N-Ethylmaleimide Chemical Properties

Melting point:

43-46 °C(lit.)

Boiling point:

210 °C(lit.)

Density 

1.2500 (rough estimate)

refractive index 

1.4430 (estimate)

Flash point:

73 °C

storage temp. 

2-8°C

solubility 

methanol: 1 M at 20 °C, clear, colorless

pka

-2.18±0.20(Predicted)

form 

Crystalline Powder

color 

White to off-white

Water Solubility 

1 g/L (20 ºC)

Sensitive 

Light Sensitive

Merck 

14,3822

BRN 

112448

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents. Refrigerate.

InChIKey

HDFGOPSGAURCEO-UHFFFAOYSA-N

CAS DataBase Reference

128-53-0(CAS DataBase Reference)

NIST Chemistry Reference

1H-pyrrole-2,5-dione, 1-ethyl-(128-53-0)

EPA Substance Registry System

N-Ethylmaleimide (128-53-0)

Safety Information

Hazard Codes 

T+

Risk Statements 

21-28-34-43-20/21

Safety Statements 

26-28-36/37/39-45-28A

RIDADR 

UN 2928 6.1/PG 2

WGK Germany 

3

RTECS 

UX9625000

F 

19

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29251900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-Ethylmaleimide Usage And Synthesis

Chemical Properties

White solid

Uses

Reagent for the covalent modification of cysteine residues in proteins. NEM gives a clear solution in ethanol at 50 mg/ml. NEM dissolves in water (>50 mg in 4 ml); however, aqueous solutions are unstable. The rate of hydrolysis is pseudo-first order and significantly dependent on pH.

Uses

N-Ethylmaleimide is a protein thiol modifier which inhibits apoptotic DNA fragmentation. It is a sulfhydryl reagent and finds application in experimental biochemical studies as well as in enzymology. It is involved in the modification of cysteine residues in proteins and peptides. It acts as a Michael acceptor and reacts with nucelophiles like thiols. It is employed in the inhibition of Mg2+ dependent internucleosomal DNA fragmentation.

Uses

In cancer research (possible antimitotic activity.)

Definition

ChEBI: N-ethylmaleimide is a member of the class of maleimides that is the N-ethyl derivative of maleimide. It has a role as an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor, an EC 2.7.1.1 (hexokinase) inhibitor, an EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor and an anticoronaviral agent. It is functionally related to a maleimide.

Hazard

Lachrymator when liquid, a strong irritant.

Biochem/physiol Actions

Augments currents from native M-channels in sympathetic neurons and acts as an opener for KCNQ2, KCNQ4 and KCNQ5 channels.

Safety Profile

Poison by intraperitoneal route. Human mutation data reported. Vapors are hlghly irritating. When heated to decomposition it emits toxic fumes of NOx.

N-Ethylmaleimide(128-53-0)Related Product Information

• O-Phthalimide
• Bismaleimide
• Succinimide
• Maleimide
• N-Benzylmaleimide
• N,N'-1,3-Phenylene bismaleimide
• N-Phenylmaleimide
• DIALIFOS
• N-Succinimidyl 3-maleimidopropionate
• 3-MALEIMIDOPROPIONIC ACID
• 4-MALEIMIDOBUTYRIC ACID
• 3-Maleimidopropionic acid
• GMBS
• N-PROPYLMALEIMIDE
• N-Succinimidyl 6-maleimidohexanoate
• N-Butylmaleimide
• 6-Maleimidocaproic acid
• 4-MALEIMIDO-TEMPO