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Hydroxyethyl vinyl ether

HCID 12995
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
764-48-7
Standard SMILES
C=COCCO
InChIKey
VUIWJRYTWUGOOF-UHFFFAOYSA-N
Molecular formula
C4H8O2
Average molar mass
88.11 g/mol
Monoisotopic mass
88.05242949

Names & identifiers

Preferred name
Hydroxyethyl vinyl ether
IUPAC
2-ethenoxyethanol
English name
2-(Vinyloxy)ethanol
Molecular formula
C4H8O2
Molecular weight
88.11

Names & synonyms

2-(Vinyloxy)ethanol764-48-7Ethylene glycol vinyl etherEthylene glycol monovinyl etherEthanol, 2-(ethenyloxy)-2-Hydroxyethyl vinyl etherMveeg2-(Ethenyloxy)ethanolETHANOL, 2-(VINYLOXY)-Ethylenglycol monovinyl ester34CNR2NAC8hydroxyethyl vinyl ether
Show more names
VINYL GLYCOLVINYL CELLOSOLVE
DTXSID4075457RefChem:596631DTXCID4047880212-124-4Vinyloxyethanol2-Vinyloxyethanol2-ethenoxyethanol2-(Vinyloxy)ethan-1-ol

Database identifiers

CAS
764-48-7
PubChem CID
12995
DTXSID
DTXSID4075457
UNII
34CNR2NAC8
EC Number
212-124-4
Nikkaji
J92.981F

Properties

Computed structural properties

XLogP
0.1
Topological polar surface area
29.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
6
Formal charge
0
Complexity
34.5

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Ethylene Glycols
SpringerMaterials PropertiesMolecular structure
Density0.9821 @ 20 °C
SolubilitySoluble in ethanol, ether, and benzene
Boiling Point141.6 °C
DecompositionWhen heated to decomposition it emits acird smoke and irritating fumes.
Refractive IndexIndex of refraction: 1.4564 @ 17 °C
Physical DescriptionClear colorless liquid; [MSDSonline]

Physicochemical properties

Boiling point
143 °C · 143 °C(lit.)
Density
0.982 g/mL · 0.982 g/mL at 25 °C(lit.)

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

This chemical does not meet GHS hazard criteria for 10% (6 of 60) of reports.

Warning

H226 (90%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 60 reports by companies from 3 notifications to the ECHA C&L Inventory.

Warning

Hazard information

Regulatory InformationREACH registered substance: 2-(vinyloxy)ethanol (EC: 212-124-4)
Hazards SummaryEffects in high-dose animal studies include general anesthesia and liver injury; [RTECS] May cause irritation; [MSDSonline]
Hazard Classes and Categories · 2 items

Flam. Liq. 3 (90%)

Flammable liquids - Category 3

Safety & protection

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.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that ethylene glycol monovinyl ether is expected to have very high mobility in soil(SRC). Volatilization of ethylene glycol monovinyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of ethylene glycol monovinyl ether from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 2.2 mm Hg(SRC), determined from a fragment constant method(4).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

/2-(Vinyloxy)ethanol/ metab in the body occurs via hydrolysis to form acetaldehyde which is rapidly oxidized and is therefore not important in the pathogenesis of intoxication. The detached ethylene glycol selectively attacks the kidneys- either itself or through its separation products.

Uses & manufacturing

Uses · 3 items

Used to make plastics, lacquers, and protective coatings; [HSDB]

Painting (Solvents) [Category: Paint]

Used in the manufacture of plastics and lacquers and also in the production of protective coatings.

Applications

UsesAccording to HSDB , EGME has been used in the manufacture of plastics and lacquers and also in the production of protective coatings.

Upstream & downstream products

Upstream raw materials

2-Bromomethyl-1,3-dioxolane

Downstream products

Ethylene glycol divinyl ether, 962-Methyl-1,3-dioxolaneDi(ethylene glycol) vinyl etherDiethylene glycol divinyl ether

Suppliers100 total

Related reactions

13 records
New reaction record
HRID 111032 reaction equation
HRID 111032As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 145486 reaction equation
HRID 145486As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 545257 reaction equation
HRID 545257As reactantuspto-grants-2011_05
HRID 922449 reaction equation
HRID 922449As reactantuspto-grants-2016_03
HRID 953129 reaction equation
HRID 953129As reactantValidation data from https://doi.org/10.1039/C8SC04228D
HRID 1007520 reaction equation
HRID 1007520As reactantuspto-grants-2004_09
HRID 1108854 reaction equation
HRID 1108854As reactantuspto-grants-2000_05
HRID 1172643 reaction equation
HRID 1172643As reactantuspto-grants-2010_11
Page 1 of 2

