Oxobis[tris Dimethylamino Phosphonium] Bis(Tetrafluoroborate)
Author(s)
Jenkins, Ian
Griffith University Author(s)
Year published
1995
Metadata
Show full item recordAbstract
[55881‐03‐3] C12H36B2F8N6OP2 (MW 516.10)
InChI = 1S/C12H36N6OP2.2BF4/c1‐13(2)20(14(3)4,15(5)6)19‐21(16(7)8,17(9)10)18(11)12;2*2‐1(3,4)5/h1‐12H3;;/q+2;2*‐1
InChIKey = MSSSPRSPUHPRKJ‐UHFFFAOYSA‐N
(a mild dehydrating agent, useful in peptide synthesis,2 dehydration of aldoximes to nitriles3 and Beckmann or Lossen‐type rearangements3)
Alternate Name: Bates’ reagent.
Physical Data: mp 194–204 °C.
Solubility: insol ether, EtOAc, THF, CH2Cl2, CHCl3; sol MeCN, DMF, HMPA.
Form Supplied in: white crystalline solid; limited commercial availability.
Preparative Methods: by treatment of Hexamethylphosphoric Triamide with ...
View more >[55881‐03‐3] C12H36B2F8N6OP2 (MW 516.10) InChI = 1S/C12H36N6OP2.2BF4/c1‐13(2)20(14(3)4,15(5)6)19‐21(16(7)8,17(9)10)18(11)12;2*2‐1(3,4)5/h1‐12H3;;/q+2;2*‐1 InChIKey = MSSSPRSPUHPRKJ‐UHFFFAOYSA‐N (a mild dehydrating agent, useful in peptide synthesis,2 dehydration of aldoximes to nitriles3 and Beckmann or Lossen‐type rearangements3) Alternate Name: Bates’ reagent. Physical Data: mp 194–204 °C. Solubility: insol ether, EtOAc, THF, CH2Cl2, CHCl3; sol MeCN, DMF, HMPA. Form Supplied in: white crystalline solid; limited commercial availability. Preparative Methods: by treatment of Hexamethylphosphoric Triamide with p‐toluenesulfonic anhydride at 55 °C for 3 h, isolation of the bis(p‐toluenesulfonate), then treatment with NaBF4 in MeCN.2 Handling, Storage, and Precautions: can be used with care without special precautions; however, it reacts with water to produce HMPA (carcinogenic) and HBF4 (corrosive).
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View more >[55881‐03‐3] C12H36B2F8N6OP2 (MW 516.10) InChI = 1S/C12H36N6OP2.2BF4/c1‐13(2)20(14(3)4,15(5)6)19‐21(16(7)8,17(9)10)18(11)12;2*2‐1(3,4)5/h1‐12H3;;/q+2;2*‐1 InChIKey = MSSSPRSPUHPRKJ‐UHFFFAOYSA‐N (a mild dehydrating agent, useful in peptide synthesis,2 dehydration of aldoximes to nitriles3 and Beckmann or Lossen‐type rearangements3) Alternate Name: Bates’ reagent. Physical Data: mp 194–204 °C. Solubility: insol ether, EtOAc, THF, CH2Cl2, CHCl3; sol MeCN, DMF, HMPA. Form Supplied in: white crystalline solid; limited commercial availability. Preparative Methods: by treatment of Hexamethylphosphoric Triamide with p‐toluenesulfonic anhydride at 55 °C for 3 h, isolation of the bis(p‐toluenesulfonate), then treatment with NaBF4 in MeCN.2 Handling, Storage, and Precautions: can be used with care without special precautions; however, it reacts with water to produce HMPA (carcinogenic) and HBF4 (corrosive).
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Journal Title
Encyclopedia of Reagents for Organic Synthesis
Issue
1
Subject
Chemical Sciences