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Home > Encyclopedia > 2-Pentenedioic acid, 3-[(dimethoxyphosphinyl)oxy]-, 1,5-dimethyl ester

2-Pentenedioic acid, 3-[(dimethoxyphosphinyl)oxy]-, 1,5-dimethyl ester

2-Pentenedioic acid, 3-[(dimethoxyphosphinyl)oxy]-, 1,5-dimethyl ester structure

2-Pentenedioic acid, 3-[(dimethoxyphosphinyl)oxy]-, 1,5-dimethyl ester 

structure
  • CAS No:

    122-10-1

  • Formula:

    C9H15O8P

  • Chemical Name:

    2-Pentenedioic acid, 3-[(dimethoxyphosphinyl)oxy]-, 1,5-dimethyl ester

  • Synonyms:

    2-Pentenedioic acid,3-[(dimethoxyphosphinyl)oxy]-,1,5-dimethyl ester;Glutaconic acid,3-hydroxy-,dimethyl ester,dimethyl phosphate;2-Pentenedioic acid,3-[(dimethoxyphosphinyl)oxy]-,dimethyl ester;Phosphoric acid,dimethyl ester,ester with dimethyl 3-hydroxyglutaconate;GC 3707;ENT 24,833;Bomyl;Dimethyl-1,3-di(carbomethoxy)-1-propen-2-yl phosphate;Dimethyl 3-hydroxyglutaconate dimethyl phosphate;General Chemicals 3707

2-Pentenedioic acid, 3-[(dimethoxyphosphinyl)oxy]-, 1,5-dimethyl ester Basic Attributes

282.18400

282.18

DTXSID3041875

LIQUID|YELLOW OIL

2931900090

Characteristics

107.17000

1.02390

1.2 g/cm3

<25 °C

155-164 °C @ Press: 17 Torr

166.8ºC

1.45

MISCIBLE WITH METHANOL, ETHANOL, ACETONE, XYLENE; PRACTICALLY INSOL IN WATER, PETROLEUM ETHER, KEROSENE

Keep cool and dry.

25 MM HG @ 25 °C

It exists as two geometric isomers which, in contrast to other vinyl phosphates, have similar insecticidal and anticholinesterase properties.

CORROSIVE TO IRON, STEEL, & BRASS

Safety Information

II

6.1(a)

3018

R36/37/38:Irritating to eyes, respiratory system and skin .

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .

LZ9450000

Xi

STABLE WHEN STORED IN GLASS

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.

Wear rubber gloves when handling...

Nonflammable

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/|If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/

DO NOT GET ON SKIN, IN EYES, OR ON CLOTHING. IN CASE OF CONTACT, WASH THOROUGHLY WITH LARGE AMT OF SOAP & WATER.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, NOS/|Personnel protection: Keep upwind. Wear appropriate chemical protective gloves, boots and goggles. Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organophosphorus pesticides, liquid, NOS/|Special aircraft should preferably be used for spraying or dusting toxic organophosphorus pesticides. ... aerial spraying or dusting gives rise to clouds which spread over larger surfaces than clouds produced by ground application. Aerial spraying should therefore be carried out on windless days only. Residential areas, water supply sources, etc must be avoided. ... When aircraft approaches, signalmen /guiding the aircraft/ should leave the windward side. ... The local population should be informed about the site & time of aerial pesticide treatment. Access of unauthorized persons & especially children to the area to be treated must be ... forbidden. Warning signs should be placed at the limits of the area. Ground spraying must be carried out with compressed-air spraying equipment towed by tractors with closed cabs. /Organophosphorus pesticides/|For more Preventive Measures (Complete) data for BOMYL (6 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

After inhalation of demeton, wheezing, aching in and behind the eyes, blurring of vision, and tearing occurred.

Toxicity

Contraindications for work with /organophosphorus pesticides/ are organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/|Persons with a history of reduced pulmonary function, convulsive disorders, or recent exposure to anticholinesterase agents would be expected to be at increased risk from exposure.

Drug Information

5= EXTREMELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG, BETWEEN 7 DROPS & 1 TEASPOONFUL FOR 70 KG PERSON (150 LB).

Rapidly absorbed through skin.

