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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:
7782-92-5
Molecular Weight:
39.01
MDL number:
MFCD00011117
UNSPSC Code:
12352301
PubChem Substance ID:
24857541
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

Signal Word

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

Supplementary Hazards

EUH014,EUH019,EUH029

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

39.2 °F - closed cup

Flash Point(C)

4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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