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Methacryloylchlorid

Methacryloyl chloride

HCID 13528
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Grundinformationen

CAS
920-46-7
Standard-SMILES
C=C(C)C(=O)Cl
InChIKey
VHRYZQNGTZXDNX-UHFFFAOYSA-N
Summenformel
C4H5ClO
Durchschnittliche Molmasse
104,53 g/mol
Monoisotopische Masse
104,00289246

Überblick

Methacryloyl chloride appears as a liquid of density 1.07 g / cm3, boiling point 95-96 °C, and flash point 55 °F. Highly toxic. Supplied in technical grades of varying purity.

Namen und Bezeichner

Bevorzugter Name
Methacryloyl chloride
IUPAC
2-methylprop-2-enoyl chloride
Lokaler Name
Methacryloylchlorid
Englischer Name
Methacryloyl chloride
Summenformel
C4H5ClO
Molmasse
104.53

Namen und Synonyme

METHACRYLOYL CHLORIDE920-46-7Methacrylyl chloride2-Methyl-2-propenoyl chlorideMethacrylic acid chlorideMethacryl chloride2-Propenoyl chloride, 2-methyl-Methacrylic chloride2-Methylpropenoyl chlorideMethylacryloyl chloride2-Methylpropenoic acid chlorideL76O6653IO
Weitere Namen anzeigen
Methacryloyl chlorid2-METHYL-ACRYLOYL CHLORIDEmethylacryloylchloridemethacrylchloridemethacrylolchloridemethacrylicchloride
alpha-Methylacryloyl chlorideDTXSID6061280RefChem:811289DTXCID8048785213-058-9Methacryloylchloride2-methylprop-2-enoyl chloride.alpha.-Methylacryloyl chloride

Datenbank-Bezeichner

CAS
920-46-7
PubChem CID
13528
DTXSID
DTXSID6061280
UNII
L76O6653IO

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,7
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
1
Schwere Atome
6
Formalladung
0
Komplexität
85,5

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Toxic Gases & Vapors -> Other Toxic Gases & Vapors

Corrosives

SpringerMaterials PropertiesSchoenflies notation
Density · 2 Einträge

1.0871 at 68 °F (EPA, 1998) - Denser than water; will sink

1.0871 g/cu cm @ 20 °C

SolubilitySol in ether, acetone, chloroform
Boiling Point · 3 Einträge

205 °F at 760 mmHg (EPA, 1998)

96 °C

96 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits toxic fumes of /hydrogen chloride/.
Melting Point · 2 Einträge

-60 °C

-60 °C

Vapor Pressure · 2 Einträge

45.5 [mmHg]

40 [mm Hg] @25 °C

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

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P320, P321, P330, P333+P317, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 53 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

Gefahrenhinweise

Regulatory Information · 2 Einträge

Status: Active Update: 12-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23665

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.)

DOT LabelFlammable Liquid Poison Corrosive
Fire HazardsExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Health HazardsExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Hazards Summary · 1 Eintrag

Flammable and corrosive; [Hawley] A strong skin irritant; [HSDB] Reacts with water evolving hydrogen chloride gas; Highly flammable and toxic; [CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline]

Chemie und Industrie

Verwendung und Herstellung

Uses · 2 Einträge

Used in the production of hydrogel for contact lenses; [HSDB]

A hydrogel with 80% water absorption was obtained from reaction of 2-hydroxyethyl methacrylate, containing small amounts of ethylene glycol dimethacrylate with the reaction product of poly(vinylpyrrolidinone) & methacryloyl chloride /contact lenses/

Formulations/PreparationsAvailable forms: Technical 90% stabilized with phenothiazine
General Manufacturing Information2-Propenoyl chloride, 2-methyl-: ACTIVE

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Binapacryl (ISO)CHLORANOCRYLoptical plastics based on coplymer of diene macromoleculeBenzylmethacrylat4-Benzoylphenyl Methacrylate2-[2-(2-Methoxyethoxy)ethoxy]ethylmethacrylat2-Methyl-N-(4-sulfaMoyl-phenyl)-acrylaMideDecylmethacrylatIsopropylmethacrylatTEMPO MethacrylateN-Succinimidyl Methacrylate

Zugehörige Reaktionen

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Reaktionsaufzeichnung erstellen
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Reaktionsgleichung von HRID 41846
HRID 41846als Eduktuspto-grants-2013_09
Reaktionsgleichung von HRID 41848
HRID 41848als Eduktuspto-grants-2013_09
Reaktionsgleichung von HRID 44126
HRID 44126als Eduktuspto-grants-2013_09
Reaktionsgleichung von HRID 45411
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Reaktionsgleichung von HRID 45706
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EC Number
213-058-9
Nikkaji
J38.880G
Refractive Index
Index of refraction: 1.4435 at 20 °C/D
Physical Description · 2 Einträge

Methacryloyl chloride appears as a liquid of density 1.07 g / cm3, boiling point 95-96 °C, and flash point 55 °F. Highly toxic. Supplied in technical grades of varying purity.

