Information

• Acyl Group Substitution • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Ester Cleavage • Fischer Indole Synthesis • Grignard Reaction • Heat of Combustion • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
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Response
Code	Phrase
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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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P342	If experiencing respiratory symptoms:
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P401
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H200	Unstable explosive
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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 3715-29-5

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CAS No.: 3715-29-5

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