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Hexachloraceton

Hexachloroacetone

HCID 8303
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Grundinformationen

CAS
116-16-5
Standard-SMILES
O=C(C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
InChIKey
DOJXGHGHTWFZHK-UHFFFAOYSA-N
Summenformel
C3Cl6O
Durchschnittliche Molmasse
264,7 g/mol
Monoisotopische Masse
261,8080307

Überblick

Hexachloroacetone appears as a yellow-colored liquid. Slightly soluble in water and denser than water. Vapors are much heavier than air. Irritates skin and eyes. May be toxic by ingestion or inhalation. Used to make other chemicals.

Namen und Bezeichner

Bevorzugter Name
Hexachloroacetone
IUPAC
1,1,1,3,3,3-hexachloropropan-2-one
Lokaler Name
Hexachloraceton
Englischer Name
Hexachloroacetone
Summenformel
C3Cl6O
Molmasse
264.75

Namen und Synonyme

HEXACHLOROACETONE116-16-5HexachloropropanoneHexachloro-2-propanonePerchloroacetoneHCA weedkillerKureha HCABis(trichloromethyl) ketoneAcetone, hexachloro-1,1,1,3,3,3-Hexachloro-2-propanone2-Propanone, hexachloro-2-Propanone, 1,1,1,3,3,3-hexachloro-
Weitere Namen anzeigen
1,1,1,3,3,3-hexachloro-propan-2-oneHCAhcaweedkillerHexachloroacethexachloro-aceton
GC-11061,1,1,3,3,3-HexachloropropanoneDTXSID7021601RU0LGU279YNSC-6852DTXCID701601RefChem:145903204-129-5

Datenbank-Bezeichner

CAS
116-16-5
PubChem CID
8303
DTXSID
DTXSID7021601
ChEMBL
CHEMBL3182582
ChEBI
CHEBI:82243
UNII
RU0LGU279Y
EC Number

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3,7
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
10
Formalladung
0
Komplexität
124

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Halogenated Ketones
SpringerMaterials PropertiesSchoenflies notation
OdorMUSTY ODOR
Density · 2 Einträge

1.444 AT 12 °C/12 °C

1.74 @ 12°C

Color/FormVERY LIGHT YELLOW LIQUID
Solubility · 4 Einträge

Slightly sol in water; sol in acetone

MISCIBLE WITH ALIPHATIC HYDROCARBONS, VEGETABLE OILS, 2-PROPANOL AT 25 °C

MISCIBLE WITH METHANOL, AROMATIC HYDROCARBONS, MONOCHLOROBENZENE, ISOPROPANOL AT 25 °C

Sol in benzene

Boiling Point · 2 Einträge

202-204 °C

202.2 °C @760 [mm Hg]

DecompositionWhen heated to decomp it emits toxic fumes of /hydrogen chloride/.
Melting Point · 4 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

H302 (91.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 4 Einträge

2-Propanone, 1,1,1,3,3,3-hexachloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanone, 1,1,1,3,3,3-hexachloro- 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)

Status: Active Update: 27-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/17343

Hexachloroacetone: Does not have an individual approval but may be used under an appropriate group standard

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.)

Other Safety InformationIMAP assessments - 2-Propanone, 1,1,1,3,3,3-hexachloro-: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 2 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Health Hazards · 2 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 6 Einträge

Used as reagent for N-trichloroacetylation of dipeptides, to produce chloroform, and formerly as a herbicide and pre-harvest desiccant on alfalfa seed crops; [HSDB]

Farming (Pesticides) [Category: Industry]

Reagent for N-trichloroacetylation of dipeptides under neutral conditions.

Hexafluoroacetone is manufactured by the reaction of hexachloroacetone and hydrogen fluoride in the presence of a chromium catalyst.

Chloroform may be produced from acetone by intermediate production of hexachloroacetone.

Hexachloroacetone was once used as a weedkiller, but it is currently believed to be of little commercial interest.

ImpuritiesTechnical product contains ... 4% pentachloroacetone & 8% compounds of higher boiling points.
U.S. Production2023: 1,000,000 - <8,500,000 lb
Industry UsesIntermediate
Methods of Manufacturing · 2 Einträge

BY DIRECT CHLORINATION OF ACETONE.

