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Home > Encyclopedia > 2,4,5-T isobutyl ester

2,4,5-T isobutyl ester

2,4,5-T isobutyl ester structure

2,4,5-T isobutyl ester 

structure
  • CAS No:

    4938-72-1

  • Formula:

    C12H13Cl3O3

  • Chemical Name:

    2,4,5-T isobutyl ester

  • Synonyms:

    Acetic acid,2-(2,4,5-trichlorophenoxy)-,2-methylpropyl ester;Acetic acid,(2,4,5-trichlorophenoxy)-,isobutyl ester;Acetic acid,(2,4,5-trichlorophenoxy)-,2-methylpropyl ester;Isobutyl 2,4,5-T;2,4,5-Trichlorophenoxyacetic acid isobutyl ester;2,4,5-T isobutyl ester

  • Categories:

    Analytical Chemistry  >  Standard

Description

off-white solid


2,4,5-t isobutyl ester is an off-white solid. (NTP, 1992)


2,4,5-t isobutyl ester is an off-white solid. (NTP, 1992)

2,4,5-T isobutyl ester Basic Attributes

311.59

311.59

225-580-4

08K7Z0G1Q5

3077

DTXSID2026074

Characteristics

35.53000

4.22480

2,4,5-t isobutyl ester is an off-white solid. (NTP, 1992)

1.322 g/cm3

366.2ºC at 760 mmHg

139.1ºC

1.527

less than 1 mg/mL at 75° F (NTP, 1992)

AMBER OR DARK AMBER COLORED LIQUID /2,4,5-T ESTERS/|Very weak odor; mixtures with kerosene or diesel oil have odor of the solvent /2,4,5-T esters/

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

2,4,5-T, ISOBUTYL ESTER is an ester of a chlorinated organic acid. May react exothermically with acids to generate isobutyl alcohol and 2,4,5-trichlorophenoxyacetic. Strong oxidizing acids may cause a reaction that is sufficiently exothermic to ignite the reaction products. Heat may also be generated with caustic solutions.

May attack some forms of plastics /2,4,5-T esters/|The salts & esters of 2,4,5-T are non-corrosive under normal application conditions /2,4,5-T/

Safety Information

UN30779/PG3

22-36/37/38-50/53

24-60-61

Xn,N

Stable. Hydrolyzes under acidic conditions. Keep cool.

P261-P273-P305 + P351 + P338-P501

H302-H315-H319-H335-H410

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number F027, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /2,4,5-T cmpd/|Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/|Group II Containers: Noncombustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/

Nat'l Research Council Canada; Phenoxy Herbicides Their Effects on Environmental Quality (1978) NRCC No. 16075|Vet Admin Rev Lit on Herbicides (1981) VA Contract No. V101(93) p-823

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 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 away from mineral acids and bases. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Wear appropriate chemical protective ... boots and goggles. /2,4,5-T amine, ester, or salt/|... Rubber gloves ... /2,4,5-T esters/

They will burn, though they may take some effort to ignite. /2,4,5-T amine, ester, or salt/

Extinguish fire using agent suitable for type of surrounding fire. /2,4,5-T amine, ester, or salt/|WATER, FOAM, DRY CHEM, CARBON DIOXIDE. ... WATER OR FOAM MAY CAUSE FROTHING. /2,4,5-T ESTERS/

Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. /2,4,5-T amine, ester, or salt/|Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /2,4,5-T amine, ester, or salt/

If material /is not/ involved in a fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. /2,4,5-T amine, ester, or salt/|Keep upwind. ... Avoid breathing vapors or dusts. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /2,4,5-T amine, ester, or salt/|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

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.

Irritating to skin and eyes. /2,4,5-T esters/

F027; A hazardous waste from nonspecific sources when a component of a discarded unused formulation. /2,4,5-T/

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). /2,4,5-T Esters/

F027; As stated in 40 CFR 261.31, discarded unused formulations containing tri-, tetra-, or pentachlorophenol or discarded unused formulation containing compounds derived from these chlorophenols. (This listing does not include formulations containing hexachlorophene synthesized from prepurified 2,4,5-trichlorophenol as the sole component.). /2,4,5-T/

During mixing & spraying operations along power line right-of-way, airborne concn of 2,4,5-T esters were < 10-60 ug/cu m. /Chlorophenoxy herbicides/

