Vinyl isobutyl ether
Basic information
- CAS
109-53-5- Standard SMILES
C=COCC(C)C- InChIKey
OZCMOJQQLBXBKI-UHFFFAOYSA-N- Molecular formula
- C6H12O
- Average molar mass
- 100.16 g/mol
- Monoisotopic mass
- 100.088815
Overview
Vinyl isobutyl ether appears as a clear colorless liquid. May polymerize if contaminated or subjected to heat. If polymerization take place inside a container, the container may violently rupture. Vapors are heavier than air.
Names & identifiers
- Preferred name
- Vinyl isobutyl ether
- IUPAC
- 1-ethenoxy-2-methylpropane
- English name
- Isobutyl vinyl ether
- Molecular formula
- C6H12O
- Molecular weight
- 100.16
Names & synonyms
ISOBUTYL VINYL ETHER109-53-5Vinyl isobutyl etherPropane, 1-(ethenyloxy)-2-methyl-IsobutoxyetheneEther, isobutyl vinyl1-(ethenyloxy)-2-methylpropaneIsobutanol vinyl etherLutanol LR 85002-Methyl-1-vinyloxypropaneVinoflex MO 400*NSC 8265
Show more names
IVEvinoflexmo400*isobutoxy-ethene1-IsobutoxyetheneIsobutyl vinyl ethAllylisobutylether
Vinoflex MO 400iso-butyl vinyl etherDTXSID8029608EINECS 203-678-88HQ2X2D0TMUN1304BRN 1560159Vinyl isobutyl ether, inhibited
Database identifiers
- CAS
109-53-5- PubChem CID
- 7992
- DTXSID
DTXSID8029608- ChEMBL
CHEMBL3183612- UNII
- 8HQ2X2D0TM
- EC Number
- 203-678-8
- Nikkaji
- J48.642F
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 9.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 48.1
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Ethers, Other
Flammable agents - 3rd degree
SpringerMaterials PropertiesBoiling point
Flash Point15 °F (NFPA, 2010)
Vapor Pressure59.5 [mmHg]
Physical Description
Vinyl isobutyl ether appears as a clear colorless liquid. May polymerize if contaminated or subjected to heat. If polymerization take place inside a container, the container may violently rupture. Vapors are heavier than air.
Liquid
Clear colorless liquid; [CAMEO]
Physicochemical properties
- Melting point
- -112 °C · -112 °C
- Boiling point
- 83 °C · 83 °C
- Density
- 0.769 · 0.769
- vapor density
- 3.45 · 3.45 (vs air)
- vapor pressure
- 68 mm · 68 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.395(lit.)
- Flash point
- 8 °F · 8 °F
- storage temp.
- Flammables area
- form
- clear liquid
- color
- Colorless to Almost colorless
- Water Solubility
- 0.7 g/L · 0.7 g/L (25 ºC)
- BRN
- 1560159 · 1560159
- Henry's Law Constant
- 3.9 · 3.9×10-3 mol/(m3Pa) at 25℃, Raventos-Duran et al. (2010)
- Dielectric constant
- 3.34 · 3.3399999999999999
- InChI
- 1S/C6H12O/c1-4-7-5-6(2)3/h4,6H,1,5H2,2-3H3
- InChIKey
- OZCMOJQQLBXBKI-UHFFFAOYSA-N
- SMILES
- CC(C)COC=C
- LogP
- 3.07 at · 3.07 at 25℃
- CAS DataBase Reference
- 109 · 109-53-5(CAS DataBase Reference)
- FDA UNII
- 8 HQ2X2D0TM · 8HQ2X2D0TM
- NIST Chemistry Reference
- Vinylisobutyl ether(109-53-5)
- EPA Substance Registry System
- 1 · Propane, 1-(ethenyloxy)-2-methyl- (109-53-5)
- UNSPSC Code
- 12162002 · 12162002
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 315 · H315-H319-H225
- Precautionary statements
- 501 · P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-38-52/53
- Safety Statements
- 16 · 16-23-24/25-33-37-61
- RIDADR
- 1304 · UN 1304 (VINYL ISOBUTYL ETHER, STABILIZED)
- WGK Germany
- 1 · 1
- RTECS
- 1300000 · KO1300000
- F
- 9 · 9
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29091990 · 29091990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 Flam · Aquatic Chronic 3Flam. Liq. 2Skin Irrit. 2
- Toxicity
- 50 · rabbit,LD50,skin,20mL/kg (20mL/kg),American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
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
This chemical does not meet GHS hazard criteria for 3.8% (8 of 213) of reports.
