highly corrosive, pyrophoric in air, reacts violently with water
Safety data sheet
External MSDS
GHS pictograms
GHS signal word
DANGER
GHS hazard statements
H260
NFPA 704
Flash point
combustible
Related compounds
Other cations
Lithium hydride Potassium hydride
Related compounds
Sodium borohydride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Nverify (what is YN ?)
Infobox references
Sodium hydride is the chemical compound with the empirical formula NaH. This alkali metal hydride is primarily used as a strong, yet combustible base in organic synthesis. NaH is representative of the saline hydrides, meaning it is a salt-like hydride, composed of Na+ and H− ions, in contrast to the more molecular hydrides such as borane, methane, ammonia and water. It is an ionic material that is insoluble in organic solvents (although soluble in molten Na), consistent with the fact that H− remains an unknown anion in solution. Because of the insolubility of NaH, all reactions involving NaH occur at the surface of the solid.
Contents
1Basic properties and structure
1.1"Inverse sodium hydride"
2Applications in organic synthesis
2.1As a strong base
2.2As a reducing agent
2.3Hydrogen storage
3Practical considerations
4Safety
5References
Basic properties and structure
NaH is produced by the direct reaction of hydrogen and liquid sodium.[4] Pure NaH is colorless, although samples generally appear grey. NaH is ca. 40% denser than Na (0.968 g/cm3).
NaH, like LiH, KH, RbH, and CsH, adopts the NaCl crystal structure. In this motif, each Na+ ion is surrounded by six H− centers in an octahedral geometry. The ionic radii of H− (146 pm in NaH) and F− (133 pm) are comparable, as judged by the Na−H and Na−F distances.[5]
"Inverse sodium hydride"
A very unusual situation occurs in a compound dubbed "inverse sodium hydride", which contains Na− and H+ ions. Na− is an alkalide, and this compound differs from ordinary sodium hydride in having a much higher energy content due to the net displacement of two electrons from hydrogen to sodium. A derivative of this "inverse sodium hydride" arises in the presence of the base adamanzane. This molecule irreversibly encapsulates the H+ and shields it from interaction with the alkalide Na−.[6] Theoretical work has suggested that even an unprotected protonated tertiary amine complexed with the sodium alkalide might be metastable under certain solvent conditions, though the barrier to reaction would be small and finding a suitable solvent might be difficult.[7]
Applications in organic synthesis
As a strong base
NaH is a base of wide scope and utility in organic chemistry.[8] As a superbase, it is capable of deprotonating a range of even weak Brønsted acids to give the corresponding sodium derivatives. Typical "easy" substrates contain O-H, N-H, S-H bonds, including alcohols, phenols, pyrazoles, and thiols.
NaH most notably is employed to deprotonate carbon acids such as 1,3-dicarbonyls and analogues such as malonic esters. The resulting sodium derivatives can be alkylated. NaH is widely used to promote condensation reactions of carbonyl compounds via the Dieckmann condensation, Stobbe condensation, Darzens condensation, and Claisen condensation. Other carbon acids susceptible to deprotonation by NaH include sulfonium salts and DMSO. NaH is used to make sulfur ylides, which in turn are used to convert ketones into epoxides, as in the Johnson–Corey–Chaykovsky reaction.
As a reducing agent
NaH reduces certain main group compounds, but analogous reactivity is very rare in organic chemistry (see below).[9] Notably boron trifluoride reacts to give diborane and sodium fluoride:[4]
6 NaH + 2 BF3 → B2H6 + 6 NaF
Si-Si and S-S bonds in disilanes and disulfides are also reduced.
A series of reduction reactions, including the hydrodecyanation of tertiary nitriles, reduction of imines to amines, and amides to aldehydes, can be effected by a composite reagent composed of sodium hydride and an alkali metal iodide (NaH:MI, M = Li, Na).[10]
Hydrogen storage
The use of sodium hydride has been proposed for hydrogen storage for use in fuel cell vehicles, the hydride being encased in plastic pellets which are crushed in the presence of water to release the hydrogen.[11]
Practical considerations
Sodium hydride is sold by many chemical suppliers usually as a mixture of 60% sodium hydride (w/w) in mineral oil. Such a dispersion is safer to handle and weigh than pure NaH. The compound is often used in this form but the pure grey solid can be prepared by rinsing the oil with pentane or THF, with care being taken because the washings will contain traces of NaH that can ignite in air. Reactions involving NaH require an inert atmosphere, such as nitrogen or argon gas. Typically NaH is used as a suspension in THF, a solvent that resists deprotonation but solvates many organosodium compounds.
Safety
NaH can ignite in air, especially upon contact with water to release hydrogen, which is also flammable. Hydrolysis converts NaH into sodium hydroxide (NaOH), a caustic base. In practice, most sodium hydride is dispensed as a dispersion in oil, which can be safely handled in air.[12]
References
^ abZumdahl, Steven S. (2009). Chemical Principles 6th Ed. Houghton Mifflin Company. p. A23. ISBN 0-618-94690-X..mw-parser-output cite.citationfont-style:inherit.mw-parser-output qquotes:"""""""'""'".mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em
^Index no. 001-002-00-4 of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 340.
^Inc, New Environment,. "New Environment Inc. - NFPA Chemicals". www.newenv.com. Archived from the original on 2016-08-27.
^ abHolleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
^Mikhail Y. Redko; et al. (2002). ""Inverse Sodium Hydride": A Crystalline Salt that Contains H+ and Na-". J. Am. Chem. Soc. 124 (21): 5928–5929. doi:10.1021/ja025655+.
^Agnieszka Sawicka; Piotr Skurski & Jack Simons (2003). "Inverse Sodium Hydride: A Theoretical Study" (PDF). J. Am. Chem. Soc. 125 (13): 3954–3958. doi:10.1021/ja021136v. PMID 12656631. Archived (PDF) from the original on 2013-02-09.
^Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289.
^Too, Pei Chui; Chan, Guo Hao; Tnay, Ya Lin; Hirao, Hajime; Chiba, Shunsuke (2016-03-07). For early examples of NaH acting as a hydride donor, see ref. [3] therein. "Hydride Reduction by a Sodium Hydride–Iodide Composite". Angewandte Chemie International Edition. 55 (11): 3719–3723. doi:10.1002/anie.201600305. ISSN 1521-3773. PMC 4797714. PMID 26878823.
^Ong, Derek Yiren; Tejo, Ciputra; Xu, Kai; Hirao, Hajime; Chiba, Shunsuke (2017-01-01). "Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite". Angewandte Chemie International Edition: n/a–n/a. doi:10.1002/anie.201611495. ISSN 1521-3773.
^J. Philip DiPietro; Edward G. Skolnik (October 1999). "Analysis of the Sodium Hydride-based Hydrogen Storage System being developed by PowerBall Technologies, LLC" (PDF). US Department of Energy, Office of Power Technologies. Archived (PDF) from the original on 2006-12-13. Retrieved 2009-09-01.
^"The Dow Chemical Company - Home". www.rohmhaas.com.
v
t
e
Sodium compounds
NaAlO2
NaBH4
NaBH3(CN)
NaBO2
NaBiO3
NaBr
NaBrO
NaBrO3
NaCH3COO
NaC6H5CO2
NaC6H4(OH)CO2
NaCN
NaCl
NaClO
NaClO2
NaClO3
NaClO4
NaF
Na2FeO4
NaH
NaHCO3
NaH2PO4
NaHSO3
NaHSO4
NaI
NaIO3
NaIO4
Na5IO6
NaMnO4
NaN3
NaNH2
NaNO2
NaNO3
NaOCN
NaO2
NaO3
NaOH
NaPO2H2
NaReO4
NaSCN
NaSH
NaTcO4
NaVO3
Na2CO3
Na2C2O4
Na2CrO4
Na2Cr2O7
Na2GeO3
Na2MnO4
Na3MnO4
Na2MoO4
Na2MoS4
Na2N2O2
Na2O
Na2O2
Na2O(UO3)2
Na2PO3F
Na2S
Na2SO3
Na2SO4
Na2S2O3
Na2S2O4
Na2S2O5
Na2S2O6
Na2S2O7
Na2S2O8
Na2S4O6
Na2Se
Na2SeO3
Na2SeO4
Na2SiO3
Na2Si2O5
Na4SiO4
Na2Te
Na2TeO3
Na2TeO4
Na2Po
Na2Ti3O7
Na2U2O7
Na2WO4
Na2Zn(OH)4
Na3N
Na3P
Na3PO4
Na3VO4
Na4Fe(CN)6
Na4P3O7
Na5P3O10
Chemical formulas
v
t
e
Binary compounds of hydrogen
Alkali metal hydrides
LiH
NaH
KH
RbH
CsH
Lithium hydride, LiH ionic metal hydride
Beryllium hydride Left (gas phase): BeH2 covalent metal hydride Right: (BeH2)n (solid phase) polymeric metal hydride
0 I'm wondering if I can run a Node.js script in my Jekyll page from GitHub Pages or Amazon S3? I think it can't run on GitHub Pages since it doesn't support server side code. Not too sure. The code is below: var Airtable = require('airtable'); var base = new Airtable(apiKey: 'YOUR_API_KEY').base('appAnZVyYqusNPV5Q'); base('Invitee list').select( // Selecting the first 3 records in Complete list: maxRecords: 3, view: "Complete list" ).eachPage(function page(records, fetchNextPage) // This function (`page`) will get called for each page of records. records.forEach(function(record) console.log('Retrieved', record.get('Email')); ); // To fetch the next page of records, call `fetchNextPage`. // If there are more records, `page` will get called again. // If there are no more records, `done` will get called. fetchNextPage(); , function done(err) if (err) console.error(err); return; ); node.js ...
Art museum in Rovereto TN, Italy Museum of Modern and Contemporary Art of Trento and Rovereto Museo d'arte moderna e contemporanea di Trento e Rovereto MART, Entrance Location Corso Angelo Bettini, 43, 38068 Rovereto TN, Italy Coordinates 45°53′38″N 11°02′42″E / 45.8940°N 11.0450°E / 45.8940; 11.0450 Coordinates: 45°53′38″N 11°02′42″E / 45.8940°N 11.0450°E / 45.8940; 11.0450 Type Art museum Director Gianfranco Maraniello Public transit access Trento train station. Taxis outside station. Website mart.trento.it The Museum of Modern and Contemporary Art of Trento and Rovereto (MART) ( Museo d'Arte Moderna e Contemporanea di Trento e Rovereto , in Italian) is a museum centre in the Italian province of Trento. The main site is in Rovereto, and contains mostly modern and contemporary artworks, including works from renowned Giorgio Morandi, Giorgio de...