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	{{Chembox new		{{Chembox
			|Verifiedfields = changed
	| ImageFile = Sodium-amide-3D-balls-C.png
			|Watchedfields = changed
	| Name = Sodium amide
			|verifiedrevid = 265528656
	| OtherNames = Sodamide
			|ImageFile1 = Sodium amide.png
	| Section1 = {{Chembox Identifiers
			|ImageFile1_Ref =
	| CASNo = 7782-92-5
			|ImageName1 =
	| CASNo_Ref = {{cascite}}
			|ImageFile2 = Sodium-amide-3D-balls-B.png
	| RTECS =
			|ImageFile2_Ref = {{Chemboximage|correct|??}}
	}}
			|ImageName2 = Ball and stick, unit cell model of sodium amide
	| Section2 = {{Chembox Properties
			|IUPACName = Sodium amide, sodium azanide<ref>{{GoldBookRef |title=amides |file=A00266}}</ref>
	| Formula = NaNH<sub>2</sub>
			|OtherNames = Sodamide
	| MolarMass = 39.01 g/mol
			|Section1={{Chembox Identifiers
	| Appearance = gray powder (colourless when pure)
			|CASNo = 7782-92-5
	| Density = 1.37 g/cm<sup>3</sup>, solid
			|CASNo_Ref = {{cascite|correct|CAS}}
	| Solubility = reacts
			|UNII_Ref = {{fdacite|correct|FDA}}
	| MeltingPt = 210 °C
			|UNII = 5DB3G6PX9D
	| BoilingPt = 400 °C
			|PubChem = 24533
	| pKa = 38 <ref>Buncel; Menon J. Organomet. Chem. 1977, 141, 1</ref>
			|ChEBI = 176791
	}}
			|ChemSpiderID = 22940
	| Section3 = {{Chembox Structure
			|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
	| Coordination =
			|EINECS = 231-971-0
	}}
			|UNNumber = 1390
	| Section7 = {{Chembox Hazards
			|SMILES = N
	| EUIndex = Not listed
			|SMILES2 = .
	| FlashPt = Non-flammable
			|StdInChI = 1S/H2N.Na/h1H2;/q-1;+1
	}}
			|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
	| Section8 = {{Chembox Related
			|StdInChIKey = ODZPKZBBUMBTMG-UHFFFAOYSA-N
	| OtherAnions = ]
			|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}}}
	| OtherCations = ]
			|Section2={{Chembox Properties
	| OtherCpds = ]
			|Formula = {{chem2|NaNH2}}
	}}
			|Na=1|N=1|H=2
			|Appearance = Colourless crystals
			|Odor = Ammonia-like
			|Density = 1.39 g/cm<sup>3</sup>
			|MeltingPtC = 210
			|BoilingPtC = 400
			|Solubility = Reacts
			|SolubleOther = 40 mg/L (liquid ammonia), reacts with ]
			|pKa = 38 (])<ref>{{cite journal |author1=Buncel, E. |author2=Menon, B. |title=Carbanion mechanisms: VII. Metallation of hydrocarbon acids by potassium amide and potassium methylamide in tetrahydrofuran and the relative hydride acidities |journal=Journal of Organometallic Chemistry |year=1977 |volume=141 |issue=1 |pages=1–7 |doi=10.1016/S0022-328X(00)90661-2}}</ref>
	}}		}}
			|Section3={{Chembox Structure
			|CrystalStruct = orthorhombic
	'''Sodium amide''', commonly called sodamide, is the ] with the ] NaNH<sub>2</sub>. 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 ]. NaNH<sub>2</sub> has been widely employed as a strong base in ].
			}}
			|Section4={{Chembox Thermochemistry
			|DeltaHf = -118.8 kJ/mol
			|DeltaGf = -59 kJ/mol
			|Entropy = 76.9 J/(mol·K)
			|HeatCapacity = 66.15 J/(mol·K)
			}}
			|Section5={{Chembox Hazards
			|NFPA-H = 3
			|NFPA-F = 2
			|NFPA-R = 3
			|NFPA-S = W
			|FlashPtC = 4.44
			|AutoignitionPtC = 450
			}}
			|Section6={{Chembox Related
			|OtherAnions = ]
			|OtherCations = ]<br>]
			|OtherCompounds = ]
			}}
			}}
			'''Sodium amide''', commonly called '''sodamide''' (systematic name '''sodium azanide'''), is the ] with the ] {{chem2|NaNH2}}. It is a ] composed of the sodium cation and the ] anion. This solid, which is dangerously reactive toward water, is white, 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 ].{{citation needed|date=September 2015}} {{chem2|NaNH2}} conducts electricity in the fused state, its conductance being similar to that of NaOH in a similar state. {{chem2|NaNH2}} has been widely employed as a ] in ].
