N-Hydroxysuccinimide

Base Information

• Chemical Name: N-Hydroxysuccinimide
• CAS No.: 6066-82-6
• Molecular Formula: C4H5NO3
• Molecular Weight: 115.089
• Hs Code.: 29251995
• European Community (EC) Number: 228-001-3
• NSC Number: 74335
• UNII: MJE3791M4T
• DSSTox Substance ID: DTXSID7064102
• Nikkaji Number: J26.034G
• Wikipedia: N-Hydroxysuccinimide
• Wikidata: Q408833
• ChEMBL ID: CHEMBL403753
• Mol file: 6066-82-6.mol

Synonyms:N-hydroxysuccinimide

Chemical Property of N-Hydroxysuccinimide

Chemical Property:

• Appearance/Colour: white to pale yellow
• Vapor Pressure: 0.00155mmHg at 25°C
• Melting Point: 95-98 °C(lit.)
• Refractive Index: 1.599
• Boiling Point: 262.4 °C at 760 mmHg
• PKA: 7.81±0.20(Predicted)
• Flash Point: 112.5 °C
• PSA: 57.61000
• Density: 1.649 g/cm³
• LogP: -0.53750
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: DMSO (Soluble), Methanol (Slightly)
• Water Solubility.: SOLUBLE
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 115.026943022
• Heavy Atom Count: 8
• Complexity: 126

Purity/Quality:

98% ^*data from raw suppliers

N-Hydroxysuccinimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Succinimides
• Canonical SMILES: C1CC(=O)N(C1=O)O
• Description: N-hydroxysuccinimide is a synthetic ingredient used in cosmetics as an ester to soften and condition skin. It's also a reagent, a substance used to trigger a reaction that leads to a new substance, such as peptides and polymers.N-Hydroxysuccinimide is used in cosmetics and beauty products as an ester often seen in eye creams. N-hydroxysuccinimide activates the elimination of blood originated pigments responsible for dark color and inflammation that causes under eye circles. "Infra-orbital shadows are due to the accumulation of hemoglobin and its coloured degradation products - biliverdin, bilirubin and iron - in the dermis and epidermis ... N-hydroxysuccinimide renders the iron soluble for natural elimination" (source).
• Uses: Reagent for preparation of active esters of amino acids. N-Hydroxysuccinimide is used for improved amidations in the carbodiimide method. It is also used to activate a carboxyl group and reacts with amine to form amide. It is involved in the preparation of N-hydroxymaleimide-styrene copolymer. Further, it finds use in analytical chemistry. As an additive, it is used in the carbodiimide method for improved amidations and peptide couplings. N-hydroxysuccinimide (NHS) is often used to assist carbodiimide-mediated peptide coupling by forming an active ester intermediate via condensation of the surface carboxyl group and NHS. The NHS-reactive ester intermediate is susceptible to nucleophilic attack by primary amines and results in the formation of stable amide bonds between the biomaterial surface and the N-terminus of the peptide.

Technology Process of N-Hydroxysuccinimide

There total 63 articles about N-Hydroxysuccinimide 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: 99.0%

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate + girard's reagent T (123-46-6) + isobutylamine (78-81-9) → 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + diisopropyl (2-(isobutylamino)-2-oxoethyl)phosphonate (1426294-35-0) + C13H29N3O5P(1+)*Cl(1-)

Guidance literature:

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; isobutylamine; In dichloromethane; at 20 ℃; for 4h;

girard's reagent T; In methanol; dichloromethane;

DOI:10.1021/co400003d

Reference yield: 99.0%

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate + girard's reagent T (123-46-6) + 6-amino-3,4-benzodioxane (22013-33-8) → 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + diisopropyl (2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)amino)-2-oxoethyl)phosphonate (1426294-37-2) + C13H29N3O5P(1+)*Cl(1-)

Guidance literature:

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; 6-amino-3,4-benzodioxane; In dichloromethane; at 20 ℃; for 4h;

girard's reagent T; In methanol; dichloromethane;

DOI:10.1021/co400003d

Reference yield: 98.2%

4-azidobenzoic acid N-hydroxysuccinimide ester (53053-08-0) → 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6)

Guidance literature:

With chitosan; In aq. phosphate buffer; dichloromethane; at 50 ℃; for 5h; Solvent; Temperature; Microwave irradiation;

upstream raw materials:

succinic acid anhydride

N-hydroxysuccinimide

1-(benzyloxy)pyrrolidine-2,5-dione

4-methoxybenzoic acid 2,5-dioxo-1-pyrrolidinyl ester

Downstream raw materials:

3,4-Bis-ethoxycarbonyloxy-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester

succinimido 4-(2-formylphenoxy)butanoate

12-(4-Nitro-phenylamino)-dodecanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

5-Acetoxy-2-benzyloxycarbonylamino-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Refernces

• 1、 Zhou, Wei,Yao, Lan,Liu, Yongxiurong,Shen, Lichun,Chen, Jie,Deng, Hongmei,Shao, Min,Zhang, Hui,Tang, Xiaojun,Cao, Weiguo. "A Catalyst-Free Synthesis of Fused Perfluoroalkylated 2,3-Dihydroisoxazoles via Oxa-Michael-Aldol Annulation". supporting information. p. 429 - 438. Retrieved 2021/10/01.
• 2、 -. "DLL3-TARGETING MULTISPECIFIC ANTIGEN-BINDING MOLECULES AND USES THEREOF". . . Retrieved 2021/10/02.