Basic information
- CAS
80-63-7- Standard SMILES
C=C(Cl)C(=O)OC- InChIKey
AWJZTPWDQYFQPQ-UHFFFAOYSA-N- Molecular formula
- C4H5ClO2
- Average molar mass
- 120.53 g/mol
- Monoisotopic mass
- 119.99780708
Overview
Methyl 2-chloroacrylate is a colorless liquid. Used to make acrylic high polymer with properties closely resembling those of polymethylmethacrylate. Monomer for specialty polymers (e.g., aircraft glazing). (EPA, 1998)
Names & identifiers
- Preferred name
- Methyl 2-chloroacrylate
- IUPAC
- methyl 2-chloroprop-2-enoate
- English name
- Methyl alpha-chloroacrylate
- Molecular formula
- C4H5ClO2
- Molecular weight
- 120.53
Names & synonyms
Show more names
Database identifiers
- CAS
80-63-7- PubChem CID
- 6659
- DTXSID
DTXSID4025585- UNII
- 47PG4L077J
- EC Number
- 201-298-7
- Nikkaji
- J55.128G
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 97.9
Experimental & physicochemical properties
Density
1.189 at 68 °F (EPA, 1998) - Denser than water; will sink
1.189 @ 20 °C/4 °C
1.189 @ 20°C
Solubility
less than 1 mg/mL at 72 °F (NTP, 1992)
> 10% in ether
Boiling Point
126 °F at 51 mmHg (EPA, 1998)
52 °C @ 51 mm Hg
140 °C @760 [mm Hg]
Polymerization
METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/
Vapor Pressure
29.0 [mmHg]
12 [mm Hg] @25 °C
Physical Description
Methyl 2-chloroacrylate is a colorless liquid. Used to make acrylic high polymer with properties closely resembling those of polymethylmethacrylate. Monomer for specialty polymers (e.g., aircraft glazing). (EPA, 1998)
Colorless liquid; [HSDB] Chlorine-like odor; [MSDSonline]
Physicochemical properties
- Melting point
- -37 °C · -37 °C
- Boiling point
- 52 °C · 52 °C (50 mmHg)
- Density
- 1.189 · 1.189
- refractive index
- 1.442 · 1.442-1.444
- Flash point
- 33 °C · 33 °C
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- form
- Liquid
- color
- Clear colorless to slightly brown
- InChI
- InChI=1S/C4H5ClO2/c1-3(5)4(6)7-2/h1H2,2H3
- InChIKey
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N
- SMILES
- C(OC)(=O)C(Cl)=C
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 47 PG4L077J · 47PG4L077J
- EPA Substance Registry System
- 2 · Methyl 2-chloroacrylate (80-63-7)
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 330 · H330-H301-H311-H314-H226
- Precautionary statements
- 260 · P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501-P280-P302+P352-P312-P322-P361-P363-P405-P501-P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501
- Hazard Codes
- T+
- Risk Statements
- 34 · 34-26-24/25-10
- Safety Statements
- 45 · 45-38-36/37/39-26-16
- RIDADR
- 2927 · 2927
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- II
- HS Code
- 29161995 · 29161995
- Hazardous Substances Data
- 80 · 80-63-7(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (80%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P361+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 10 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard 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. Methyl 2-chloroacrylate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
Skin, Eye, and Respiratory Irritations
... AT VERY LOW CONCN (5-10 PPM) THE VAPORS OF THIS MONOMER HAVE VERY IRRITATING ACTION ON EYES.
A severe skin irritant.
Safety & protection
Fire Fighting
Fight fire from maximum distance. 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.
Nonfire Spill Response
(Non-Specific -- Poisonous Liquid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Remove and isolate contaminated clothing at the site. Stop leak if you can do so without risk. Use water spray to reduce vapors.
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
IT IS NECESSARY TO TAKE STRONG PREVENTIVE MEASURES IN FACTORY, BOTH WITH REGARD TO SKIN & RESPIRATORY TRACT.
... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/
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.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Protective Action Criteria (PAC)
0.45 [mg/m3]
5.0 [mg/m3]
17 [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)
SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/
Toxicology
Human Toxicity Excerpts
IT IS ... A RESPIRATORY POISON, & BREATHING ITS VAPORS CAN CAUSE PULMONARY EDEMA. EVEN AT VERY LOW CONCN (5-10 PPM) THE VAPORS OF THIS MONOMER HAVE VERY IRRITATING ACTION ON EYES.
REPLACEMENT OF A CH3 GROUP ... BY A CHLORINE ATOM CONSIDERABLY INCREASES THE IRRITANT PROPERTIES.
Methyl-alpha-chloroacrylate is a strong vesicant; a trace on the skin causes large blisters.
Non-Human Toxicity Values
LC50 Rat ihl 500 mg/cu m/2 hr
LC50 Mouse ihl 500 mg/cu m/2 hr
LC50 Cat ihl 500 mg/cu m/2 hr
LC50 Rabbit ihl 500 mg/cu m/2 hr
LC50 Guinea Pig ihl 500 mg/cu m/2 hr
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. Methyl 2-chloroacrylate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
Safety data
- ridadr
- 2927
- hs_code
- 29161995
- risk_code
- 34-26-24/25-10
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS06
- hazard_code
- T+
- safety_code
- 45-38-36/37/39-26-16
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard statements
- H330-H301-H311-H314-H226
- Precautionary statements
- P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501-P280-P302+P352-P312-P322-P361-P363-P405-P501-P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501
- Hazardous Substances Data
- 80-63-7(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Monomer for specialty polymers; research chemical; [HSDB]
USED TO MAKE ACRYLIC HIGH POLYMER WITH PROPERTIES CLOSELY RESEMBLING THOSE OF POLYMETHYLMETHACRYLATE.
MONOMER FOR SPECIALTY POLYMERS, EG, FOR AIRCRAFT GLAZING.
RESEARCH CHEMICAL.
Applications
DescriptionMethyl 2-chloroacrylate is a colorless liquid.Molecular weight = 120.54; Boiling point = 52℃ at51 mmHg. Hazard Identification (based on NFPA-704 MRating System): Health 3, Flammability 3, Reactivity 0.Slightly soluble in water; solubility 5 ,1 mg/mL at 22℃.
UsesMethyl 2-Chloroacrylate is used as a reagent in various coupling reactions.
General DescriptionColorless liquid. Used to make acrylic high polymer with properties closely resembling those of polymethylmethacrylate. Monomer for specialty polymers (e.g., aircraft glazing).
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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