sodium hydride

• ChemBase ID: 129527
• Molecular Formular: Na+
• Molecular Mass: 22.98977
• Monoisotopic Mass: 22.98976928
• SMILES: [Na+]
• Canonical SMILES: [Na+]
• InChI: InChI=1S/Na/q+1
• InChIKey: FKNQFGJONOIPTF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium hydride
• IUPAC Traditional name: sodium hydride
• Synonyms: Sodium hydride; Sodium hydride; 氢化钠

Database IDs

• CAS Number: 7646-69-7
• EC Number: 231-587-3
• MDL Number: MFCD00003471
• Merck Index: 148625
• PubChem SID: 162223819
• PubChem CID: 24758
• Chemspider ID: 23144
• Wikipedia Title: Sodium_hydride

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• Molar Refractivity: 0.0 cm^3
• Polarizability: 0.394384 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: insoluble in ammonia, benzene, CCl₄, CS₂; reacts in water
• Apperance: colorless to grey solid; Powder
• Melting Point: 800 °C (decomposes); 800°C dec.
• Flash Point: combustible
• Density: 0.92; 1.396 g/cm^3
• Refractive Index: 1.470
• Std enthalpy of formation: -56 kJ·mol^-1
• Std molar entropy: 40 J·mol^-1·K^-1

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Flammable (F)
• UN Number: UN1427
• Hazard Class: 4.3
• Packing Group: I
• Risk Statements: 15
• Safety Statements: 7/8-24/25-43
• TSCA Listed: 是
• EU Index: 001-003-00-X
• GHS Pictograms: GHS02; : Water-react. 1
• GHS Signal Word: DANGER
• NFPA704:
  

  1

  3

  0

  W
• GHS Hazard statements: 260; H260
• GHS Precautionary statements: P231+P232-P280-P233-P370+P378I-P402+P404-P501A

Product Information

• Purity: 57-63% oil dispersion

REFERENCES

• Used in the deprotonation of DMSO to form "dimsyl sodium", a useful strong base for e.g. the Wittig reaction: J. Org. Chem., 28, 1128 (1963).
• For a review of sodium hydride-based complex reducing agents, see: Acta Chem. Scand., 44, 274 (1990).
• Widely used strong base for the irreversible formation of Na derivatives. If required, the protective oil can be removed by repeated washing and decantation with low-boiling petroleum, see, e.g.: Org. Synth. Coll., 6, 684 (1988), but for many purposes, this is not necessary, and the oil can be removed by incorporating a suitable extraction or washing step in the work-up. There are numerous Organic Syntheses references to reactions using NaH.
• CAUTION! Many literature procedures employ NaH in DMF, and this system is often used routinely by research workers as a 'convenient' general purpose strong base. It should be noted, especially when considering scale-up of such reactions, that thermal runaways have been observed with NaH/ DMF, with self-heating beginning at temperatures as low as 26^oC in some cases: Chem. Eng. News, 60(28), 5; 60(37), 5 (1982). A similar effect was also noted with N,N-dimethylacetamide. More recently also, incidents have been reported with other dipolar aprotic solvents 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) and Dimethyl sulfoxide (DMSO): Org. Process. Res. Dev., 7, 1030 (2003).