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Neopentyl alcohol

From Wikipedia, the free encyclopedia
(Redirected from2,2-Dimethylpropan-1-ol)
Neopentyl alcohol[1]
Ball-and-stick model of the neopentyl alcohol molecule
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 InfoCard100.000.826Edit this at Wikidata
EC Number
  • 200-907-3
UNII
UN number1325
  • 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 mass88.150 g·mol−1
Density0.812 g/mL at 20 °C
Melting point52.5 °C (126.5 °F; 325.6 K)
Boiling point113.5 °C (236.3 °F; 386.6 K)
36 g/L
Solubilityvery soluble inethanol,diethyl ether
Thermochemistry
−399.4kJ·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 point37 °C (99 °F; 310 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Neopentyl alcohol is acompound with formula (CH3)3CCH2OH. It is a colorless solid. The compound is one of the eight isomers ofpentyl alcohol.

Preparation and reactions

[edit]

Neopentyl alcohol can be prepared from the hydroperoxide of diisobutylene.[3]It can also be prepared by the reduction oftrimethylacetic acid withlithium 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 withtriphenylphosphite/methyl iodide:[5]

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

See also

[edit]

References

[edit]
  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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