기본 정보
- 표준 SMILES
O=C(C(F)(F)F)C(F)(F)F- InChIKey
VBZWSGALLODQNC-UHFFFAOYSA-N- 분자식
- C3F6O
- 평균 분자량
- 166.02 g/mol
- 단동위원소 질량
- 165.98533394
개요
Hexafluoroacetone can cause developmental toxicity and male reproductive toxicity according to an independent committee of scientific and health experts.
이름 및 식별자
- 우선 이름
- Hexafluoroacetone
- IUPAC
- 1,1,1,3,3,3-hexafluoropropan-2-one
- 현지명
- 헥사플루오로아세톤
- 영어명
- Hexafluoroacetone
- 분자식
- C3F6O
- 분자량
- 166.02
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
684-16-2- PubChem CID
- 12695
- DTXSID
DTXSID9043778- ChEBI
CHEBI:39429- UNII
- AKU9463N1Y
- EC Number
- 211-676-3
- Nikkaji
- J1.724H
물성
구조 계산 물성
- XLogP
- 1.5
- 극성 표면적
- 17.1 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 7
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 10
- 형식 전하
- 0
- 복잡도
- 124
실험 및 물리화학적 성질
Chemical Classes
Toxic Gases & Vapors -> Corrosive Gases
Reactive agents - 2nd degree
LogP
Log Kow = 1.46
1.46
Odor
MUSTY ODOR BECOMES ACRID IN PRESENCE OF ACIDIC IMPURITIES
Musty odor.
Density
1.33 G/ML @ 25 °C (LIQUID)
DENSITY: 1.65 @ 25 °C (LIQUID)
1.33 @25 °C
5.76(relative gas density)
Color/Form
COLORLESS GAS
Colorless gas [Note: Shipped as a liquefied compressed gas].
Solubility
Reacts with water (NIOSH, 2024)
Solubility in water: reaction, releasing heat
Reacts
Boiling Point
-18 °F at 760 mmHg (NIOSH, 2024)
-27 °C
-28 °C
-18 °F
-27.4 °C @760 [mm Hg]
-18 °F
Decomposition
DANGEROUS; WHEN HEATED TO DECOMP, OR ON CONTACT WITH ACID OR ACID FUMES, THEY EMIT HIGHLY TOXIC FUMES. /FLUORIDES/
550 °C. This produces toxic and corrosive fumes. Reacts vigorously with water and moisture. This produces a highly acidic hydrate. Attacks glass and most metals.
Melting Point
-188 °F (NIOSH, 2024)
-125.45 °C @ 101.3 kPa
-129 °C
-188 °F
-125.45 °C
-188 °F
Vapor Density
5.76 (NIOSH, 2024) - Heavier than air; will sink (Relative to Air)
Relative vapor density (air = 1): 5.7
물리화학적 성질
- 녹는점
- 129 °C · −129 °C(lit.)
- 끓는 점
- 26 °C · −26 °C(lit.)
- 밀도
- 1 · 1,32 g/cm3
- 증기 밀도
- 1.65 · 1.65 (vs air)
- 증기압
- 4525 mm · 4525 mm Hg ( 21.1 °C)
- 저장 조건
- Refrigerator
- 용해도
- 클로로포름에 용해됨
- 물리적 상태
- Colorless gas, which reacts vigorously with water to form hydrates
- Henry's Law Constant
- 3.2 · 3.2×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
- NIST
- 2 · 2-Propanone, 1,1,1,3,3,3-hexafluoro-(684-16-2)
- EPA
- Hexafluoroacetone (684-16-2)
화학적 성질
Hexafluoroacetone is a colorless, nonflamma ble poison gas. Musty odor. Shipped as a liquefied com pressed gas.
안전 및 규제
GHS 분류
GHS Classification
Danger
H280 (73.8%): Contains gas under pressure; may explode if heated [Warning Gases under pressure]
P203, P260, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P308+P316, P316, P317, P318, P319, P320, P321, P330, P332+P317, P361+P364, P362+P364, P363, P403+P233, P405, P410+P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 187 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H280: Contains gas under pressure; may explode if heated [Warning Gases under pressure]
유해성 정보
Regulatory Information
Hazard Traits - Developmental Toxicity; Reproductive Toxicity
2-Propanone, 1,1,1,3,3,3-hexafluoro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanone, 1,1,1,3,3,3-hexafluoro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
2-Propanone, 1,1,1,3,3,3-hexafluoro- (hexafluoro acetone): HSNO Approval: HSR001060 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Excerpt from ERG Guide 125 [Gases - Toxic and/or Corrosive]:
· Some may burn but none ignite readily.
Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Health Hazards
Excerpt from ERG Guide 125 [Gases - Toxic and/or Corrosive]:
· TOXIC and/or CORROSIVE; may be fatal if inhaled, ingested or absorbed through skin.
Hazards Summary
In 4-hour inhalation studies of rats, 300 ppm is lethal, 200 ppm causes liver and kidney injury, and 100 ppm causes testicular damage; evidence of bone marrow injury is also seen; [ACGIH] Possible frostbite from contact with liquid; [NIOSH] Inhalation of vapor can cause pulmonary edema; A skin, eye, and respiratory tract irritant; [ICSC]
DOT ID and Guide
2420 125
2420 125
Special Reports
Kennedy GL Jr; Crit Rev Toxicol 21 (2): 149-70 (1990). Toxicology of fluorine containing monomers. /A toxicological review covering metabolism, acute toxicity, repeated dose toxicity, genetic toxicity, developmental toxicity, carcinogenicity and environmental toxicology/.
안전 및 보호
Fire Fighting
Excerpt from ERG Guide 125 [Gases - Toxic and/or Corrosive]:
In case of fire in the surroundings, use appropriate extinguishing media. In case of fire: keep cylinder cool by spraying with water.
First Aid Measures
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . ON FROSTBITE: rinse with plenty of water, do NOT remove clothes.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· Do not touch or walk through spilled material.
First Aid
Excerpt from NIOSH Pocket Guide for Hexafluoroacetone:
General First Aid:
(General first aid procedures)
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].
Disposal Methods
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.
Preventive Measures
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.
Isolation and Evacuation
Excerpt from ERG Guide 125 [Gases - Toxic and/or Corrosive]:
Immediate precautionary measure
Small spill:
Small spill:
독성 정보
Environmental Fate
TERRESTRIAL FATE: An estimated Koc of 150(1,SRC), based on an experimental log Kow(2), indicates that 1,1,1,3,3,3-hexafluoro-2-propanone will have moderate mobility in soil(3,SRC). In moist soils, 1,1,1,3,3,3-hexafluoro-2-propanone is expected to vigorously react with water producing 1,1,1,3,3,3-hexafluoro-2,2-propanediol, a stable solid hydrate as well as liquid hydrates(4,5). If released to dry soils, 1,1,1,3,3,3-hexafluoro-2-propanone may quickly volatilize based on a vapor pressure of 5 mm Hg at 25 °C(6,SRC). 1,1,1,3,3,3-Hexafluoro-2-propanone on soil surfaces may photolyse(SRC); this compound decomposes under UV irradiation to trifluoromethyl radicals and carbon monoxide(7).
AQUATIC FATE: 1,1,1,3,3,3-Hexafluoro-2-propanone is expected to vigorously react with water producing 1,1,1,3,3,3-hexafluoro-2,2-propanediol, a stable solid hydrate as well as liquid hydrates(1,2). This is expected to be a major fate process for 1,1,1,3,3,3-hexafluoro-2-propanone in aquatic systems(SRC). An estimated BCF value of 8(4), based on an experimental log Kow(3), indicates that 1,1,1,3,3,3-hexafluoro-2-propanone should not bioconcentrate in aquatic organisms(SRC).
ATMOSPHERIC FATE: Based on a vapor pressure of 5.0 mm Hg at 25 °C(1,SRC), as extrapolated from experimentally derived coefficients, 1,1,1,3,3,3-hexafluoro-2-propanone will exist solely in the vapor phase(2,SRC). 1,1,1,3,3,3-hexafluoro-2-propanone absorbs in the 220 to 400 nm region with a lambda max of 302 nm(2) and may thus directly photolyse(3,SRC). This compound decomposes under UV irradiation to trifluoromethyl radicals and carbon monoxide(3). The rate constant for the vapor-phase reaction of 1,1,1,3,3,3-hexafluoro-2-propanone with photochemically produced hydroxyl radicals has been estimated to be less than 1X10-16 cu cm/molecule-sec at 25 °C(4,SRC) indicating that 1,1,1,3,3,3-hexafluoro-2-propanone is essentially non-reactive and that degradation via hydroxyl radical reaction is not a major fate process for this compound in the atmosphere(SRC).
