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Home > Encyclopedia > Propanal, 2-methyl-2-(methylthio)-, oxime

Propanal, 2-methyl-2-(methylthio)-, oxime

Propanal, 2-methyl-2-(methylthio)-, oxime structure

Propanal, 2-methyl-2-(methylthio)-, oxime 

structure
  • CAS No:

    1646-75-9

  • Formula:

    C5H11NOS

  • Chemical Name:

    Propanal, 2-methyl-2-(methylthio)-, oxime

  • Synonyms:

    Propanal,2-methyl-2-(methylthio)-,oxime;Propionaldehyde,2-methyl-2-(methylthio)-,oxime;2-Methyl-2-(methylthio)propionaldoxime;Aldicarb oxime;Temik oxime;2-(Methylthio)-2-methylpropionaldehyde oxime;2-Methyl-2-(methylthio)propionaldehyde oxime;2-Methyl-2-(methylthio)propanal oxime;2-Methyl-2-methylsulfanyl-propionaldehyde oxime

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

ChEBI: The oxime resulting from the formal condensation of 2-methyl-2-(methylsulfanyl)propanal with hydroxylamine. Addition of the oxime group to methyl isocyanate forms the final step in the synthesis of the systemic insecticide aldicarb.Clear colorless,viscous liquid with an unpleasant sulfurous or musty odor.


Aldicarb oxime appears as clear colorless,viscous liquid with an unpleasant sulfurous or musty odor. (NTP, 1992)


Aldicarb oxime appears as clear colorless,viscous liquid with an unpleasant sulfurous or musty odor. (NTP, 1992)

Propanal, 2-methyl-2-(methylthio)-, oxime Basic Attributes

133.21

133.21

216-709-5

DTXSID9024431

2930909090

Characteristics

57.9

1.58800

1.05 (NTP, 1992)

70° F (NTP, 1992)

78-81 °C @ Press: 5 Torr

244.4° F (NTP, 1992)

1.5216 (estimate)

10 to 50 mg/mL at 68° F (NTP, 1992)

0-6°C

less than 0.1 mm Hg at 68° F (NTP, 1992)

4.6 (estimated) (NTP, 1992) (Relative to Air)

Sensitive to heat. Water soluble. May decompose with prolonged exposure to moisture.

Sulfides, Organic

Peroxidizable Compound

ALDICARB OXIME is incompatible with oxidizers, acids and alkalis [(NTP, 1992]. Several explosions or violent decompositions have occurred during distillation of alkoxides, which may be attributable to the formation of peroxides of various types. This is especially the case in the presence of acid, Chem. Eng. News, 1974, 52(35), 3. A nickel catalyzed aldoxime rearrangement to an amide, went out of control after changing the solvent employed, J. Loss Prev., 1993, 6(2), 69.

545 °F (NTP, 1992)

Safety Information

This chemical is combustible. (NTP, 1992)

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and protect it from moisture. If possible, it would be prudent to store this compound under inert atmosphere. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor and high efficiency particulate filter cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. (NTP, 1992)

Toxicity

... Aldicarb oxime ... was recommended for immunotoxicological evaluation /using female B6C3F1 mice/. Aldicarb oxime was administered by gavage at doses of 1, 7.5 or 15 mg/kg daily for 14 consecutive days. The highest dose was the maximum tolerated dose. Doses of 20 mg/kg or higher produced major central nervous system effects and lethality. ... Aldicarb oxime produced no overt pharmacotoxicological signs. There was no alteration in body weight or body weight gain, and no change in weight, gross or histopathology of the liver, spleen, lungs, thymus, kidneys or brain. The hematological parameters measured were not affected. The changes observed in the serum chemistries were minimal and not considered biologically meaningful. There was a slight increase in bone marrow cellularity. This increase was accompanied by an increase in the CFU-GM stem cells, based on a trend analysis, but no exposure group reached statistical significance. In summary, aldicarb oxime, administered in doses between 1 and 15 mg/kg by gavage, produced no detectable adverse effects on basic toxicological parameters. ... Aldicarb oxime produced no changes in the number or function of T cells which are considered biologically meaningful. T cell responses to mitogens (Con A and PHA) and allogeneic cells (MLR) were all unaffected by exposure to aldicarb oxime. The slight change (7%) in the CTL response is not considered a biologically meaningful change. The slight decrease in B cells (7%) does not translate into functional changes as measured by proliferative response to mitogen stimulation or F(ab') receptor driven proliferation or in the spleen antibody-forming cell response to the T-dependent antigen sheep erythrocytes. With respect to innate immunity, natural killer cell function and peritoneal macrophage number and functions were unaffected by aldicarb oxime exposure. ... Streptococcus pneumoniae, Listeria monocytogenes, and the B16F10 pulmonary metastatic melanoma models were all unaffected by exposure to aldicarb oxime. In summary, aldicarb oxime, in doses below those that produced major central nervous system action, administered daily for 14 days, did not alter any of the toxicological, immunological or host resistance parameters measured.

