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| CAS No.: | 18197-26-7 |
| Formula: | C2h2nnao2 |
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Common Name: Sodium Formamide (often referred to as Formamide Sodium Salt or Sodioformamide)
Systematic Name: More accurately described as a sodium amide-formamide adduct or disodium formamide derivative.
Typical Representation: NaNHCHO, HCONHNa, or more precisely as a complex like NaNH2·HCONH2or NaNH2·HCOONa.
CAS No.: 20654-11-7 (commonly associated, but CAS may vary with exact composition)
State: Off-white to grayish or tan powder.
Basic Description:
Sodium formamide is not a simple salt but a complex reagent or adduct formed between sodium amide (NaNH2) and formamide or its decomposition products. It is commercially available as a safer and more handleable solid alternative to pure, pyrophoric sodium amide.
Its key feature is that it serves as a strong base and nucleophilic amination agent, equivalent. Compared to pure sodium amide, it is:
Less pyrophoric and less moisture-sensitive
Easier to weigh and handle
Soluble in some polar aprotic solvents (like DMF, DMSO) when fresh, but decomposes over time.
It is exclusively used as a specialized reagent in organic synthesis, valued for its dual functionality:
As a Strong, Non-Nucleophilic Base:
For deprotonating weakly acidic C-H bonds (e.g., terminal alkynes, active methylene groups).
To generate carbanions for alkylation or condensation reactions.
As a Nucleophilic Amination Source ( Equivalent):
For direct amination of alkyl halides to produce primary amines.
For ring-opening of epoxides to yield amino alcohols.
In some heterocyclic syntheses requiring amide anion introduction.
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