Trifluoroacetic acid

114.02

114.02

742035

200-929-3

E5R8Z4G708

1673

77366

2699

TSCA listed

DTXSID9041578

Colorless

29159080

λ: 260 nm Amax: 0.9λ: 270 nm Amax: 0.10λ: 280 nm Amax: 0.05λ: 290 nm Amax: 0.04λ: 300 nm Amax: 0.03λ: 320 nm Amax: 0.025

37.30000

0.63330

Trifluoroacetic acid appears as a colorless fuming liquid with a pungent odor. Soluble in water and denser than water. Corrosive to skin, eyes and mucous membranes. Used to make other chemicals and as a solvent.

1.489 g/mL at 20 °C (lit.)

-15.4 °C (lit.)

72.4 °C (lit.)

-3ºC

n20/D1.3(lit.)

miscible

2-8ºC

97.5 mm Hg ( 20 °C)

3.9 (vs air)

LD50 i.v. in mice: 1200 mg/kg (Airaksinen, Tammisto)

Sharp, pungent odor

1 (10g/l, H2O)

-0.3(at 25℃)

5.7×101mol/(m3Pa) at 25℃, Burkholder et al. (2019)

pKa = 0.3

Strong, non-oxidizing acid|Hydroxyl radical reaction rate constant = 5.2X10-13 cu cm/molec-sec at 25 °C (est)

Fumes in air. Soluble in water.

Acids, Carboxylic

Trifluoroacetic acid is a strong acid; attacks many metals [Handling Chemicals Safely 1980. p. 935]. A 30% solution of hydrogen peroxide in Trifluoroacetic acid is often used to destructively oxidize aromatic rings in preference to the side chains. Explosions have occurred, if the excess peroxide is not catalytically destroyed, prior to removal of solvent, [Tetrahedron Lett., 1977, 1703-1704]. The reduction of amides of Trifluoroacetic acid with lithium aluminum hydride are dangerous at all phases of the process, explosions have occurred, [Chem. Eng. News, 1955, 33, 1368].

The vapour is heavier than air.

Corrosive

Store at +15°C to +25°C.

I

8

UN 2699

2

C,T,Xi

9-26-27-28-45-61-28A-36/37/39

AJ9625000

C

trifluoroacetic acid should be stored in an acid cabinet away from other classes of compounds. Because of its high vapor pressure, fumes of trifluoroacetic acid can destroy labels on other bottles if the container is not tightly sealed.

Stable. Incompatible with combustible material, strong bases, water, strong oxidizing agents. Non-combustible. Hygroscopic. May react violently with bases.

P273-P280-P305 + P351 + P338-P310

20-35-52/53-34

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Mixing trifluoroacetic acid and water evolves considerable heat.

UN 2699

P261; P273; P280; P303 + P361 + P353; P304 + P340 + P310; P305 + P351 + P338

Trifluoroacetic acid is not combustible. Nevertheless, the presence of trifluoroacetic acid at the site of a fire would be of great concern because of its high vapor pressure and extreme corrosiveness. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

|Danger|H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P261, P264, P271, P273, P280, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P363, P405, and P501|H290 (18.86%): May be corrosive to metals [Warning Corrosive to Metals]|P234, P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P390, P404, P405, and P501|Aggregated GHS information provided by 525 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H290: May be corrosive to metals [Warning Corrosive to Metals]|P234, P260, P261, P264, P270, P271, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P321, P330, P363, P390, P403+P233, P404, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)|In case of fire in the surroundings, use appropriate extinguishing media. In case of fire: keep drums, etc., cool by spraying with water.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: 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)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)

Nonflammable

/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Fire or Explosion: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.|/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for TRIFLUOROACETIC ACID (8 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.

Personal protection: gas-tight chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable plastic containers. Absorb remaining liquid in sand or inert absorbent. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from strong bases, metals, oxidants and food and feedstuffs. Keep in a well-ventilated room. Store in an area without drain or sewer access.

A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.

The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of fumes may cause lung oedema.

NO contact with bases, oxidizing agents or reducing agents.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

Data suggest that the total trifluoroacetic acid in air and precipitation exceeds the formation potential of currently known sources. Trifluoroacetic acid in atmosphere and rain is regionally associated with industrial or population density and that other unresolved sources must contribute to the present concentrations(1).

URBAN/SUBURBAN: Average trifluoroacetic acid concentration in air samples collected from Bayreuth, Germany from March 1995 to September 1996 was 44 pg/cu m with a range of 10 to 126 pg/cu m(1).

