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^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL458630
ChemSpider	6164^Y
ECHA InfoCard	100.000.826
EC Number	200-907-3
PubChem CID	6404
UNII	5I067PJD7S^Y
UN number	1325
CompTox Dashboard (EPA)	DTXSID9052501
InChI InChI=1S/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3^Y Key: KPSSIOMAKSHJJG-UHFFFAOYSA-N^Y 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 (Δ_fH^⦵₂₉₈)	-399.4 kJ·mol⁻¹
Hazards
GHS labelling:^[2]
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). N verify (what is ^YN ?) Infobox references

Chemical compound

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.

Alcohols

By consumption

Alcohols found in alcoholic drinks	1-Propanol 2-Methyl-1-butanol Ethanol Isoamyl alcohol Isobutanol Phenethyl alcohol tert-Amyl alcohol tert-Butyl alcohol Tryptophol
Medical alcohol	Ethchlorvynol Methylpentynol Methanol poisoning Ethanol
Toxic alcohols	Isopropyl alcohol Methanol

Primary
alcohols (1°)

Methanol	4-Methylcyclohexanemethanol Aminomethanol Cyclohexylmethanol Methoxymethanol Methylazoxymethanol Trifluoromethanol
Ethanol	1-Aminoethanol 2,2,2-Trichloroethanol 2,2,2-Trifluoroethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-Butoxyethanol 2-Chloroethanol 2-Ethoxyethanol 2-Fluoroethanol 2-Mercaptoethanol 2-Methoxyethanol Aminoethylethanolamine Diethylethanolamine Dimethylethanolamine Ethanol Ethanolamine N,N-Diisopropylaminoethanol N-Methylethanolamine Phenoxyethanol Tribromoethanol
Butanol	2-Methyl-1-butanol Isobutanol n-Butanol
Straight-chain saturated C₁ — C₉	Methanol Ethanol 1-Propanol 1-Butanol 1-Pentanol 1-Hexanol 1-Heptanol 1-Octanol (capryl) 1-Nonanol (pelargonic)
Straight-chain saturated C₁₀ — C₁₉	1-Decanol (capric) 1-Undecanol (hendecyl) 1-Dodecanol (lauryl) 1-Tridecanol 1-Tetradecanol (myristyl) 1-Pentadecanol 1-Hexadecanol (cetyl / palmityl) 1-Heptadecanol 1-Octadecanol (stearyl) 1-Nonadecanol
Straight-chain saturated C₂₀ — C₂₉	1-Icosanol (arachidyl) 1-Heneicosanol 1-Docosanol (behenyl) 1-Tricosanol 1-Tetracosanol (lignoceryl) 1-Pentacosanol 1-Hexacosanol (ceryl) 1-Heptacosanol 1-Octacosanol (cluytyl / montanyl) 1-Nonacosanol
Straight-chain saturated C₃₀ — C₃₉	1-Triacontanol (melissyl / myricyl) 1-Hentriacontanol 1-Dotriacontanol (lacceryl) 1-Tritriacontanol 1-Tetratriacontanol (geddyl) 1-Pentatriacontanol 1-Hexatriacontanol 1-Heptatriacontanol 1-Octatriacontanol 1-Nonatriacontanol
Straight-chain saturated C₄₀ — C₄₉	1-Tetracontanol 1-Hentetracontanol 1-Dotetracontanol 1-Tritetracontanol 1-Tetratetracontanol 1-Pentatetracontanol 1-Hexatetracontanol 1-Heptatetracontanol 1-Octatetracontanol 1-Nonatetracontanol

Secondary
alcohols (2°)

2-Deoxyerythritol

Propylene glycol methyl ether

Tertiary
alcohols (3°)

2-Methyl-2-pentanol
2-Methylheptan-2-ol
2-Methylhexan-2-ol
3-Methyl-3-pentanol
3-Methyloctan-3-ol
Diacetone alcohol
Ethchlorvynol
Methylpentynol
Nonafluoro-tert-butyl alcohol
tert-Amyl alcohol
tert-Butyl alcohol
Triphenylethanol
Triphenylmethanol

Hydric alcohols

Monohydric alcohols	Methanol (C₁) Ethanol (C₂) Isopropanol (C₃) 1-Butanol (C₄) 1-Pentanol (C₅) Cetyl alcohol (C₁₆)
Dihydric alcohols	Ethylene glycol Propylene glycol
Trihydric alcohols	Glycerol
Polyhydric alcohols (sugar alcohols)	Pentaerythritol Ethylene glycol (C₂) Glycerol, Propylene glycol (C₃) Erythritol, Threitol (C₄) Xylitol (C₅) Mannitol, Sorbitol (C₆) Volemitol (C₇)

Amyl alcohols

Aromatic alcohols

Saturated
fatty alcohols

Branched and
unsaturated
fatty alcohols

3-Methyl-3-pentanol
Erucyl alcohol
Linolenyl alcohol
Linoleyl alcohol
Oleyl alcohol
Palmitoleyl alcohol
tert-Amyl alcohol
tert-Butyl alcohol

Sugar alcohols

C₁ — C₇	Methylene glycol (C₁) Ethylene glycol (C₂) Glycerol (C₃) Erythritol (C₄) Threitol (C₄) Arabitol (C₅) Ribitol (C₅) Xylitol (C₅) Mannitol (C₆) Sorbitol (C₆) Galactitol (C₆) Iditol (C₆) Volemitol (C₇)
Deoxy sugar alcohols	Fucitol
Cyclic sugar alcohols	Inositol
Glycylglycitols	Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol

Terpene alcohols

Monoterpene alcohols	Borneol Citronellol Geraniol Linalool Menthol Nerol Rhodinol Terpineol
Sesquiterpene alcohols	Bisabolol Farnesol Nerolidol Patchoulol
Diterpene alcohols	Phytol