18342-66-0

Basic information

• Product Name: N-Succinimidyl-N-methylcarbamate
• Synonyms: 2,5-PYRROLIDINEDIONE, 1-[[(METHYLAMINO)CARBONYL]OXY]-;N-SUCCINIMDYL-N-METHYLCARBAMATE;N-SUCCINIMIDYL-N-METHYLCARBAMATE;N-Succinimidyl-N-methylcarbama;methyl isocyanate substitute;Methyl isocyanate substitute, MIC substitute;2,5-dioxopyrrolidin-1-yl MethylcarbaMate;SuO-NM
• CAS NO: 18342-66-0
• Molecular Formula: C₆H₈N₂O₄
• Molecular Weight: 172.14
• Product Categories: Medical Intermediates;Norbornene Derivatives
• Mol File: 18342-66-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 148-153 °C
• Appearance: /Solid
• Density: 1.416 g/cm³
• Refractive Index: 1.527
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane (Slightly), DMSO (Slightly)
• PKA: 11.00±0.46(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 1531863
• CAS DataBase Reference: N-Succinimidyl-N-methylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: N-Succinimidyl-N-methylcarbamate(18342-66-0)
• EPA Substance Registry System: N-Succinimidyl-N-methylcarbamate(18342-66-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 18342-66-0(Hazardous Substances Data)

Usage

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.

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

Upstream product

• 15149-73-2 2,5-dioxopyrrolidin-1-yl carbonochloridate 
• 593-51-1 methylamine hydrochloride 
• 74124-79-1 di(succinimido) carbonate 
• 74-89-5 methylamine 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 624-83-9 methyl isocyanate 

Downstream Products

• 903556-18-3 C₁₄H₂₁N₃O₃ 
• 868840-76-0 (2R,5S,8S,11S,15S)-8-Benzyl-5-(3-guanidino-propyl)-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentaaza-cycloheptadecane-11,15-dicarboxylic acid 
• 1115069-00-5 C₃₁H₄₄N₁₀O₁₁ 
• 243975-37-3 cyclo(N^w-(N-methylcarbamoyl)-L-arginyl-N-methyl-L-phenylalanyl-β-L-aspartyl-β-L-aspartyl-D-alanyl) 
• 1115068-97-7 C₃₃H₄₉N₉O₁₀ 
• 188612-53-5 5-amino-N₁-methyl-1H-imidazole-1,4-dicarboxamide 
• 1408329-68-9 N-(4-fluoro-3-methoxybenzyl)-2-methyl-6-(5-(1-(methylcarbamoyl)piperidin-4-yl)-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide 
• 1408330-56-2 N-(4-fluoro-3-methoxybenzyl)-2-methyl-6-(5-(1-(2-(3-methylureido)acetyl)piperidin-4-yl)-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide 
• 857275-30-0 benzyl (3R,4R)-3-{7-bromo-3-methyl-1-[2-(3-methylureido)ethyl]-1H-indol-6-ylmethoxy}-4-{4-[3-(2-methoxybenzyl)oxypropoxy]phenyl}piperidine-1-carboxylate 

Relevant articles and documents

Synthesis and in vitro antitumor activity of novel 2-alkyl-5- methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine.

A convenient method for the synthesis of activated N-methylcarbamates

An investigation of methods to efficiently prepare activated N-methylcarbamates is reported. N-(Methylcarbamoyloxy)succinimide (3a), aryl N-methylcarbamates 3b-d and 2,2,2-trifluoro-1-(trifluoromethyl)ethyl N-methylcarbamate (3e) have been prepared in 70-80% yields from the corresponding chloroformates 5a-e, which were prepared as crystalline solids by the condensation of trichloromethylchloroformate (1) or bis(trichloromethyl)carbonate (2) with hydroxy compounds 4a-e in high yields.

Activated N-Nitrosocarbamates for Regioselective Synthesis of N-Nitrosoureas

A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N-nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed.N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N-nitrosoureas.As an interesting example, N,N'-biscystamine, a new attractive oncostatic derivative, has been prepared.The cytotoxic activity of these various compounds were tested on L1210 leukemia.