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N-Hydroxysuccinimide

CAS No.
6066-82-6
Chemical Name:
N-Hydroxysuccinimide
Synonyms
NHS;HOSU;1-HYDROXY-PYRROLIDINE-2,5-DIONE;Hydroxysuccinimide;HONSU;2,5-PYRROLIDINEDIONE, 1-HYDROXY-;N-HYDROXYSUCCINIMDE;N-HYDROXYSUCCINAMIDE;1-Hydroxysuccinimide;1-HYDROXY-2,5-PYRROLIDINEDIONE
CBNumber:
CB0391283
Molecular Formula:
C4H5NO3
Molecular Weight:
115.09
MDL Number:
MFCD00005516
MOL File:
6066-82-6.mol
MSDS File:
SDS
Last updated:2024-03-22 17:12:53

N-Hydroxysuccinimide 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)
form Liquid or Solid
pka 7.81±0.20(Predicted)
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.
InChIKey NQTADLQHYWFPDB-UHFFFAOYSA-N
LogP -2.01
CAS DataBase Reference 6066-82-6(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII MJE3791M4T
NIST Chemistry Reference N-hydroxylsuccinimide(6066-82-6)
EPA Substance Registry System 2,5-Pyrrolidinedione, 1-hydroxy- (6066-82-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS05
Signal word  Danger
Hazard statements  H315-H318
Precautionary statements  P264-P280-P302+P352-P305+P351+P338-P332+P313-P362+P364
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  22-24/25-26-36
WGK Germany  3
Hazard Note  Irritant
TSCA  Yes
HS Code  29251995
NFPA 704
1
2 1

N-Hydroxysuccinimide price More Price(74)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.51056 HOSu Novabiochem? 6066-82-6 25g $33.2 2024-03-01 Buy
Sigma-Aldrich 8.04518 N-Hydroxysuccinimide for synthesis 6066-82-6 25g $46.3 2024-03-01 Buy
Sigma-Aldrich 8.51056 HOSu Novabiochem? 6066-82-6 100g $80.6 2024-03-01 Buy
Sigma-Aldrich 8.04518 N-Hydroxysuccinimide for synthesis 6066-82-6 100g $143 2024-03-01 Buy
Sigma-Aldrich 8.04518 N-Hydroxysuccinimide for synthesis 6066-82-6 500g $462 2024-03-01 Buy
Product number Packaging Price Buy
8.51056 25g $33.2 Buy
8.04518 25g $46.3 Buy
8.51056 100g $80.6 Buy
8.04518 100g $143 Buy
8.04518 500g $462 Buy

N-Hydroxysuccinimide Chemical Properties,Uses,Production

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

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.

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.

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.

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.]

53053-08-0
6066-82-6
Synthesis of N-Hydroxysuccinimide from N-HYDROXYSUCCINIMIDYL-4-AZIDOBENZOATE
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N-Hydroxysuccinimide pictures 2024-03-29 N-Hydroxysuccinimide
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US $0.00 / Kg/Drum 1KG 99% 500kg Jinan Finer Chemical Co., Ltd
N-Hydroxysuccinimide pictures 2024-03-28 N-Hydroxysuccinimide
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US $30.00 / kg 1kg 98% 2000kg hebei hongtan Biotechnology Co., Ltd
N-HYDROXYSUCCINIMIDE pictures 2023-11-21 N-HYDROXYSUCCINIMIDE
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US $0.00-0.00 / kg 1kg 99% 50000kg Hebei Yibangte Import and Export Co. , Ltd.
N-HYDROXY-2,5-PYRROLIDINEDIONE N-HYDROXYSUCCINIMIDE N-HYDROXYSUCCINIMIDE POLYMER-BOUND NHS N-HYDROXYSUCCINIMIDE, NHS OR HONSU HOSu~1-Hydroxy-2,5-pyrrolidinedione N-Hydroxysuccinimide (HOSu) N-HYDROXYSUCCINIMIDE, 99+% N-HYDROXYSUCCINIMIDE, 98+% Hosu,Nhs(N-Hydroxysuccinimide) 9,10-Bis(Phenthynyl)Anthracene HOSU (N-Hydroxysuccinimide) N-HYDOXYSUCCINIMIDE, NHS HOSU (N-HYDROXYSUCCINIMIDE,NHS) N-Hydroxysuccinimide >97% N-HYDROXYSUCCINIMIDE pure 1-Hydroxy-2,5-pyrrolidinedione, HOSu N-Hydroxysuccinic acid imide Succinimidyl alcohol N-Hydroxysuccinimide [Coupling Reagent for Peptide] O-Hydroxysucc Inimide N-Hydroxysuccinimide,1-Hydroxy-2,5-pyrrolidinedione, HOSu, NHS N-Hydroxysuccinimide≥ 99% (Assay) HOSu Novabiochem 1-hydroxy-5-pyrrolidinedione 5-Pyrrolidinedione,1-hydroxy-2 Succinimide, N-hydroxy- AKOS 91864 4-HYDROXY-2,5-PYRROLIDINEDIONE N-HydroxysucciniMide, 98+% 100GR N-HydroxysucciniMide, 98+% 250GR N-HydroxysucciniMide, 98+% 25GR N-Hydroxy-2,5-dioxopyrrolidine N-HYDROXYSUCCINIMIDE FOR SYNTHESIS 1-Hydroxy-2,5-pyrrolidione 1-Hydroxypyrrolidine-2,5-dione, 2,5-Dioxo-1-hydroxypyrrolidine N-HydroxysucciniMide 98% N-HydroxysucciniMide puruM, >=97.0% (T) N - butyl hydroxy diiMide N-Hydroxysuccinimide N- hydroxyl Ji Dingya diamide 1-Hydroxy-2,5-pyrrolidinedione, NHS, N-Hydroxybutanimide, N-гидроксибутанимид N-Hydroxysuccinimide> N-Hydroxysuccinimide [Coupling Reagent for Peptide]> NHS N-Hydroxysuccinimide,98% HOSU 25 G HOSU/NHS N-Hydroxysuccinimide USP/EP/BP NHS N-HYDROXYSUCCINIMDE N-HYDROXYSUCCINAMIDE 1-Hydroxysuccinimide Hydroxysuccinimide 1-HYDROXY-PYRROLIDINE-2,5-DIONE HONSU HOSU 1-HYDROXY-2,5-PYRROLIDINEDIONE 2,5-PYRROLIDINEDIONE, 1-HYDROXY-