The primary source of trifluoroacetic acid in the environment is believed to be through the atmospheric oxidation of the CFC-replacement gases, HCFC-123 and HFC-134a(2). Trifluoroacetic acid is formed as an important breakdown product by atmospheric degradation of chlorofluorocarbons replacement compounds(1).

LD50 Rat oral rat 200 mg/kg|LC50 Rat inhalation rat 10 g/cu m (duration unspecified)|LC50 Mouse inhalation 13500 mg/cu m (Duration of exposure unspecified)|LD50 Mouse iv 1200 mg/kg

Trifluoroacetic acid's production and use in organic synthesis(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a structure estimation method(2), indicates that trifluoroacetic acid is expected to have very high mobility in soil(SRC). The pKa of trifluoroacetic acid is 0.52(3), indicating that this compound will primarily exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of trifluoroacetic acid from moist soil surfaces is not expected to be an important fate process as anions do not volatilize(SRC). Trifluoroacetic acid is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 110 mm Hg(5). Certain oxic conditions do suggest that biodegradation is possible in soil; however, one of the products of degradation is fluoroform, a potential ozone-depleting compound with much longer atmospheric persistence than the parent compound(6).|TERRESTRIAL FATE: In a throughput study at the Hubbard Brook Experimental Forest in New Hampshire, the fate of trifluoroacetic acid within northern hardwood forest soils is suggested as follows: loss via soil water flow, 40-80%; soil retention, 5-30%; and plant uptake, 50-35%. These results indicate that transport of this compound is controlled primarily by hydrologic processes in upland forest ecosystems(1).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a structure estimation method(2), indicates that trifluoroacetic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 0.52(3) indicates trifluoroacetic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.50(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Trifluoroacetic acid was not biodegraded during a year-long study using laboratory aquatic microcosms and ecosystem sediment-water systems(8). Certain oxic conditions do suggest that biodegradation is possible in soil; trifluoroacetic acid degraded 9, 2.4, 1.9 and 25.5%, respectively, O2 as electron acceptor(9).|AQUATIC FATE: Trifluoroacetic acid is extremely persistent in water, showing no degradation during a year-long study using field aquatic microcosms and ecosystem sediment-water systems(1). Observations of the field ponds showed a reduction of trifluoroacetic acid over the winter months with levels rising again toward spring. Reaction with hydroxyl radicals in water is slow, with an estimated half-life of over 100 years(1). Trifluoroacetic acid was added to aquatic microcosms at concentrations of 10, 100, 300 and 1000 ug/L; a concentration of 20 ug/mL was added to laboratory sediment microcosms(1).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trifluoroacetic acid, which has an estimated vapor pressure of 110 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase trifluoroacetic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 31 days(SRC), calculated from its rate constant of 5.2X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Trifluoroacetic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

The rate constant for the vapor-phase reaction of trifluoroacetic acid with photochemically-produced hydroxyl radicals has been estimated as 5.2X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 31 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Trifluoroacetic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Trifluoroacetic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(3).

An estimated BCF of 3 was calculated in fish for trifluoroacetic acid(SRC), using an estimated log Kow of 0.50(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of trifluoroacetic acid can be estimated to be 3(SRC). According to a classification scheme(2), this estimated Koc value suggests that trifluoroacetic acid is expected to have very high mobility in soil. The pKa of trifluoroacetic acid is 0.52(3), indicating that this compound will primarily exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). In a throughput study at the Hubbard Brook Experimental Forest in New Hampshire, calculated outflows of trifluoroacetic acid from the organic layers were 57% of the total added concentration of 0.81 g/sq m(5). Thirty-five soils ranging from acrtic (Toolik Lake) and boreal (Bonanza Creek) sites in Alaska to a tropical rain forest in Puerto Rico (Luquillo) as well as soils from Lake Agissaz Peatlands, MN, near Found Lake, WI, Lysina and Pluhuv Bor, Czech Republic, Manaus, Balem, a Brazilian carton in Brazil, and the Hubbard Brook Experimental Forest, NH, were utilized to ascertain the fate of trifluoroacetic acid(6). Retention ranged from 25 to 260 umol/kg (60-0% of added trifluoroacetic acid) with 43 of 54 soils not retaining this compound strongly; soils with high organic matter and some mineral soils with high iron and aluminum content exhibited strong retention (20-60% of added trifluoroacetic acid); generally though, mineral soils exhibited less retention (0-15% of added trifluoroacetic acid)(6). The retention of trifluoroacetic acid increased with decreasing pH(6).|Trifluoroacetic acid adsorption parameters(1). [Table#7195]

A pKa of 0.52(1) indicates trifluoroacetic acid will exist almost entirely in the anion form at pH values of 5 to 9(2) and therefore volatilization from water surfaces is not expected to be an important fate process. Trifluoroacetic acid is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 110 mm Hg(3).

