Neopentyl alcohol

Neopentyl alcohol^[1]
Names
	Preferred IUPAC name 2,2-Dimethylpropan-1-ol
	Other names tert-Butyl carbinol; tert-Butylmethanol; Neoamyl alcohol; Neopentanol
Identifiers
CAS Number	75-84-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL458630;
ChemSpider	6164 ;
ECHA InfoCard	100.000.826
EC Number	200-907-3;
PubChem CID	6404;
UNII	5I067PJD7S ;
UN number	1325
CompTox Dashboard (EPA)	DTXSID9052501 ;
	InChI InChI=1S/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3 Key: KPSSIOMAKSHJJG-UHFFFAOYSA-N ; InChI=1/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3 Key: KPSSIOMAKSHJJG-UHFFFAOYAJ;
	SMILES CC(CO)(C)C;
Properties
Chemical formula	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)
Solubility in water	36 g/L
Solubility	very soluble in ethanol, diethyl ether
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	-399.4 kJ·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H228, H319, H332, H335
Precautionary statements	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). verify (what is ?) Infobox references

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.

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

References

^ 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
^ "Neopentyl alcohol". pubchem.ncbi.nlm.nih.gov.
^ Joseph Hoffman (1960). "Neopentyl Alcohol". Organic Syntheses. 40: 76. doi:10.15227/orgsyn.040.0076.
^ Comptes Rendus, 1891, 112, p. 1065
^ H. N. Rydon (1971). "Alkyl Iodides: Neopentyl Iodide and Iodocyclohexane". Organic Syntheses. 51: 44. doi:10.15227/orgsyn.051.0044.

[hand-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.

[1]

[2]

[3]

[4]

[5]

Preparation and reactions

See also

References