Neopentyl alcohol

Last updated
Neopentyl alcohol [1]
Neopentyl-alcohol-2D-structure.svg
Ball-and-stick model of the neopentyl alcohol molecule Neopentyl-alcohol-from-xtal-Mercury-3D-bs.png
Ball-and-stick model of the neopentyl alcohol molecule
Names
Preferred IUPAC name
2,2-Dimethylpropan-1-ol
Other names
tert-Butyl carbinol
tert-Butylmethanol
Neoamyl alcohol
Neopentanol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.826 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-907-3
PubChem CID
UNII
UN number 1325
  • InChI=1S/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3 Yes check.svgY
    Key: KPSSIOMAKSHJJG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3
    Key: KPSSIOMAKSHJJG-UHFFFAOYAJ
  • CC(CO)(C)C
Properties
C5H12O
Molar mass 88.150 g·mol−1
Density 0.812 g/mL at 20 °C
Melting point 52.5 °C (126.5 °F; 325.6 K)
Boiling point 113.5 °C (236.3 °F; 386.6 K)
36 g/L
Solubility very soluble in ethanol, diethyl ether
Thermochemistry
−399.4 kJ·mol−1
Hazards
GHS labelling: [2]
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H228, H319, H332, H335
P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, P501
Flash point 37 °C (99 °F; 310 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Neopentyl alcohol is a compound with formula (CH3)3CCH2OH. It is a colorless solid. The compound is one of the eight isomers of pentyl alcohol.

Contents

Preparation and reactions

Neopentyl alcohol can be prepared from the hydroperoxide of diisobutylene. [3] It can also be prepared by the reduction of trimethylacetic acid with lithium aluminium hydride. Neopentyl alcohol was the first described in 1891 by L. Tissier, who prepared it by reduction of a mixture of trimethyl acetic acid and trimethylacetyl chloride with sodium amalgam. [4]

Neopentyl alcohol can be converted to neopentyl iodide by treatment with triphenylphosphite/methyl iodide: [5]

(CH3)3CCH2OH + [CH3(C6H5O)3P]+I− → (CH3)3CCH2I + [CH3(C6H5O)2PO + C6H5OH

See also

References

  1. ↑ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–228, 5–42, 8–102, 16–22, ISBN   0-8493-0594-2
  2. ↑ "Neopentyl alcohol". pubchem.ncbi.nlm.nih.gov.
  3. ↑ Joseph Hoffman (1960). "Neopentyl Alcohol". Organic Syntheses. 40: 76. doi:10.15227/orgsyn.040.0076.
  4. ↑ Comptes Rendus, 1891, 112, p. 1065
  5. ↑ H. N. Rydon (1971). "Alkyl Iodides: Neopentyl Iodide and Iodocyclohexane". Organic Syntheses. 51: 44. doi:10.15227/orgsyn.051.0044.
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