N-Succinimidyl-N-methylcarbamate Chemical Properties

Melting point:

148-153 °C

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Dichloromethane (Slightly), DMSO (Slightly)

pka

11.00±0.46(Predicted)

form 

Solid

color 

White to Off-White

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture Sensitive

BRN 

1531863

Major Application

peptide synthesis

InChI

InChI=1S/C6H8N2O4/c1-7-6(11)12-8-4(9)2-3-5(8)10/h2-3H2,1H3,(H,7,11)

InChIKey

XMNGSPOWUCNRMO-UHFFFAOYSA-N

SMILES

N1(OC(NC)=O)C(=O)CCC1=O

CAS DataBase Reference

18342-66-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-21

HS Code 

2928.00.5000

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich

N-Succinimidyl-N-methylcarbamate Usage And Synthesis

Uses

N-Succinimidyl N-Methylcarbamate is used as a reagent in the synthesis of Argifin, a natural product chitinase inhibitor with chemotherapeutic potential. N-Succinimidyl N-Methylcarbamate is also used as a reagent in the preparation of 5-Amino-N1-methyl-1H-imidazole-1,4-dicarboxamide (A616300); a metabolite of Temozolomide (T017775) which is an imidazotetrazine alkylating agent and antineoplastic.

Definition

ChEBI: N-succinimidyl N-methylcarbamate is a member of the class of pyrrolidinones that is N-hydroxysuccinimide in which the hydroxyl hydrogen is replaced by a methylcarbamoyl group. It has a role as an apoptosis inducer. It is a carbamate ester, a dicarboximide, a pyrrolidinone and a N-hydroxysuccinimide ester. It is functionally related to a succinimide.

Synthesis

GENERAL STEPS: N-hydroxysuccinimide (5.83 g, 50.7 mmol) and ethyl acetate (20 mL) were added as solvents to a dry round-bottomed flask, and the mixture was cooled to 0 °C. Triethylamine (4.76 g) and methyl isocyanate (6.39 g, 0.112 mmol) were slowly added to the mixture at the same temperature. Subsequently, the reaction system was slowly warmed up to room temperature and stirred continuously at room temperature for 24 hours. Upon completion of the reaction, the volatiles were removed by distillation under reduced pressure. The crude product obtained was recrystallized with ethyl acetate/ether mixed solvent to afford the target compound N-succinimidyl-N-methylcarbamate (86% yield). The product was colorless needle-like crystals with a melting point of 148.0-149.0 °C (literature value: 148.0-152.0 °C).1H NMR (300 MHz, CDCl3) δ: 8.15 (1H, br, NH), 2.76 (4H, s, CH2CH2), 2.67 (3H, s, CH3); 13C NMR (22.5 MHz. CDCl3) δ: 170.66, 151.98, 27.98, 25.47; MS (FAB+) m/z: 173 (M + H).

References

[1] European Journal of Medicinal Chemistry, 2014, vol. 82, p. 16 - 35
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 2, p. 178 - 182
[3] Journal of the American Chemical Society, 1995, vol. 117, # 4, p. 1240 - 1245

N-Succinimidyl-N-methylcarbamate(18342-66-0)Related Product Information

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• TERT-BUTYL N-SUCCINIMIDYL N,N'-HEXAMETHYLENEDICARBAMATE
• CARBAMIC ACID, (2-CHLOROETHYL)NITROSO-, 2,5-DIOXO-1-PYRROLIDINYL ESTER
• TERT-BUTYL N-SUCCINIMIDYL N,N'-TETRAMETHYLENEDICARBAMATE
• N-Succinimidyl-N-methylcarbamate