Toxicity

... Assuming the densities of Purple and Pink were similar to Orange, one gallon of Purple or Pink would have weighed approximately 10.7 pounds. The specified formulation of Purple was ... 20% by weight the isobutyl ester of 2,4,5-T, so one gallon of the specified formulation of Purple would contain approximately ... 2.1 pounds of the isobutyl ester of 2,4,5-T. Therefore, Purple applied at 1.5 gallons per acre is estimated to have released a maximum of ... 3.2 pounds per acre of the isobutyl ester of 2,4,5-T. The specified formulation of Pink was 40% by weight the isobutyl ester of 2,4,5-T, so one gallon of the specified formulation of Pink would contain approximately 4.3 pounds of the isobutyl ester of 2,4,5-T. Therefore, Pink applied at 1.5 gallons per acre is estimated to have released a maximum of 6.5 pounds per acre of the isobutyl ester of 2,4,5-T.

2,4,5-T ESTERS ARE RAPIDLY HYDROLYZED AFTER SPRAYING, & THE 2,4,5-T IS THEN FURTHER DECOMPOSED BY BACTERIAL ACTION. THE MAJOR PRODUCT OF 2,4,5-T PHOTODECOMPOSITION IS 2,4,5-TRICHLOROPHENOL. OTHER PRODUCTS IDENTIFIED INCLUDED 4,6-DICHLORORESORCINOL, 4-CHLORORESORCINOL, 2,4,5-TRICHLOROANISOLE. /2,4,5-T ESTERS/

From limited data available, it may be concluded that any phenoxy herbicide, whether applied as ester or as dimethylamine salt formulations, may be chemically transformed to the same phenoxyalkanoic anion in soil and water at rates dependent on pH. These anions would presumably reassociate with a variety of inorganic cations present in the soil to maintain electrical neutrality, and then undergo leaching and biological degradation. /Phenoxy esters/

Exposure to chlorophenoxy herbicides may occur through inhalation, skin contact or ingestion. /Chlorophenoxy herbicides/|... Occupational exposure to chlorophenoxy herbicides ... is known to have occurred during their production, formulation, application & disposal. /Chlorophenoxy herbicides/

Drug Information

THE CHLOROPHENOXY COMPOUNDS ARE ABSORBED ACROSS THE GUT WALL, LUNG, & THE SKIN. THEY ARE NOT SIGNIFICANTLY FAT STORABLE. EXCRETION OCCURS WITHIN HOURS, OR AT MOST DAYS, PRIMARILY IN THE URINE. /CHLOROPHENOXY CMPD/|IN SHEEP GIVEN ORAL DOSE OF 25 MG/KG OF 2,4,5-T ESTER PEAK PLASMA CONCN OF 10 PPM ... FOUND 3-4 HR LATER; 86% OF ADMIN DOSE WAS RECOVERED FROM URINE IN UNALTERED FORM, & 1.4% AS FREE ACID, WITHIN 72 HR. THERE WAS LESS THAN 0.1 PPM OF 2,4,5-T IN TISSUES, BUT IN SHEEP POISONED BY REPEATED DOSES OF 2,4,5-T TISSUE LEVELS WERE 368 PPM. /2,4,5-T ESTERS/

THESE HERBICIDES /CHLOROPHENOXY CMPD/ DO NOT ACCUM IN ANIMALS. THEY ARE NOT EXTENSIVELY METAB BUT ARE ACTIVELY EXCRETED INTO THE URINE ... THEIR PLASMA HALF-LIFE IN MAN IS ABOUT 1 DAY. /CHLOROPHENOXY HERBICIDES/

They exert their herbicidal action by acting as a growth hormone in plants. They have no hormonal action in animals, but their mechanism of toxic action is poorly understood. /Chlorophenoxy compounds/

2,3,7,8-Tetrachlorodibenzo-1,4-dioxin (I) ... was detected in technical samples of ... 2,4,5-T alkyl esters. ... Thirty-two samples of 50% 2,4,5-T alkyl esters in mineral oil, 8 contained <0.05 ppm 2,3,7,8-tetrachlorodibenzo-1,4-dioxin, and 18 <0.5 ppm 2,3,7,8-tetrachlorodibenzo-1,4-dioxin. The maximum found was 28.3 ppm.|... Dioxins ... still are present /but to lesser extent/ as impurities in commercial preparations of the trichlorophenoxy herbicides. /Trichlorophenoxy herbicides/|IT WAS CONCLUDED @ STOCKHOLM CONF, FEB 7-9, 1977, THAT THE ONLY DIOXIN FOUND IN PHENOXY ACID HERBICIDES WHICH IS OF ENVIRONMENTAL CONCERN IS TCDD /2,3,7,8-TETRACHLORODIBENZO-P-DIOXIN/; IT IS FOUND IN 2,4,5-T & 2,4,5-TP. /PHENOXY ACID HERBICIDES/

