291587

Sigma-Aldrich

Sodium amide

50 wt. % suspension in toluene

Linear Formula:
NaNH2
CAS Number:
Molecular Weight:
39.01
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

concentration

50 wt. % suspension in toluene

bp

400 °C (lit.)

mp

210 °C (lit.)

SMILES string

N[Na]

InChI

1S/H2N.Na/h1H2;/q-1;+1

InChI key

ODZPKZBBUMBTMG-UHFFFAOYSA-N

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General description

Sodium amide, an inorganic compound used in organic synthesis, is generally prepared by heating sodium metal in gaseous ammonia. It is used in some organic reactions like dehalogenation, deprotonation, anionic polymerization of ionic chains, and in cleavage of ketones.

Application

Reagent for:
Synthesis of allylic amines and amides
Synthesis of antibacterials
Aggregative activation and heterocyclic chemistry
Phenylation with diphenyliodonium chloride

Packaging

100, 750 g in glass bottle

Signal Word

Danger

Target Organs

Central nervous system

Supp Hazards

EUH014 - EUH019 - EUH029

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3129 8(4.3) / PGII

WGK Germany

WGK 2

Flash Point(F)

39.2 °F - closed cup

Flash Point(C)

4 °C - closed cup

Sodium Amide
Ullmann's Encyclopedia of Industrial Chemistry (2000)
M. Bakavoli, et al.,
Journal of Heterocyclic Chemistry, 48, 149-152 (2010)
Christian Bukovec et al.
Organic & biomolecular chemistry, 9(8), 2743-2750 (2011-03-08)
Stannylated allylic carbonates are suitable substrates for Pd-catalyzed allylic aminations. In DMF and with [allylPdCl](2) as catalyst the stannylated allyl amines formed can be directly coupled with electrophiles according to the Stille protocol, giving rise to highly functionalized building blocks...
C. Caubere, et al.,
Tetrahedron, 50, 11903-11920 (1994)
K. G. Hampton, et al.,
Organic Syntheses, 51, 128-132 (1971)

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