Exposure Routes
The substance can be absorbed into the body by inhalation and through the skin.
inhalation, skin absorption, skin and/or eye contact
Signs and Symptoms
Cough. Sore throat. Burning sensation. Laboured breathing. Shortness of breath. Symptoms may be delayed.
MAY BE ABSORBED! Redness. Pain. ON CONTACT WITH LIQUID: FROSTBITE.
Redness. Pain.
irritation eyes, skin, mucous membrane, respiratory system; pulmonary edema; liquid: frostbite; In Animals: teratogenic, reproductive effects; kidney injury
Soil Adsorption/Mobility
Based on an experimental log Kow of 1.46(1), the Koc of 1,1,1,3,3,3-hexafluoro-2-propanone is estimated as approximately 150 using a regression-derived equation(2,SRC). According to a suggested classification scheme(3), this estimated Koc value suggests that 1,1,1,3,3,3-hexafluoro-2-propanone has moderate mobility in soil(SRC).
Artificial Pollution Sources
1,1,1,3,3,3-Hexafluoro-2-propanone is widely used in the synthesis of polymers, medicinals, agriculture chemicals, and as a component of high-performance fluoropolymers and in the manufacture of the solvent 1,1,1,3,3,3-hexafluoro-2-propanol(1). It is also used as a chemical intermediate for hexafluoroisopropanol, polyacrylates used for textile coating, and polyester coatings for textiles; a solvent for acetal resins and polyamides; and a polymer adhesive(2). During 1,1,1,3,3,3-hexafluoro-2-propanone's production and subsequent use in the above products, it may be released to the environment through various waste streams(SRC).
Environmental Bioconcentration
A BCF of 8 was calculated for 1,1,1,3,3,3-hexafluoro-2-propanone, using an experimental log Kow of 1.46(1) and a recommended regression-derived equation(2,SRC). This BCF value suggests that 1,1,1,3,3,3-hexafluoro-2-propanone will not bioconcentrate in aquatic organisms(2,SRC).
Volatilization from Water/Soil
The Henry's Law constant for 1,1,1,3,3,3-hexafluoro-2-propanone is estimated as 3.07X10-3 atm-cu m/mole(1,SRC). This indicates that 1,1,1,3,3,3-hexafluoro-2-propanone will volatilize from water surfaces(2,SRC). This compound's rapid rate of hydrolysis(3) indicates that hydrolysis should preclude volatilization in aquatic environments(SRC).
Non-Human Toxicity Excerpts
INHALATION EXPOSURES OF RATS INDICATED A 4-HR LETHAL CONCN OF 300 PPM; 200 PPM HFA (GAS) FOR 4 HR PRODUCED INJURY TO THE LIVER, KIDNEY, TESTES & THYMUS; & 100 PPM DAMAGED THE TESTES ONLY. DAILY, 6-HR REPEATED EXPOSURES OF RATS AT 60 PPM RESULTED IN DECREASED SPERMATOGENESIS AFTER 10 EXPOSURES & DECREASED BONE-MARROW ERYTHROPOIESIS AFTER TERMINATION OF EXPOSURE. TESTICULAR REGENERATION WAS STILL INCOMPLETE AT 57 DAYS FOLLOWING A SINGLE, 4-HR EXPOSURE AT 60 PPM HFA.