SYMPTOMS: Symptoms of exposure to this compound may include skin and eye irritation. ACUTE/CHRONIC HAZARDS: This compound may cause irritation on contact. When heated to decomposition it emits toxic fumes. (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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)

The chlorophenoxy herbicides have produced contact dermatitis in man ... . /Chlorophenoxy compounds/|INHALATION OF SPRAY MAY CAUSE BURNING SENSATIONS IN THE NASOPHARYNX & CHEST, & COUGHING MAY RESULT. PROLONGED INHALATION SOMETIMES CAUSES DIZZINESS. /CHLOROPHENOXY COMPOUNDS/|WHEN INGESTED, HIGH CONCENTRATIONS OF CHLOROPHENOXY COMPOUNDS MAY IRRITATE THE MOUTH & THROAT, & GI TRACT. ... CHEST PAIN (FROM ESOPHAGITIS), ABDOMINAL PAIN & DIARRHEA COMMONLY ENSUE. ... ABSORBED CHLOROPHENOXY COMPOUNDS HAVE CAUSED FIBRILLARY MUSCLE TWITCHING, SKELETAL MUSCLE TENDERNESS, & MYOTONIA ... INGESTION OF VERY LARGE AMOUNTS HAS PRODUCED METABOLIC ACIDOSIS, FEVER, TACHYCARDIA, HYPERVENTILATION, VASODILATATION & SWEATING. PARTICULAR CASES HAVE BEEN CHARACTERIZED BY COMA & CONVULSIONS. /CHLOROPHENOXY COMPOUNDS/|Phenoxyherbicides including (2,4,5-trichlorophenoxy)acetic acid have been widely used in New Zealand for over 30 years. In the light of Swedish studies reporting an association between exposure to phenoxyherbicides or chlorophenols and soft tissue sarcoma, a case-control study was undertaken that involved interviewing 82 subjects (cases) with soft tissue sarcoma and 92 controls with other types of cancer. For those potentially exposed to phenoxyherbicides for more than 1 day not in the 5 years before cancer registration, the estimate of relative risk was 1.3, with 90% confidence limits of 0.6-2.5. The comparable relative risk estimate for chlorophenol exposure was 1.5, with 90% confidence limits of 0.5-4.5. The discovery of cases in trichlorophenol manufacturing plants in the United States lended support to the Swedish findings but further studies are needed to conclude whether human exposure to these chemicals truly increases the risk of soft tissue sarcoma. /Phenoxyherbicides/|A previous case-control study which used the occupational information available on the New Zealand Cancer Registry found that agricultural workers were at increased risk of developing non-Hodgkin's lymphoma. The findings are now presented for the second phase of the study which entailed interviewing 83 cases of non-Hodgkin's lymphoma registered under code 202 of the International Classification of Diseases together with 168 controls with other types of cancer and 228 general population controls. The findings for the two control groups were similar, and there were no significant differences between cases and controls regarding potential exposure to phenoxyherbicides (odds ratio= 1.4, 90% confidence limits 0.7-2.5, p= 0.26) or chlorophenols (odds ratio= 1.3, 90% confidence limits 0.6-2.7, p= 0.39). The odds ratio for fencing work, necessitating exposure to several potential risk factors including arsenic and sodium pentachlorophenate was 2.0 (90% confidence limits 1.3-3.0, p= 0.01). The odds ratio for employment in a meat works, necessitating potential exposure to 2,4,6-trichlorophenol and zoonotic viruses, was 1.8 (90% confidence limits 1.1-3.1, p= 0.04). There was a significant statistical interaction between the risks associated with these two activities, the odds ratio for involvement in both activities compared with involvement in neither being 5.7 (90% confidence limits 2.3, p= 0.03). /Phenoxyherbicides, chlorophenols, arsenic, and sodium pentachlorophenate/

2,4,5-T isobutyl ester Use and Manufacturing

Methods of Manufacturing

Esters of 2,4,5-T are synthesized by esterification of acid with appropriate alkyl alcohol. /2,4,5-T esters/|Chlorophenoxy ester herbicides can ... be produced by direct reaction of chlorophenol with appropriate chloroacetic esters ... /Chlorophenoxy herbicides/

Uses

In March 1985 the EPA terminated all registrations for the use of this herbicide on rice fields, orchards, sugarcane, rangeland and other noncrop sites. This follows the 1970 of the Department of Agriculture halting the use of the pesticide on all food crops except rice ... . /2,4,5-T/|For Trichlorophenoxyacetic Acid, Isobutyl Ester (USEPA/OPP Pesticide Code: 082062) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./|2,4,5-T: U.S. Banned. /2,4,5-T; From table/|2,4,5-T salts & esters are used widely to control woody plants on industrial sites & rangeland /2,4,5-T salts and esters; former use/|For more Uses (Complete) data for 2,4,5-T, ISOBUTYL ESTER (6 total), please visit the HSDB record page.

