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2-Isocyanatoethyl methacrylate

HCID 35409
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Basic information

CAS
30674-80-7
Standard SMILES
C=C(C)C(=O)OCCN=C=O
InChIKey
RBQRWNWVPQDTJJ-UHFFFAOYSA-N
Molecular formula
C7H9NO3
Average molar mass
155.15 g/mol
Monoisotopic mass
155.05824315

Overview

Methacryloyloxyethyl isocyanate is a liquid. (EPA, 1998)

Names & identifiers

Preferred name
2-Isocyanatoethyl methacrylate
IUPAC
2-isocyanatoethyl 2-methylprop-2-enoate
English name
2-Isocyanatoethyl methacrylate
Molecular formula
C7H9NO3
Molecular weight
155.15

Names & synonyms

2-Isocyanatoethyl methacrylate30674-80-72-isocyanatoethyl 2-methylprop-2-enoateIsocyanoethyl methacrylateMETHACRYLOYLOXYETHYL ISOCYANATE2-Propenoic acid, 2-methyl-, 2-isocyanatoethyl esterbeta-Isocyanatoethyl methacrylateMetharcyclic acid, 2-isocyanatoethyl esterKARENZ MOI2-methacryloyloxyethyl isocyanateMethacrylic acid, 2-isocyanatoethyl esterMetharcylic acid, 2-isocyanatoethyl ester
Show more names
MOIiemISOCYANATOETHYL METHACRYLATE2-IsocyanatoethylKarenz MOI (IEM)isocyanoethylmethacrylateEthyl2-isocyanatoacrylate2-Isocyatoethyl methacrylatemethacryloyloxyethylisocyanate
828DBI7X912-(Methacryloyloxy)ethyl isocyanateDTXSID6051986ISOCYANIC ACID, 2-HYDROXYETHYL ESTER METHACRYLATE (ESTER)RefChem:156846DTXCID9030549METHACRYLIC ACID BETA-ISOCYANATOETHYL ESTER250-284-7

Database identifiers

CAS
30674-80-7
PubChem CID
35409
DTXSID
DTXSID6051986
UNII
828DBI7X91
EC Number
250-284-7
Nikkaji
J60.904H

Properties

Computed structural propertiesFilling in

XLogP
2.3
Topological polar surface area
55.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
11
Formal charge
0
Complexity
204

Experimental & physicochemical properties

Chemical ClassesToxic Gases & Vapors -> Monoisocyanates
Physical Description · 2 items

Methacryloyloxyethyl isocyanate is a liquid. (EPA, 1998)

Colorless liquid with a peppery odor; [CHEMINFO]

Other Experimental Properties · 2 items

Compound is stable in moist air for up to 5.2 hours at 5% and 2.6 hours at 50% RH.

Compound is readily hydrolyzed in dilute water solution.

Physicochemical properties

Melting point
-45 °C · -45 °C
Boiling point
211 °C · 211 °C
Density
1.1 · 1.10
vapor pressure
18 Pa · 18Pa at 20℃
refractive index
1.45 · 1.45
Flash point
97 °C · 97 °C
storage temp.
2 · 2-8°C
form
clear liquid

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 53 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information · 3 items

Chemical: 2-Propenoic acid, 2-methyl-, 2-isocyanatoethyl ester

Status: Active Update: 20-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5762

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 LabelPoison
Fire Hazards · 1 item

(Non-Specific -- Isocyanates and Solutions, n.o.s. (Flammable, Poisonous)) May be ignited by heat, sparks, or flames. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff from fire control or dilution water may cause pollution. (EPA, 1998)

Health Hazards(Non-Specific -- Isocyanates and Solutions, n.o.s. (Flammable, Poisonous)) Poisonous; may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. (EPA, 1998)
Hazards Summary

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

Uses & manufacturing

Uses · 2 items

Used in adhesives, epoxy resins, and marine and automotive coatings; [CHEMINFO]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

General Manufacturing Information2-Propenoic acid, 2-methyl-, 2-isocyanatoethyl ester: ACTIVE

Applications

UsesA latent cross-linker for resins.1

General DescriptionLiquid.