NINETY DAYS EXPOSURE AT 0.1 PPM RESULTED IN NO GROSS BIOCHEMICAL, HEMATOLOGIC OR HISTOPATHOLOGIC CHANGES IN EITHER RATS OR DOGS, ALTHOUGH THE LUNG WEIGHTS OF THE DOGS EXCEEDED THAT OF THE CONTROLS. AT 1 PPM, REVERSIBLE RENAL DYSFUNCTION IN RATS & INCREASED LUNG WEIGHT IN DOGS OVER THAT OF CONTROLS WAS ALL THAT WAS NOTED OF SIGNIFICANCE, NO HISTOPATHOLOGIC CHANGES. AT 12 PPM, SERIOUS TISSUE DAMAGE OCCURRED; THE RATE OF WEIGHT GAIN, ADRENAL & TESTES WEIGHTS OF MALE RATS, WERE LESS THAN THOSE OF CONTROLS. TRENDS TOWARD INCREASED WEIGHTS OF HEART, STOMACH, LIVER & LUNG WERE OBSERVED. IN ADDITION, THERE WAS EVIDENCE OF A TREND TOWARD LYMPHOCYTOSIS & RENAL DYSFUNCTION. HISTOPATHOLOGICALLY, SEVERE, BUT REVERSIBLE, TESTICULAR DAMAGE, & SLIGHT HYPERPLASIA OF THE SPLEEN, THYMUS, LYMPH NODES & BONE MARROW OCCURRED.
... SEVERE INJURY FROM 12 PPM LEVEL /HAS/ RESULTED IN DOGS; THE TESTES WEIGHT DECREASED, & THE WEIGHTS OF PITUITARY & LUNG INCREASED. DOGS ALSO DEVELOPED NEUTROPHILIA, HYPERGLYCEMIA, HYPOALBUMINERIA, & ANEMIA. AS WITH RATS, THE DOGS DEVELOPED SEVERE, BUT REVERSIBLE, TESTICULAR DAMAGE & SLIGHT HYPOPLASIA OF THE SPLEEN, THYMUS & LYMPH NODES. /FROM 90 DAYS INHALATION/
Testicular degeneration and atrophy were seen in rats given dermal doses of 65, 130, or 260 mg/kg 5 days/wk for 2 wk. These changes were still apparent 14 days after the last dose. They were not produced by a dermal dosage of 13 mg/kg for 14 days. The dose of 13 mg/kg/day HFA was considered a no-observed-effect level (NOEL). The structural changes (testicular atrophy) and altered lipid metabolism correlated well. In these studies, changes in steroidogenesis was due to inhibition in Leydig cells and was not due to a direct or immediate effect of HFA nor by hormonal mediation. HFA (as the sesquihydrate) was applied to the skin of pregnant rats at various dosages on days 6 through 16 of gestation. Maternal toxicity was observed at 90 mg/kg/day. The number of resorptions and live fetuses per litter suggested fetal toxicity at 25 mg/kg with fetal size being reduced at the 5 and 25 mg/kg doses (but not at 1 mg/kg). A small increase in soft tissue and external abnormalities was seen, but a definite teratogenic response could not be concluded. /Sesquihydrate/
For more Non-Human Toxicity Excerpts (Complete) data for 1,1,1,3,3,3-HEXAFLUORO-2-PROPANONE (11 total), please visit the HSDB record page.
Environmental Abiotic Degradation
1,1,1,3,3,3-Hexafluoro-2-propanone reacts readily with nucleophilic reagents(1). 1,1,1,3,3,3-Hexafluoro-2-propanone reacts vigorously with water(2). In water, this compound forms 1,1,1,3,3,3-hexafluoro-2,2-propanediol, a stable solid hydrate. Further addition of water produces liquid hydrates. With ammonia and primary or secondary amines it forms stable 2,2-amino alcohols(1). 1,1,1,3,3,3-Hexafluoro-2-propanone absorbs in the 220 to 400 nm region with a lambda max of 302 nm(3). This compound decomposes under UV irradiation to trifluoromethyl radicals and carbon monoxide(3). Small amounts of CF3CO radical have also been detected in low temperature flash photolysis(3). The rate constant for the vapor phase reaction of 1,1,1,3,3,3-hexafluoro-2-propanone with photochemically produced hydroxyl radicals has been estimated to be less than 1X10-16 cu cm/molecule-sec at 25 °C(4,SRC); this indicates that 1,1,1,3,3,3-hexafluoro-2-propanone is essentially non-reactive and that degradation via hydroxyl radical reaction is not a major fate process for this compound in the atmosphere(SRC).
규제 정보
DHS Chemicals of Interest (COI)
Hexafluoroacetone
15.67
45
Weapons of Mass Effect chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques.