Drug Information

ORAL ADMIN OF ALDICARB TO RATS RESULTED IN 80 % OF THE DOSE BEING ELIMINATED IN URINE WITHIN 24 HR. AN ADDITIONAL 4 % WAS DETECTED IN FECES. ONLY A TRACE AMOUNT OF ALDICARB ITSELF WAS FOUND IN THE EXCRETA, INDICATING A VERY RAPID DEGRADATION WITHIN THE ANIMALS. THE ALDICARB METABOLITES ISOLATED FROM THE URINE INCLUDED ALDICARB OXIME.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and respiratory tract, central nervous system effects, kidney and hematological disorders, and corneal damage on eye contact. ACUTE/CHRONIC HAZARDS: This compound may cause irritation of the skin, eyes and respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide and nitrogen oxides. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Propanal, 2-methyl-2-(methylthio)-, oxime Use and Manufacturing

Methods of Manufacturing

It is prepared by the reaction of 2-chloro-2-methyl-propionaldehyde oxime dimer and sodium methyl mercaptan in the synthesis kettle, adding industrial ethanol, then adding 20% ​​sodium methyl mercaptan, heating to 45 ℃, at a certain temperature Put 60$ dimer in the temperature range and keep the temperature for 30 min. Use a vacuum pump to lift the reaction material into the ethanol-removing kettle, dilute ethanol is evaporated under a vacuum of 46-60 kPa, when the liquid temperature reaches 85°C and the temperature is 75°C, stop heating, and cool the cold water. Use a vacuum pump to lift the materials into the glass-lined neutralization kettle, add hydrochloric acid dropwise to neutralize when the liquid temperature is lower than 45℃, adjust pH=5~6, let stand and separate, put the oil layer in the detoluene kettle, and the water layer Put it in the extraction kettle, extract with toluene, put the toluene layer in the detoluene kettle, remove the toluene under a vacuum of 46-60 kPa, reduce the temperature, and put the product in the propionaldoxime storage tank. Isobutyraldehyde method 2-Chloro-2-methylpropanal was dropped into equimolar sodium methyl mercaptan under agitation. The reaction was carried out in an aqueous solution. After the addition, the water layer was separated and the oil layer was distilled to obtain 2-methyl 2-methylthiopropionaldehyde is a colorless liquid with a boiling point of 140-144°C and a yield of 84.9%-95.2%. Use 2-methyl-2-methylthiopropionaldehyde and 0.5mol hydroxylamine sulfate to react with stirring at 80°C for 1h. The reaction is carried out in an aqueous solution. After the reaction is completed, it is cooled, the water layer is separated, and the oil layer is distilled under reduced pressure to obtain 2-methyl 2-methylthiopropionaldoxime is a colorless liquid with a boiling point of 76-78°C/800Pa and a yield of 83.0%-90.1%. The isobutylene method reacts isobutylene and nitrosyl chloride in dichloromethane at a material ratio of 1.1:1.0 at a temperature of -5 to 0°C. After removing the solvent, a dimer with a yield of 66% is obtained. The melting point is 104 to 105. ℃. Dissolve the dimer in hot sodium ethoxide ethanol solution, reflux for 5 hours, remove the solvent and distill it twice to obtain a colorless oily propionaldoxime.

Uses

2-Methyl-2-(methylthio) propionaldehyde oxime is abbreviated as propionaldehyde oxime. It is an important intermediate for the synthesis of carbamate insecticide aldicarb, and it can also be used to manufacture medical drugs. Nematodes.

Production

(1986) No Data

Propanal, 2-methyl-2-(methylthio)-, oxime: ACTIVE|AN ALDICARB FORMULATION IS PREPARED BY REACTING METHYL ISOCYANATE WITH ALDICARB OXIME, USING ME3-N CATALYST, IN THE PRESENCE OF CORN COB GRITS, & A VINYL RESIN BINDER.|/Prior to May 1985, Union Carbide Corp/ produced aldicarb in the U.S. at Woodbine, Georgia with MIC shipped from Institute /West Virginia/ and aldicarb oxime, which Carbide buys from Allied Corp. Under the new system, aldicarb in solution is shipped by Carbide from Institute to Woodbine, where it is formulated into Temik

DETERMINATION OF ALDICARB OXIME IN WATER BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY/MASS SPECTROMETRY.

Computed Properties

Molecular Weight:133.21
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:133.05613515
Monoisotopic Mass:133.05613515
Topological Polar Surface Area:57.9
Heavy Atom Count:8
Complexity:90.4
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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