Danger
H225 (96.2%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P264, P264+P265, P273, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 213 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: Propane, 1-(ethenyloxy)-2-methyl-
Propane, 1-(ethenyloxy)-2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 1-(ethenyloxy)-2-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 31-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/2053
Propane, 1-(ethenyloxy)-2-methyl-: Does not have an individual approval but may be used under an appropriate group standard
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
Fire Hazards
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible); polymerization hazard]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible); polymerization hazard]:
· Inhalation or contact with material may irritate or burn skin and eyes.
Hazards Summary
May polymerize; Forms explosive peroxides on exposure to air; [CAMEO] A skin, eye, nose, and throat irritant; [NJ-HSFS] May form explosive peroxides; An irritant; [Sigma-Aldrich MSDS] Vinyl isobutyl ether, stabilized (UN1304) has warning of explosive polymerization; [ERG 2016]
DOT ID and Guide1304 127P
Reactive GroupEthers
Reactivity AlertsHighly Flammable
Reactivity ProfileVINYL ISOBUTYL ETHER is a colorless, moderately toxic liquid, highly flammable. A very dangerous fire hazard when exposed to heat, flame or strong oxidizing agents. Highly explosive in the form of vapor when exposed to open flame or sparks.
DOT Hazard Classification
Vinyl isobutyl ether, stabilized
UN1304
Class 3 Flammable and combustible liquid (49 eCFR § 173.120)
PG II: the degree of danger presented by the material is medium
Air and Water ReactionsHighly flammable. Less dense than water and very slightly soluble in water. Tends to form explosive peroxides when exposed to air. When ethers containing peroxides are heated (distilled) they can detonate [Lewis, 3rd ed., 1993, p. 728].
Peroxide Forming Chemical
Isobutyl vinyl ether
B: Compounds that form peroxides on concentration (distillation/evaporation)
Kelly
Safety & protection
Fire FightingExcerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible); polymerization hazard]:
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible); polymerization hazard]:
General First Aid:
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
20.0 [ppm]
Nonfire Spill ResponseExcerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible); polymerization hazard]:
Isolation and Evacuation
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible); polymerization hazard]:
Immediate precautionary measure
Personal Protective Equipment (PPE)Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible); polymerization hazard]:
Emergency Response Planning GuidelinesCAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.
Toxicology
Toxicity DataLCLo (rat) = 16,000 ppm/4hr
Safety data
- F
- 9
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- KO1300000
- ridadr
- UN 1304 (VINYL ISOBUTYL ETHER, STABILIZED)
- hs_code
- 29091990
- Toxicity
- rabbit,LD50,skin,20mL/kg (20mL/kg),American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
- risk_code
- 11-38-52/53
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xi
- safety_code
- 16-23-24/25-33-37-61
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H315-H319-H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 3Flam. Liq. 2Skin Irrit. 2
- Precautionary statements
- P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235
Chemistry & industry
Uses & manufacturing
Uses
Used in adhesives, coatings, and lacquers, as a resin modifier, plasticizer, and to make other chemicals; [NJ-HSFS]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
U.S. Production2023: <50,000 lb
Industry UsesIntermediate
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Propane, 1-(ethenyloxy)-2-methyl-: ACTIVE
Applications
UsesIsobutyl vinyl ether is use in preparation method and formula of bulk polymerized Chloroether resin.
UsesPolymer and copolymers used in surgical adhesives, coatings, and lacquers; modifier for alkyd and polystyrene resins; plasticizer for nitrocellulose and other plastics; chemical intermediate.
General DescriptionA clear colorless liquid. Flash point 15°F. May polymerize if contaminated or subjected to heat. If polymerization take place inside a container, the container may violently rupture. Vapors are heavier than air.
Upstream & downstream products
Downstream products
Related reactions
27 records
Compound notes
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