	==Preparation and structure==		==Preparation and structure==
	Sodium amide can be prepared by the reaction of ] with ammonia gas,<ref>Bergstrom, F. W. (1955). "". ''] Coll. Vol.'' '''3''':778.</ref> but it is usually prepared by the reaction in liquid ammonia using ] as a ]. The reaction is fastest at the boiling point of the ammonia, ca. -33 °C.<ref>Greenlee, K. W.; Henne, A. L. (1946). "Sodium Amide". ''Inorganic Syntheses'' '''2''':128&ndash;35.</ref>		Sodium amide can be prepared by the reaction of ] with ammonia gas,<ref>{{OrgSynth |author=Bergstrom, F. W. |title=Sodium amide |year=1955 |collvol=3 |collvolpages=778 |prep=cv3p0778}}</ref> but it is usually prepared by the reaction in ] using ] as a ]. The reaction is fastest at the boiling point of the ammonia, c. −33&nbsp;°C. An ], {{chem2|+e−}}, is formed as a ].<ref>{{cite book |author1=Greenlee, K. W. |author2=Henne, A. L. |title=Inorganic Syntheses |chapter=Sodium Amide |year=1946 |volume=2 |pages=128–135 |doi=10.1002/9780470132333.ch38 |isbn=9780470132333}}</ref>
	:2 Na + 2 NH<sub>3</sub> → 2 NaNH<sub>2</sub> + H<sub>2</sub>
			:{{chem2|2 Na + 2 NH3 → 2 NaNH2 + H2}}
	NaNH<sub>2</sub> is a salt-like material and as such, crystallizes as an infinite polymer.<ref>Zalkin, A.; Templeton, D. H. "The Crystal Structure Of Sodium Amide" Journal of Physical Chemistry 1956, Volume 60, pp 821 - 823. DOI: 10.1021/j150540a042</ref> The geometry about sodium is tetrahedral.<ref>Wells, A.F. (1984) Structural Inorganic Chemistry, Oxford: Clarendon Press. ISBN 0-19-855370-6.</ref> In ammonia, NaNH<sub>2</sub> forms conductive solutions, consistent with the presence of Na(NH<sub>3</sub>)<sub>6</sub><sup>+</sup> and NH<sub>2</sub><sup>-</sup> anions.
			{{chem2|NaNH2}} is a salt-like material and as such, crystallizes as an infinite polymer.<ref>{{cite journal |author1=Zalkin, A. |author2=Templeton, D. H. |title=The Crystal Structure Of Sodium Amide |journal=Journal of Physical Chemistry |year=1956 |volume=60 |issue=6 |pages=821–823 |doi=10.1021/j150540a042 |hdl=2027/mdp.39015086484659 |hdl-access=free}}</ref> The geometry about sodium is tetrahedral.<ref>{{cite book |author=Wells, A. F. |year=1984 |title=Structural Inorganic Chemistry |location=Oxford |publisher=Clarendon Press |isbn=0-19-855370-6}}</ref> In ammonia, {{chem2|NaNH2}} forms conductive solutions, consistent with the presence of {{chem2|+}} and {{chem2|NH2−}} ions.
	==Uses==		==Uses==
			Sodium amide is mainly used as a ] in organic chemistry, often ] (it is insoluble<ref>{{cite book|url=https://archive.org/details/cftri.2662nonaqueoussolven0000ludw/page/79/|page=79|title=Non-aqueous solvents|first1=Ludwig&nbsp;F.|last1=Audrieth|first2=Jacob|last2=Kleinberg|publisher=John Wiley & Sons|location=New York|year=1953|lccn=52-12057}}</ref>) in liquid ammonia solution. One of the main advantages to the use of sodium amide is its relatively low ]. In the industrial production of ], sodium amide is a component of the highly basic mixture that induces cyclisation of ]. The reaction produces ammonia, which is recycled typically.<ref>L. Lange, W. Treibel "Sodium Amide" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a24_267}}</ref>
	Sodium amide is used in the industrial production of ], ], and ].<ref>{{Merck12th}}</ref> It is the reagent of choice for the drying of ] (liquid or gaseous) and is also widely used as a strong ] 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 ], ] (NaHMDS), and ] (LDA).
