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- W1844432528 abstract "[1075198-30-9] C12H19F6N4O4P (MW 428.27)InChI = 1S/C12H19N4O4.F6P/c1-4-19-11(17)10(9-13)14-20-12(15(2)3)16-5-7-18-8-6-16;1-7(2,3,4,5)6/h4-8H2,1-3H3;/q+1;-1/b14-10-;InChIKey = GPDHNZNLPKYHCN-DZOOLQPHSA-N(stand-alone coupling reagent for peptide bond formation1, 2 and transformation of α-amino acids into their corresponding Weinreb amides3)Alternate Name: COMU.Physical Data: sample decomposes without melting at 143–144 °C (color transition to dark brown) in a standard melting point device. A more accurate onset for the decomposition (159.90 °C) is obtained from dynamic DSC (differential scanning calorimetry) assays.2 COMU contains less than 1% water according to Karl-Fischer studies when sodium tartrate is used as reference.Solubility: sol DMF (1.44 mol L−1), NMP/DCM 3:1 (0.5 mol L−1) and most organic solvents.Form Supplied in: white to off-white crystalline solid, commercially available.Analysis of Reagent Purity: 1H NMR is the most reliable technique for an accurate determination; an approximate purity can also be obtained from HPLC.Preparative Method: COMU is easily accessed from (dimethylaminomorpholino)chloroformamidinium hexafluorophosphate, generated in three steps from morpholine, N,N-dimethylcarbamoyl chloride, and ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) in the presence of Et3N in DCM.2Purification: crystallization or precipitation from acetonitrile.Handling, Storage and Precautions: this reagent is sensitive to hydrolysis. The use of DMF dried over molecular sieves and bubbled with N2 is common for long-term storage in solution. In solid form, it is stable at 4 °C for several months. COMU displays an opposite decomposition profile to explosive benzotriazole-based analogs. Although conservative calorimetric parameters recommend working at temperatures below 41 °C, the sample can be safely dried for several hours at 60 °C and used in microwave syntheses at 80 °C.2, 4 Median lethal dose (LD50) is estimated at 2000 mg kg−1. The title compound presents low potential as allergenic agent." @default.
- W1844432528 created "2016-06-24" @default.
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- W1844432528 date "2011-09-15" @default.
- W1844432528 modified "2023-10-09" @default.
- W1844432528 title "(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholino-carbenium Hexafluorophosphate" @default.
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- W1844432528 doi "https://doi.org/10.1002/047084289x.rn01360" @default.
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