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29684-56-8 - Burgess Reagent, 96% - (Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt - Methyl N-(triethylammoniosulfonyl)carbamate - L20155 - Alfa Aesar

L20155 Burgess Reagent, 96%

CAS-Nummer
29684-56-8
Synonyme
(Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt
Methyl N-(triethylammoniosulfonyl)carbamate

Größe Preis ($) Menge Verfügbarkeit
1g 65,10
5g 224,54
25g 815,76
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Burgess Reagent, 96%

MDL
MFCD00077815

Chemische Eigenschaften

Formel
C8H18N2O4S
Molmasse
238.30
Schmelzpunkt
72-82°
Sensitivität
Moisture Sensitive
Löslichkeit
Soluble in organic solvents.

Anwendungen

Burgess reagent is a selective dehydrating reagent used in organic synthesis. It is used to convert secondary and tertiary alcohol, with an adjacent proton, into alkenes. Burgess reagent is also utilized to promote great synthetic values in medicinal chemistry. It has been used in dehydration of primary amides, formamides and primary nitroalkanes to generate nitriles, isocyanides and nitrile oxides respectively. It forms urethanes when it reacts with primary alcohols.

Bemerkungen

Store in cool place. Moisture sensitive. Incompatible with strong oxidizing agents.

Literaturverweise

Mild, efficient dehydrating agent. Primary alcohols are converted to carbamates, which can be hydrolyzed to primary amines, thus providing a valuable alcohol to amine transformation. Secondary and tertiary alcohols afford olefins in synthetically useful yields: J. Org. Chem., 38, 26 (1973); Org. Synth. Coll., 6, 788 (1988). For further discussion, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 5, p. 3345.

Primary amides undergo facile dehydration to nitriles, even in the presence of other functional groups including alcohols: Tetrahedron Lett., 29, 2155 (1988). Aldoximes are also dehydrated to nitriles: Synth. Commun., 30, 1509 (2000); Synlett, 1169 (2000). Formamides afford isonitriles: J. Chem. Soc., Perkin 1, 1015 (1998). 2-Acylamino carbonyl compounds undergo the Robinson-Gabriel cyclodehydration to give oxazoles, avoiding conventional harsh dehydrating agents (e.g. P2 O5, POCl3 or SOCl2 ): Synlett, 1642 (1999):

The cyclization of 1,2-diacylhydrazines to 1,3,4-oxadiazoles has also been reported: Tetrahedron Lett., 40, 3275 (1999).

Majid, M. H.; Tahereh, A.; Azadeh, F.; Nasim, M. K. Recent Advances in the Application of the Burgess Reagent in Organic Synthesis. Curr. Org. Synth. 2015, 12 (3), 328-357.

Maki, T.; Tsuritani, T.; Yasukata, T. A Mild Method for the Synthesis of Carbamate-Protected Guanidines Using the Burgess Reagent. Org. Lett. 2014, 16 (7), 1868-1871.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H315-H319-H335

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

Sicherheitshinweise: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
1432131
Harmonized Tariff Code
2930.90
TSCA
No

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