Diethyl fumarate

Diethyl fumarate Basic information
Product Name:Diethyl fumarate
Synonyms:Diethyl fuMarat;Diethyl (2E)-but-2-ene-1,4-dioate;FuMaric acidethyl ester two;Diethyl fuMara;diethyl furmarate;trans-2-butenedioicaciddiethylester;DIETHYL TRANS-BUTENEDIOATE;DIETHYL FUMARATE
CAS:623-91-6
MF:C8H12O4
MW:172.18
EINECS:210-819-7
Product Categories:Building Blocks;C8 to C9;Acids & Esters;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;straight chain compounds;C8 to C9;Carbonyl Compounds;Esters;C8 to C9Alphabetic;D;DID - DIN;intermediates;bc0001
Mol File:623-91-6.mol
Diethyl fumarate Structure
Diethyl fumarate Chemical Properties
Melting point 1-2 °C (lit.)
Boiling point 218-219 °C (lit.)
density 1.052 g/mL at 25 °C (lit.)
refractive index n20/D 1.44(lit.)
Fp 197 °F
storage temp. Sealed in dry,Room Temperature
solubility 3.1g/l
form Liquid
color Clear colorless to slightly yellow
Water Solubility immiscible
BRN 775347
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, acids, bases, reducing agents.
InChIKeyIEPRKVQEAMIZSS-AATRIKPKSA-N
LogP2.200 (est)
CAS DataBase Reference623-91-6(CAS DataBase Reference)
NIST Chemistry Reference2-Butenedioic acid (E)-, diethyl ester(623-91-6)
EPA Substance Registry SystemDiethyl fumarate (623-91-6)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 23-24/25
RIDADR NA 1993 / PGIII
WGK Germany 3
RTECS EM5950000
TSCA Yes
HS Code 29171990
Hazardous Substances Data623-91-6(Hazardous Substances Data)
MSDS Information
ProviderLanguage
(E)-2-Butenedioic acid diethyl ester English
SigmaAldrich English
ACROS English
ALFA English
Diethyl fumarate Usage And Synthesis
Chemical Propertiescolourless liquid
UsesIt is used as a pesticide or comonomer for the production of polystyrene.
UsesDiethyl fumarate is unsaturated polyester resins are used in applications, such as reinforced glass fiber for boats, piping, bathtubs, roof panels, etc., and as protective coatings, finishes, and lacquers.
UsesDiethyl Fumarate is a reagent in the preparation of chiral hydroisoindolines via Diels-Alder cycloaddition which are potent, brain-penetrant, human neurokinin-1 receptor antagonists.
Production MethodsDiethyl fumarate is manufactured via esterification of ethanol with fumaric acid.
DefinitionChEBI: A dieter obtained by the formal condensation of fumaric acid with ethanol.
Synthesis Reference(s)The Journal of Organic Chemistry, 52, p. 323, 1987 DOI: 10.1021/jo00378a045
Tetrahedron Letters, 28, p. 6649, 1987 DOI: 10.1016/S0040-4039(00)96936-3
Purification MethodsWash the fumarate with aqueous 5% Na2CO3, then with saturated CaCl2 solution, dry with CaCl2 and distil it. [Beilstein 2 IV 2207.]
Diethyl fumarate Preparation Products And Raw materials
Raw materialsFumaric acid
Preparation ProductsMonoethyl fumarate-->2-BUTENE-1,4-DIOL-->Diethyl malate-->Ethyl ethoxyacetate-->ALPHA-CHLOROFUMARICACIDDIETHYLESTER
Dimethyl fumarate Monoethyl fumarate DIPENTYL FUMARATE Ferrous fumarate Diethyl phthalate Tris(trimethylsilyl)phosphate FUMARATE Diisooctyl fumarate Ketotifen fumarate Fumaric acid Diethyl fumarate Diethyl ether DIETHYL PHOSPHATE BUTYL OLEATE Methyl acrylate Diethyl malonate Quetiapine fumarate TETRAETHYL ETHYLENETETRACARBOXYLATE Ethyl Fumarate

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