57-71-6

Basic information

• Product Name: 2,3-Butanedione monoxime
• Synonyms: Biacetyl Monoxime 2,3-Butanedione 2-Oxime Isonitrosoethyl Methyl Ketone;(E)-3-(hydroxyiMino)butan-2-one;2,3-Butanedione monoxime 97%;3-(Hydroxyimino)butan-2-one;Diacetyl Monoxime 〔2,3-Butanedione-2-oxime〕;ISONITROSOETHYL METHYL KETONE;DAM;DIACETYL MONOOXIME
• CAS NO: 57-71-6
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• EINECS: 200-348-5
• Product Categories: Inhibitors
• Mol File: 57-71-6.mol

Chemical Properties

• Melting Point: 75-78 °C(lit.)
• Boiling Point: 185-186 °C(lit.)
• Flash Point: 185-186°C
• Appearance: White to almost white/Crystalline Powder
• Density: 1.2085 (rough estimate)
• Vapor Pressure: 0.315mmHg at 25°C
• Refractive Index: 1.4340 (estimate)
• Storage Temp.: Store at +15°C to +25°C.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.32±0.10(Predicted)
• Water Solubility: 5 g/100 mL (20 ºC)
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 605582
• CAS DataBase Reference: 2,3-Butanedione monoxime(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Butanedione monoxime(57-71-6)
• EPA Substance Registry System: 2,3-Butanedione monoxime(57-71-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-36/37/39-26
• WGK Germany: 3
• RTECS: EK3150000
• TSCA: Yes
• Hazardous Substances Data: 57-71-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Butanedione monoxime is used as a pharmaceutical agent for its ability to inhibit myosin ATPase. This property makes it valuable in the development of drugs targeting muscle contraction and related conditions.
Used in Chemical Analysis:
In the field of chemical analysis, 2,3-Butanedione monoxime is used as a reagent for the colorimetric determination of urea. Its effectiveness in this application aids in the accurate measurement and analysis of urea levels in various samples.

Preparation

Approximately 9 moles of ethyl nitrite are required for this preparation. The literature indicates a suitable apparatus for its generation. In a well-ventilated hood, to freshly dried and distilled methyl ethyl ketone (620 gm, 8.6 moles) is added, with stirring, 40 ml of cone, hydro-chloric acid. The temperature of the reaction system is raised to 40°C. Without delay the addition of ethyl nitrite is initiated and the flow of the reagent is regulated to such a rate that the reaction temperature never exceeds 55°C. About 1.5 hr are required for the addition. The ethanol formed in the reaction, as well as unreacted methyl ethyl ketone, is separated by distillation until the pot temperature just reaches 90°C. The product is separated from the residue by rapid steam distillation. Virtually all of the product will be found in the first 5 liters of the distillate. The distillate is saturated with 1.5 kg of sodium chloride and cooled to 0°C. The product, which precipitates out, is filtered off. If necessary, the pro-duct may be recrystallized from water to afford 500 gm (58%), m.p. 76.5°C.

Air & Water Reactions

Soluble in water.

Reactivity Profile

2,3-Butanedione monoxime may react violently during vacuum distillation above 130 pascals.

Fire Hazard

Flash point data for 2,3-Butanedione monoxime are not available, but 2,3-Butanedione monoxime is probably combustible.

Biological Activity

2,3-butanedione-2-monoxime is a myosin atpase inhibitor.myosin, an atpase, can convert chemical energy into directed movement and is regarded as a molecular motor. myosin has various shapes and sizes. more than 11 myosin classes have been identified, and more will be found. the common feature of all of these molecules is a section close to the n terminus, which can be identified as a motor domain.

Biochem/physiol Actions

DRK1 is a delayed rectifier (Kv2.1) cloned K+ channel from rat brain with consensus sites for protein kinase-dependent phosphorylation that might be expected to be functionally regulated by phosphorylation. 2,3-Butanedione monoxime (BDM) chemically removes phosphate groups from many proteins, and its action on DRK1 channels was examined after expression of DRK1 cRNA in Xenopus oocytes. In two-microelectrode voltage-clamp experiments, the application of 2,3-Butanedione monoxime to the bath inhibited DRK1 current (ki = 16.6 mM, H = 0.96) rapidly and reversibly, with a time course similar to the time course of solution change within the bath. DRK1 current was inhibited at all potentials; the time course of current activation, deactivation and inactivation were unaffected by 2,3-Butanedione monoxime. In inside-out patch-clamp experiments, the application of 2,3-Butanedione monoxime to the cytoplasmic surface similarly inhibited channel activity rapidly and reversibly (ki = 10.7 mM, H = 1.01) in the absence of rephosphorylating substrates. These results are inconsistent with a phosphatase effect, because such an effect should be irreversible in cell-free, ATP-free patches. Instead, the results suggest that 2,3-Butanedione monoxime can inhibit DRK1 channels directly from inside or outside of the membrane.

