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)

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

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.

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.

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.]