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H27719 1,1'-(Azodicarbonyl)dipiperidine, 97%

CAS Number
10465-81-3
Synonyms
ADDP

Stock No. Size Price ($) Quantity Availability
H27719-06 5g 89.30
H27719-14 25g 266.00
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1,1'-(Azodicarbonyl)dipiperidine, 97%

MDL
MFCD00010111

Chemical Properties

Formula
C12H20N4O2
Formula Weight
252.32
Melting point
133-136°
Storage & Sensitivity
Ambient temperatures.
Solubility
Slightly soluble in water.

Applications

It is used in a study of the copper-catalyzed addition of aryboronic acids to azodicarboxyl derivatives providing aryl-substituted hydrazides. It is widely used reagent for the Mitsunobu reaction. It is reactant for preparation of polyfluoroalkylated tripyrazolylmethane ligands, (-)-Hygromycin A via Mitsunobu glycosylation, optically active α,α-disubstituted amino acids via Mitsunobu reaction, aza-β-lactams through [2+2] cycloaddition reactions, glycosyl disulfides, pyridine ether PPAR agonists, S-glycosyl amino acid, building blocks for combinatorial neoglycopeptide synthesis and is a histamine H3 receptor antagonists. It is a reactant for Mitsunobu inversion reactions.

Notes

Store in cool dry conditions. Incompatible with oxidizing agents.

Literature References

Tetsuto Tsunoda.; Yoshiko Yamamiya.; Shô Itô. 1,1?-(azodicarbonyl)dipiperidine-tributylphosphine, a new reagent system for mitsunobu reaction.Tetrahedron Lett. 1993, 34 (10),1639-1642 .

Robert A. Falconera.; Istvan Jablonkaia.; Istvan Toth. Efficient synthesis of thioglycosides via a Mitsunobu condensation.Tetrahedron Lett. 1999, 40 (39),8663-8666 .

Reagent for the Mitsunobu reaction (see Diethyl­ azodicarboxyl­ate, L19348), used in combination with tri-n-butylphosphine as a more powerful system than DEAD for higher pKa nucleophiles: Tetrahedon Lett., 34, 1639 (1993); Tetrahedron, 61, 6218 (2005). Has also been utilized in a selective method for converting primary and secondary alcohols to carbonyl compounds, by reaction of the alcohol with a Grignard reagent, followed by oxidation of the intermediate magnesio-derivative with ADDP: J. Org. Chem., 38, 1652 (1973); Bull. Chem. Soc. Jpn., 2773 (1977).

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

Harmonized Tariff Code
2933.39
TSCA
No

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