			].]]
	===Preparation of alkynes===		===Dehydrohalogenation===
	Sodium amide induces the loss of two molecules of ] from a ] dibromoalkane to give a ], as in the preparation of ] below.<ref>Campbell, Kenneth N.; Campbell, Barbara K. (1950). "". '']'' '''30''':72; ''Coll. Vol.'' '''4''':763.</ref>		Sodium amide is a standard base for dehydrohalogenations.<ref name=eEROS>{{cite book |doi=10.1002/047084289X.rs041 |chapter=Sodium Amide |title=Encyclopedia of Reagents for Organic Synthesis |date=2001 |last1=Belletire |first1=John L. |last2=Rauh |first2=R. Jeffery |isbn=0-471-93623-5 }}</ref> It induces the loss of two equivalents of ] from a ] dibromoalkane to give a ], as in a preparation of ].<ref>{{OrgSynth |author=Campbell, K. N.; Campbell, B. K. |title=Phenylacetylene |year=1950 |volume=30 |pages=72 |collvol=4 |collvolpages=763 |prep=cv4p0763}}</ref>
	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.		Usually two equivalents of sodium amide yields the desired alkyne. Three equivalents are necessary in the preparation of a terminal alkynes because the terminal CH of the resulting alkyne protonates an equivalent amount of base.
	]		]
	] and/or ] can also be eliminated in this way,<ref>Jones, E. R. H.; Eglinton, Geoffrey; Whiting, M. C.; Shaw, B. L. (1954). "". '']'' '''34''':46; ''Coll. Vol.'' '''4''':404.<br />		] and ] can also be eliminated in this way,<ref>{{OrgSynth |author=Jones, E. R. H.; ]; Whiting, M. C.; Shaw, B. L. |title=Ethoxyacetylene |year=1954 |volume=34 |pages=46 |collvol=4 |collvolpages=404 |prep=cv4p0404}}<br>
	Bou, Anna; Pericàs, Miquel A.; Riera, Antoni; Serratosa, Fèlix (1987). "". '']'' '''65''':68; ''Coll. Vol.'' '''8''':161.<br />		{{OrgSynth |author=Bou, A.; Pericàs, M. A.; Riera, A.; Serratosa, F. |title=Dialkoxyacetylenes: di-''tert''-butoxyethyne, a valuable synthetic intermediate |year=1987 |volume=65 |pages=58 |collvol=8 |collvolpages=161 |prep=cv8p0161}}<br>
	Magriotis, Plato A.; Brown, John T. (1995). "". '']'' '''72''':252; ''Coll. Vol.'' '''9''':656.<br />		{{OrgSynth |author=Magriotis, P. A.; Brown, J. T. |title=Phenylthioacetylene |year=1995 |volume=72 |pages=252 |collvol=9 |collvolpages=656 |prep=cv9p0656}}<br>
	Ashworth, P. J.; Mansfield, G. H.; Whiting, M. C. (1955). "". '']'' '''35''':20; ''Coll. Vol.'' '''4''':128.</ref> as in the preparation of ].<ref>Newman, Melvin S.; Stalick, W. M. (1977). "". '']'' '''57''':65; '''6''':564.</ref>		{{OrgSynth |author=Ashworth, P. J.; Mansfield, G. H.; Whiting, M. C. |year=1955 |title=2-Butyn-1-ol |volume=35 |pages=20 |collvol=4 |collvolpages=128 |prep=cv4p0128}}</ref> as in the preparation of 1-ethoxy-1-butyne.<ref>{{OrgSynth |author=Newman, M. S.; Stalick, W. M. |title=1-Ethoxy-1-butyne |year=1977 |volume=57 |pages=65 |collvol=6 |collvolpages=564 |prep=cv6p0564}}</ref>
	]		]
	===Cyclization reactions===		===Cyclization reactions===
