ヘキサフルオロアセトン

Hexafluoroacetone

HCID 12695

基本情報

CAS
684-16-2
標準SMILES
O=C(C(F)(F)F)C(F)(F)F
InChIKey
VBZWSGALLODQNC-UHFFFAOYSA-N
分子式
C3F6O
平均分子量
166.02 g/mol
単同位体質量
165.98533394

概要

Hexafluoroacetone can cause developmental toxicity and male reproductive toxicity according to an independent committee of scientific and health experts.

名称と識別子

優先名称
Hexafluoroacetone
IUPAC
1,1,1,3,3,3-hexafluoropropan-2-one
現地名
ヘキサフルオロアセトン
英語名
Hexafluoroacetone
分子式
C3F6O
分子量
166.02

名称と別名

Hexafluoroacetone684-16-2PerfluoroacetonePerfluoro-2-propanoneAcetone, hexafluoro-Hexafluoro-2-propanone1,1,1,3,3,3-HEXAFLUORO-2-PROPANONENCI-C56440GC 78871,1,1,3,3,3-Hexafluoroacetone2-Propanone, 1,1,1,3,3,3-hexafluoro-AKU9463N1Y
名称をさらに表示
ヘキサフルオロアセトン (5%酢酸エチル溶液)ビス(トリフルオロメチル)ケトンペルフルオロ-2-プロパノンペルフルオロアセトンヘキサフルオロイソプロパナール1,1,1,3,3,3-ヘキサフルオロアセトンヘキサフルオロ-2-プロパノン1,1,1,3,3,3-ヘキサフルオロ-2-プロパノンヘキサフルオロアセトン(CF3)2CO6FKgc7887hexafluoro-aceton
NSC-202438DTXSID9043778CHEBI:39429RefChem:146003DTXCID7023778211-676-31,1,1,3,3,3-hexafluoropropan-2-oneHexafluoropropanone

データベース識別子

CAS
684-16-2
PubChem CID
12695
DTXSID
DTXSID9043778
ChEBI
CHEBI:39429
UNII
AKU9463N1Y
EC Number
211-676-3
Nikkaji
J1.724H

物性

構造計算による物性

XLogP
1.5
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
7
回転可能結合数
0
重原子数
10

実験および物理化学的性質

Chemical Classes · 2 件

Toxic Gases & Vapors -> Corrosive Gases

Reactive agents - 2nd degree

PFASPFAS -> Other/unspecified
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 件

Log Kow = 1.46

1.46

Odor · 2 件

MUSTY ODOR BECOMES ACRID IN PRESENCE OF ACIDIC IMPURITIES

Musty odor.

Density · 4 件

1.33 G/ML @ 25 °C (LIQUID)

DENSITY: 1.65 @ 25 °C (LIQUID)

1.33 @25 °C

5.76(relative gas density)

物理化学的性質

融点
129 °C · −129 °C(lit.)
沸点
26 °C · −26 °C(lit.)
比重(密度)
1 · 1,32 g/cm3
蒸気密度
1.65 · 1.65 (vs air)
蒸気圧
4525 mm · 4525 mm Hg ( 21.1 °C)
貯蔵温度
Refrigerator

化学的性質

化学的特性Hexafluoroacetone is a colorless, nonflamma ble poison gas. Musty odor. Shipped as a liquefied com pressed gas.

安全と法規制

GHS分類

GHS Classification · 6 件

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]

危険有害性情報

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 4 件

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.)

DOT LabelPoison Gas Corrosive
Fire Hazards · 3 件

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 · 2 件

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 · 1 件

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]

安全と保護具

Fire Fighting · 2 件

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 · 3 件

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 · 2 件

· 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 · 3 件

Excerpt from NIOSH Pocket Guide for Hexafluoroacetone:

General First Aid:

(General first aid procedures)

Safe StorageFireproof if in building. Cool.
Firefighting HazardsHIGHLY DANGEROUS; WHEN HEATED, EMITS HIGHLY TOXIC FUMES. /FLUORINE/

毒性情報

Target OrgansEyes, skin, respiratory system, kidneys, reproductive system
Environmental Fate · 3 件

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).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 2 件

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 · 4 件

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 · 1 件

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).

法規制情報

DHS Chemicals of Interest (COI) · 4 件

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.

安全データ

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

化学と産業

薬理情報

Absorption, Distribution and ExcretionMost of an injected dose of radiolabeled HFA was excreted by the rat rapidly and unmetabolized in the urine, and no unusual accumulation or retention of HFA occurred in the testes.

用途と製造

Uses · 4 件

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.

U.S. Production2023: 1,000,000 - <5,000,000 lb
Industry UsesIntermediate
Methods of Manufacturing · 3 件

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 · 2 件

AS PRESENTLY AVAIL, ITS PURITY IS AT LEAST 99.5% & COMMONLY EXCEEDS 99.9%.

MINIMUM PURITY 95%.

General Manufacturing Information · 3 件

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/

応用分野 · 3 件

用途テトラフルオロエチレン、フッ化ビニル、フッ化ビニリデン、エチレンとの共重合体として用いる。ポリエチレン、ポリプロピレン、ポリブタジエン、アクリル、スチレン等へのヘキサフルオロプロパノールの側鎖導入剤、医薬品、農薬の合成原料

使用Hexafluoroacetone 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.

一般的な説明Hexafluoroacetone 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.

調製方法 · 1 件

純化方法Dehydrate hexafluoroacetone by passing the vapours over P2O5. Ethylene is removed by passing the dried vapours through a tube containing Pyrex glass wool moistened with conc H2SO4. Further purification is by low temperature distillation using Warde-Le Roy stills. Store it in the dark at -78o. [Holmes & Kutschke Trans Faraday Soc 58 333 1962, Beilstein 1 IV 3215.]

補足説明

定義ChEBI: A ketone that is acetone in which all the methyl hydrogens are replaced by fluoro groups.

関連反応

165 件

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