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Sulfoxide

pharmaceutical raw materials
Sulfoxide structure

Sulfoxide 

structure
  • CAS No:

    120-62-7

  • Formula:

    C18H28O3S

  • Chemical Name:

    Sulfoxide

  • Synonyms:

    1,3-Benzodioxole,5-[2-(octylsulfinyl)propyl]-;Benzene,1,2-(methylenedioxy)-4-[2-(octylsulfinyl)propyl]-;5-[2-(Octylsulfinyl)propyl]-1,3-benzodioxole;1,2-(Methylenedioxy)-4-[2-(octylsulfinyl)propyl]benzene;1-Methyl-2-(3,4-methylenedioxyphenyl)ethyl octyl sulfoxide;Sulfox-cide;Sulfoxide;Isosafrole octyl sulfoxide;Sulfoxide (synergist);Piperonyl sulfoxide;Piperonyl sulfoxide (insecticide);NSC 8400;23715-11-9

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Light yellow viscous oilAn organic compound of general formula RSOR′, where R and R′ are organic radicals. An example is dimethyl sulfoxide, (CH3)2SO, commonly used as a solvent.Clear pale yellow to amber viscous liquid with a sweetish smell.


Piperonyl sulfoxide is a clear pale yellow to amber viscous liquid with a sweetish smell. (NTP, 1992)


Piperonyl sulfoxide is a clear pale yellow to amber viscous liquid with a sweetish smell. (NTP, 1992)|Piperonyl sulfoxide is a member of benzodioxoles.

Sulfoxide Basic Attributes

324.48

324.48

204-412-3

WOR3CS513R

8400

DTXSID1021168

PALE YELLOW, VISCOUS OIL|Brown liquid

2932999014

Characteristics

54.7

5.32120

Piperonyl sulfoxide is a clear pale yellow to amber viscous liquid with a sweetish smell. (NTP, 1992)

1.06-1.09 g/cm3 @ Temp: 25 °C

432.8°C (rough estimate)

greater than 200° F (NTP, 1992)

1.5460 (estimate)

Insoluble in water.

0-6°C

4.24E-09mmHg at 25°C

Oral-Rat LD50: 2000 mg/kg

Combustion produces toxic sulfur oxide gas

SWEET-SMELLING

BROWN LIQUID; DECOMP ON HEATING; DENSITY: 1.06-1.09; INDEX OF REFRACTION: 1.528-1.532 @ 25 °C/D; MILD ODOR /COMMERCIAL MATERIAL/|Vapor pressure is very low at room temp; Practically insol in water; Readily sol or miscible with organic solvents, eg alcohol, acetone, xylene, methylene chloride; In mineral oils 2-2.5%; pale yellow liquid /technical 88%/

Insoluble in water.

Sulfonates, Phosphonates, and Thiophosphonates, Organic

PIPERONYL SULFOXIDE reacts violently with perchloric acid. (NTP, 1992). With strong reducing agents it will produce hydrogen sulfide.

Safety Information

S24/25

F;T;N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable. Combustible. Incompatible with strong oxidizing agents. Reacts violently with perchloric acid.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Bioassay of Piperonyl Sulfoxide for Possible Carcinogenicity (1979) Technical Rpt Series No. 124 DHEW Pub No. (NIH) 79-1379, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014

This chemical is probably combustible. (NTP, 1992)

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (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 material under ambient temperatures. (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: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Toxicity

moderately toxic

...SYNERGIST TO INCR INSECTICIDAL POTENCY OF PYRETHRINS.|OF THE METHYLENEDIOXYPHENYL SYNERGISTS, AT LEAST THE FOLLOWING HAVE BEEN SHOWN TO INCR SLEEPING TIME FOLLOWING ADMIN OF CERTAIN BARBITURATES &/OR TO INHIBIT MAMMALIAN MICROSOMAL ENZYMES: PIPERONYL BUTOXIDE; PIPERONYL CYCLONENE; SULFOXIDE...|PRESUMABLY AS A RESULT OF INHIBITING LIVER ENZYMES, BOTH PIPERONYL BUTOXIDE & SULFOXIDE REDUCED THE RATE AT WHICH RADIOACTIVITY INTRODUCED IN THE FORM OF 7,10-(14)C-BENZPYRENE WAS CLEARED FROM THE BLOOD & EXCRETED IN THE BILE.|WHEN ADMINISTERED ORALLY, INTRAPERITONEALLY OR INTRAVENOUSLY PIPERONYL SULFOXIDE INTERFERRED WITH RAPID ELIMINATION OF INTRAVENOUSLY INJECTED 3,4-BENZPYRENE IN RATS.|For more Interactions (Complete) data for PIPERONYL SULFOXIDE (6 total), please visit the HSDB record page.

