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A10312 N-Hydroxysuccinimide, 98+%

CAS Number
6066-82-6
Synonyms
HOSu
1-Hydroxy-2,5-pyrrolidinedione

Stock No. Size Price ($) Quantity Availability
A10312-14 25g 35.50
A10312-22 100g 95.30
A10312-36 500g 380.00
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N-Hydroxysuccinimide, 98+%

MDL
MFCD00005516
EINECS
228-001-3

Chemical Properties

Formula
C4H5NO3
Formula Weight
115.09
Melting point
94-99°
Storage & Sensitivity
Hygroscopic. Ambient temperatures.
Solubility
Soluble in water, dimethyl formamide, alcohols and ethyl acetate. Insoluble in cold ether.

Applications

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.

Notes

Hygroscopic. Moisture sensitive. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides and strong bases. Store in a cool place.

Literature References

Reagent for the preparation of active N-hydroxysuccinimide esters for peptide coupling with minimum racemization: J. Am. Chem. Soc., 86, 1839 (1964), or as an additive in the DCC method (see N,N'-Dicyclohexyl­carbodiimide, A10973 ) to suppress racemization: J. Am. Chem. Soc., 89, 7151 (1967). For peptide reagents, see Appendix 6.

For a study of the aminolysis of N-hydroxysuccinimide esters, see: J. Org. Chem., 53, 3583 (1988).

Park, C.; Vo, C. L. N.; Kang, T.; Oh, E.; Lee, B. J. New method and characterization of self-assembled gelatin-oleic nanoparticles using a desolvation method via carbodiimide/N-hydroxysuccinimide (EDC/NHS) reaction. Eur. J. Pharm. Biopharm. 2015, 89, 365-373.

Peng, Z.; McGee, W. M.; Bu, J.; Barefoot, N. Z.; McLuckey, S. A. Gas phase reactivity of carboxylates with N-hydroxysuccinimide esters. J. Am. Soc. Mass. Spectrom. 2015, 26 (1), 174-180.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
113913
Harmonized Tariff Code
2925.19
TSCA
Yes

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