	Where there is no β-hydrogen to be eliminated, cyclic compounds may be formed, as in the preparation of ] below.<ref>Salaun, J. R.; Champion, J.; Conia, J. M. (1977). "". '']'' '''57''':36; ''Coll. Vol.'' '''6''':320.</ref>		Where there is no β-hydrogen to be eliminated, cyclic compounds may be formed, as in the preparation of ] below.<ref>{{OrgSynth |author=Salaun, J. R.; Champion, J.; Conia, J. M. |title=Cyclobutanone from methylenecyclopropane ''via'' oxaspiropentane |year=1977 |volume=57 |pages=36 |collvol=6 |collvolpages=320 |prep=cv6p0320}}</ref>
	]		]
	]s,<ref>Nakamura, Masuharu; Wang, Xio Qun; Isaka, Masahiko; Yamago, Shigeru; Nakamura, Eiichi (2003). "". '']'' '''80''':144.</ref> ]s<ref>Bottini, Albert T.; Olsen, Robert E. (1964). "". '']'' '''44''':53; ''Coll. Vol.'' '''5''':541.</ref>		]s,<ref>{{OrgSynth |author=Nakamura, M.; Wang, X. Q.; Isaka, M.; Yamago, S.; Nakamura, E. |title=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(2''H'')-pentalen-2-one |year=2003 |volume=80 |pages=144 |prep=v80p0144}}</ref> ]<ref>{{OrgSynth |author=Bottini, A. T.; Olsen, R. E. |title=''N''-Ethylallenimine |year=1964 |volume=44 |pages=53 |collvol=5 |collvolpages=541 |prep=cv5p0541}}</ref>
	and ]s<ref>Skorcz, J. A.; Kaminski, F. E. (1968). "". '']'' '''48''':55; ''Coll. Vol.'' '''5''':263.</ref> may be formed in a similar manner.		and ]s<ref>{{OrgSynth |author=Skorcz, J. A.; Kaminski, F. E. |title=1-Cyanobenzocyclobutene |year=1968 |volume=48 |pages=55 |collvol=5 |collvolpages=263 |prep=cv5p0263}}</ref> may be formed in a similar manner.
	===Deprotonation of carbon and nitrogen acids===		===Deprotonation of carbon and nitrogen acids===
	Carbon acids which can be ] by sodium amide in liquid ammonia include terminal ]s,<ref>Saunders, J. H. (1949). "". '']'' '''29''':47; ''Coll. Vol.'' '''3''':416.<br />		Carbon acids which can be ] by sodium amide in liquid ammonia include terminal ]s,<ref>{{OrgSynth |author=Saunders, J. H. |title=1-Ethynylcyclohexanol |year=1949 |volume=29 |pages=47 |collvol=3 |collvolpages=416 |prep=cv3p0416}}<br>
	Peterson, P. E.; Dunham, M. (1977). "". '']'' '''57''':26; ''Coll. Vol.'' '''6''':273.<br />		{{OrgSynth |author=Peterson, P. E.; Dunham, M. |title=(''Z'')-4-Chloro-4-hexenyl trifluoroacetate |year=1977 |volume=57 |pages=26 |collvol=6 |collvolpages=273 |prep=cv6p0273}}<br>
	Kauer, J. C.; Brown, M. (1962). "". '']'' '''42''':97; ''Coll. Vol.'' '''5''':1043.</ref>		{{OrgSynth |author=Kauer, J. C.; Brown, M. |title=Tetrolic acid |year=1962 |volume=42 |pages=97 |collvol=5 |collvolpages=1043 |prep=cv5p1043}}</ref>
			methyl ]s,<ref>{{OrgSynth |author=Coffman, D. D. |title=Dimethylethynylcarbinol |year=1940 |volume=20 |pages=40 |collvol=3 |collvolpages=320 |prep=cv3p0320}}{{OrgSynth |author=Hauser, C. R.; Adams, J. T.; Levine, R. |title=Diisovalerylmethane |year=1948 |volume=28 |pages=44 |collvol=3 |collvolpages=291 |prep=cv3p0291}}</ref>
	methyl ]s,<ref>Coffman, Donald D. (1940). "". '']'' '''20''':40; ''Coll. Vol.'' '''3''':320.<br />
