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Diacetylmonoxime is an important organic compound. Its molecular formula is C4H7NO2, molecular weight is 101.1, CAS number is 57-71-6, EINECS number is 200-348-5, and it is a white to light yellow crystalline powder. Slightly soluble in water, but easily soluble in organic solvents such as ethanol, ether, and chloroform. This property allows the compound to be dissolved, extracted, and separated in the laboratory by selecting appropriate solvents. It also has some special physical phenomena and effects. For example, the compound can exhibit fluorescence under specific conditions, which makes it potentially valuable in fields such as fluorescence analysis, biomarkers, and optical materials. At the same time, it can also undergo special chemical reaction types such as complexation or coordination reactions with other substances, which are of great significance for understanding the chemical properties of substances, preparing new compounds, and developing new application fields.

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Chemical Formula |
C4H7NO2 |
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Exact Mass |
101 |
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Molecular Weight |
101 |
|
m/z |
101 (100.0%), 102 (4.3%) |
|
Elemental Analysis |
C, 47.52; H, 6.98; N, 13.85; O, 31.65 |
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|

Diacetylmonoxime (CAS number: 57-71-6) is an important organic compound with unique chemical properties, which makes it widely applied in various fields. The following elaborates on its specific applications from four aspects: analytical chemistry, pharmaceutical field, biological research, and industrial applications.
Applications in Analytical Chemistry
Diacetylmonoxime is mainly used as a color developer and chelating agent in analytical chemistry. Its core value lies in forming stable complexes with specific metal ions, thereby enabling qualitative or quantitative detection.

Metal ion detection
Diacetylmonoxime can form pale yellow to orange complexes with transition metal ions such as nickel ions (Ni²⁺), cobalt ions (Co²⁺), and palladium ions (Pd²⁺). These complexes have high solubility in organic solvents (such as trichloromethane) and can be separated and enriched by extraction methods. For example, in the detection of nickel ions, the complex formed by diacetylmonoxime and Ni²⁺ has a strong absorption peak at a specific wavelength, and can be precisely determined by spectrophotometry for nickel content.
Urea and carbamate determination
Diacetylmonoxime is a classic reagent for spectrophotometric determination of urea and carbamate compounds. Under acidic conditions, urea reacts with diacetylmonoxime to form a red complex, and its absorbance is proportional to the concentration of urea. This method is highly sensitive and simple to operate, and is widely used in clinical urine analysis, agricultural soil nitrogen content detection, and industrial wastewater treatment, etc.

Applications in the pharmaceutical field
The application of diacetylmonoxime in the pharmaceutical field is mainly based on its regulatory effect on biological enzyme activity, especially in myocardial protection and neurotoxin detoxification.
Myocardial protectant
Diacetyl orthoformate is a non-competitive inhibitor of myosin ATPase, which can reduce myocardial oxygen consumption by inhibiting the activity of myocardial contractile proteins. In cardiac surgery, the perfusate containing diacetyl orthoformate can significantly prolong the myocardial tolerance to ischemia and reduce postoperative complications. Its mechanism of action includes:
Inhibiting the activity of L-type calcium channels, reducing calcium ion influx;
Inducing the release of calcium ions from the sarcoplasmic reticulum, reducing the risk of intracellular calcium overload;
Inhibiting the activity of myosin light chain kinase (MLCK), blocking the transmission of contraction signals.
Neurotoxin antidote
Early studies have shown that diacetyl orthoformate has an antagonistic effect on organophosphorus nerve agent poisoning such as sarin. Its detoxification mechanism may involve:
Activating plasma carboxylesterase (CarbE) to accelerate the clearance of toxic agent metabolites;
Inhibiting irreversible inhibition of acetylcholinesterase (AChE), restoring the balance of neurotransmitters.
Although subsequent studies have raised doubts about the detoxification effect of diacetyl orthoformate, its exploration as a potential antidote provides new ideas for nerve agent protection.
Applications in the field of biological research
Diacetyl orthoformate is an important tool compound in biological research, mainly used for studying cell signal transduction and ion channel functions.
Calcium Signal Regulation Research
Diacetylone can induce the release of calcium ions from the sarcoplasmic reticulum, and this property makes it an ideal model for studying intracellular calcium signal regulation. For example, in the study of cardiac muscle cells, diacetylone is used to simulate the calcium overload state and explore the relationship between abnormal calcium signals and diseases such as arrhythmia and heart failure.


Analysis of Ion Channel Function
Diacetylone has concentration-dependent inhibitory effects on L-type calcium channels and sodium channels, and the electrical physiological characteristics of ion channels can be studied by regulating the extracellular concentration of diacetylone. Moreover, its inhibitory effect is reversible, making it suitable for dynamic monitoring of changes in channel activity.
Research on Cell Contraction Mechanism
As an inhibitor of skeletal muscle and cardiac muscle contraction, diacetylone is widely used to study the interaction between myosin and actin and the regulatory mechanism of contraction. For example, in in vitro muscle fiber experiments, diacetylone can block the ATPase activity of contraction proteins, thereby separating the relationship between contraction signal transduction and energy metabolism.

Industrial Applications
The application of diacetylone in the industrial field mainly focuses on the preparation of highly toxic disinfectants and organic synthesis intermediates.

