Nicotinic Acid N-Hydroxysuccinimide Ester

Base Information

• Chemical Name: Nicotinic Acid N-Hydroxysuccinimide Ester
• CAS No.: 78348-28-4
• Molecular Formula: C10H8 N2 O4
• Molecular Weight: 220.185
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID60357880
• Nikkaji Number: J1.360.741I
• Wikidata: Q82138054
• Mol file: 78348-28-4.mol

Synonyms:78348-28-4;Nicotinic Acid N-Hydroxysuccinimide Ester;Succinimidyl Nicotinate;(2,5-dioxopyrrolidin-1-yl) pyridine-3-carboxylate;2,5-dioxopyrrolidin-1-yl nicotinate;Nicotinic acid hydroxysuccinimidyl ester;3-PYRIDINECARBOXYLIC ACID, 2,5-DIOXO-1-PYRROLIDINYL ESTER;NIC-OSU;N-Nicotinoyloxysuccinimide;CBMicro_022223;N-(Nicotinoyloxy)succinimide;n-nicotinoyloxy-succinimide;Cambridge id 5488023;Oprea1_363702;SCHEMBL2504660;2,5-dioxopyrrolidinyl nicotinate;DTXSID60357880;CCG-9413;MFCD00619111;STK524762;AKOS005458417;Nicotinic acid?N-hydroxysuccinimide ester;AS-53694;BIM-0022288.P001;CS-0210315;FT-0672719;P16897;AB00086867-01;1-[(pyridin-3-ylcarbonyl)oxy]pyrrolidine-2,5-dione;2,5-Pyrrolidinedione, 1-[(3-pyridinylcarbonyl)oxy]-

Chemical Property of Nicotinic Acid N-Hydroxysuccinimide Ester

Chemical Property:

• Vapor Pressure: 1.12E-05mmHg at 25°C
• Melting Point: 127-130°C
• Refractive Index: 1.602
• Boiling Point: 370.3°C at 760 mmHg
• Flash Point: 177.7°C
• PSA: 76.57000
• Density: 1.46g/cm³
• LogP: 0.24030
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 220.04840674
• Heavy Atom Count: 16
• Complexity: 313

Purity/Quality:

98% ^*data from raw suppliers

Nicotinic acid N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)C2=CN=CC=C2
• Uses: Nicotinic Acid N-Hydroxysuccinimide Ester (cas# 78348-28-4) is a compound useful in organic synthesis.

Technology Process of Nicotinic Acid N-Hydroxysuccinimide Ester

There total 8 articles about Nicotinic Acid N-Hydroxysuccinimide Ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

nicotinic acid (59-67-6) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) → nicotinic acid succinimidyl ester (78348-28-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,4-dioxane;

DOI:10.1246/bcsj.56.564

Reference yield: 83.0%

3-iodopyridine (1120-90-7) + 2,5-dioxopyrrolidin-1-yl formate (17592-54-0) → nicotinic acid succinimidyl ester (78348-28-4)

Guidance literature:

With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 2-methyltetrahydrofuran; at 60 ℃; for 10h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.5b01119

Reference yield: 61.0%

3-iodopyridine (1120-90-7) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + carbon monoxide (201230-82-2) → nicotinic acid succinimidyl ester (78348-28-4)

Guidance literature:

With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In dimethyl sulfoxide; at 70 ℃; for 17h; under 760 Torr;

DOI:10.1016/S0040-4039(03)00337-X

upstream raw materials:

nicotinic acid

1-hydroxy-pyrrolidine-2,5-dione

3-iodopyridine

carbon monoxide

Downstream raw materials:

N-[2-(3-indolyl)ethyl]nicotinamide

N-nicotinoyltri(hydroxymethyl)aminomethane

nicotinoylglycine

(S)-2-(nicotinamido)-3-phenylpropanoic acid

Refernces

• 1、 Wada, Yasuaki,Yamaguchi, Isomaro,Takahashi, Michiko,Nakanishi, Hiromi,Mori, Satoshi,Nishizawa, Naoko K.. "Highly sensitive quantitative analysis of nicotianamine using LC/ESI-TOF-MS with an internal standard". . p. 435 - 441. Retrieved 2007.
• 2、 -. "SIRT1 ACTIVATING COMPOUNDS". Page/Page column 63; 65-66. . Retrieved 2020/05/21.
• 3、 Falcone, Natashya,She, Zhe,Syed, Jebreil,Lough, Alan,Kraatz, Heinz-Bernhard. "Synthesis and Biochemical Evaluation of Nicotinamide Derivatives as NADH Analogue Coenzymes in Ene Reductase". . p. 838 - 845. Retrieved 2019/02/07.