LD50 Rat oral 2 g/kg

A bioassay of technical-grade piperonyl sulfoxide for possible carcinogenicity was conducted by administering the test chemical in feed to Fischer 344 rats and B6C3F1 mice. Groups of 50 rats of each sex were administered piperonyl sulfoxide in the diet at one of several doses, either 1,500 or 3,000 ppm for the males and either 3,000 or 6,000 ppm for the females, for 105 weeks. Matched controls consisted of 20 untreated rats of each sex. All surviving rats were killed at the end of the period of administration of the test chemical. Groups of 50 male mice were administered one of two doses, either 350 or 700 ppm, for 104 or 105 weeks. Groups of 50 female mice were initially administered one of two doses, either 700 or 1,400 ppm. Due to excessive weight depression in the dosed female mice, the doses for this sex were reduced after week 20 to 200 and 600 ppm, respectively, and administration of the test chemical at the lower doses was continued for 84 or 85 weeks. The time-weighted average doses for the females were 295 and 754 ppm. Matched controls consisted of 20 untreated mice of each sex. All surviving mice were killed at the end of the period of administration of the test chemical. ... It is concluded that under the conditions of this bioassay, technical-grade piperonyl sulfoxide was not carcinogenic for male or female Fischer 344 rats or for female B6C3F1 mice, but was carcinogenic for male B6C3F1 mice, producing an increased incidence of hepatocellular carcinomas. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Positive; Female Mice: Negative.

Drug Information

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

MAJOR METABOLIC PATHWAY FOR A & B SULFOXIDE DIASTEREOMERS OF 1,2-METHYLENEDIOXY-4-(2-OCTYLSULFINYL PROPYL)BENZENE AFTER ORAL ADMINISTRATION TO MICE INVOLVED THE CLEAVAGE OF THE METHYLENEDIOXYPHENYL (MDP) MOIETY & EXPIRATION OF THE METHYLENE CARBON AS CARBON DIOXIDE. MIXED-FUNCTION OXIDASES OF LIVER MICROSOMES DEMETHYLATED SEVERAL COMPOUNDS CONTAINING THE MDP MOIETY.

Piperonyl butoxide, like other methylenedioxybenzene synergists (eg, sesamex, sulfoxide, n-propyl isome, piperonyl cyclonene, etc), inhibits hepatic microsomal oxidase enzymes in lab rodents & by inference in man; it also inhibits a related group of enzymes in insects apparently by serving as a competitive substrate. Because these enzymes act to detoxify many drugs & other exogenous chemicals, a heavy exposure to one of these insecticidal synergists might make a person temporarily vulnerable to a variety of toxic insults that would normally be tolerated with ease.

SYMPTOMS: Symptoms of exposure to this compound may include tremors, central nervous system depression and prolonged coma 10 to 20 minutes after exposure. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of sulfur 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: DO NOT INDUCE VOMITING. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

