Basic information
- Standard SMILES
O=C(CCl)CCl- InChIKey
SUNMBRGCANLOEG-UHFFFAOYSA-N- Molecular formula
- C3H4Cl2O
- Average molar mass
- 126.97 g/mol
- Monoisotopic mass
- 125.96392011
Overview
1,3-dichloroacetone appears as a crystalline solid. Denser than water and insoluble in water. Inhalation of dust or powder may cause adverse health reactions.
Names & identifiers
- Preferred name
- 1,3-Dichloroacetone
- IUPAC
- 1,3-dichloropropan-2-one
- English name
- 1,3-Dichloroacetone
- Molecular formula
- C3H4Cl2O
- Molecular weight
- 126.97
Names & synonyms
Show more names
Database identifiers
- CAS
534-07-6- PubChem CID
- 10793
- DTXSID
DTXSID2021577- ChEMBL
CHEMBL1231783- ChEBI
CHEBI:156485- UNII
- UFH8559WS5
- EC Number
- 208-585-6
- Nikkaji
- J1.590C
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 46.8
Experimental & physicochemical properties
Density
1.3826 at 114.8 °F (EPA, 1998) - Denser than water; will sink
1.3826 at 46 °C/4 °C
1.3826 @ 46°C
Color/Form
Prisms or needles
Plates, needles on distillation
Solubility
> 10% in water
> 10% in ethanol
> 10% in ether
Boiling Point
343 °F at 760 mmHg (EPA, 1998)
173.4 °C
173 °C @760 [mm Hg]
Melting Point
113 °F (EPA, 1998)
45 °C
45 °C
Physicochemical properties
- Melting point
- 43 °C · 43 °C
- Boiling point
- 73 °C733.4 · 73 °C733.4 mm Hg(lit.)
- Density
- 1.383 g/mL · 1.383 g/mL at 25 °C(lit.)
- vapor density
- 4.38 · 4.38 (vs air)
- vapor pressure
- 0.1 mm · <0.1 mm Hg ( 20 °C)
- refractive index
- 1.44 · 1.4400
- Flash point
- 193 °F · 193 °F
- storage temp.
- Refrigerator (+4°C) + Poison room
- solubility
- alcohol: very soluble
- form
- Crystals
- color
- White or colorless
- Specific Gravity
- 1.383 · 1.383
- PH
- 4.2 · 4.2 (10g/l, H2O, 20℃)
- Water Solubility
- 27.9 g/L · 27.9 g/L (20 º C)
- Merck
- 14 · 14,3052
- BRN
- 605456 · 605456
- Dielectric constant
- 14 · 14.0(20℃)
- InChI
- 1S/C3H4Cl2O/c4-1-3(6)2-5/h1-2H2
- InChIKey
- SUNMBRGCANLOEG-UHFFFAOYSA-N
- SMILES
- ClCC(=O)CCl
- CAS DataBase Reference
- 534 · 534-07-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 8559 WS5 · UFH8559WS5
- NIST Chemistry Reference
- 1 · 1,3-Dichloro-2-propanone(534-07-6)
- EPA Substance Registry System
- Bis(chloromethyl) ketone (534-07-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300+H310+H330-H314
- Precautionary statements
- 501 · P501-P260-P270-P262-P271-P264-P280-P284-P361+P364-P303+P361+P353-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P405
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- T+,F
- Risk Statements
- 24 · 24-26/28-34-68-36/37/38-11
- Safety Statements
- 26 · 26-36/37/39-45-28A-1-28-16
- RIDADR
- 2649 · UN 2649
- WGK Germany
- 3 · 3
- RTECS
- 1430000 · UC1430000
- F
- 19 · 19
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- HS Code
- 29147090 · 29147090
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 1 InhalationAcute · Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 2 OralMuta. 2Skin Corr. 1B
- Hazardous Substances Data
- 534 · 534-07-6(Hazardous Substances Data)
- Toxicity
- 1250 ng/plate · mmo-sat 1250 ng/plate MUREAV 157,111,85
- REACH Registrations
- Active
- Limited Quantities
- 100 ml · 100ml (liquid) or 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P203, P260, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P320, P321, P330, P361+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 82 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Propanone, 1,3-dichloro-
Status: Active Update: 15-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/17083
1,3-Dichloroacetone: 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.)
Fire Hazards
When heated to decomposition, it emits highly toxic fumes of chlorides. This material may burn but does not ignite readily. Container may explode in heat of fire. (EPA, 1998)
· Combustible material: may burn but does not ignite readily.
