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Neopentyl alcohol

(Redirected from 2,2-Dimethylpropan-1-ol)

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.

Neopentyl alcohol[1]
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 Edit this at Wikidata
EC Number
  • 200-907-3
UNII
UN number 1325
  • InChI=1S/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3 checkY
    Key: KPSSIOMAKSHJJG-UHFFFAOYSA-N checkY
  • 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]
GHS02: FlammableGHS07: Exclamation mark
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).
☒N verify (what is checkY☒N ?)

Preparation and reactions

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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

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References

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  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 0-8493-0863-2
  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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