in vitro

2,3-butanedione-2-monoxime (bdm), a general probe of myosin function, was widely used in muscle research as a low-affinity but specific chemical phosphatase that could reversibly inhibit the myosin cross-bridge cycle. it was found that wild-type cells treated with bdm at 20 mm for around two generation times were smaller than untreated controls and showed a septation index about twice that observed in the absence of the inhibitor. moreover, the organization of actin at the cell poles was disorganized in the presence of bdm, however, cells formed a cytokinetic actin ring. in addition, when nitrogen-starved stationary-phase cells were reinoculated into fresh medium in the presence of bdm, the time taken to repolarize the actin cytoskeleton and to resume the characteristic vegetative cell shape were both delayed substantially [1].

references

[1] may km, wheatley sp, amin v, hyams js. the myosin atpase inhibitor 2,3-butanedione-2-monoxime (bdm) inhibits tip growth and cytokinesis in the fission yeast, schizosaccharomyces pombe. cell motil cytoskeleton. 1998;41(2):117-25.

InChI:InChI=1/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3/b5-3+

Upstream product

• 431-03-8 dimethylglyoxal 
• 78-93-3 butanone 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 100-02-7 4-nitro-phenol 
• 71087-81-5 (E)-mono(O-acetyloxime)-2,3-butanedione 
• 80957-49-9 3-hydroxyomono-2-phenylhydrazonobutane 
• 521267-05-0 (2S)-1-({1-[2-(2-Chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile 
• 521267-04-9 (2S)-1-({1-[2-(3-Chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile 
• 521267-03-8 (2S)1-({1-[2-(4-Fluoro-3-methyl-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile 
• 328918-80-5 4,5-dimethyl-2-(4-bromophenyl)-oxazole oxide 
• 328918-93-0 2-(3-Bromophenyl)-4,5-dimethyloxazole-3-oxide 
• 7063-98-1 3-acetyl-5-phenyl-isoxazole 
• 109544-27-6 2-(4-chlorophenyl)-4,5-dimethyl-1,3-oxazole-3-oxide 
• 521266-99-9 (2S)-1-({2-[2-(4-Fluoro-3-methyl-phenyl)-5-methyl-oxazol-4-yl]-1,1-dimethyl-ethylamino}-acetyl)-pyrrolidine-2-carbonitrile 
• 521267-02-7 (2S)-1-({2-[2-(2-Chloro-phenyl)-5-methyl-oxazol-4-yl]-1,1-dimethyl-ethylamino}-acetyl)-pyrrolidine-2-carbonitrile 
• 773845-35-5 (2S)-1-({2-[2-(3-Chloro-phenyl)-5-methyl-oxazol-4-yl]-1,1-dimethyl-ethylamino}-acetyl)-pyrrolidine-2-carbonitrile 

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Effects of counter cations of base catalysts on nitrosation mechanisms

Reaction of 2-butanone (1) with tert-butyl nitrite (tert-BuONO) was performed using base catalysts (RO-M+: R=CH3, C2H5; M+=Li+, Na+, K+) in alcohols (CH3OH or C2H5OH). In this report, the effects of M+ of RO-M+ on the nitrosation mechanisms were investigated. The yield of E-hydroxyimino compound (5E) increases much better in the reaction using Na+ or K+ as M+ compared with that using Li+. It is also observed that the yield of 5E increases by addition of crown ether as a cation-capturing agent. The experimental results suggested that under the conditions lowering the effects of M+ of RO-M+ on the nitrosation mechanisms, because the reactivity of naked enolate of 1 increases and the reaction in the C-N bond formation process tends to proceed via open-chain transition state without M+, the yield of 5E tends to increase.

Nitrosation of ketone dianions

Nitrosation of α,α'-dianions produced from ketones using a couple of bases was carried out with tert-butyl nitrite(tert-BuONO) in ether, and then two regioisomers of oximes(but notacetone)were obtained simultaneously. The ratio of these regioisomers was remarkably reversed by the addition of hexamethylphosphoric triamide (HMPA).