Diallyl carbonate

Diallyl carbonate
Names
	IUPAC name Bis(prop-2-enyl) carbonate
Identifiers
CAS Number	15022-08-9;
3D model (JSmol)	Interactive image;
ChemSpider	76468;
EC Number	239-106-9;
PubChem CID	84764;
UNII	J9P2G65CXJ;
CompTox Dashboard (EPA)	DTXSID6065846 ;
	InChI InChI=1S/C7H10O3/c1-3-5-9-7(8)10-6-4-2/h3-4H,1-2,5-6H2 Key: JKJWYKGYGWOAHT-UHFFFAOYSA-N;
	SMILES C=CCOC(=O)OCC=C;
Properties
Chemical formula	C7H10O3
Molar mass	142.154 g·mol−1
Density	0.991 g/mL
Melting point	−70 °C (−94 °F; 203 K)
Boiling point	95–97 °C (203–207 °F; 368–370 K) 60 mmHg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diallyl carbonate (DAC) is a colorless liquid with a pungent odor. Its structure contains allyl groups and a functional carbonate group. The presence of double bonds in the allyl groups makes it reactive in various chemical processes. This compound plays a key role in the production of polymers, including polycarbonates and polyurethanes. Diallyl carbonate is soluble in ethanol, methanol, toluene, and chloroform. Diallyl carbonate reacts with amines, alcohols, and thiols.

DAC is also used as an acrylate agent. Allyl carbonates are widely used in Tsuji-Trost allylation, promoting the formation of carbanions, boronates, phosphides, amides, and alkoxides. They act as in situ nucleophiles, increasing the reaction rate compared to allyl acetate. These compounds are of great interest for the design of intramolecular decarboxylate asymmetric compounds.