|Jmol-3D images||Image 1|
|Molar mass||39.01 g mol-1|
|Density||1.39 g cm-3|
210 °C, 483 K, 410 °F
400 °C, 673 K, 752 °F
|Acidity (pKa)||38 (conjugate acid) |
|EU Index||Not listed|
|Flash point||4.44 °C|
|Other anions||Sodium bis(trimethylsilyl)amide|
|Other cations||Potassium amide|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Sodium amide, commonly called sodamide, is the chemical compound with the formula NaNH2. This solid, which is dangerously reactive toward water, is white when pure, but commercial samples are typically gray due to the presence of small quantities of metallic iron from the manufacturing process. Such impurities do not usually affect the utility of the reagent. NaNH2 conducts electricity in the fused state, its conductance being similar to that of NaOH in a similar state. NaNH2 has been widely employed as a strong base in organic synthesis.
Preparation and structure 
Sodium amide can be prepared by the reaction of sodium with ammonia gas, but it is usually prepared by the reaction in liquid ammonia using iron(III) nitrate as a catalyst. The reaction is fastest at the boiling point of the ammonia, c. −33 °C. An electride, [Na(NH3)6]+e-, is formed as an intermediate.
- 2 Na + 2 NH3 → 2 NaNH2 + H2
NaNH2 is a salt-like material and as such, crystallizes as an infinite polymer. The geometry about sodium is tetrahedral. In ammonia, NaNH2 forms conductive solutions, consistent with the presence of Na(NH3)6+ and NH2- anions.
Sodium amide is used in the industrial production of indigo, hydrazine, and sodium cyanide. It is the reagent of choice for the drying of ammonia (liquid or gaseous) and is also widely used as a strong base in organic chemistry, often in liquid ammonia solution. One of the main advantages to the use of sodamide is that it is an excellent base and rarely serves as a nucleophile. It is however poorly soluble and its use has been superseded by the related reagents such as sodium hydride, sodium bis(trimethylsilyl)amide (NaHMDS), and lithium diisopropylamide (LDA).
Preparation of alkynes 
Sodium amide induces the loss of two molecules of hydrogen bromide from a vicinal dibromoalkane to give a carbon-carbon triple bond, as in a preparation of phenylacetylene. Normally two equivalents of sodium amide yields the desired alkyne. However, three equivalents are necessary in the preparation of a terminal alkyne because, as this alkyne forms, its acidic terminal hydrogen immediately protonates an equivalent amount of base.
Cyclization reactions 
Deprotonation of carbon and nitrogen acids 
Carbon acids which can be deprotonated by sodium amide in liquid ammonia include terminal alkynes, methyl ketones, cyclohexanone, phenylacetic acid and its derivatives and diphenylmethane. Acetylacetone loses two protons to form a dianion.
Other reactions 
- Rearrangement with orthodeprotonation
- Oxirane synthesis (by carbene reaction?)
- Indole synthesis
- Chichibabin reaction
- NaNH2 + H2O → NH3 + NaOH
- 2 NaNH2 + 4 O2 → Na2O + 2 NO2 + 2 H2O
In the presence of limited quantities of air and moisture, such as in a poorly closed container, explosive mixtures of peroxides may form. This is accompanied by a yellowing or browning of the solid. As such, sodium amide should always be stored in a tightly closed container, under an atmosphere of nitrogen gas. Sodium amide samples which are yellow or brown in color should be dealt with immediately. These containers should not be handled and proper safety authorities should be notified.
Sodium amide may be expected to be corrosive to the skin, eyes and mucous membranes. Care should be taken to avoid dispersal of the dust.
See also 
- Buncel, E.; Menon, B. (1977). "Carbanion mechanisms: VII. Metallation of hydrocarbon acids by potassium amide and potassium methylamide in tetrahydrofuran and the relative hydride acidities". Journal of Organometallic Chemistry 141 (1): 1–7. doi:10.1016/S0022-328X(00)90661-2.
- Bergstrom, F. W. (1955), "Sodium amide", Org. Synth.; Coll. Vol. 3: 778
- Greenlee, K. W.; Henne, A. L.; Fernelius, W. C. (1946). "Sodium Amide". Inorganic Syntheses 2: 128–135. doi:10.1002/9780470132333.ch38.
- Zalkin, A.; Templeton, D. H. (1956). "The Crystal Structure Of Sodium Amide". Journal of Physical Chemistry 60 (6): 821–823. doi:10.1021/j150540a042.
- Wells, A. F. (1984). Structural Inorganic Chemistry. Oxford: Clarendon Press. ISBN 0-19-855370-6.
- Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
- Campbell, K. N.; Campbell, B. K. (1950), "Phenylacetylene", Org. Synth. 30: 72; Coll. Vol. 4: 763
- Jones, E. R. H.; Eglinton, G.; Whiting, M. C.; Shaw, B. L. (1954), "Ethoxyacetylene", Org. Synth. 34: 46; Coll. Vol. 4: 404
Bou, A.; Pericàs, M. A.; Riera, A.; Serratosa, F. (1987), "Dialkoxyacetylenes: di-tert-butoxyethyne, a valuable synthetic intermediate", Org. Synth. 65: 58; Coll. Vol. 8: 161
Magriotis, P. A.; Brown, J. T. (1995), "Phenylthioacetylene", Org. Synth. 72: 252; Coll. Vol. 9: 656
Ashworth, P. J.; Mansfield, G. H.; Whiting, M. C. (1955), "2-Butyn-1-ol", Org. Synth. 35: 20; Coll. Vol. 4: 128
- Newman, M. S.; Stalick, W. M. (1977), "1-Ethoxy-1-butyne", Org. Synth. 57: 65; Coll. Vol. 6: 564
- Salaun, J. R.; Champion, J.; Conia, J. M. (1977), "Cyclobutanone from methylenecyclopropane via oxaspiropentane", Org. Synth. 57: 36; Coll. Vol. 6: 320
- Nakamura, M.; Wang, X. Q.; Isaka, M.; Yamago, S.; Nakamura, E. (2003), "Synthesis and (3+2)-cycloaddition of a 2,2-dialkoxy-1-methylenecyclopropane: 6,6-dimethyl-1-methylene-4,8-dioxaspiro(2.5)octane and cis-5-(5,5-dimethyl-1,3-dioxan-2-ylidene)hexahydro-1(2H)-pentalen-2-one", Org. Synth. 80: 144
- Bottini, A. T.; Olsen, R. E. (1964), "N-Ethylallenimine", Org. Synth. 44: 53; Coll. Vol. 5: 541
- Skorcz, J. A.; Kaminski, F. E. (1968), "1-Cyanobenzocyclobutene", Org. Synth. 48: 55; Coll. Vol. 5: 263
- Saunders, J. H. (1949), "1-Ethynylcyclohexanol", Org. Synth. 29: 47; Coll. Vol. 3: 416
Peterson, P. E.; Dunham, M. (1977), "(Z)-4-Chloro-4-hexenyl trifluoroacetate", Org. Synth. 57: 26; Coll. Vol. 6: 273
Kauer, J. C.; Brown, M. (1962), "Tetrolic acid", Org. Synth. 42: 97; Coll. Vol. 5: 1043
- Coffman, D. D. (1940), "Dimethylethynylcarbinol", Org. Synth. 20: 40; Coll. Vol. 3: 320
Hauser, C. R.; Adams, J. T.; Levine, R. (1948), "Diisovalerylmethane", Org. Synth. 28: 44; Coll. Vol. 3: 291
- Vanderwerf, C. A.; Lemmerman, L. V. (1948), "2-Allylcyclohexanone", Org. Synth. 28: 8; Coll. Vol. 3: 44
- ; Coll. Vol. 5: 526
Kaiser, E. M.; Kenyon, W. G.; Hauser, C. R. (1967), "Ethyl 2,4-diphenylbutanoate", Org. Synth. 47: 72; Coll. Vol. 5: 559
Wawzonek, S.; Smolin, E. M. (1951), "α,β-Diphenylcinnamonitrile", Org. Synth. 31: 52; Coll. Vol. 4: 387
- Murphy, W. S.; Hamrick, P. J.; Hauser, C. R. (1968), "1,1-Diphenylpentane", Org. Synth. 48: 80; Coll. Vol. 5: 523
- Hampton, K. G.; Harris, T. M.; Hauser, C. R. (1971), "Phenylation of diphenyliodonium chloride: 1-phenyl-2,4-pentanedione", Org. Synth. 51: 128; Coll. Vol. 6: 928
Hampton, K. G.; Harris, T. M.; Hauser, C. R. (1967), "2,4-Nonanedione", Org. Synth. 47: 92; Coll. Vol. 5: 848
- Potts, K. T.; Saxton, J. E. (1960), "1-Methylindole", Org. Synth. 40: 68; Coll. Vol. 5: 769
- Bunnett, J. F.; Brotherton, T. K.; Williamson, S. M. (1960), "N-β-Naphthylpiperidine", Org. Synth. 40: 74; Coll. Vol. 5: 816
- Brazen, W. R.; Hauser, C. R. (1954), "2-Methylbenzyldimethylamine", Org. Synth. 34: 61; Coll. Vol. 4: 585
- Allen, C. F. H.; VanAllan, J. (1944), "Phenylmethylglycidic ester", Org. Synth. 24: 82; Coll. Vol. 3: 727
- Allen, C. F. H.; VanAllan, J. (1942), "2-Methylindole", Org. Synth. 22: 94; Coll. Vol. 3: 597
- "Sodium Amide". Princeton, NJ: Princeton University. 3/16/2011. Retrieved 7/20/2011.