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Basic Information

Molecular Structure:
CAS No.:	141-05-9
Name:	Diethyl maleate
Article Data:	201

Formula:	C₈H₁₂O₄
Molecular Weight:	172.181
Synonyms:	2-Butenedioicacid (2Z)-, diethyl ester (9CI);2-Butenedioic acid (Z)-, diethyl ester;Maleicacid, diethyl ester (6CI,8CI);(2Z)-2-Butenedioic acid diethyl ester;Diethyl(Z)-2-butenedioate;2-Butenedioicacid (2Z)-, 1,4-diethyl ester;Ethyl maleate;Staflex DEM;
EINECS:	205-451-9
Density:	1.068 g/cm³
Melting Point:	-10 °C
Boiling Point:	214 °C at 760 mmHg
Flash Point:	93.3 °C
Solubility:	insoluble in water
Appearance:	colourless liquid
Hazard Symbols:	Xi
Risk Codes:	36-43
Safety:	26-36/37-37-24
PSA:	52.60000
LogP:	0.66880

Synthetic route

: 763-51-9
diethyl 2-bromosuccinate

: 327-62-8
potassium propionate

: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 20h;	100%

: 327-62-8
potassium propionate

: 99967-60-9
2-(Methylsulfonyloxy)-diethylester

: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 20h;	100%

: 608-82-2, 1114-30-3, 1114-31-4, 40205-59-2
diethyl dl-dibromosuccinate

A: 623-91-6
diethyl Fumarate

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With N-benzyl-1,4-dihydronicotinamide In acetonitrile at 49.9℃; for 7h;	A 100% B n/a

: 623-73-4
diazoacetic acid ethyl ester

: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With trans-IICl2(pyboxip)(=CHSiMe3)> Ambient temperature;	98%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 15h;	95%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃;	95%

: 623-73-4
diazoacetic acid ethyl ester

: 104575-54-4
N-(2-naphthalenylmethylene)butane-1-amine

: (2R,3S)-1-Butyl-3-naphthalen-2-yl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 96% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 172367-39-4
N-(2-naphthalenylmethylene)hexane-1-amine

: (2R,3S)-1-Hexyl-3-naphthalen-2-yl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 96% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 627463-17-6
4-bromo-2-fluoro-1-vinylbenzene

A: 934995-82-1
C12H12BrFO2

: C12H12BrFO2

C: 623-91-6
diethyl Fumarate

D: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
With aluminum oxide; potassium carbonate; copper(I) trifluoromethanesulfonate benzene; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] In chloroform at 0 - 20℃; for 24 - 25h; Product distribution / selectivity;	A n/a B 96% C n/a D n/a
copper(I) trifluoromethanesulfonate benzene; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] In ethyl acetate at 0 - 20℃; for 24 - 25h; Product distribution / selectivity;	A n/a B n/a C n/a D n/a
copper(I) trifluoromethanesulfonate benzene; 2,2'-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] In toluene at 0 - 20℃; for 24 - 25h; Product distribution / selectivity; Molecular sieve;	A n/a B n/a C n/a D n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 3910-55-2
N-(p-methoxybenzylidene)butylamine

: (2R,3S)-1-Butyl-3-(4-methoxy-phenyl)-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 94% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 53054-00-5
N-hexyl-1-(4-methoxyphenyl)methanimine

: (2R,3S)-1-Hexyl-3-(4-methoxy-phenyl)-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 94% B n/a

...Expand

: 623-73-4
diazoacetic acid ethyl ester

: 19340-96-6
N-benzylidenehexylamine

: (2R,3S)-1-Hexyl-3-phenyl-aziridine-2-carboxylic acid ethyl ester

B: 141-05-9
Diethyl maleate

Conditions

Conditions	Yield
methyltrioxorhenium(VII)	A 93% B n/a

...Expand

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Chemistry

Structure of Diethyl maleate (CAS NO.141-05-9):

IUPAC Name: diethyl (Z)-but-2-enedioate
Empirical Formula: C₈H₁₂O₄
Molecular Weight: 172.1785
EINECS: 205-451-9
Index of Refraction: 1.442
Molar Refractivity: 42.71 cm³
Molar Volume: 161.1 cm³
Polarizability: 16.93×10^-24cm³
Surface Tension: 33.2 dyne/cm
Density: 1.068 g/cm³
Flash Point: 93.3 °C
Enthalpy of Vaporization: 45.03 kJ/mol
Melting point: -10 ºC
Boiling Point: 214 °C at 760 mmHg
Vapour Pressure: 0.159 mmHg at 25°C
Water Solubility: insoluble
Physical Appearance: colourless liquid
Stability: Stable. Combustible. Incompatible with oxidizing agents, bases, acids, reducing agents.
Product Categories: Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer
Synonyms of Diethyl maleate (CAS NO.141-05-9): 2-Butenedioic acid (Z)-, diethyl ester ; 4-02-00-02207 (Beilstein Handbook Reference) ; Diethylester kyseliny maleinove ; Ethyl maleate
Canonical SMILES: CCOC(=O)C=CC(=O)OCC
Isomeric SMILES: CCOC(=O)/C=C\C(=O)OCC
InChI: InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
InChIKey: IEPRKVQEAMIZSS-WAYWQWQTSA-N

Toxicity Data With Reference

1.	skn-rbt 10 mg/24H open MLD	JIHTAB Journal of Industrial Hygiene and Toxicology. 31 (1949),60.
2.	skn-rbt 530 mg open MLD	UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 10/29 ,1957.
3.	eye-rbt 500 mg open	JIHTAB Journal of Industrial Hygiene and Toxicology. 31 (1949),60.
4.	orl-rat LD50:3200 mg/kg	JIHTAB Journal of Industrial Hygiene and Toxicology. 31 (1949),60.
5.	ipr-rat LD50:3070 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 52 (1980),422.
6.	skn-rbt LD50:4000 mg/kg	UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 10/29 ,1957.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36-43
R36:Irritating to eyes.
R43:May cause sensitization by skin contact.
Safety Statements: 26-36/37-37-24
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S37:Wear suitable gloves.
S24:Avoid contact with skin.
RIDADR: 3334
WGK Germany: 2
RTECS: ON1225000
HS Code: 29171990
Moderately toxic by ingestion, skin contact, and intraperitoneal routes. A skin and eye irritant. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO₂, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Specification

Diethyl maleate's Handling and Storage
Storage: Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Avoid contact with heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.