			],<ref>{{OrgSynth |author=Vanderwerf, C. A.; Lemmerman, L. V. |title=2-Allylcyclohexanone |year=1948 |volume=28 |pages=8 |collvol=3 |collvolpages=44 |prep=cv3p0044}}</ref> ] and its derivatives<ref>{{OrgSynth |author=Hauser, C. R.; Dunnavant, W. R. |title=α,β-Diphenylpropionic acid |year=1960 |volume=40 |pages=38 |collvol=5 |collvolpages=526 |prep=cv5p0526}}<br>
	Hauser, C. R.; Adams, J. T.; Levine, R. (1948). "". '']'' '''28''':44; ''Coll. Vol.'' '''3''':291.</ref>
			{{OrgSynth |author=Kaiser, E. M.; Kenyon, W. G.; Hauser, C. R. |title=Ethyl 2,4-diphenylbutanoate |year=1967 |volume=47 |pages=72 |collvol=5 |collvolpages=559 |prep=cv5p0559}}<br>
	],<ref>Vanderwerf, Calvin A.; Lemmerman, Leo V. (1948). "". '']'' '''28''':8; ''Coll. Vol.'' '''3''':44.</ref>
			{{OrgSynth |author=Wawzonek, S.; Smolin, E. M. |title=α,β-Diphenylcinnamonitrile |year=1951 |volume=31 |pages=52 |collvol=4 |collvolpages=387 |prep=cv4p0387}}</ref>
	] and its derivatives<ref>Hauser, Charles R.; Dunnavant, W. R. (1960). "". '']'' '''40''':38; ''Coll. Vol.'' '''5''':526.<br />
			and ].<ref>{{OrgSynth |author=Murphy, W. S.; Hamrick, P. J.; Hauser, C. R. |title=1,1-Diphenylpentane |year=1968 |volume=48 |pages=80 |collvol=5 |collvolpages=523 |prep=cv5p0523}}</ref> ] loses two protons to form a ].<ref>{{OrgSynth |author=Hampton, K. G.; Harris, T. M.; Hauser, C. R. |title=Phenylation of diphenyliodonium chloride: 1-phenyl-2,4-pentanedione |year=1971 |volume=51 |pages=128 |collvol=6 |collvolpages=928 |prep=cv6p0928}}<br>
	Kaiser, Edwin M.; Kenyon, William G.; Hauser, Charles R. (1967). "". '']'' '''47''':72; ''Coll. Vol.'' '''5''':559.<br />
			{{OrgSynth |author=Hampton, K. G.; Harris, T. M.; Hauser, C. R. |title=2,4-Nonanedione |year=1967 |volume=47 |pages=92 |collvol=5 |collvolpages=848 |prep=cv5p0848}}</ref> Sodium amide will also deprotonate ]<ref>{{OrgSynth |author=Potts, K. T.; Saxton, J. E. |title=1-Methylindole |year=1960 |volume=40 |pages=68 |collvol=5 |collvolpages=769 |prep=cv5p0769}}</ref> and ].<ref>{{OrgSynth |author=Bunnett, J. F.; Brotherton, T. K.; Williamson, S. M. |title=''N''-β-Naphthylpiperidine |year=1960 |volume=40 |pages=74 |collvol=5 |collvolpages=816 |prep=cv5p0816}}</ref>
	Wawzonek, Stanley; Smolin, Edwin M. (1951). "". '']'' '''31''':52; ''Coll. Vol.'' '''4''':387.</ref>
	and ].<ref>Murphy, William S.; Hamrick, Phillip J.; Hauser, Charles R. (1968). "". '']'' '''48''':80; ''Coll. Vol.'' '''5''':523.</ref>
	] loses two protons to form a ].<ref>Hampton, K. Gerald; Harris, Thomas M.; Hauser, Charles R. (1971). "". '']'' '''51''':128; ''Coll. Vol.'' '''6''':928.<br />
	Hampton, K. Gerald; Harris, Thomas M.; Hauser, Charles R. (1967).</ref>
			===Related non-nucleophilic bases===
	]
			It is however poorly soluble in solvents other than ammonia. Its use has been superseded by the related reagents ], ] (NaHMDS), and ] (LDA).
