N-Hydroxysuccinimide CAS 6066-82-6
Introduction：Basic information about N-Hydroxysuccinimide CAS 6066-82-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
N-Hydroxysuccinimide Basic information
| Product Name: | N-Hydroxysuccinimide |
| Synonyms: | N-HYDROXY-2,5-PYRROLIDINEDIONE;NHS;N-HYDROXYSUCCINIMDE;N-HYDROXYSUCCINIMIDE;N-HYDROXYSUCCINIMIDE POLYMER-BOUND;NHS N-HYDROXYSUCCINIMIDE,;NHS OR HONSU;HOSu~1-Hydroxy-2,5-pyrrolidinedione |
| CAS: | 6066-82-6 |
| MF: | C4H5NO3 |
| MW: | 115.09 |
| EINECS: | 228-001-3 |
| Product Categories: | Zero-Length Crosslinker;heteroXlink;APIS;Coupling ReagentsSynthetic Reagents;Coupling;Others;Supported Reagents;Supported Synthesis;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Succinimides;Peptide Synthesis;Synthetic Organic Chemistry;Miscellaneous Reagents;Other Reagents;Heterocycles;Peptide coupling agents;Medical Intermediates;bc0001;6066-82-6 |
| Mol File: | 6066-82-6.mol |
N-Hydroxysuccinimide Chemical Properties
| Melting point | 95-98 °C(lit.) |
| Boiling point | 215.33°C (rough estimate) |
| density | 1.4769 (rough estimate) |
| vapor pressure | 0Pa at 25℃ |
| refractive index | 1.4080 (estimate) |
| storage temp. | Store at +2°C to +8°C. |
| solubility | DMSO (Soluble), Methanol (Slightly) |
| pka | 7.81±0.20(Predicted) |
| form | Liquid or Solid |
| color | Clear yellow-brown to brown |
| PH | 5-7 (50g/l, H2O, 20℃) |
| Water Solubility | SOLUBLE |
| Sensitive | Hygroscopic |
| BRN | 113913 |
| Stability: | Stable. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, strong bases. Protect from moisture. |
| Cosmetics Ingredients Functions | SKIN CONDITIONING |
| InChI | 1S/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2 |
| InChIKey | NQTADLQHYWFPDB-UHFFFAOYSA-N |
| SMILES | ON1C(=O)CCC1=O |
| LogP | -2.01 |
| CAS DataBase Reference | 6066-82-6(CAS DataBase Reference) |
| NIST Chemistry Reference | N-hydroxylsuccinimide(6066-82-6) |
| EPA Substance Registry System | 2,5-Pyrrolidinedione, 1-hydroxy- (6066-82-6) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 22-24/25-26-36 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| TSCA | TSCA listed |
| HS Code | 29251995 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Dam. 1 Skin Irrit. 2 |
| 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). |
| Chemical Properties | White to pale yellow |
| Uses | Reagent for preparation of active esters of amino acids. |
| Uses | 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. |
| Uses | 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. |
| Application | N-Hydroxysuccinimide has been used in the synthesis of intermediates such as: N-succinimidyl 3-(di-tert-butylfluorosilyl)benzoate 4-[2,2-bis[(p-tolylsulfonyl)-methyl] acetyl]benzoic acid-NHS ester N-succinimidyl 3-iodobenzoate It has also been used in a protocol for the surface modification of microchannels of a microfluidic-integrated surface plasmon resonance (SPR) platform for the detection and quantification of bacterial pathogens. Additive used in the carbodiimide method for improved amidations and peptide couplings. N-Hydroxysuccinimide can be used in the synthesis of N-hydroxysuccinimide ester via dehydration reaction in the presence of dicyclohexylcarbodiimide in carboxylic acid. |
| reaction suitability | reaction type: Coupling Reactions |
| Synthesis | N-Hydroxysuccinimide can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride. |
| Purification Methods | Recrystallise the imide from EtOH/ethyl acetate [Manesis & Goodmen J Org Chem 52 5331 1987]. [Beilstein 21/9 V 498.] |
N-Hydroxysuccinimide Preparation Products And Raw materials
| Raw materials | Hydroxylamine hydrochloride-->Succinic anhydride-->NSC81536-->estradiol-3-sulfate-->1-Pyrrolidinecarboxylic acid, 2,5-dioxo-, 1,1-dimethylethyl ester-->1-Hydroxypiperidine-2,6-dione-->N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE-->N,N'-Disuccinimidyl carbonate-->N-(3-aminopropyl)benzamide-->BZ-OSU-->Girard's Reagent T-->N-Succinimidyl 3-maleimidopropionate-->2-METHYLBUTYLAMINE |
| Preparation Products | Enalapril-->Imidapril-->N-ACRYLOXYSUCCINIMIDE-->Arbekacin-->Aspoxicillin-->GUSPERIMUS-->Cy5 |