1. WASH CONTAMINATING PESTICIDE FROM THE EYE WITH COPIOUS AMOUNTS OF WATER. WASH CONTAMINATED SKIN WITH SOAP & WATER. 2. FOR LIFE-THREATENING ALLERGIC REACTION TO PYRETHRUM (SEVERE ASTHMA OR ANAPHYLAXIS), GIVE 0.1 TO 0.5 ML OF 1:1000 ADRENALIN INTRAMUSCULARLY, OR SLOWLY INTRAVENOUSLY. REPEAT IF NECESSARY TO RELIEVE RESPIRATORY DISTRESS & MAINTAIN BLOOD PRESSURE. INTRAVENOUS AMINOPHYLLINE (10 ML, SLOWLY) MAY BE INDICATED. GIVE HYDROCORTISONE (50-100 MG), OR EQUIVALENT STEROID, INTRAVENOUSLY. LESS SEVERE REACTIONS (RHINITIS) CAN BE MANAGED WITH ANTIHISTAMINES & DECONGESTANTS, GIVEN ORALLY. HYPERSENSITIVITY PNEUMONITIS MAY REQUIRE OXYGEN, STEROIDS, ANTIBIOTICS & SEVERAL DAYS BEDREST, DEPENDING ON SEVERITY. /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/|3. INGESTION OF SMALL AMOUNT OF PYRETHRIN OR PYRETHROID FORMULATION IS NOT LIKELY TO CAUSE POISONING. EXAMINE LABEL TO IDENTIFY ADDITIONAL INSECTICIDES, WHICH MAY BE MORE TOXIC. BASE TREATMENT ON THE MOST TOXIC INGREDIENTS. A. IF FORMULATION CONTAINS ONLY PYRETHRINS, OR PYRETHROIDS, & SYNERGISTS, INGESTION OF A SMALL AMOUNT (UP TO ABOUT 5 MG/KG) IS PROBABLY BEST TREATED BY LARGE DOSES OF ACTIVATED CHARCOAL.../PRC: 30 G IN 3-4 OZ OF WATER (CHILDREN), 100 G IN 8-10 OZ OF WATER (ADULTS)/, FOLLOWED BY CATHARTIC DOSES OF SODIUM OR MAGNESIUM SULFATE, 0.25 G/KG BODY WEIGHT IN 1-6 OZ WATER. /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/|4. IF LARGE AMOUNTS OF PYRETHRIN OR PYRETHROIDS FORMULATION HAVE BEEN INGESTED, THE STOMACH & INTESTINE MUST BE EVACUATED: A. IF VICTIM IS ALERT & RESPIRATION IS NOT DEPRESSED, GIVE SYRUP OF IPECAC, FOLLOWED BY 1-2 GLASSES OF WATER, TO INDUCE VOMITING (ADULTS & CHILDREN 12 YEARS & OLDER: 30 ML; CHILDREN UNDER 12 YEARS: 15 ML). CAUTION: OBSERVE VICTIM CLOSELY AFTER ADMINISTERING IPECAC. IF CONSCIOUSNESS LEVEL DECLINES OR VOMITING HAS NOT OCCURRED IN 15 MINUTES, INTUBATE THE STOMACH IMMEDIATELY. FOLLOWING EMESIS, HAVE VICTIM DRINK SUSPENSION OF...ACTIVATED CHARCOAL /PRC: 30 G IN 3-4 OZ OF WATER (CHILDREN), 100 G IN 8-10 OZ OF WATER (ADULTS)/ TO LIMIT ABSORPTION OF TOXICANT REMAINING IN THE GUT. /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/|B. IF VICTIM...NOT FULLY ALERT, EMPTY STOMACH IMMEDIATELY BY INTUBATION, ASPIRATION, & LAVAGE /PRC: WATER IN CHILDREN & SALINE IN ADULTS/... BECAUSE MANY PESTICIDES ARE DISSOLVED IN PETROLEUM DISTILLATES, EMESIS & INTUBATION OF THE STOMACH INVOLVE RISK THAT SOLVENT WILL BE ASPIRATED, LEADING TO CHEMICAL PNEUMONITIS. FOR THIS REASON: (A) IF VICTIM IS UNCONSCIOUS OR OBTUNDED & FACILITIES ARE AT HAND, INSERT AN ENDOTRACHEAL TUBE (CUFFED, IF AVAILABLE) PRIOR TO GASTRIC INTUBATION. (B) KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING INTUBATION & LAVAGE /PRC: WATER IN CHILDREN & SALINE IN ADULTS/ (TRENDELENBURG, OR LEFT LATERAL DECUBITUS, WITH HEAD OF TABLE TIPPED DOWNWARD). KEEP VICTIM'S HEAD TURNED TO LEFT. (C) ASPIRATE PHARYNX AS REGULARLY AS POSSIBLE TO REMOVE GAGGED OR VOMITED STOMACH CONTENTS. (D) AFTER ASPIRATION OF GASTRIC CONTENTS & WASHING OF STOMACH, INSTILL...ACTIVATED CHARCOAL.../PRC: 30 G IN 3-4 OZ OF WATER (CHILDREN), 100 G IN 8-10 OZ OF WATER (ADULTS)/ THROUGH STOMACH TUBE TO LIMIT ABSORPTION... (E) IF BOWEL MOVEMENT HAS NOT OCCURRED IN 4 HR & PATIENT IS FULLY CONSCIOUS, GIVE SODIUM OR MAGNESIUM SULFATE AS CATHARTIC... /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/|5. DO NOT ADMINSTER OR INSTILL MILK, CREAM, OR OTHER SUBSTANCES CONTAINING VEGETABLE OR ANIMAL FATS, WHICH ENHANCE ABSORPTION OF LIPOPHILIC SUBSTANCES, SUCH AS PYRETHRINS & PYRETHROIDS. 6. DIAZEPAM...5-10 MG IN ADULTS, 0.1 MG/KG IN CHILDREN, GIVEN ORALLY OR SLOWLY IV, SHOULD CONTROL NERVOUSNESS & TREMORS IN RARE CASES HAVING SYMPTOMS AFTER EXTRAORDINARY EXPOSURE TO PYRETHRINS & PYRETHROIDS. /PYRETHRUM, PYRETHRINS, PYRETHROIDS, & PIPERONYL BUTOXIDE/

