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Methyl-2-chloracrylat

Methyl 2-chloroacrylate

HCID 6659
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Grundinformationen

CAS
80-63-7
Standard-SMILES
C=C(Cl)C(=O)OC
InChIKey
AWJZTPWDQYFQPQ-UHFFFAOYSA-N
Summenformel
C4H5ClO2
Durchschnittliche Molmasse
120,53 g/mol
Monoisotopische Masse
119,99780708

Überblick

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)

Namen und Bezeichner

Bevorzugter Name
Methyl 2-chloroacrylate
IUPAC
methyl 2-chloroprop-2-enoate
Lokaler Name
Methyl-2-chloracrylat
Englischer Name
Methyl alpha-chloroacrylate
Summenformel
C4H5ClO2
Molmasse
120.53

Namen und Synonyme

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
Weitere Namen anzeigen
METHYL CHLOROACRYLATEmethyl2-chloro-2-propenoateAcrylichloro-2acrylatedemethyleMethyl 2-chloropropenoate
Methyl .alpha.-chloroacrylatePropenoic acid, 2-chloro-, methyl estermethyl-a-chloroacrylateMethylester kyseliny 2-chlorakryloveMFCD0005136847PG4L077JNSC-32608HSDB 5238

Datenbank-Bezeichner

CAS
80-63-7
PubChem CID
6659
DTXSID
DTXSID4025585

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,5
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
7
Formalladung
0
Komplexität
97,9

Experimentelle und physikochemische Eigenschaften

PolymersPlastics & Rubber -> Other Monomers
Density · 3 Einträge

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 Einträge

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

> 10% in ether

Boiling Point · 3 Einträge

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/.
Polymerization · 1 Eintrag

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

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 · 4 Einträge

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.

Gefahrenhinweise

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
Reactivity Alerts

Chemie und Industrie

Verwendung und Herstellung

Uses · 4 Einträge

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

Anwendungen

VerwendenMethyl 2-Chloroacrylate is used as a reagent in various coupling reactions.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2-Propen-1-ol, 2,3,3-trichloro-Propanoic acid, 3-bromo-2-chloro-, methyl ester1,1,2,3-Tetrachlor-1-propenDalapon-methyl esterBenzaldehydMethanolEthylenFormaldehydMethylchloracetatTrichlorethylenacrylic acid methyl ester

Zugehörige Reaktionen

31
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 143796
HRID 143796als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 271043
HRID 271043als Eduktuspto-grants-2008_11
Reaktionsgleichung von HRID 271044
HRID 271044als Eduktuspto-grants-2008_11
Reaktionsgleichung von HRID 374246
HRID 374246als Eduktuspto-grants-1992_11
Reaktionsgleichung von HRID 399258
HRID 399258als Eduktuspto-grants-1998_10
Reaktionsgleichung von HRID 421941
HRID 421941als Eduktuspto-grants-2012_01
Reaktionsgleichung von HRID 465682
HRID 465682als Eduktuspto-grants-1992_10
Reaktionsgleichung von HRID 465685
HRID 465685als Eduktuspto-grants-1992_10
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UNII
47PG4L077J
EC Number
201-298-7
Nikkaji
J55.128G
· 2 Einträge

29.0 [mmHg]

12 [mm Hg] @25 °C

Refractive IndexIndex of refraction: 1.4420 @ 20 °C/D
Physical Description · 2 Einträge

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]

Physikochemische Eigenschaften

Schmelzpunkt
-37 °C · -37 °C
Siedepunkt
52 °C · 52 °C (50 mmHg)
Dichte
1.189 · 1.189
Brechungsindex
1.442 · 1.442-1.444
Flammpunkt
33 °C · 33 °C
storage temp.
2 · Keep in dark place,Inert atmosphere,2-8°C
Aggregatzustand
Liquid
Farbe
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
EPA chemische Informationen
2 · Methyl 2-chloroacrylate (80-63-7)
Highly Flammable
Reactivity ProfileMETHYL 2-CHLOROACRYLATE is sensitive to prolonged exposure to light, moisture and heat. This chemical is incompatible with oxidizers and polymerizers. (NTP, 1992)
Air and Water ReactionsHighly flammable. Insoluble in water.
CERCLA Reportable Quantities · 1 Eintrag

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.

Hazard Classes and CategoriesFlam. Liq. 3 (80%)
Skin, Eye, and Respiratory Irritations · 2 Einträge

... AT VERY LOW CONCN (5-10 PPM) THE VAPORS OF THIS MONOMER HAVE VERY IRRITATING ACTION ON EYES.

A severe skin irritant.

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

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 Eintrag

(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 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.

Preventive Measures · 4 Einträge

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]:
Protective Action Criteria (PAC) · 3 Einträge

0.45 [mg/m3]

5.0 [mg/m3]

17 [mg/m3]

Personal Protective Equipment (PPE) · 2 Einträge

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/

Acute Exposure Guideline Levels (AEGLs)The compound is currently at the Holding Status AEGLs which have been reviewed by the NAC/AEGL Committee and are on hold due to insufficient data to develop AEGL values.
AEGLs NotesAEGLs Status: Holding

Toxikologische Informationen

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

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 Einträge

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

Regulatorische Informationen

CERCLA Reportable Quantities · 1 Eintrag

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.

Sicherheitsdaten

ridadr
2927
hs_code
29161995
risk_code
34-26-24/25-10
hazard_code
T+
safety_code
45-38-36/37/39-26-16
hazard_class
6.1(a)
packing_group
II
Giftige Stoffe Daten
80-63-7(Hazardous Substances Data)

Nachgelagerte Produkte

Methyl 3-hydroxythiophene-2-carboxylate1H-Pyrrole-2-carboxylicacid,3-hydroxy-,methylester(9CI)