IN PRESENCE OF MOUSE LIVER ENZYMES & GLUTATHIONE, CIS- OR TRANS-BOMYL WAS HYDROLYZED WITH PRODUCTION OF DIMETHYL PHOSPHATE.

The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase ... /Organophosphorus pesticides/

1. INSURE THAT A CLEAR AIRWAY EXISTS BY ASPIRATION OF SECRETIONS IF NECESSARY. ADMIN OXYGEN BY MECHANICALLY ASSISTED PULMONARY VENTILATION IF RESPIRATION IS DEPRESSED. IMPROVE TISSUE OXYGENATION AS MUCH AS POSSIBLE BEFORE ADMIN ATROPINE TO MINIMIZE RISK OF VENTRICULAR FIBRILLATION. IN SEVERE POISONINGS, IT MAY BE NECESSARY TO SUPPORT PULMONARY VENTILATION MECHANICALLY FOR SEVERAL DAYS. 2. ADMIN ATROPINE SULFATE IV, OR IM IF IV INJECTION IS NOT POSSIBLE. ... IN MODERATELY SEVERE POISONING: ADULT DOSAGE AND CHILDREN OVER 12 YR: 0.4-2.0 MG REPEATED EVERY 15 MIN UNTIL ATROPINIZATION IS ACHIEVED. MAINTAIN ATROPINIZATION WITH REPEATED DOSAGE OF 0.02-0.05 MG/KG BODY WEIGHT. /ORGANOPHOSPHATE PESTICIDES/|2. SEVERELY POISONED INDIVIDUALS MAY EXHIBIT REMARKABLE TOLERANCE TO ATROPINE; TWO OR MORE TIMES THE DOSAGES SUGGESTED ABOVE MAY BE NEEDED. THE DOSE OF ATROPINE MAY BE INCREASED AND THE DOSING INTERVAL DECREASED AS NEEDED TO CONTROL SYMPTOMS. CONTINUOUS INTRAVENOUS INFUSION OF ATROPINE MAY BE NECESSARY WHEN ATROPINE REQUIREMENTS ARE MASSIVE. REVERSAL OF MUSCARINIC SYMPTOMS AND SIGNS, NOT AN ARBITRARY DOSE LIMIT, IS THE DESIRED END-POINT. PRESERVATIVE-FREE ATROPINE PRODUCTS SHOULD BE USED WHENEVER POSSIBLE. NOTE: PERSONS NOT POISONED OR ONLY SLIGHTLY POISONED BY ORGANOPHOSPHATES MAY DEVELOP SIGNS OF ATROPINE TOXICITY FROM SUCH LARGE DOSES. FEVER, MUSCLE FIBRILLATIONS, AND DELIRIUM ARE THE MAIN SIGNS OF ATROPINE TOXICITY. IF THESE APPEAR WHILE THE PATIENT IS FULLY ATROPINIZED, ATROPINE ADMINISTRATION SHOULD BE DISCONTINUED, AT LEAST TEMPORARILY, WHILE THE SEVERITY OF POISONING IS REEVALUATED. /ORGANOPHOSPHATE PESTICIDES/|3. DRAW BLOOD SAMPLE (HEPARINIZED) FOR CHOLINESTERASE ANALYSIS BEFORE ADMINISTRATION OF PRALIDOXIME, WHICH TENDS TO REVERSE THE CHOLINESTERASE DEPRESSION. 4. ADMIN PRALIDOXIME (PROTOPAM, 2-PAM) IN CASES OF SEVERE POISONING...IN WHICH RESP DEPRESSION, MUSCLE WEAKNESS & TWITCHINGS ARE SEVERE. ... ADULT DOSAGE AND CHILDREN OVER 12): GIVE 1.0-2.0 G IV @ NO MORE THAN 0.2 G/MIN. CHILD'S DOSE (UNDER 12 YR): GIVE 20-50 MG/KG (DEPENDING ON SEVERITY) IV, INJECTING NO MORE THAN HALF TOTAL DOSE/MIN. DOSAGE...MAY BE REPEATED IN 1-2 HR, THEN @ 10-12 HR INTERVAL IF NEEDED. IN VERY SEVERE POISONINGS, DOSAGE...MAY BE DOUBLED. /ORGANOPHOSPHATE PESTICIDES/|4. BE PREPD TO ASSIST PULMONARY VENTILATION MECHANICALLY IF RESP ... DEPRESSED ... . 5. IN PATIENTS WHO HAVE BEEN POISONED BY ORGANOPHOSPHATE CONTAMINATION OF SKIN, CLOTHING, HAIR, AND/OR EYES, DECONTAMINATION MUST PROCEED CONCURRENTLY WITH WHATEVER RESUSCITATIVE AND ANTIDOTAL MEASURES ARE NECESSARY TO PRESERVE LIFE. ... 6. IF ... INGESTED IN QUANTITY PROBABLY SUFFICIENT TO CAUSE POISONING, THE STOMACH AND INTESTINE MUST BE EMPTIED. A. EMPTY THE STOMACH BY INTUBATION, ASPIRATION, AND LAVAGE, USING SLURRY OF ACTIVATED CHARCOAL IN ISOTONIC SALINE. RIGOROUS PRECAUTIONS MUST BE TAKEN TO PROTECT THE AIRWAY FROM ASPIRATION OF REGURGITATED. IF VICTIM IS UNCONSCIOUS OR OBTUNDED, INSERT A CUFFED ENDOTRACHEAL TUBE PRIOR TO GASTRIC INTUBATION. KEEP VICTIM'S HEAD BELOW LEVEL OF STOMACH DURING GASTRIC INTUBATION AND LAVAGE ... . KEEP VICTIM'S HEAD TURNED TO THE LEFT. /ORGANOPHOSPHATE PESTICIDES/|For more Antidote and Emergency Treatment (Complete) data for BOMYL (8 total), please visit the HSDB record page.

