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291587

Sigma-Aldrich

Sodium amide

50 wt. % suspension in toluene

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About This Item

Linear Formula:
NaNH2
CAS Number:
Molecular Weight:
39.01
MDL number:
UNSPSC Code:
12352301
PubChem Substance ID:
NACRES:
NA.22

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

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3 - Water-react 2

target_organs

Central nervous system

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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Sodium Amide
Ullmann's Encyclopedia of Industrial Chemistry (2000)
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
M. Bakavoli, et al.,
Journal of Heterocyclic Chemistry, 48, 149-152 (2010)
C. Caubere, et al.,
Tetrahedron, 50, 11903-11920 (1994)
K. G. Hampton, et al.,
Organic Syntheses, 51, 128-132 (1971)

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