Health Hazards
It may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating or poisonous gases. Runoff from fire control water may give off poisonous gases. Runoff from fire control or dilution water may cause pollution. (EPA, 1998)
· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.
Hazards Summary
The major hazards encountered in the use and handling of bischloromethyl ketone stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal absorption), exposure to this crystalline substance may occur from its use as vesicant or in the synthesis of citric acid. Effects from exposure may include contact burns to the skin and eyes, and even death with sufficiently high concentrations. In activities or situations where over exposure may occur, wear a self-contained breathing apparatus and chemical protective clothing which is specifically recommended by the shipper or producer. If contact should occur. immediately flush affected skin or eyes with running water for at least 15 minutes, and remove contaminated clothing and shoes at the site. While bischloromethyl ketone does not ignite easily, it may burn with the production of irritating and poisonous gases. Also, containers may explode violently in the heat of a fire. Fires involving bischloromethyl ketone may be extinguished with dry chemical, CO2, Halon, water spray, fog, or standard foam. Fight the fire from as far a distance as possible, and dike runoff from fire control water. Containers for international shipment by air and water must bear the labels, "Corrosive" and "Poison", respectively. Small spills of bischloromethyl ketone may be taken up and placed into containers for later disposal (liquid solutions are first absorbed by sand or other noncombustible material). Large liquid spills should be diked far ahead of the spill area for later disposal. Prior to implementing land disposal of bischloromethyl ketone, consult with environmental regulatory agencies for guidance.
Reactivity Profile
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
/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 BISCHLOROMETHYL KETONE (8 total), please visit the HSDB record page.
DOT Hazard Classification
1,3-Dichloroacetone
UN2649
Div 6.1 Poisonous materials (49 eCFR § 173.132)
PG II: the degree of danger presented by the material is medium
CERCLA Reportable Quantities
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Bis(chloromethyl) ketone is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10/10,000 lbs.
Safety & protection
Fire Fighting
Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site. If water pollution occurs, notify appropriate authorities.
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.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Warning: Bis(chloromethyl) ketone may be fatal if inhaled, swallowed, or absorbed through skin.
General First Aid:
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.
Isolation and Evacuation
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Immediate precautionary measure
Protective Action Criteria (PAC)
0.025 [mg/m3]
0.27 [mg/m3]
1.0 [mg/m3]
Personal Protective Equipment (PPE)
For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
Toxicology
Regulatory information
CERCLA Reportable Quantities
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Bis(chloromethyl) ketone is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10/10,000 lbs.
Safety data
- F
- 19
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UC1430000
- ridadr
- UN 2649
- hs_code
- 29147090
- Toxicity
- mmo-sat 1250 ng/plate MUREAV 157,111,85
- risk_code
- 24-26/28-34-68-36/37/38-11
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- T+,F
- safety_code
- 26-36/37/39-45-28A-1-28-16
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- Hazard statements
- H300+H310+H330-H314
- Limited Quantities
- 100ml (liquid) or 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 2 OralMuta. 2Skin Corr. 1B
- Precautionary statements
- P501-P260-P270-P262-P271-P264-P280-P284-P361+P364-P303+P361+P353-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P405
- Hazardous Substances Data
- 534-07-6(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Vesicant
Synthesis of citric acid based on the reaction of glycerol derived 1,3-dichloroacetone with cyanide.
Applications
Description1,3-Dichloroacetone is a chemical substance with the molecular formula C3H4Cl2O. TLC has discovered that it is a metabolite of 1,3-dichloropropanol. The crystalline solid is denser than water and is not water-soluble.
DescriptionBis(chloromethyl)ketone is a crystalline solid.Molecular weight=127.02; Freezing/Melting point=45℃;Boiling point=173℃. Hazard Identification (based onNFPA-704 M Rating System): Health 3, Flammability 1,Reactivity 0. Soluble in water.
Uses1,3-Dichloroacetone was used as acceptor substrate in the cross-aldol reaction with donor substrates such as acetone, cyclopentanone and cyclohexanon
General DescriptionA crystalline solid. Denser than water and insoluble in water. Inhalation of dust or powder may cause adverse health reactions.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: 1,3-dichloroacetone is a ketone that is propan-2-one in which a hydrogen at positions 1 and 3 have been replaced by chloro groups. It is used in the synthesis of citric acid. Also used as a solvent and as an intermediate in organic synthesis. It is an organochlorine compound and a ketone. It is functionally related to a 1,3-dichloropropan-2-ol.
Related reactions
Linked notes
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