... Chlorination /of isopropyl alcohol/ at 70-100 °C provides nearly complete conversion of lower chloroacetones into 1,1,1,3,3-pentachloroacetone and hexachloroacetone.

Formulations/Preparations · 5 Einträge

20% TECHNICAL IN AROMATIC PETROLEUM OILS, USED 1 PART TO 9 PARTS BY VOLUME OF AROMATIC PETROLEUM OILS, AT RATES OF 50-150 US GALLONS/ACRE.

FORMULATED AS AN EMULSIFIABLE CONCENTRATE, GRANULAR, & WETTABLE POWDER.

TECHNICAL PRODUCT IS ABOUT 85% PURE.

Discontinued mixture: Urox 379, (bromacil + hexachloracetone).

GC 1106

General Manufacturing Information

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204-129-5
Nikkaji
J5.276K

-2 °C

MP: 15 °C /HEXACHLOROACETONE HYDRATE/

-2 °C

-2 °C

Vapor Density9.2 (AIR= 1)
Vapor Pressure · 3 Einträge

0.12 [mmHg]

0.376 MM HG AT 20 °C

0.376 [mm Hg] @20 °C

Refractive IndexINDEX OF REFRACTION: 1.5112 AT 20 °C/D

Physikochemische Eigenschaften

Schmelzpunkt
-3 °C · -3 °C
Siedepunkt
66 · 66-70 °C6 mm Hg(lit.)
Dichte
1.743 g/mL · 1.743 g/mL at 25 °C(lit.)
Dampfdruck
10 · 10-130Pa at 20-50℃
Brechungsindex
20 · n20/D 1.511(lit.)
Flammpunkt
230 °F · >230 °F
storage temp.
30 °C · Store below +30°C.
Aggregatzustand
clear liquid
Farbe
Colorless to Almost colorless
Wasserlöslichkeit
SLIGHTLY SOLUBLE
BRN
1707475 · 1707475
Henry's Law Constant
1 · 1.0×102 mol/(m3Pa) at 25℃, Zhang et al. (2010)
Dielectric constant
3.99 · 3.9900000000000002
InChI
1S/C3Cl6O/c4-2(5,6)1(10)3(7,8)9
InChIKey
DOJXGHGHTWFZHK-UHFFFAOYSA-N
SMILES
ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl
LogP
2.48 · 2.48-2.59 at 30℃
CAS Datenbank
116 · 116-16-5(CAS DataBase Reference)
NIST chemische Informationen
2 · 2-Propanone, 1,1,1,3,3,3-hexachloro-(116-16-5)
EPA chemische Informationen
Hexachloroacetone (116-16-5)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 2 Einträge

Highly irritating; Produces phosgene when heated; [Hawley] A skin and mucous membrane irritant; A mild lachrymator; Oral LD50 (rat) = 1550 mg/kg; In animal studies, caused pulmonary edema after inhalation and liver and kidney injury after ingestion; Can cause burns of skin and eyes; [HSDB] Oral TDLo (rat) = 450.8 mg/kg (1-14D preg) for maternal effects (oogenesis); [RTECS] Contact with molten substance may cause severe burns; [CAMEO] An irritant; Effects in high-dose animal studies include pulmonary edema; [MSDSonline]

The major hazards encountered in the use and handling of hexachloroacetone stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal contact), exposure to this musty-smelling liquid may occur from its use as an intermediate in the production of chloroform and hexafluoroacetone. Effects from exposure may include contact burns to the skin and eyes, and irritation of the mucous membranes. If contact should occur, immediately flush affected eyes with running water for at least 15 minutes, and wash skin with soap and water. Remove contaminated clothing and shoes at the site. While hexachloroacetone does not ignite easily, it may burn with the production of irritating and poisonous gases. Also, heating of this substance may give rise to toxic thermal decomposition products such as chlorine or phosgene. Fires involving hexachloroacetone may be extinguished with dry chemical, CO2, Halon, water spray, fog, or standard foam. Hexachloroacetone should be stored in well-ventilated areas, away from heat and sources of ignition. Containers for international shipment by air and by water must bear the labels, "Keep away from food" and "Poison", respectively. Small spills of hexachloroacetone may be taken up with sand or other noncombustible absorbent and placed into containers for later disposal. Before implementing land disposal of waste hexachloroacetone, consult with environmental regulatory agencies for guidance.

