ChemicalBook > CAS DataBase List > N-Hydroxysuccinimide

N-Hydroxysuccinimide

Product Name
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
Formula Weight
115.09
MOL File
6066-82-6.mol
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N-Hydroxysuccinimide Property

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.
InChIKey
NQTADLQHYWFPDB-UHFFFAOYSA-N
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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H318Causes serious eye damage

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.51056
Product name
HOSu
Purity
Novabiochem?
Packaging
25g
Price
$33.2
Updated
2024/03/01
Sigma-Aldrich
Product number
8.04518
Product name
N-Hydroxysuccinimide
Purity
for synthesis
Packaging
25g
Price
$46.3
Updated
2024/03/01
Sigma-Aldrich
Product number
8.51056
Product name
HOSu
Purity
Novabiochem?
Packaging
100g
Price
$80.6
Updated
2024/03/01
Sigma-Aldrich
Product number
8.04518
Product name
N-Hydroxysuccinimide
Purity
for synthesis
Packaging
100g
Price
$143
Updated
2024/03/01
Sigma-Aldrich
Product number
8.04518
Product name
N-Hydroxysuccinimide
Purity
for synthesis
Packaging
500g
Price
$462
Updated
2024/03/01
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N-Hydroxysuccinimide Chemical Properties,Usage,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

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

Succinic anhydride Hydroxylamine hydrochloride

Preparation Products

Enalapril Aspoxicillin Imidapril N-ACRYLOXYSUCCINIMIDE GUSPERIMUS Arbekacin
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View Lastest Price from N-Hydroxysuccinimide manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
N-Hydroxysuccinimide 6066-82-6
Price
US $62.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/week
Release date
2024-05-24
Jinan Finer Chemical Co., Ltd
Product
N-Hydroxysuccinimide 6066-82-6
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
500kg
Release date
2022-02-10
hebei hongtan Biotechnology Co., Ltd
Product
N-Hydroxysuccinimide 6066-82-6
Price
US $30.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
2000kg
Release date
2024-05-14

6066-82-6, N-HydroxysuccinimideRelated Search:

Bismaleimide Diethyl succinosuccinate N-Chlorosuccinimide CHLOROPHOSPHONAZO III N-Iodosuccinimide N-Bromosuccinimide Succinimide Dispersing agent 155 O-Phthalimide N-ALLYLPHTHALIMIDE 3-CHLORO-PROPANE-1-SULFONIC ACID TERT-BUTYLAMIDE Methyldiallylamine 2-Oxo-1-imidazolidinecarbonyl chloride 2-Anilinoethanol tert-Butyl N-hydroxycarbamate N-octadecylstearamide 4-(Hydroxyamino)-4-oxobutanoic acid 1-Benzyl-4-methyl-piperidin-3-one hydrochloride

  • 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
  • N-Hydroxysuccinimide (HOSu)
  • N-HYDROXYSUCCINAMIDE
  • 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-2,5-pyrrolidinedione, NHS, N-Hydroxybutanimide, N-гидроксибутанимид
  • 1-hydroxy-5-pyrrolidinedione
  • 1-Hydroxysuccinimide
  • 5-Pyrrolidinedione,1-hydroxy-2
  • Hydroxysuccinimide
  • Succinimide, N-hydroxy-
  • AKOS 91864
  • 4-HYDROXY-2,5-PYRROLIDINEDIONE
  • 2,5-PYRROLIDINEDIONE, 1-HYDROXY-
  • 1-HYDROXY-2,5-PYRROLIDINEDIONE
  • 1-HYDROXY-PYRROLIDINE-2,5-DIONE
  • HONSU
  • HOSU
  • 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
  • <i>N</i>-Hydroxysuccinimide
  • N- hydroxyl Ji Dingya diamide
  • N-Hydroxysuccinimide&gt
  • N-Hydroxysuccinimide [Coupling Reagent for Peptide]&gt
  • NHS N-Hydroxysuccinimide,98%
  • HOSU 25 G
  • HOSU/NHS
  • N-Hydroxysuccinimide USP/EP/BP