Acrylic anhydride

HCID 74919

Notes Reactions

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Basic information

CAS: 2051-76-5
Standard SMILES: C=CC(=O)OC(=O)C=C
InChIKey: ARJOQCYCJMAIFR-UHFFFAOYSA-N
Molecular formula: C6H6O3
Average molar mass: 126.11 g/mol
Monoisotopic mass: 126.03169405

Names & identifiers

Preferred name: Acrylic anhydride
IUPAC: prop-2-enoyl prop-2-enoate
English name: Acrylic anhydride
Molecular formula: C6H6O3
Molecular weight: 126.11

Names & synonyms

Acrylic anhydride2051-76-5Acrylic acid anhydrideM4BYS5VWG32-Propenoic acid, anhydride2-Propenoic acid, 1,1'-anhydrideEINECS 218-128-2NSC-32616NSC 32616RefChem:552847218-128-2prop-2-enoyl prop-2-enoate

Show more names

JACS-2051-76-5Diacrylic anhydridePROPENOIC ANHYDRIDEAcyrlic acid anhydride2-PROPENOIC ACID ANHYDRIDEacrylic acid acryloyl ester2-Propenoic acid,1,1'-anhydride

AcryloxideMFCD0004814661932-59-0acrylic anhydride (stabl. with 10% 4-methoxyphenol)Acrylicanhydride2-acrylic anhydrideprop-2-enoic anhydrideDiacrylic acid anhydride

Database identifiers

CAS: 2051-76-5、61932-59-0
PubChem CID: 74919
DTXSID: DTXSID70942685
UNII: M4BYS5VWG3
EC Number: 218-128-2
Nikkaji: J149.603D

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 43.4 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 9
Formal charge: 0
Complexity: 140

Physicochemical properties

Melting point: -20 °C · -20 °C
Boiling point: 85 · 85-86°C 17mm
Density: 1 · 1,094 g/cm3
Flash point: 77 °C · 77°C
storage temp.: 2 · 2-8°C
solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
form: clear liquid
color: Colorless to Almost colorless
Stability: Moisture sensitive
InChI: InChI=1S/C6H6O3/c1-3-5(7)9-6(8)4-2/h3-4H,1-2H2
InChIKey: ARJOQCYCJMAIFR-UHFFFAOYSA-N
SMILES: C(=O)(C=C)OC(=O)C=C
CAS DataBase Reference: 2051 · 2051-76-5(CAS DataBase Reference)
FDA UNII: 4 BYS5VWG3 · M4BYS5VWG3
UNSPSC Code: 43211915 · 43211915
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H317-H319-H335
Precautionary statements: 261 · P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
target organs: Respiratory system
Risk Statements: 14 · 14-20/21/22-34
Safety Statements: 26 · 26-36/37/39-45
RIDADR: 3265 · 3265
WGK Germany: 3 · WGK 3
HazardClass: 8 · 8
PackingGroup: II
HS Code: 2916199590 · 2916199590
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
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)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H290 (20%): May be corrosive to metals [Warning Corrosive to Metals]

P234, P260, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesMet. Corr. 1 (20%)

Safety data

wgk: WGK 3
ridadr: 3265
hs_code: 2916199590
risk_code: 14-20/21/22-34
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 26-36/37/39-45
hazard_class: 8
Storage Class: 10 - Combustible liquids
packing_group: II
target organs: Respiratory system
Hazard statements: H302-H315-H317-H319-H335
Limited Quantities: 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
Precautionary statements: P261-P264-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

DescriptionAcrylic anhydride is used to prepare specialty acrylate, acrylamide monomers. Forms cyclic anhydrides on polymerization and does not produce crosslinks in polymers. It is used in the preparation of acrylic resin. And it is also used in organic synthesis. For example: it can react with adamantan-1-ol to get acrylic acid adamantan-1-yl ester. This reaction needs catalytic agent acidic catalyst and solvent cyclohexane by heating. The yield is 95%.

UsesAcrylic anhydride can be used to prepare specialty acrylate, acrylamide monomers or acrylic resin. It forms cyclic anhydrides on polymerization and can not be used as a crosslinker.