Disinfectant raw materials
The sodium or potassium salt of diacetylone is the main active ingredient of the new type of skin disinfectant. This type of disinfectant has the advantages of being non-toxic, non-irritating, and easy to store, and can effectively kill various pathogenic microorganisms, suitable for disinfection needs in medical, food processing, and public places.
Organic synthesis intermediates
Diacetylone is a key intermediate for the synthesis of various complex organic compounds. For example, it can be reduced to diacetylone alcohol through a reduction reaction, which can be further used to prepare drug molecules or functional materials. In addition, the oxime group structure of diacetylone can participate in ring formation reactions to construct heterocyclic compounds with specific biological activities.


Diacetylmonoxime (a type of organic compound) has the chemical formula C₄H₇NO₂ and a molecular weight of approximately 101.10. It exhibits stable chemical properties and unique reactivity. The following provides an explanation from four aspects: physical properties, solubility, chemical reactivity, and thermal stability.
Physical Properties
Diacetylone is a white to pale yellow crystalline powder with a melting point range of 74°C to 78°C. Its boiling point is approximately 185-186°C. Its density is about 1.1 g/cm³ and it has a definite crystal structure, existing in a solid state at room temperature. During storage, this substance should be protected from high temperatures and direct sunlight to prevent physical changes or decomposition. Its crystalline form and melting point characteristics enable it to serve as a characteristic identifier in qualitative analysis. For example, the melting point determination can be used to preliminarily determine the purity of the sample.
Solubility
The solubility of 2,6-diaminohexanedione shows significant polarity differences:
Slightly soluble in water
The solubility in water at 20℃ is approximately 5 g/100 mL. This property limits its direct application in aqueous-phase reactions, but it can be improved by adjusting the pH or adding solubilizers.

Easy to dissolve in organic solvents
It can be completely dissolved in common organic solvents such as ethanol, ether, and chloroform, especially in ethanol where the solubility is significant. This property makes it convenient for it to participate in reactions as a reactant or intermediate in organic synthesis, for example, through recrystallization purification using ethanol solutions.

Solvent selection affects the reaction pathway
In different solvents, the molecular conformation and reactivity of diacetylmonoxime may change. For instance, in polar solvents, it may be more prone to form hydrogen bonds, thereby affecting its coordination ability with metal ions.

Chemical Reactivity
The core reactivity of diacetylmonoxime is manifested in the following aspects:
Coordination with metal ions
Diacetyl oxime is an effective chelating agent for transition metal ions such as nickel (Ni²⁺), cobalt (Co²⁺), and palladium (Pd²⁺). The oxime group (-C=NOH) in its molecule can provide lone pairs of electrons, forming stable five-membered ring complexes with the metal ions. The complexes usually present a pale yellow to orange color and are easily extracted by chloroform. This property makes it a key reagent for photometric detection of metal ions, for example, quantitative analysis can be achieved by measuring the absorbance of the nickel-diacetyl oxime complex.
Reactivity of the oxime group
The oxime group can participate in various organic reactions, such as reduction to form amine compounds, or reaction with acyl reagents to form oxime ethers. Additionally, in acidic conditions, diacetyl oxime can undergo a condensation reaction with urea to form a red dione derivative, which is the basis for photometric determination of urea.
As an organic synthesis intermediate
Diacetyl oxime can be reduced to diacetyl oxime alcohol, which can be further used for the synthesis of drug molecules or functional materials. Its oxime structure can also participate in ring formation reactions to construct heterocyclic compounds with specific biological activity.
Thermal stability
Diacetyl oxime is chemically stable at room temperature, but it may decompose under high-temperature conditions:
Stable below boiling point
In an environment below 185℃, its crystal structure and reactivity remain unchanged, making it suitable for long-term storage and transportation.


Risk of high-temperature decomposition
When the temperature approaches or exceeds the boiling point, diacetylmonoxime may decompose to form small volatile substances, resulting in quality loss or an increase in reaction by-products. Therefore, during high-temperature operations (such as distillation for purification), the temperature and time must be strictly controlled.
Thermal stability application
Its thermal stability makes it a stable ligand for certain high-temperature reactions, such as serving as an extractant for metal ions in high-temperature molten salt systems.

FAQ
1. What are the basic details of diacetyl orthoformate?
Diacetylmonoxime is an important ketoxime compound with the CAS number 57-71-6 and the molecular formula C₄H₇NO₂, having a molecular weight of approximately 101.10 g/mol. It usually appears as a white to light green or light orange crystalline powder.
2. What are its main purposes?
This compound has important applications in multiple fields:
- Analytical Chemistry: It is a commonly used chromogenic agent, and its most classic application is for the detection and quantification of urea, and it can also be used to determine metal ions such as nickel, cobalt, and palladium.
- Biochemical Research: As a myosin ATPase inhibitor, it is widely used in basic research in muscle physiology and cell biology.
- Organic Synthesis: As an intermediate, it is used to prepare other more complex compounds.
- Other Industrial Applications: It can also be used as a crosslinking agent in polymer materials and a dyeing aid for textiles.
3. What should be noted when storing?
To ensure its stability, diacetylone should be stored in a sealed and dry environment and placed in a cool and dark place. The recommended storage temperature is 2-8°C. During operation, it should be avoided from coming into contact with strong oxidants.
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