Dimethyl adipate

Dimethyl adipate is the organic compound with the formula (CH₂CH₂CO₂CH₃)₂. It is a colorless oily liquid. Although the main commercial interest in adipates is related to the production of nylons, this diester is used as a plasticizer, a solvent for paint stripping and resins, and a pigment dispersant.^[2][3]

Dimethyl adipate

Names
Preferred IUPAC name Dimethyl hexanedioate
Identifiers
CAS Number	627-93-0 Y
3D model (JSmol)	Interactive image
ChemSpider	11824
ECHA InfoCard	100.010.019
PubChem CID	12329
UNII	BY71RX0R62 Y
CompTox Dashboard (EPA)	DTXSID8025096
InChI InChI=1S/C8H14O4/c1-11-7(9)5-3-4-6-8(10)12-2/h3-6H2,1-2H3 Key: UDSFAEKRVUSQDD-UHFFFAOYSA-N
SMILES COC(=O)CCCCC(=O)OC
Properties
Chemical formula	C8H14O4
Molar mass	174.196 g·mol−1
Appearance	Colorless liquid[1]
Density	1.06 g/cm3 (20 °C)[1]
Melting point	10.3 °C (50.5 °F; 283.4 K)[1]
Boiling point	227 °C (441 °F; 500 K)[1]
Solubility in water	< 1 g/L[1]
Viscosity	2.5 cP @ 25°C
Hazards
Flash point	107 °C (225 °F; 380 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Preparation

Dimethyl adipate is prepared by esterification of adipic acid with methanol. Less conventional routes include the hydroesterification of butadiene and the carbonylation of 1,4-dimethoxy-2-butene.^[2]

It reacts with concentrated ammonia to give the diamide (CH₂CH₂C(O)NH₂)₂.

Toxicity

Esters of adipic acid exhibit low acute toxicities in animal models. The LD50 of this dimethyl ester is estimated at 1800 mg/kg (rat, i.p.).^[2]