| Identification | More | [Name]
2,3-Butanedione monoxime | [CAS]
57-71-6 | [Synonyms]
2,3-BUTANEDIONE 2-MONOXIME
2,3-BUTANEDIONE 2-OXIME
2,3-BUTANEDIONE, MONO-OXIME
2,3-BUTANEDIONE MONOXIME
2,3-BUTANEDIONE OXIME
BDM
BIACETYL MONOOXIME
BIACETYL MONOXIME
DAM
DIACETYL MONOOXIME
DIACETYL MONOXIME
ISONITROSOETHYL METHYL KETONE
(2E)-2,3-Butanedione 2-oxime
,3-Butanedione monooxime
2,3-Butanedione 3-monoxime
2-oxime2,3-butanedione
2-Oximino-3-Butanone
3-Oximino-2-butanone
iso-Nitroethylmethylketone
iso-Nitromethylethylketone | [EINECS(EC#)]
200-348-5 | [Molecular Formula]
C4H7NO2 | [MDL Number]
MFCD00002116 | [Molecular Weight]
101.1 | [MOL File]
57-71-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystals | [Melting point ]
75-78 °C(lit.)
| [Boiling point ]
185-186 °C(lit.)
| [density ]
1.2085 (rough estimate) | [refractive index ]
1.4340 (estimate) | [Fp ]
185-186°C | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
9.32±0.10(Predicted) | [color ]
White to almost white | [Odor]
Odorless | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
5 g/100 mL (20 ºC) | [Sensitive ]
Hygroscopic | [BRN ]
605582 | [InChIKey]
FSEUPUDHEBLWJY-HWKANZROSA-N | [CAS DataBase Reference]
57-71-6(CAS DataBase Reference) | [NIST Chemistry Reference]
2,3-Butanedione, monooxime(57-71-6) | [EPA Substance Registry System]
57-71-6(EPA Substance) |
| Questions And Answer(Q&A) | Back Directory | [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, hydrochloric 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 product may be recrystallized from water to afford 500 gm (58%), m.p. 76.5°C.
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| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
EK3150000
| [TSCA ]
Yes | [HS Code ]
29280090 | [Toxicity]
LD50 ipr-mus: 51 mg/kg JPMSAE 53,1143,64 |
| Hazard Information | Back Directory | [General Description]
Cream-colored powder. | [Reactivity Profile]
2-OXIME 2,3-BUTANEDIONE(57-71-6) may react violently during vacuum distillation above 130 pascals. | [Air & Water Reactions]
Soluble in water. | [Fire Hazard]
Flash point data for this chemical are not available, but 2-OXIME 2,3-BUTANEDIONE is probably combustible. | [Chemical Properties]
white crystals | [Uses]
2,3-Butanedione monoxime is a reversible inhibitor of myosin ATPase. It is also used as a reagent for colorimetric determination of urea. | [Definition]
ChEBI: Diacetylmonoxime is a ketoxime obtained via formal condensation of butane-2,3-dione with hydroxylamine. It is a reversible myosin ATPase inhibitor. It has a role as a cholinesterase reactivator, a chromogenic compound and an EC 3.6.1.3 (adenosinetriphosphatase) inhibitor. | [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. | [Safety Profile]
Poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx. | [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]. | [storage]
Store at -20°C | [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. |
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