DOT ID and Guide2661 153
Reactive GroupHalogenated Organic Compounds
Reactivity Profile · 1 Eintrag

HEXACHLOROACETONE is a halogenated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

DOT Emergency Guidelines · 5 Einträge

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (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 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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 153: SUBSTANCES - TOXIC and/or CORROSIVE (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 HEXACHLOROACETONE (8 total), please visit the HSDB record page.

DOT Hazard Classification · 4 Einträge

Hexachloroacetone

UN2661

Div 6.1 Poisonous materials (49 eCFR § 173.132)

PG III: the degree of danger presented by the material is minor

Air and Water ReactionsSlightly soluble in water.

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Accidental Release Measures · 2 Einträge

· 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.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 1 Eintrag

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.

Isolation and Evacuation · 2 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Protective Action Criteria (PAC) · 3 Einträge

0.14 [mg/m3]

3.0 [mg/m3]

18 [mg/m3]

Personal Protective Equipment (PPE)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Emergency Response Planning GuidelinesSmall Fire

Toxikologische Informationen

Interactions · 1 Eintrag

Hexachloroacetone without solvent was mutagenic, and this activity was enhanced when it was dissolved in dimethyl sulfoxide; in acetone it was not mutagenic. A time dependent reaction of hexachloroacetone with dimethyl sulfoxide was the only test material solvent interaction found. Results show clearly that dimethyl sulfoxide is not an appropriate solvent for hexachloroacetone.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Hexachloroacetone has a vapor pressure of 0.376 mm Hg at 20 °C(2) indicating that the chemical is expected to evaporate significantly from dry surfaces(SRC). The estimated Koc of 1,886(3,SRC) suggests that hexachloroacetone will have low mobility in soil and will not leach(1). No data are available regarding biodegradation or other chemical processes in soil(SRC).

AQUATIC FATE: If released to water, hexachloroacetone is expected to evaporate into the atmosphere with a volatilization half-life of 6.5 hours from a model river(SRC). No data are available on other potential degradation processes in water. Based on the estimated Koc of 1,886(1,SRC), hexachloroacetone may partition from the water column to the sediment.

ATMOSPHERIC FATE: Based on a vapor pressure of 0.376 at 20 °C(1), hexachloroacetone will exist almost entirely in the vapor phase in the ambient atmosphere(2,SRC). Hexachloroacetone will not react with photochemically produced hydroxyl radicals in the ambient atmosphere(3,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.
Effluent Concentrations · 2 Einträge

Concentration of hexachloroacetone in chlorination stage effluent from a bleached kraft pulp mill in the interior of British Columbia was approximately 1.1 mg/l. (Fresh sample taken immediately prior to analysis) /From table/

Hexachloroacetone was deteted in pulp mill effluents with a concentration of approximately 30 g hexachloroacetone per ton pulp(1) and a concentration of approximately 0.2 g hexachloroacetone in the spent chlorination liquor per ton pulp(2) after the chlorination process. Hexachloroacetone was found in chlorinated municipal sewage effluents at a concentration of 30 ppb(3).

Soil Adsorption/MobilityBased on an estimated log Kow of 3.490(2) and a regression derived equation(1), the Koc for hexachloroacetone can be estimated to be 1,886(SRC) indicating that hexachloroacetone has low mobility in soil(3).
Natural Pollution SourcesHexachloroacetone is a constituent of the edible Hawaiian (USA) seaweed, Asparagopsis taxiformis (Limu kohu).
Human Toxicity ExcerptsNO CLINICAL POISONINGS KNOWN. IRRITATING TO MUCOUS MEMBRANES AND SKIN, SLIGHT LACRIMATORY ACTION.
Artificial Pollution Sources · 2 Einträge

ANALYSIS OF A SAMPLE OF CHLORINATION STAGE EFFLUENT FROM A BLEACHED KRAFT PULP MILL REVEALED THE PRESENCE OF HEXACHLOROACETONE.

Hexachloroacetone was detected after the chlorination process in pulp mill effluents with a concentration of approximately 30 g hexachloroacetone per ton pulp(1) and a concentration of approximately 0.2 g hexachloroacetone in the spent chlorination liquor per ton pulp(2). Hexachloroacetone was found in chlorinated municipal sewage effluents at a concentration of 30 ppb(3). Hexachloroacetone was once used as a weedkiller, but it is currently believed to be of little commercial interest(4).