Compound notes

Loading…

On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
refractive index
20 · n20/D 1.436(lit.)
Flash point
120 °F · 120 °F
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
form
clear liquid
pka
14.2 · 14.20±0.10(Predicted)
color
Colorless to Almost colorless
Henry's Law Constant
3.9 · 3.9×101 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
InChI=1S/C4H8O2/c1-2-6-4-3-5/h2,5H,1,3-4H2
InChIKey
VUIWJRYTWUGOOF-UHFFFAOYSA-N
SMILES
C(O)COC=C
CAS DataBase Reference
764 · 764-48-7(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
34 CNR2NAC8 · 34CNR2NAC8
NIST Chemistry Reference
Ethylene glycol monovinyl ether(764-48-7)
EPA Substance Registry System
Ethylene glycol monovinyl ether (764-48-7)
UNSPSC Code
12162002 · 12162002
NACRES
23 · NA.23
Symbol(GHS)
2 · GHS02
Signal word
Warning
Hazard statements
226 · H226
Precautionary statements
210 · P210-P233-P240-P241+P242+P243-P280-P303+P361+P353-P403+P235-P501
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Risk Statements
10 · 10
Safety Statements
16 · 16-36
RIDADR
3271 · UN 3271 3/PG 3
WGK Germany
2 · 2
RTECS
5495000 · KM5495000
HazardClass
3.2 · 3.2
PackingGroup
III
HS Code
29094400 · 29094400
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
3 · Flam. Liq. 3
Hazardous Substances Data
764 · 764-48-7(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 3910mg/kg
REACH Registrations
Active
Limited Quantities
5 L · 5.0 L (1.3 gallons) (liquid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that ethylene glycol monovinyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.8X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.55(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene glycol monovinyl ether, which has an estimated vapor pressure of 2.2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase ethylene glycol monovinyl ether is degraded in the atmosphere by reactions with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions in air are estimated to be 2.8 and 31 hrs, respectively(SRC), calculated from their rate constants of 4.5X10-11 cu cm/molecule-sec and 0.88X10-17 cu cm/molecule-sec at 25 °C, respectively(SRC), that were derived using a structure estimation method(3).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for ethylene glycol monovinyl ether can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethylene glycol monovinyl ether is expected to have very high mobility in soil(SRC).

Artificial Pollution SourcesEthylene glycol monovinyl ether's production and use in the manufacture of plastics and lacquers(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated for ethylene glycol monovinyl ether(SRC), using an estimated log Kow of -0.55(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for ethylene glycol monovinyl ether is estimated as 2.5X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ethylene glycol monovinyl ether is expected to be essentially nonvolatile from water surfaces(2). The potential for volatilization of ethylene glycol monovinyl ether from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 2.2 mm Hg(SRC), determined from a fragment constant method(3).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of ethylene glycol monovinyl ether with photochemically-produced hydroxyl radicals has been estimated as 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of ethylene glycol monovinyl ether with photochemically-produced ozone has been estimated as 0.88X10-17 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 31 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Ethylene glycol monovinyl ether is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

Probable Routes of Human ExposureOccupational exposure to ethylene glycol monovinyl ether may occur through inhalation and dermal contact with this compound at workplaces where ethylene glycol monovinyl ether is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 item

Ethylene glycol monovinyl ether's production and use in the manufacture of plastics and lacquers may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 2.2 mm Hg at 25 °C indicates ethylene glycol monovinyl ether will exist solely as a vapor in the ambient atmosphere. Vapor-phase ethylene glycol monovinyl ether will be degraded in the atmosphere by reactions with photochemically-produced hydroxyl radicals and ozone; the half-lives for these reactions in air are estimated to be 2.8 and 31 hrs, respectively. If released to soil, ethylene glycol monovinyl ether is expected to have very high mobility based upon an estimated Koc of 3.2. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.8X10-7 atm-cu m/mole. If released into water, ethylene glycol monovinyl ether is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to ethylene glycol monovinyl ether may occur through inhalation and dermal contact with this compound at workplaces where ethylene glycol monovinyl ether is produced or used. (SRC)

Antidote and Emergency Treatment · 4 items

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 ... . /Poison 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 /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 ... . /Poison A and B/

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. 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. Administer activated charcoal ... . /Ethylene glycol, glycols, and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /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 ... . Consider vasopressors to treat hypotension without signs of hypovolemia ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethylene glycol, glycols, and related compounds/

Toxicity DataLC50 (mice) = 29,000 mg/m3
Non-Human Toxicity Values · 2 items

LD50 Mouse oral 2900 mg/kg

LD50 Rat oral 3910 mg/kg

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
rtecs
KM5495000
ridadr
UN 3271 3/PG 3
hs_code
29094400
Toxicity
LD50 oral in rat: 3910mg/kg
risk_code
10
Signal word
Warning
Symbol(GHS)
GHS02
safety_code
16-36
hazard_class
3.2
Storage Class
3 - Flammable liquids
packing_group
III
Hazard statements
H226
Limited Quantities
5.0 L (1.3 gallons) (liquid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations
Active
Hazard Classifications
Flam. Liq. 3
Precautionary statements
P210-P233-P240-P241+P242+P243-P280-P303+P361+P353-P403+P235-P501
Hazardous Substances Data
764-48-7(Hazardous Substances Data)
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