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Burgess Reagent, 96%
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Catalog number L20155.06
also known as L20155-06
Price (USD)/ Each
256.65
Online exclusive
285.00 Save 28.35 (10%)
-
Quantity:
5 g
Price (USD)/ Each
256.65
Online exclusive
285.00 Save 28.35 (10%)
Burgess Reagent, 96%
Catalog numberL20155.06
Price (USD)/ Each
256.65
Online exclusive
285.00 Save 28.35 (10%)
-
Chemical Identifiers
CAS29684-56-8
IUPAC Name(methoxycarbonyl)[(triethylazaniumyl)sulfonyl]azanide
Molecular FormulaC8H18N2O4S
InChI KeyYSHOWEKUVWPFNR-UHFFFAOYSA-N
SMILESCC[N+](CC)(CC)S(=O)(=O)[N-]C(=O)OC
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Specifications
Specification Sheet
Specification SheetFormCrystals or powder or crystalline powder or lumps
Appearance (Color)White to cream to yellow
Assay (HPLC)≥95.0%
Identification (FTIR)Conforms
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Soluble in organic solvents.
Notes
Store in cool place. Moisture sensitive. Incompatible with strong oxidizing agents.
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.
Solubility
Soluble in organic solvents.
Notes
Store in cool place. Moisture sensitive. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- 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.