Related reactions

52 records
New reaction record
HRID 2677 reaction equation
HRID 2677As reactantuspto-grants-1998_03
HRID 3077 reaction equation
HRID 3077As reactantuspto-grants-1998_03
HRID 4694 reaction equation
HRID 4694As reactantuspto-grants-1988_02
HRID 124454 reaction equation
HRID 124454As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 212771 reaction equation
HRID 212771As productTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 215696 reaction equation
HRID 215696As reactantuspto-grants-2012_06
HRID 222454 reaction equation
HRID 222454As reactantuspto-grants-2012_06
HRID 234081 reaction equation
HRID 234081As reactantuspto-grants-1997_01
Page 1 of 7

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
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color
Colorless to Almost colorless
Water Solubility
4.214 g/L · 4.214g/L at 25℃
InChI
InChI=1S/C7H9NO3/c1-6(2)7(10)11-4-3-8-5-9/h1,3-4H2,2H3
InChIKey
RBQRWNWVPQDTJJ-UHFFFAOYSA-N
SMILES
C(OCCN=C=O)(=O)C(C)=C
LogP
1.72 · 1.72
FDA UNII
828 DBI7X91 · 828DBI7X91
EPA Substance Registry System
Methacryloyloxyethyl isocyanate (30674-80-7)
UNSPSC Code
12162002 · 12162002
NACRES
23 · NA.23
Symbol(GHS)
5 · GHS05,GHS06,GHS08
Signal word
Danger
Hazard statements
302 · H302-H315-H317-H318-H330-H334
Precautionary statements
260 · P260-P280-P301+P312-P302+P352-P304+P340+P310-P305+P351+P338
Hazard Codes
T+,T
Risk Statements
21 · 21/22-26-37/38-41-42-42/43-36/37/38-23-22
Safety Statements
26 · 26-36/37/39-45-36/37-23
RIDADR
2206 · UN 2206 6.1/PG 3
WGK Germany
3 · 3
RTECS
4950000 · OZ4950000
TSCA
TSCA listed
HazardClass
6.1 · 6.1(a)
PackingGroup
II
HS Code
2929109000 · 2929109000
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. 4 OralEye Dam. 1Resp. Sens. 1Skin Irrit. 2Skin Sens. 1
Hazardous Substances Data
30674 · 30674-80-7(Hazardous Substances Data)
Toxicity
50 · rat,LC50,inhalation,4ppm/6H (4ppm),Drug and Chemical Toxicology. Vol. 3, Pg. 381, 1980.
REACH Registrations
Active
Limited Quantities
5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
May cause eye injury and skin burns; Inhalation of high concentrations may cause pulmonary edema although this effect has not been reported in the workplace. [CHEMINFO]
Reactive GroupIsocyanates and Isothiocyanates
TSCA Requirements · 2 items

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Propenoic acid, 2-methyl-,2-isocyanatoethyl ester is included on this list.

Reactivity AlertsPolymerizable
Reactivity Profile · 1 item

Isocyanates and thioisocyanates, such as METHACRYLOYLOXYETHYL ISOCYANATE, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide.

Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
Highly Hazardous SubstanceChemical: Methacryloyloxyethyl Isocyanate
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. Methacryloyloxyethyl isocyanate 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.

Safety & protection

Fire Fighting · 1 item

(Non-Specific -- Isocyanates and Solutions, n.o.s. (Flammable, Poisonous)) 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. Move container from fire area if you can do it without risk. Cool containers that are exposed to flames with water from the side until well after fire is out. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

First AidWarning: Methacryloyloxyethyl isocyanate is an irritant.
Nonfire Spill Response · 1 item

(Non-Specific -- Isocyanates and Solutions, n.o.s. (Flammable, Poisonous)) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Shut off ignition sources; no flares, smoking or flames in hazard area. Do not touch spilled material; 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 · 1 item

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.

Isolation and EvacuationExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Protective Action Criteria (PAC) · 3 items

0.0091 [ppm]

0.10 [ppm]

1.0 [ppm]

Personal Protective Equipment (PPE) · 1 item

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)

Emergency Response Planning GuidelinesERPG-1: Insufficient data - one hour exposure limit: 1 = mild transient health effects or objectionable odor [AIHA]
Other Standards Regulations and GuidelinesEmergency Response Planning Guidelines (ERPG): ERPG(1) Not appropriate; ERPG(2) 0.1 ppm (without serious, adverse effects) for up to 1 hr exposure; ERPG(3) 1 ppm (not life threatening) up to 1 hr exposure.

