Basic information
- 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 properties
- 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]
Other Experimental Properties
BEGINS TO VOLATILIZE @ 400 °C & DECOMP INTO ITS ELEMENTS BETWEEN 500 & 600 °C; HEAT OF FORMATION (FOR SOLID) @ 18 °C & 1 ATM: -32.26 KCAL/MOLE; HEAT OF SOLN: -31.06 KCAL/MOLE @ 21 °C. ... FUSED NaNH2 DISSOLVES METALLIC MAGNESIUM, ZINC, MOLYBDENUM, TUNGSTEN, QUARTZ, GLASS, SILICATES & OTHER SUBSTANCES.
DECOMP IN WATER & ALCOHOL
WHITE TO OLIVE-GREEN SOLID WITH SEA-SHELL FRACTURE /COMMERCIAL PRODUCT/
Physicochemical properties
- Melting point
- 210 °C · 210 °C (lit.)
- Boiling point
- 400 °C · 400 °C (lit.)
- Density
- 1.39 g/cm3 · 1.39 g/cm3 (25℃)
- Flash point
- 85 °F · 85 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 2 O · reacts with H2O
- form
- crystalline
- color
- Greyish white powder
- Odor
- Ammonia like
- Water Solubility
- REACTS VERY VIOLENTLY, EVEN EXPLOSIVELY
- Specific Heat Capacity
- 1.7 J/ · Cp(crystal): 1.7 J/(g·K), at 25℃
- Sensitive
- Air & Moisture Sensitive
- Merck
- 14 · 14,8576
- Stability
- Stability Flammable. Reacts violently with water producing very toxic fumes. In case of fire do not use water, but instead smother with soda ash. May form explosive peroxides if heated, or if stored for extended periods in contact with air or oxygen. Incompatible with water and aqueous solutions, carbon dioxide, halogenated hydrocarbo
- InChI
- 1S/H2N.Na/h1H2;/q-1;+1
- InChIKey
- ODZPKZBBUMBTMG-UHFFFAOYSA-N
- SMILES
- N[Na]
- CAS DataBase Reference
- 7782 · 7782-92-5(CAS DataBase Reference)
- FDA UNII
- 5 DB3G6PX9D · 5DB3G6PX9D
- EPA Substance Registry System
- Sodium amide (Na(NH2)) (7782-92-5)
- UNSPSC Code
- 26111700 · 26111700
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H261-H304-H314-H336-H361d-H373-H412
- Precautionary statements
- 210 · P210-P231+P232-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- F,C,Xi,N
- Risk Statements
- 14 · 14/15-19-34-20/21-10-67-65-63-48/20-11-36/37-15/29-14-50-29
- Safety Statements
- 26 · 26-43-45-62-7/8-43D-36/37/39-27-16-61
- RIDADR
- 3129 · UN 3129 4.3/PG 2
- WGK Germany
- 2 · 2
- F
- 3 · 3-10-23
- Autoignition Temperature
- 450 °C · 450 °C
- TSCA
- TSCA listed
- HS Code
- 2853 · 2853 90 90
- HazardClass
- 4.3 · 4.3
- PackingGroup
- II
- Storage Class
- 4.3 · 4.3 - Hazardous materials which set free flammable gases upon contact with water
- Hazard Classifications
- 3 Eye · Aquatic Chronic 3Eye Dam. 1Skin Corr. 1BWater-react 2
- Hazardous Substances Data
- 7782 · 7782-92-5(Hazardous Substances Data)
- REACH Registrations
- Active
- Limited Quantities
- 0.5 Kg · 0.5 Kg (1.1 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
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
Emergency treatment: Corrosives- alkaline; [HSDB] Reacts violently with water producing sodium hydroxide and ammonia; Oxidation products after air exposure may be highly explosive; A severe skin, eye, and mucous membrane irritant; [Merck Index] A strong reducing agent; An explosive peroxide may be produced on storage; May cause caustic burns to skin and eyes; [CAMEO] Reacts violently with water evolving highly flammable gases; Explosive on contact with oxidizing substances; A highly corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [Alfa Aesar MSDS]
Reactive GroupBases, Strong
Reactivity AlertsHighly Flammable
Reactivity Profile
SODIUM AMIDE is a powerful reducing agent. Reacts violently with oxidizing agents. Reacts violently with steam and water to form caustic NaOH and NH3 vapors [Bergstrom et al., Chem. Reviews, 12:6 1932]. May form explosive compounds in the presence of water and carbon dioxide [Handling Chemicals Safely 1980 p 826]. Liable to deflagration upon heating and friction. Forms an explosive peroxide on storage. When sodium amide and chromic anhydride are mixed together a vigorous reaction results; the same occurs with other oxidizing agents including dinitrogen tetraoxide, potassium chlorate, sodium nitrite. [Mellor 11:234 1946-47]. Reaction with 1,1-diethoxy-2- chloroethane produces sodium ethoxyacetylide, which is extremely pyrophoric [Rutledge 1968 p. 35]. Reactions with halogenated hydrocarbons may be violently explosive. Sodium amide forms toxic and flammable H2S gas with CS2. (714).