/FORMER USES:/ INDUSTRIAL & COMMERCIAL USES, 63%; RANGELAND, 26%; RICE (EXCLUDING ISOOCTYL ESTER) 8%; LAWNS & TURF, 3% (1983-INCL 2,4,5-TRICHOROPHENOXYACETIC ACID, ESTERS, & SALTS)

Agent Purple (n-butyl esters of 2,4-D and 2,4,5-T, and isobutyl ester of 2,4,5-T). /Former/|Monsanto 2,4,5-T Butyl Ester (isobutyl & n-butyl esters of 2,4,5-T). /Former/|GRADES: TECHNICAL, 96-99%; 55-65% SOLUTIONS IN KEROSENE OR DIESEL OIL. /2,4,5-T ESTERS; FORMER/

Chlorophenoxy herbicides are applied alone or as mixtures with other herbicides, in solutions, dispersions, or emulsions in water &/or oil, using equipment that produces large droplets to avoid spray drift. /Chlorophenoxy herbicides/|Relatively high volatility esters ... /of 2,4,5-T incl/ methyl, ethyl, isopropyl, butyl, amyl & others known to possess relatively high vapor activity. These esters ... are liquids which, when properly formulated form emulsions when mixed with water. Because they are highly volatile, they should not be used under high temp conditions for weed control in areas adjacent to susceptible plants, such as cotton, tomatoes, grapes, flowers, & ornamentals.|New Zealand: The spraying of phenoxyherbicides is restricted within prescribed distances of vineyards. /Phenoxyherbicides/|THE ACTION ... OF /2,4,5-T SALTS & ESTERS/ ARE SIMILAR TO 2,4-D PREPARATIONS, ALTHOUGH ESTER FORMULATIONS ARE SOMEWHAT LESS VOLATILE. /2,4,5-T/

Product analysis is by ... GLC of a suitable ester ... . Residues may be determined by GLC of a suitable ester. /2,4,5-T/|Samples of phenoxyalkanoic herbicides in whole plants are acidified, hydrolyzed, and extracted into ether, and analyzed by electron capture gas chromatography (EC/GC) ... using a pyrex column ... packed with 1:1 10% DC 200/15% QF-1 on 80/100 mesh Chromosorb W (AW-DMCS). The injector, column, and (63)Ni electron capture detector temperatures are 220, 195, and 220 °C, respectively. The flow rate of nitrogen carrier is 80 ml/min. /Phenoxyalkanoic Herbicides/|2,4,5-T and /its esters/ in pesticide formulations are determined by automated liquid chromatographic method after extraction of sample into hexane. (Method is modification of liq chromatography method of 2,4-D, 6.288-6.292) ...by collecting major portion extracted with hexane ... .|CHLOROPHENOXYALKANOIC ACID HERBICIDES WERE ANALYZED ON UNMODIFIED SILICA GEL & ON REVERSE PHASE SILICA GEL. AN EFFECTIVE RETENTION OF THE SUBSTANCES AS WELL AS GOOD SEPARATION ON THE REVERSE PHASE PERISORB RP-2 WAS OBTAINED BY ADDING 60 MMOLES TETRAMETHYLAMMONIUM BROMIDE/L OF MOBILE PHASE. THE UV SPECTRA OF 7 ACTIVE INGREDIENTS & 3 CHLOROPHENOLS WERE RECORDED. IN MANY CASES THEY SHOWED AN ABSORPTION MIN NEAR THE MOST APPLIED UV WAVELENGTH OF 254 NM. /CHLOROPHENOXYALKANOIC ACID HERBICIDES/|For more Analytic Laboratory Methods (Complete) data for 2,4,5-T, ISOBUTYL ESTER (6 total), please visit the HSDB record page.

Computed Properties

Molecular Weight:311.6
XLogP3:5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:309.993027
Monoisotopic Mass:309.993027
Topological Polar Surface Area:35.5
Heavy Atom Count:18
Complexity:273
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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