Symptomatology: 1. Nausea...vomiting, abdominal cramps, diarrhea, excessive salivation... 2. Headache, giddiness, vertigo & weakness. 3. Rhinorrhea & sensation of tightness in chest are common in inhalation exposure. 4. Blurring or dimness of vision, miosis... Tearing, ciliary muscle spasm, loss of accommodation & ocular pain... Mydriasis...sometimes seen...probably due to sympatho-adrenal discharge. 5. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations & twitching of muscles (particularly of tongue & eyelids, & generalized profound weakness. 7. Mental confusion, disorientation & drowsiness. /Parathion/|Symptomatology: 8. Difficulty in breathing, excessive secretion of saliva & of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi & hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, & coma. 10. Death primarily due to resp arrest arising from failure of resp center, paralysis of resp muscles, intense bronchoconstriction or all three. /Parathion/|Highly toxic to humans...by ingestion, inhalation, or skin contact.

2-Pentenedioic acid, 3-[(dimethoxyphosphinyl)oxy]-, 1,5-dimethyl ester Use and Manufacturing

Methods of Manufacturing

PRODUCED BY REACTING DIMETHYL 3-OXOPENTANEDIOATE WITH SULFURYL CHLORIDE & RESULTING CHLORO CMPD WITH TRIMETHYL PHOSPHITE...

THESE INCL: WP (250 G AI/KG); EC (120, 240 & 480 G/L); BAIT (10 & 22 G/KG).|GRADES: GRANULAR, TECHNICAL, & CONCENTRATED.|Technical liquid (80% and 90%), 1% fly baits

TWO GEOMETRICAL ISOMERS ARE VERY SIMILAR IN INSECT TOXICITY & ANTICHOLINESTERASE ACTIVITY...

PRODUCT ANALYSIS IS BY GLC & IR SPECTROSCOPY.|PESTICIDE RESIDUES; MULTIRESIDUE METHODS: RESIDUES IN CONCENTRATED ELUATES ARE MEASURED BY GLC & IDENTIFIED BY COMBINATIONS OF GAS CHROMATOGRAPHY, THIN-LAYER CHROMATOGRAPHY... /ORGANOPHOSPHORUS PESTICIDES/|MULTIPLE RESIDUE METHODS FOR ORGANOPHOSPHORUS PESTICIDES. GAS-LIQUID CHROMATOGRAPHY. /ORGANOPHOSPHORUS PESTICIDES/

INSECTICIDES

Computed Properties

Molecular Weight:282.18
XLogP3:0.6
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:9
Exact Mass:282.05045443
Monoisotopic Mass:282.05045443
Topological Polar Surface Area:97.4
Heavy Atom Count:18
Complexity:367
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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