Seyferth-Gilbert Reagent
Title: Seyferth-Gilbert Reagent
CAS Registry Number: 27491-70-9
CAS Name: (Diazomethyl)phosphonic acid dimethyl ester
Additional Names: dimethyl diazomethylphosphonate
Molecular Formula: C3H7N2O3P
Molecular Weight: 150.07
Percent Composition: C 24.01%, H 4.70%, N 18.67%, O 31.98%, P 20.64%
Literature References: Divalent carbon transfer reagent. Prepn: D. Seyferth, R. S. Marmor, Tetrahedron Lett. 11, 2493 (1970); and applications in organophosphorus syntheses: D. Seyferth et al., J. Org. Chem. 36, 1379 (1971). Reactions with aldehydes and aryl ketones to form alkynes: J. C. Gilbert, U. Weerasooriya, ibid. 47, 1837 (1982). Improved prepn: D. G. Brown et al., ibid. 61, 2540 (1996).
Properties: Distillable yellow liquid, bp0.42 59°. nD25 1.4585.
Boiling point: bp0.42 59°
Index of refraction: nD25 1.4585
Use: Reagent for one-carbon homologation of aldehydes and ketones to alkynes.

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