N-Succinimidyl-N-methylcarbamate

Product Name: N-Succinimidyl-N-methylcarbamate
CAS No.: 18342-66-0
Chemical Name: N-Succinimidyl-N-methylcarbamate
Synonyms: SuO-NM;methyl isocyanate substitute;N-Succinimidyl-N-methylcarbame;N-Succinimidyl Methylcarbamate;N-Succinimidyl-N-methylcarbama;N-SUCCINIMDYL-N-METHYLCARBAMATE;N-SUCCINIMIDYL-N-METHYLCARBAMATE;2,5-dioxopyrrolidin-1-yl MethylcarbaMate;Methylcarbamic Acid N-Succinimidyl Ester;N-Succinimidyl N-methylcarbamate >=97.0% (N)
CBNumber: CB7301533
Molecular Formula: C6H8N2O4
Formula Weight: 172.14
MOL File: 18342-66-0.mol

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N-Succinimidyl-N-methylcarbamate Property

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
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)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
F: 10-21
HS Code: 2928.00.5000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 66181
Product name: N-Succinimidyl N-methylcarbamate
Purity: ≥97.0% (N)
Packaging: 5g
Price: $225.4
Updated: 2025/07/31

Sigma-Aldrich

Product number: 66181
Product name: N-Succinimidyl N-methylcarbamate
Purity: ≥97.0% (N)
Packaging: 25g
Price: $638
Updated: 2023/06/20

TCI Chemical

Product number: U0108
Product name: N-Succinimidyl Methylcarbamate
Purity: >98.0%(N)
Packaging: 1g
Price: $23
Updated: 2025/07/31

TCI Chemical

Product number: U0108
Product name: N-Succinimidyl Methylcarbamate
Purity: >98.0%(N)
Packaging: 5g
Price: $63
Updated: 2025/07/31

TRC

Product number: S688845
Product name: N-Succinimidyl N-methylcarbamate
Packaging: 2.5g
Price: $130
Updated: 2021/12/16

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N-Succinimidyl-N-methylcarbamate Chemical Properties,Usage,Production

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

6066-82-6

624-83-9

18342-66-0

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 Preparation Products And Raw materials

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N-Succinimidyl-N-methylcarbamate Suppliers

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View Lastest Price from N-Succinimidyl-N-methylcarbamate manufacturers

Henan Aochuang Chemical Co.,Ltd.

Product: N-Succinimidyl-N-methylcarbamate 18342-66-0
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 1ton
Release date: 2022-09-26

Zhuozhou Wenxi import and Export Co., Ltd

Product: N-Succinimidyl-N-Methylcarbamate 18342-66-0
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

Zhuozhou Wenxi import and Export Co., Ltd

Product: N-Succinimidyl-N-Methylcarbamate 18342-66-0
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-08

18342-66-0, N-Succinimidyl-N-methylcarbamateRelated Search:

POLYURETHANE Methyl anthranilate Urethane Dithiooxamide 4-Aminobenzoic acid 6-Aminoquinolyl-N-hydroxysuccinimidylcarbamate Anthranilic acid TERT-BUTYL N-SUCCINIMIDYL N,N'-TRIMETHYLENEDICARBAMATE TERT-BUTYL N-SUCCINIMIDYL N,N'-(1,4-PHENYLENE)DICARBAMATE TERT-BUTYL-N-SUCCINIMIDYL N N'-ETHYLENE- N-SucciniMidoxycarbonyl-β-alanine N-SucciniMidyl Ester 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

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

N-Succinimidyl Methylcarbamate

N-Succinimidyl-N-methylcarbame

N-Succinimidyl N-methylcarbamate >=97.0% (N)

Methylcarbamic Acid N-Succinimidyl Ester

1-[[(Methylamino)carbonyl]oxy]-2,5-pyrrolidinedione

1-[(Methylcarbamoyl)oxy]-2,5-pyrrolidinedione

<i>N</i>-Succinimidyl <i>N</i>-methylcarbamate

18342-66-0

8342-66-0

C6H8N2O4

Synthetic Reagents

Coupling

Active Esters/Additives

Norbornene Derivatives

Medical Intermediates