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.

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)

Safety Information

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

MSDS

• Language:English Provider:1-Hydroxy-2,5-pyrrolidinedione
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-Hydroxysuccinimide Usage And Synthesis

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.

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(6066-82-6)Related Product Information

• 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