Liquid; [Hawley] Colorless liquid; [MSDSonline]

Other Experimental PropertiesHydrolyzed by water

Physikochemische Eigenschaften

Schmelzpunkt
-60 °C · -60°C
Siedepunkt
95 to · 95 to 96 °C (203 to 205 °F; 368 to 369 K)
Dichte
1.07 g/mL · 1.07 g/mL
Brechungsindex
1.45 · 1.45
Flammpunkt
12.8 °C · 12.8 °C
storage temp.
2 · 2-8°C
Löslichkeit
Chloroform
Aggregatzustand
clear liquid
Farbe
Colorless to Red to Green
Wasserlöslichkeit
Miscible with alcohols, ethers and organic solvents. Slightly miscible with water.
BRN
878175 · 878175
Stabilität
Light and Moisture Sensitive
InChIKey
VHRYZQNGTZXDNX-UHFFFAOYSA-N
CAS Datenbank
920 · 920-46-7(CAS DataBase Reference)
NIST chemische Informationen
Methacryloyl chloride(920-46-7)
EPA chemische Informationen
Methacryloyl chloride (920-46-7)
Reactive Group
Acyl Halides, Sulfonyl Halides, and Chloroformates
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 Eintrag

METHACRYLOYL CHLORIDE is incompatible with strong oxidizing agents, alcohols, bases (including amines). Can polymerize violently; but the polymerization reaction can be inhibited by the addition of phenolthiazine. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Air and Water ReactionsHighly flammable. Reacts with water to produce gaseous hydrogen chloride (corrosive and toxic).
Highly Hazardous SubstanceChemical: Methacryloyl Chloride
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. Methacryloyl chloride is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 lbs.

Hazard Classes and Categories · 3 Einträge

Flam. Liq. 2 (100%)

Flammable liquids - Category 2

Corrosives, Flammable agents - 3rd degree, Reactive agents - 1st degree

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
First AidNote: No information on specific clinical effects of acute exposure to methacryloyl chloride was found.
Nonfire Spill ResponseExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
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 EvacuationExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Protective Action Criteria (PAC) · 3 Einträge

0.055 [mg/m3]

0.60 [mg/m3]

2.6 [mg/m3]

Personal Protective Equipment (PPE) · 1 Eintrag

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)

Toxikologische Informationen

Adverse EffectsDermatotoxin - Skin burns.
Human Toxicity ExcerptsConcn of up to 113 ppm were found in a plant handling the material. Medical reports of acute exposures revealed no resp symptoms, but skin toxicity and a severe corneal burn. /Methacrylic acid/
Non-Human Toxicity Excerpts · 2 Einträge

... severe corneal burns have been reported after acute exposure to methacrylic acid. /Methacrylic acid/

Direct contact with liquid methacrylic acid can result in blindness ... /Methacrylic acid/

Antidote and Emergency Treatment · 2 Einträge

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

Toxicity DataLC50 (rat) = 60 mg/m3/4h
Non-Human Toxicity Values · 2 Einträge

LC50 Rat ihl 60 mg/cu m/4 hr

LC50 Mouse ihl 115 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. Methacryloyl chloride is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 lbs.

Sicherheitsdaten

F
21
wgk
3
tsca
TSCA listed
ridadr
UN 3383 6.1/PG 1
hs_code
2916190090
RTECS-Nr.
OZ5791000
risk_code
11-26/27/28-34-26-22-43-52/53
hazard_code
F,T+,Xi
hazard_note
Irritant
safety_code
26-28-36/37/39-45-27-16-33-29
hazard_class
6.1
packing_group
I
Giftige Stoffe Daten
920-46-7(Hazardous Substances Data)
2-Ethyl-2-adamantyl methacrylate
3-Chlor-2-hydroxypropylmethacrylat
2-Ethoxyethyl Methacrylate
12-hydroxydodecyl methacrylate