안전 데이터
- OEB
- C
- OEL
- TWA: 0.1 ppm (0.7 mg/m3) [skin]
- wgk
- 3
- IDLA
- 9 ppm (61 mg/m3)
- tsca
- TSCA listed
- rtecs
- UC2450000
- ridadr
- UN 2420
- 독성
- LD50 (mg/kg) in rats: 190 orally (trihydrate), 670 dermally (sesquihydrate); in mice: 250 i.p., 180 i.v.; in rabbits: 113 dermally (trihydrate) (Kennedy)
- risk_code
- 60-14-23/24/25-34-63
- hazard_code
- T
- safety_code
- 53-26-28-36-45-7/9
- 위험 등급
- 2.3
- 기존화학 물질
- KE-05-0695
- 위험 참고 사항
- Highly Toxic
- 유해 물질 데이터
- 684-16-2(Hazardous Substances Data)
화학 및 산업
약리 정보
용도 및 제조
Uses
Used in the synthesis of organic chemicals and polymers; [ACGIH]
CHEM INT FOR HEXAFLUOROISOPROPANOL, POLYACRYLATES FOR TEXTILE COATING & POLYESTER COATING FOR TEXTILES; SOLVENT FOR ACETAL RESINS & POLYAMIDES; POLYMER ADHESIVE
1,1,1,3,3,3-Hexafluoro-2-propanone is widely used in the synthesis of polymers, medicinals, agriculture chemicals, and as a component of high-performance fluoropolymers and in the manufacture of the solvent 1,1,1,3,3,3-hexafluoro-2-propanol.
1,1,1,3,3,3-Hexafluoro-2-propanone is employed in organic synthesis. It is also used as a chemical intermediate for hexafluoroisopropanol, polyacrylates used for textile coating, and polyester coating for textiles; a solvent for acetal resins and polyamides; and a polymer adhesive.
Methods of Manufacturing
1,1,1,3,3,3-Hexafluoro-2-propanone is prepared from acetone in low yield by direct fluorination
1,1,1,3,3,3-Hexafluoro-2-propanone is manufactured by perchlorination of acetone, followed by reaction with hydrogen fluoride and a chromium catalyst. Separation of the product from excess hydrogen fluoride requires the use of a hydrogen fluoride acceptor, such as activated sodium fluoride or acetic anhydride.
The rearrangement of hexafluoropropyleneoxide induced by Lewis acids is an attractive new route that avoids the highly toxic sym-dichlorotetrafluoro- and chloropentafluoroacetones.
Formulations/Preparations
AS PRESENTLY AVAIL, ITS PURITY IS AT LEAST 99.5% & COMMONLY EXCEEDS 99.9%.
MINIMUM PURITY 95%.
General Manufacturing Information
Miscellaneous Manufacturing
2-Propanone, 1,1,1,3,3,3-hexafluoro-: ACTIVE
...1,1,1,3,3,3-HEXAFLUOROPROPAN-2-ONE...WAS INTRODUCED IN 1967 BY ALLIED CHEM CORP AS NONSELECTIVE HERBICIDE UNDER CODE NUMBER 'GC-7887'... HEXAFLUOROACETONE IS SUGGESTED FOR CONTROL OF ANNUAL & PERENNIAL WEEDS & OF WOODY PLANTS ON UNCROPPED GROUND... /TRIHYDRATE/
응용 분야
용도Hexafluoroacetone is a protecting and activatng reagent used in the synthesis of (S)-isoserine from (S)-malic acid. It is also an intermediate used to prepare hexafluorocarbinols as liver X receptor-α agonists.
일반 설명Hexafluoroacetone is a colorless, toxic, and highly reactive gas. At ambient temperatures, Hexafluoroacetone is likely to generate a considerable amount of vapor. Hexafluoroacetone is an irritant to skin, eyes and mucous membranes and is toxic by ingestion, skin absorption, and inhalation. When heated to high temperatures Hexafluoroacetone emits toxic fluoride fumes. Prolonged exposure of the container to fire or intense heat may cause Hexafluoroacetone to violently rupture and rocket. Hexafluoroacetone is used in the production of other chemicals.
상·하류 제품 정보
상류 원료
하류 제품
추가 설명
정의ChEBI: A ketone that is acetone in which all the methyl hydrogens are replaced by fluoro groups.
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