Toxicology

Treatment · 1 item

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

Health Effects · 1 item

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1 item

Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)
Human Toxicity Excerpts · 1 item

Isocyanates are irritating to the skin and the mucous membranes, the skin conditions ranging from localized itching to more or less widespread eczema. Eye affections are less common and, although lacrimation is often found, conjunctivitis is rare. The commonest and most serious troubles, however, are those affecting the respiratory systems. /Isocyanates/

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 2 items

Guinea pigs were exposed to daily induction exposures with an aerosol of bovine serum albumin (BSA) or bovine serum albumin conjugated with isocyanatoethyl methacrylate (IEM) or isocyanatoethyl propionate (IEP). After approx 2 wk significant incr in respiratory rate occurred in the guinea pigs exposed to the isocyanate conjugates. The number of animals responding was related to the degree of conjugation of isocyanate to protein. The isocyanates conjugated to another carrier, guinea pig serum albumin (GSA), elicited responses. In guinea pigs responding to bovine serum albumin-isocyanatoethyl methacrylate, 0.01 ppm isocyanatoethyl methacrylate monomer did not elicit responses; 0.1-0.4 ppm isocyanatoethyl methacrylate vapor elicited responses similar to conjugates but which were delayed; 0.5 and 0.6 ppm induced irritation responses. Guinea pigs developing responses to either of the isocyanate conjugates displayed cross-reactions to challenge with the other. Application of bovine serum albumin-isocyanatoethyl propionate or isocyanatoethyl propionate monomer to the scratched skin of guinea pigs that responded by inhalation to bovine serum albumin-isocyanato propionate resulted in immediate wheal and flare responses not seen in unexposed animals.

The dominant lethal test was used to evaluate the mutagenic potential of isocyanatoethyl methacrylate in rats. Male Sprague-Dawley rats were exposed to 0, 25, 80, or 250 ppb of isocyanatoethyl methacrylate by inhalation for 6 hr/day for 10 wk (one spermatogenic cycle). After the exposure period, the males were bred with untreated virgin female rats. At approx mid-gestation, the females were sacrificed and the number of corpora lutea, implantations and resorptions were recorded. Statistical analysis of these data indicated that the treated males were comparable to control males in all reproductive parameters evaluated. Isocyanatoethyl methacrylate did not affect male fertility or produce dominant lethal mutations in male rats.

Antidote and Emergency Treatment · 2 items

Noncardiogenic pulmonary edema and bronchospasm are the most immediate serious clinical consequences of isocyanate exposure. Markedly symptomatic patients should receive oxygen, ventilatory support, and an intravenous line. Treatment for asthma includes inhaled sympathomimetics (salbutamol, metaproterenol), intravenous theophylline, parenteral sympathomimetics (epinephrine, terbutaline), and steroids. /Isocyanates/

Most treatment is symptomatic. Mydriatics, systemic analgesics, and topical antibiotics (Sulamyd) may be used for corneal abrasions. There is no effective therapy for sensitized workers, and these people should be moved to a work site devoid of exposure to isocyanates. /Isocyanates/

Toxicity DataLC50 (rat) = 4 ppm/6H

Regulatory information

TSCA Requirements · 2 items

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Propenoic acid, 2-methyl-,2-isocyanatoethyl ester is included on this list.

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. Methacryloyloxyethyl isocyanate 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.

Safety data

wgk
3
tsca
TSCA listed
rtecs
OZ4950000
ridadr
UN 2206 6.1/PG 3
hs_code
2929109000
Toxicity
rat,LC50,inhalation,4ppm/6H (4ppm),Drug and Chemical Toxicology. Vol. 3, Pg. 381, 1980.
risk_code
21/22-26-37/38-41-42-42/43-36/37/38-23-22
Signal word
Danger
Symbol(GHS)
GHS05,GHS06,GHS08
hazard_code
T+,T
safety_code
26-36/37/39-45-36/37-23
hazard_class
6.1(a)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
II
Hazard statements
H302-H315-H317-H318-H330-H334
Limited Quantities
5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations
Active
Hazard Classifications
Acute Tox. 1 InhalationAcute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Irrit. 2Skin Sens. 1
Precautionary statements
P260-P280-P301+P312-P302+P352-P304+P340+P310-P305+P351+P338
Hazardous Substances Data
30674-80-7(Hazardous Substances Data)