Basic information
- CAS
10476-95-6- Standard SMILES
C=C(C)C(OC(C)=O)OC(C)=O- InChIKey
QFXJBPCTHSTOPE-UHFFFAOYSA-N- Molecular formula
- C8H12O4
- Average molar mass
- 172.18 g/mol
- Monoisotopic mass
- 172.07355886
Overview
Methacrolein diacetate appears as a liquid. Density 1.04 g / cm3; highly toxic.
Names & identifiers
- Preferred name
- Methacrolein diacetate
- IUPAC
- (1-acetyloxy-2-methylprop-2-enyl) acetate
- English name
- 2-Methyl-2-propene-1,1-diol diacetate
- Molecular formula
- C8H12O4
- Molecular weight
- 172.18
Names & synonyms
METHACROLEIN DIACETATE2-Methyl-2-propene-1,1-diol diacetate2-Methylallylidene diacetateMethyl allylidene diacetateMethallylidene diacetate2-Propene-1,1-diol, 2-methyl-, diacetate3,3-diacetoxy-2-methylpropeneHSDB 6443Acetic acid, 2-methyl-2-propene-1,1-diol diesterUNII-VQ6QDI298V3,3-Diacetoxy-2-methyl-1-propeneEINECS 233-974-2
Show more names
2-methylprop-2-ene-1,1-diyl diacetatemethacroleindiacetate2-methylallyl diacetate2-MethylacroleindiacetateMETHACROLEIN DIACETYLACETAL2-methyl-2-propene-1,1-diol
VQ6QDI298VNSC 46577BRN 1775081NSC-46577DTXSID708642772-Propene-1,1-diol, 2-methyl-, 1,1-diacetate4-02-00-00292 (Beilstein Handbook Reference)METHACROLEIN DIACETATE [HSDB]
Database identifiers
- CAS
10476-95-6- PubChem CID
- 25305
- DTXSID
DTXSID70864277- UNII
- VQ6QDI298V
- EC Number
- 233-974-2
- Nikkaji
- J35.492I
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 191
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Esters, Other
Flammable agents - 2nd degree
Density
1.051 @ 20 °C/20 °C
1.051 @ 20°C
Flash Point215 °C (open cup)
Boiling Point
375.8 °F at 760 mmHg (EPA, 1998)
191 °C @760 [mm Hg]
Vapor Pressure0.35 [mm Hg] @25 °C
Physical Description
Methacrolein diacetate appears as a liquid. Density 1.04 g / cm3; highly toxic.
Liquid; [CAMEO] Clear faintly yellow liquid; [MSDSonline]
Other Experimental PropertiesConversion factors: 1 ppm= 7.03 mg/cu m @ 25 °C, 760 mm Hg; 1 mg/l= 142.3 ppm @ 25 °C, 760 mm Hg
Physicochemical properties
- Melting point
- 15 °C · −15 °C(lit.)
- Boiling point
- 191 °C · 191 °C(lit.)
- Density
- 1.039 g/mL · 1.039 g/mL at 25 °C(lit.)
- vapor pressure
- 760 mm · 760 mm Hg ( 191 °C)
- refractive index
- 20 · n20/D 1.424(lit.)
- Flash point
- 182 °F · 182 °F
- storage temp.
- 2 · 2-8°C, stored under nitrogen
- form
- Liquid
- Appearance
- Colorless to light yellow Liquid
- FDA UNII
- 6 QDI298V · VQ6QDI298V
- EPA Substance Registry System
- Methacrolein diacetate (10476-95-6)
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 302 · H302-H310-H330
- Precautionary statements
- 260 · P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P264-P270-P301+P312-P330-P501-P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501
- Hazard Codes
- T+
- Risk Statements
- 26 · 26/27/28
- Safety Statements
- 23 · 23-26-27-36/37/39-45
- RIDADR
- 2810 · UN 2810 6.1/PG 1
- WGK Germany
- 3 · 3
- RTECS
- 9800000 · UC9800000
- F
- 9 · 9-21
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- II
- Hazardous Substances Data
- 10476 · 10476-95-6(Hazardous Substances Data)
- Toxicity
- 50 orl-rat: · LD50 orl-rat: 440 mg/kg AIHAAP 30,470,69
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
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P262, P264, P270, P271, P280, P284, P301+P317, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Propene-1,1-diol, 2-methyl-, diacetate
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 HazardsWhen heated to decomposition, it emits acrid smoke and irritating fumes. (EPA, 1998)
Health HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Hazards Summary
Causes ataxia and convulsions in lethal-dose intraperitoneal studies of rats; [RTECS] A skin, eye, and respiratory tract irritant; External application to rabbit eyes scored 9 on a scale of 1-10 (10 being most severe); Animal studies indicate skin absorption, irritation, and burns; [HSDB] Very toxic; [CAMEO] A severe irritant that can cause permanent injuries in high concentrations; Can be absorbed through skin; May be fatal by inhalation, skin absorption, or ingestion; [MSDSonline]
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special ReportsUSEPA; Chemical Profile: Methacrolein diacetate (1985)
Reactivity Profile
METHACROLEIN DIACETATE reacts exothermically with acids. Strong oxidizing acids may cause a reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated with basic solutions. Flammable hydrogen may be generated by mixing with alkali metals and hydrides. Reacts readily with mercaptans. Acidic conditions favor breakdown to methacrolein, which is subject to possibly vigorous polymerization.
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
CERCLA Reportable Quantities
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. Methacrolein diacetate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Flammable agents - 2nd degree
Safety & protection
Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
First AidNote: No information on specific clinical effects of exposure was available.
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods
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 MeasuresWhen handling this material special precautions should be taken to prevent eye & skin contact & inhalation of vapor.
Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Protective Action Criteria (PAC)
0.040 [ppm]
0.44 [ppm]
2.7 [ppm]
Personal Protective Equipment (PPE)
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)
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Non-Human Toxicity Excerpts
Rabbit eye studies showed the material to cause severe irritation & corneal injury, being rated 9 on a scale of 10. It is markedly irritating to the skin & can cause a burn, but greater hazard is that of skin absorption ... It is hazardous from inhalation also. All rats exposed for 1 hr to essentially saturated vapors died, & five of six rats exposed to 63.5 ppm for 4 hr died.
Toxicity DataLCLo (rat) = 62 ppm/4h
Regulatory information
CERCLA Reportable Quantities
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. Methacrolein diacetate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs.
Safety data
- F
- 9-21
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UC9800000
- ridadr
- UN 2810 6.1/PG 1
- Toxicity
- LD50 orl-rat: 440 mg/kg AIHAAP 30,470,69
- risk_code
- 26/27/28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 23-26-27-36/37/39-45
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard statements
- H302-H310-H330
- Precautionary statements
- P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P264-P270-P301+P312-P330-P501-P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501
- Hazardous Substances Data
- 10476-95-6(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Methods of Manufacturing
The common esters & diesters of the common polyols are prepared commercially by esterifying the particular polyol with the acid, acid anhydride, or acid chloride of choice in presence of a catalyst. Mono- or diesters result, depending upon the proportions of each reactant employed. /Esters, diesters, & ether--esters of glycols/
General Manufacturing Information2-Propene-1,1-diol, 2-methyl-, 1,1-diacetate: ACTIVE
Applications
UsesChemical intermediate, can provide controlled release of methacrolein in acid solution.
General DescriptionA liquid. Density 1.04 g / cm3; highly toxic.
Related reactions
12 records
Compound notes
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