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Merck
CN

291587

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
NACRES:
NA.22
PubChem Substance ID:
24857541
UNSPSC Code:
12352301
MDL number:
MFCD00011117
Concentration:
50 wt. % suspension in toluene

Key Documents

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InChI

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

SMILES string

N[Na]

InChI key

ODZPKZBBUMBTMG-UHFFFAOYSA-N

concentration

50 wt. % suspension in toluene

bp

400 °C (lit.)

mp

210 °C (lit.)

Quality Level

200

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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

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM4778
SHBL7209
SHBK7773
SHBJ2244
SHBH8436

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