Sodium amide
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Basic information
- CAS
7782-92-5- Standard SMILES
[NH2-].[Na+]- InChIKey
ODZPKZBBUMBTMG-UHFFFAOYSA-N- Molecular formula
- H2NNa
- Average molar mass
- 39.013 g/mol
- Monoisotopic mass
- 39.00849334
Overview
Sodium amide is an odorless colorless solid. Denser than water.
Names & identifiers
- Preferred name
- Sodium amide
- IUPAC
- sodium azanide
- English name
- Sodium amide
- Molecular formula
- H2NNa
- Molecular weight
- 39.01
Names & synonyms
SODIUM AMIDE7782-92-5Sodamidesodium azanideSodium amide (Na(NH2))5DB3G6PX9DHSDB 692EINECS 231-971-0NaNH2EC 231-971-0SODIUM AMIDE [MI]SODIUM AMIDE [HSDB]
Show more names
m amideNatriumamidAminosodiumSodium aminoSodiumamide,94%SODIUM AMIDE 95%Sodium amide (8CI)
DTXSID2064816CHEBI:176791RefChem:887257DTXCID9048017UN1390231-971-0sodium;azanideUNII-5DB3G6PX9D
Database identifiers
- CAS
7782-92-5- PubChem CID
- 24533
- DTXSID
DTXSID2064816- ChEBI
CHEBI:176791- UNII
- 5DB3G6PX9D
- EC Number
- 231-971-0
- Nikkaji
- J1.296C
Properties
Computed structural propertiesFilling in
- Topological polar surface area
- 1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 2
- Formal charge
- 0
- Complexity
- 2
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds
OdorAMMONIA ODOR
Density
1.39 at 68 °F (USCG, 1999) - Denser than water; will sink
1.39 @ 20 °C
Color/FormWHITE CRYSTALLINE POWDER
Solubility
SOLUBILITY IN LIQ AMMONIA AT 20 °C= ABOUT 0.1%
Soluble in water; insoluble in alcohol.
Boiling Point
752 °F at 760 mmHg (USCG, 1999)
400 °C
Melting Point
410 °F (USCG, 1999)
210 °C
Physical Description
Sodium amide is an odorless colorless solid. Denser than water.
Solid; Commercial form is white to olive-green; Quickly absorbs water and carbon dioxide from atmosphere; [Merck Index] White solid with an odor of ammonia; [Hawley] Grey powder or granules with an ammoniacal odor; [Alfa Aesar MSDS]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H260 (42.1%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances and mixtures which in contact with water, emit flammable gases]
P223, P231+P232, P260, P264, P264+P265, P273, P280, P301+P330+P331, P302+P335+P334, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P391, P402+P404, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 297 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Sodium amide (Na(NH2))
Status: Active Update: 25-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/11165
Sodium amide: HSNO Approval: HSR004679 Approved with controls
DOT LabelDangerous When Wet
Fire HazardsSpecial Hazards of Combustion Products: Toxic and irritating ammonia gas may be formed. (USCG, 1999)
Fire Potential
FLAMMABLE, DANGEROUS FIRE RISK.
The reduction with 1,1-diethoxy-2-chloroethane in the presence of ammonia produces sodium ethoxyacetylide, which is extremely pyrophoric. Sodium amide reacts violently with water and frequently bursts into flame.
Health HazardsAmmonia gas formed by reaction of solid with moisture irritates eyes and skin. Solid causes caustic burns of eyes and skin. Ingestion burns mouth and stomach in same way as caustic soda and may cause perforation of tissue. (USCG, 1999)
Hazards Summary
Chemistry & industry
Uses & manufacturing
Uses
Used as a dehydrating agent, in ammonolysis reactions, in Claisen condensations, and for alkylation of nitriles and ketones; Also used to make indigo, hydrazine, ethynyl compounds, acetylenic carbinols, and sodium cyanide; [Merck Index]
DEHYDRATING AGENT; PRODN OF INDIGO & HYDRAZINE; INTERMEDIATE IN PREPN OF SODIUM CYANIDE; IN AMMONOLYSIS REACTIONS; IN CLAISEN CONDENSATIONS, ALKYLATION OF NITRILES & KETONES, SYNTH OF ETHYNYL CMPD, ACETYLENIC CARBINOLS
Methods of Manufacturing
PREPARED FROM SODIUM METAL & GASEOUS AMMONIA (OR LIQ AMMONIA WITH FERRIC NITRATE CATALYST): DENNIS, BROWNE, INORG SYN 1, 74 (1939); GREENLEE, HENNE, INORG SYN 2, 128 (1946). ...ALTERNATE METHOD: BERGSTROM, ORG SYN, COLL VOL III, 778 (1955).
DRY AMMONIA GAS IS PASSED OVER METALLIC SODIUM @ 350 °C.
Formulations/PreparationsGRADES OR PURITY: PURE; TECHNICAL
General Manufacturing InformationSodium amide (Na(NH2)): ACTIVE
Applications
Uses1. It can be used as the condensation accelerator in organic chemical reactions. It is raw material in synthesis of vitamin A. It can be also used as dehydrating agent, dehalogenating agent, alkylating agent, ammoniated agent. In liquid ammonia, the dissociation of NHf in liquid ammonia can be used as initiator of anionic polymerization producting polyvinyl chloride ion. It is also used in the manufacture azides, cyanide, hydrazine, and indigo. 2. It can be used as condensation-accelerating agent in organic synthesis, dehydration and the like. The above information is edited by the chemicalbook of Wang Xiaodong.
UsesSodium Amide is widely used in organic chemical synthesis as a strong base in reactions such as in the preparation of phenylacetylene from 1,2-dibromophenylethane. Also used in the synthesis of 2,6-diamination of substituted pyridines as initiator of heterogeneous chichibabin reaction.
Dehydrating agent. In the production of indigo and hydrazine. Intermediate in the preparation of sodium cyanide. In ammonolysis reactions, in Claisen condensations, alkylation of nitriles and ketones, synthesis of ethynyl Compounds, acetylenic carbinols. Fused NaNH2 dissolves metallic Mg, Zn, Mo, W, quartz, glass, silicates and other substances.
Related reactions
478 records
Compound notes
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