ChemicalBook > CAS DataBase List > 2,3-Butanedione monoxime

2,3-Butanedione monoxime

Product Name
2,3-Butanedione monoxime
CAS No.
57-71-6
Chemical Name
2,3-Butanedione monoxime
Synonyms
DAM;BDM;DIACETYL MONOXIME;3-(Hydroxyimino)butan-2-one;NSC 660;NSC 116103;BIACETYL MONOXIME;Diacety1monoxime;Biacethylmonoxime;DIACETYL MONOOXIME
CBNumber
CB2488015
Molecular Formula
C4H7NO2
Formula Weight
101.1
MOL File
57-71-6.mol
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2,3-Butanedione monoxime Property

Melting point:
75-78 °C(lit.)
Boiling point:
185-186 °C(lit.)
Density 
1.2085 (rough estimate)
refractive index 
1.4340 (estimate)
Flash point:
185-186°C
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
9.32±0.10(Predicted)
form 
Crystalline Powder
color 
White to almost white
Odor
Odorless
Water Solubility 
5 g/100 mL (20 ºC)
Sensitive 
Hygroscopic
BRN 
605582
Stability:
Stable. Incompatible with strong oxidizing agents.
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
Diacetyl monooxime (57-71-6)
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Safety

Hazard Codes 
Xn
Risk Statements 
36/37/38-20/21/22
Safety Statements 
22-24/25-36/37/39-26
WGK Germany 
3
RTECS 
EK3150000
TSCA 
Yes
HS Code 
29280090
Toxicity
LD50 ipr-mus: 51 mg/kg JPMSAE 53,1143,64
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
31550
Product name
2,3-Butanedione monoxime
Purity
for spectrophotometric det. of urea, ≥99.0%
Packaging
25g
Price
$71
Updated
2024/03/01
Sigma-Aldrich
Product number
203984
Product name
2,3-Butanedione 2-Monoxime
Purity
An inhibitor of skeletal and cardiac muscle contraction.
Packaging
500mg
Price
$56.2
Updated
2024/03/01
TCI Chemical
Product number
B0683
Product name
Diacetyl Monoxime
Purity
>98.0%(GC)
Packaging
25g
Price
$69
Updated
2024/03/01
TCI Chemical
Product number
B0683
Product name
Diacetyl Monoxime
Purity
>98.0%(GC)
Packaging
100g
Price
$148
Updated
2024/03/01
Alfa Aesar
Product number
A14339
Product name
2,3-Butanedione monoxime, 99%
Packaging
100g
Price
$73.1
Updated
2024/03/01
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2,3-Butanedione monoxime Chemical Properties,Usage,Production

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.

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.

General Description

Cream-colored powder.

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.

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].

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.

2,3-Butanedione monoxime Preparation Products And Raw materials

Raw materials

2-Butanone Ethyl nitrite

Preparation Products

Dimethylglyoxime
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2,3-Butanedione monoxime Suppliers

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View Lastest Price from 2,3-Butanedione monoxime manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
2,3-Butanedione monoxime 57-71-6
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 mt
Release date
2024-11-25
Shanxi Naipu Import and Export Co.,Ltd
Product
2,3-Butanedione monoxime 57-71-6
Price
US $10.00/ASSAYS
Min. Order
1ASSAYS
Purity
99%
Supply Ability
500tons/month
Release date
2021-09-22
Career Henan Chemical Co
Product
2,3-Butanedione monoxime 57-71-6
Price
US $1.00/KG
Min. Order
1G
Purity
98%
Supply Ability
100KG
Release date
2018-08-17

57-71-6, 2,3-Butanedione monoximeRelated Search:

2,3-Butanedione 2-Butanone oxime Tralkoxydim (Diacetoxyiodo)benzene Acetylcholine 2,6-Diacetylpyridine ISOBUTANE DIACETAMIDE Acetylspiramycin Acetaminophen Acetone oxime 4-Ethylacetophenone n-Butane 3-Pentanone Dimethylglyoxime 2-Butanone ETHYL 2-(HYDROXYIMINO)-3-OXOBUTANOATE (1S,E)-(-)-Camphorquinone 3-oxime

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