Average trifluoroacetic acid concentrations measured in Switzerland, 1996-1997(1). [Table#7197]|GROUNDWATER: Trifluoroacetic acid levels in spring waters of a young age were in the same range as surface waters. Groundwater samples of known old age, determined by radioisotope analyses, from the Antonien Quelle and Thueringer Wald Quelle, Bayreuth Germany, contained very low levels of the compound, generally less than 1%(1). The Bayern Quells and Rennsteig Quelle with young water content of 10 and 15%, respectively, had trifluoroacetic acid levels of 13 and 25 ng/L, respectively(1).|DRINKING WATER: Trifluoroacetic acid concentrations in drinking water originating from Lake Ontario for Hamilton and Burlington, Ontario, Canada were 183 and 120 ng/L, respectively(1).|SURFACE WATER: Trifluoroacetic acid concentrations in Canadian lakes, 1997(1). [Table#7198]|For more Environmental Water Concentrations (Complete) data for TRIFLUOROACETIC ACID (12 total), please visit the HSDB record page.

NIOSH (NOES Survey 1981-1983) has statistically estimated that 8,046 workers (1,731 of these are female) are potentially exposed to trifluoroacetic acid in the US(1). Occupational exposure to trifluoroacetic acid may occur through inhalation and dermal contact with this compound at workplaces where trifluoroacetic acid is produced or used(SRC). Monitoring data indicate that the general population may be exposed to trifluoroacetic acid via inhalation of ambient air, ingestion of food and drinking water(SRC).

To elucidate the possible role of biotransformation in 1,1,1,3,3-pentafluoropropane (HFC-245fa)-induced cardiotoxicity, the biotransformation of HFC-245fa was investigated in rats after inhalation exposure ... Male and female rats were exposed by inhalation to 50,000, 10,000, and 2,000 ppm 1,1,1,3,3-pentafluoropropane for 6 hr, urine was collected for 72 hr ... Trifluoroacetic acid and inorganic fluoride were identified as major urinary metabolites of 1,1,1,3,3-pentafluoropropane ... .|Trifluoroacetic acid is a known human metabolite of (R)-halothane.

Trifluoroacetic acid is a highly corrosive substance. Contact of the liquid with the skin, eyes, and mucous membranes can cause severe burns, and ingestion can result in serious damage to the digestive tract. TFA vapor is highly irritating of the eyes and respiratory tract, and inhalation of high concentrations can lead to severe destruction of the upper respiratory tract and may be fatal as a result of pulmonary edema. Symptoms of overexposure to TFA vapor include a burning feeling, coughing, headache, nausea, and vomiting.Trifluoroacetic acid has not been found to be carcinogenic or to show reproductive or developmental toxicity in humans.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

Fresh air, rest. Half-upright position. Refer immediately for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

/ALTERNATIVE and IN VITRO TESTS/ To elucidate the possible role of biotransformation in 1,1,1,3,3-pentafluoropropane (HFC-245fa)-induced cardiotoxicity, the biotransformation of HFC-245fa was investigated in rats after inhalation exposure and in rat and human liver microsomes. ... In rat and human liver microsomes, HFC-245fa was biotransformed by a cytochrome P450-dependent reaction to trifluoroacetic acid and 3,3,3-trifluoropropanoic acid. ... In human liver microsomes, rates of trifluoroacetic acid formation ranged from 0 to 11.6 pmol/mg of protein/min.

Acid, Trifluoroacetic

Serious local effects by all routes of exposure.

Cough. Sore throat. Burning sensation. Laboured breathing.

Redness. Pain. Serious skin burns.

Redness. Pain. Severe deep burns.

All other basic organic chemical manufacturing|Acetic acid, 2,2,2-trifluoro-: ACTIVE

Analyte: trifluoroacetic acid; matrix: chemical purity; procedure: dissolution in water and alcohol; potentiometric titration with sodium hydroxide

Fire Hazards -> Corrosives, Reactive - 1st degree|Environmental transformation -> Pesticide transformation products (metabolite, successor)

Trifluoroethanoic acid is a known environmental transformation product of flurtamone.|Trifluoracetat is a known environmental transformation product of Tembotrione.