	Sodium amide will also deprotonate ]<ref>Potts, K. T.; Saxton, J. E. (1960). "". '']'' '''40''':68; ''Coll. Vol.'' '''5''':769.</ref> and ].<ref>Bunnett, J. F.; Brotherton, T. K.; Williamson, S. M. (1960). "". '']'' '''40''':74; ''Coll. Vol.'' '''5''':816.</ref>
	===Other reactions===		===Other reactions===
	*Rearrangement with orthodeprotonation<ref>Brazen, W. R.; Hauser, C. R. (1954). "". '']'' '''34''':61; ''Coll. Vol.'' '''4''':585.</ref>		*Rearrangement with orthodeprotonation<ref>{{OrgSynth |author=Brazen, W. R.; Hauser, C. R. |title=2-Methylbenzyldimethylamine |year=1954 |volume=34 |pages=61 |collvol=4 |collvolpages=585 |prep=cv4p0585}}</ref>
	*Oxirane synthesis (by carbene reaction?)<ref>Allen, C. F. H.; VanAllen, J. (1944). "". '']'' '''24''':82; ''Coll. Vol.'' '''3''':727.		*Oxirane synthesis<ref>{{OrgSynth |author=Allen, C. F. H.; VanAllan, J. |title=Phenylmethylglycidic ester |year=1944 |volume=24 |pages=82 |collvol=3 |collvolpages=727 |prep=cv3p0727}}</ref>
			*Indole synthesis<ref>{{OrgSynth |author=Allen, C. F. H.; VanAllan, J. |title=2-Methylindole |year=1942 |volume=22 |pages=94 |collvol=3 |collvolpages=597 |prep=cv3p0597}}</ref>
	</ref>
	*Indole synthesis<ref> Allen, C. F. H.; VanAllen, James (1942). "". '']'' '''22''':94; ''Coll. Vol.'' '''3''':597.</ref>
	*]		*]
	==Safety==		==Safety==
	Sodium amide reacts violently with water to produce ] and ]: and will burn in air to give oxides of ] and ].		Sodium amide is a common reagent with a long history of laboratory use.<ref name=eEROS/> It can decompose violently on contact with water, producing ] and ]:
	:NaNH<sub>2</sub> + H<sub>2</sub>O → NH<sub>3</sub> + NaOH		:{{chem2|NaNH2 + H2O → NH3 + NaOH}}
	:2NaNH<sub>2</sub> + 4O<sub>2</sub> → ] + 2] + 2H<sub>2</sub>O
	In the presence of limited quantities of air and moisture, such as in a poorly closed container, explosive mixtures of oxidation products can 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, if possible under an atmosphere of nitrogen gas.
	Sodium amide samples which are yellow or brown in color should be destroyed immediately: one method for destruction is the careful addition of ] to a suspension of sodium amide in a ] solvent.
			When burned in oxygen, it will give ] (which react with the produced water, giving sodium hydroxide) along with nitrogen oxides:
	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.
			:{{chem2|4 NaNH2 + 5 O2 → 4 NaOH + 4 NO + 2 H2O}}
			:{{chem2|4 NaNH2 + 7 O2 → 4 NaOH + 4 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.<ref name="Clark2001">{{cite journal |last1=Clark |first1=Donald E |title=Peroxides and peroxide-forming compounds |journal=Chemical Health and Safety |volume=8 |issue=5 |year=2001 |pages=12–22 |issn=1074-9098 |doi=10.1016/S1074-9098(01)00247-7}}</ref> This is accompanied by a yellowing or browning of the solid. As such, sodium amide is to be stored in a tightly closed container, under an atmosphere of an inert gas. Sodium amide samples which are yellow or brown in color represent explosion risks.<ref>{{cite web |title=Sodium amide SOP |url=https://ehs.princeton.edu/laboratory-research/chemical-safety/chemical-specific-protocols/sodium-amide |publisher=Princeton |ref=SOP sodium amide Princeton}}</ref>
	==See also==
	* ]
	* ]
	==References==		==References==
			{{Reflist}}
	<references/>
			{{Sodium compounds}}
	==External links==
			{{Authority control}}
	* (from '']'')
			]
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