BECAUSE PIPERONYL BUTOXIDE & SULFOXIDE INHIBIT THE METABOLISM OF BENZPYRENE & BECAUSE OF THEIR CLOSE CHEMICAL SIMILARITY TO SESAMOL & SAFROLE, ALL METHYLENEDIOXYPHENYL SYNERGISTS ARE SUSPECT AS LIVER TUMORIGENS.

1,2-(methylenedioxy)-4-(2-(octylsulfinyl)propyl)benzene

Sulfoxide Use and Manufacturing

Methods of Manufacturing

BY ADDITION OF N-OCTYL MERCAPTAN TO ISOSAFROLE; THIOETHER SO FORMED DISTILS AT 183-186 °C/1 MM. THE THIOETHER IS OXIDIZED BY THE ADDITION OF HYDROGEN PEROXIDE TO AN ACETONE SOLUTION; ACETONE & WATER BEING REMOVED BY DISTILLATION IN VACUO.

Uses

Insecticide.

Production

(1978) NOT PRODUCED COMMERCIALLY IN US

USED IN CONJUCTION WITH PYRETHRINS FOR AEROSOL PREPARATIONS, GENERALLY AT 1% WITH 0.2% PYRETHRINS OR ALLETHRIN. PRO-NOXFISH--2.5% ROTENONE & 2.5% SULFOXIDE.

/SYNERGISTIC PROPERTIES DISCOVERED BY/ SYNERHOLM ET AL, CONTRIBS BOYCE THOMPSON INST 15, 35 (1947); SYNERHOLM, US PATENT 2,486,579 (1949 TO BOYCE THOMPSON INST FOR PLANT RES).|SULFOXIDE: PRODUCT DISCONTINUED BY PENICK CORP.|OF SLIGHT INSECTICIDAL PROPERTIES BUT MAINLY USED AS SYNERGIST FOR PYRETHRINS, ALLETHRIN WITH ROTENONE AS FISH TOXICANT.

STEAM DISTIL & MAKE TO 5-6 MG SULFOXIDE/100 ML ALCOHOL. READ OPTICAL DENSITY AT 288 NM. (WHO/INSECT/30 REV, P 170, 1955). SEPARATE BY COLUMN CHROMATOGRAPHY ON SILICIC ACID (3 ELUTING SOLUTIONS) SULFOXIDE IS REMOVED IN THE LAST ELUATE & DETERMINED BY UV SPECTROPHOTOMETRY. HAUS, JB ET AL, J ASSOC OFF AGRIC CHEM, 48, 569, 1965. (SEE ALSO HAUS, JB ET AL, J ASSOC OFF AGRIC CHEM, 47, 265, 1964).|GLC, TLC, GLC/MASS SPECTROMETRIC PROCEDURES FOR DETERMINING METHYLENEDIOXYPHENYL INSECTICIDE SYNERGISTS ARE DISCUSSED.|BASED ON THE FLUORESCENT PROPERTIES, A PROCEDURE WAS DEVISED FOR DETERMINING PIPERONYL SULFOXIDE IN RICE, FLOUR, & CORNMEAL.|Method 8270A-S,8270A-W. Semivolatile Organic compounds by Gas Chromatography/Mass Spectrometry (GC/MS): Capillary Column Technique. Capillary Gas Chromatography Mass Spectroscopy; Detection Limit = 100 ug/L (Water).

Computed Properties

Molecular Weight:324.5
XLogP3:4.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:10
Exact Mass:324.17591592
Monoisotopic Mass:324.17591592
Topological Polar Surface Area:54.7
Heavy Atom Count:22
Complexity:334
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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