Methyl 2-chloroacrylate

HCID 6659

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

METHYL 2-CHLOROACRYLATE80-63-7Methyl alpha-chloroacrylatemethyl 2-chloroprop-2-enoateMethyl 2-chloro-2-propenateMethyl-2-chloroacrylate2-Chloroacrylic acid, methyl ester2-Propenoic acid, 2-chloro-, methyl esterAcrylic acid, 2-chloro-, methyl esterMethyl-alpha-chloroacrylateMethyl 2-chloro-2-propenoateNSC 32608
Show more names
METHYL CHLOROACRYLATEmethyl2-chloro-2-propenoateAcrylichloro-2acrylatedemethyleMethyl 2-chloropropenoate
Methyl .alpha.-chloroacrylatePropenoic acid, 2-chloro-, methyl estermethyl-a-chloroacrylateMethylester kyseliny 2-chlorakryloveMFCD0005136847PG4L077JNSC-32608HSDB 5238

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

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Other Monomers
Density · 3 items

1.189 at 68 °F (EPA, 1998) - Denser than water; will sink

1.189 @ 20 °C/4 °C

1.189 @ 20°C

Color/FormCOLORLESS LIQUID
Solubility · 2 items

less than 1 mg/mL at 72 °F (NTP, 1992)

> 10% in ether

Boiling Point · 3 items

126 °F at 51 mmHg (EPA, 1998)

52 °C @ 51 mm Hg

140 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits toxic fumes of /hydrogen chloride/.

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Regulatory InformationThe 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 Flammable Liquid
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsIt is a skin, eye, and lung irritant. The least trace on skin raises large blisters. It is also a respiratory poison; breathing the vapors can cause pulmonary edema. (EPA, 1998)
Hazards SummaryMay cause severe skin, eye, and respiratory tract irritation; Can cause pulmonary edema; [HSDB] Trace amounts can cause large blisters on skin; [CAMEO] Corrosive; Causes burns; Lachrymator; [MSDSonline]
Reactive GroupHalogenated Organic Compounds

Safety & protection

Fire Fighting · 1 item

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.

First AidWarning: Methyl 2-chloroacrylate is a strong eye, skin, and lung irritant and a respiratory poison. The least trace on skin raises large blisters. Caution is advised.
Nonfire Spill Response · 1 item

(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 · 1 item

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 · 4 items

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.

Isolation and EvacuationExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Human Toxicity Excerpts · 3 items

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 ExcerptsPAINFUL KERATITIS & DERMATITIS WITH VESICATION DEVELOPS, POSTULATED DUE TO GRADUAL CHANGE TO METHYL ALPHA-CHLOROACRYLATE WHICH IS VERY IRRITATING.
Toxicity DataLC50 (rat) = 500 mg/m3/2h
Non-Human Toxicity Values · 5 items

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 · 1 item

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+

Chemistry & industry

Uses & manufacturing

Uses · 4 items

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.

U.S. Imports(1983) 1.36X10+9 g /Acrylates & Acrylic Acid/
Methods of ManufacturingREACTION OF ETHYLENE TRICHLORIDE WITH FORMALDEHYDE & METHYL ALCOHOL IN THE PRESENCE OF SULFURIC ACID
Applications · 3 items

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).

Suppliers100 total

常州帝通化工有限公司+86-0519-88298848 · [email protected]
江西益众化工有限公司15307925109 15350027073 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Related reactions

31 records

Compound notes

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