Environmental BioconcentrationBased on an estimated log Kow of 3.490(2), the BCF for hexachloroacetone can be estimated to be 264 using a recommended regression derived equation(1,SRC).
Volatilization from Water/Soil · 1 Eintrag

Based on an estimated log Kow of 3.49(2) and a recommended regression equation, the water solubility is estimated to be 154.7 mg/L(2,SRC). Based on a vapor pressure of 0.376 mm Hg at 20 °C(1) and a water solubility of 154.7 mg/L(2), the Henry's Law constant is estimated to be 8.33X10-4 atm cu-m/mole at 25 °C(SRC). This value of Henry's Law constant suggests that hexachloroacetone will volatilize significantly, but not rapidly from water. Based on this value, the volatilization half-life of hexachloroacetone from a model river 1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec has been estimated to be approximately 6.5 hours(3,SRC).

Non-Human Toxicity Excerpts · 5 Einträge

... /SRP: SIGNIFICANT/ PERCUTANEOUS TOXICITY IN RABBITS.

Inhalation exposure caused pulmonary edema, hemorrhage & congestion in laboratory rats. Only slight repair of lung tissue was noted in these animals, 15 days after exposure. Chronic feeding studies in rats revealed hypertrophy of liver & kidneys, & slight growth depression.

The oral toxicity of hexachloroacetone in adult male albino rats of the Wistar strain was CNS depression. The dermal toxicity in adult male albino rabbits was mild CNS depression and erythema at exposed area. The inhalation toxicity in adult albino rats was CNS depression manifested as hind leg instability, loss of postural and righting reflexes, and death. Gross exam of the lung immediately after death presented a picture of widespread hemorrhage. Edema, hemorrhage and congestion of the lung was evident microscopically 15 days after termination of exposure, with little indication of repair of the injury.

THE MUTAGENIC PROPERTIES OF HEXACHLOROACETONE IN SHORT TERM BACTERIAL MUTAGEN ASSAY SYSTEMS: HEXACHLOROACETONE REVERTS THE AMES SALMONELLA TYPHIMURIUM STRAINS TA98 & TA100, BUT NOT THE NON-PLASMID STRAINS TA1535, TA1537, & TA1538. IN ABSENCE OF SOLVENT, THE NUMBER OF REVERTANT COLONIES IS 5 TIMES THE SPONTANEOUS REVERSION RATE FOR TA100 & 10 TIMES THE SPONTANEOUS REVERSION RATE FOR TA98 WITH 26 MG HEXACHLOROACETONE/PLATE.

Compounds ... /including/ hexachloroacetone ... identified in pulp mill effluents were screened for genetic activity in growing cells using Saccharomyces cerevisiae strains D7 and XV185-14C without and with S9. Hexachloroacetone without solvent was mutagenic.

Environmental Abiotic DegradationHexachloroacetone will not react with photochemically produced hydroxyl radicals in the ambient atmosphere based on the fact that hexachloroacetone has no extractable protons(1,SRC).

Sicherheitsdaten

F
19
wgk
2
tsca
TSCA listed
ridadr
UN 2661
hs_code
29147090
RTECS-Nr.
UC2100000
risk_code
22-51/53
hazard_code
Xn,N
safety_code
24/25-61
hazard_class
6.1
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
116-16-5(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 2Skin Sens. 1
· 3 Einträge

Miscellaneous Manufacturing

2-Propanone, 1,1,1,3,3,3-hexachloro-: ACTIVE

Discontinued by Allied Chemical Corp.

Anwendungen · 1 Eintrag

VerwendenHexachloro-2-propanone (hexachloroacetone) was used in the synthesis of chirally deuterated benzyl chlorides and enol phosphate 2,2-dichloro-1-(trichloromethyl)ethenyl diethyl phosphate. It was also used in obtaining efficient amino acid activation by exploiting the rapid formation of acid chlorides under low temperature and acid/base free conditions.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole1,1-DichloracetonPentachloraceton1,1,1-TRICHLOROACETONE

Nachgelagerte Produkte

DiphenylcarbamoylchloridIsopropyltrichloracetatFLUOROPENTACHLOROACETONE2,2,2-trichloro-N-1,3-thiazol-2-ylacetamide