Air and Water ReactionsHighly flammable. Reacts violently with water and bursts into flame.
Peroxide Forming Chemical
Sodium amide
A: Compounds that form explosive levels of peroxides without concentration
Clark
Hazard Classes and CategoriesWater-react. 1 (42.1%)
Safety & protection
Fire FightingFire Extinguishing Agents Not to Be Used: Water
First AidINGESTION: give water or milk followed by dilute vinegar or fruit juice; do NOT induce vomiting; call a doctor.
Fire Fighting ProceduresDRY SODA ASH, GRAPHITE, SALT, OR OTHER RECOMMENDED DRY POWDER, SUCH AS DRY LIMESTONE.
Storage Conditions
SEALED CONTAINERS MUST BE STORED IN WELL-VENTILATED AREA.
SHOULD BE STORED IN SEALED CONTAINERS WHICH PREVENT ALL CONTACT WITH AIR DURING STORAGE ...
Nonfire Spill ResponseNeutralizing Agents for Acids and Caustics: Caustic solution formed by reaction with water can be diluted with water and/or neutralized by acetic acid. (USCG, 1999)
Isolation and EvacuationExcerpt from ERG Guide 139 [Substances - Water-Reactive (Emitting Flammable and Toxic Gases)]:
Personal Protective Equipment (PPE)
Goggles or face shield; dust respirator; rubber gloves and shoes. (USCG, 1999)
GOGGLES OR FACE SHIELD; DUST RESPIRATOR; RUBBER GLOVES AND SHOES.
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 3-10-23
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 2
- tsca
- TSCA listed
- ridadr
- UN 3129 4.3/PG 2
- hs_code
- 2853 90 90
- risk_code
- 14/15-19-34-20/21-10-67-65-63-48/20-11-36/37-15/29-14-50-29
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07,GHS08
- hazard_code
- F,C,Xi,N
- safety_code
- 26-43-45-62-7/8-43D-36/37/39-27-16-61
- hazard_class
- 4.3
- Storage Class
- 4.3 - Hazardous materials which set free flammable gases upon contact with water
- packing_group
- II
- Hazard statements
- H225-H261-H304-H314-H336-H361d-H373-H412
- Limited Quantities
- 0.5 Kg (1.1 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 3Eye Dam. 1Skin Corr. 1BWater-react 2
- Autoignition Temperature
- 450 °C
- Precautionary statements
- P210-P231+P232-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338
- Hazardous Substances Data
- 7782-92-5(Hazardous Substances Data)
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.
UsesDehydrating 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.
UsesReagent for: Synthesis of allylic amines and amides1 Synthesis of antibacterials2 Aggregative activation and heterocyclic chemistry3 Phenylation with diphenyliodonium chloride4
General DescriptionOdorless colorless solid. Denser than water.
Preparation methods
PreparationSodium amide is prepared by passing dry ammonia gas over sodium metal at 350°C: 2Na + 2NH3 → 2NaNH2 + H2Also, it may be prepared by reacting sodium metal with liquid ammonia in the presence of a catalyst such as iron(III) nitrate. The compound must be stored in well-sealed containers free from air or moisture.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionA white ionic solid formed by passing dry ammonia over sodium at 300–400°C. The compound reacts with water to give sodium hydroxide and ammonia. It reacts with red-hot carbon to form sodium cyanide and with nitrogen(I) oxide to form sodium azide. Sodamide is used in the Castner process and in the explosives industry.
Related reactions
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