neopentyl alcohol
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 420088148
| ImageFile1 = Neopentyl-alcohol-2D-structure.svg
| ImageSize1 = 180px
| ImageFile2 = Neopentyl-alcohol-from-xtal-Mercury-3D-bs.png
| ImageName2 = Ball-and-stick model of the neopentyl alcohol molecule
| ImageSize2 = 150px
| PIN = 2,2-Dimethylpropan-1-ol
| OtherNames = tert-Butyl carbinol
tert-Butylmethanol
Neoamyl alcohol
Neopentanol
{{Citation
| last = Lide
| first = David R.
| year = 1998
| title = Handbook of Chemistry and Physics
| edition = 87
| publication-place = Boca Raton, Florida
| publisher = CRC Press
| isbn = 0-8493-0594-2
| pages = 3-228, 5-42, 8-102, 16-22
}}
|Section1={{Chembox Identifiers
| CASNo =75-84-3
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEMBL = 458630
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6164
| EC_number = 200-907-3
| PubChem = 6404
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5I067PJD7S
| UNNumber = 1325
| InChI = 1/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3
| InChIKey = KPSSIOMAKSHJJG-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H12O/c1-5(2,3)4-6/h6H,4H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KPSSIOMAKSHJJG-UHFFFAOYSA-N
| SMILES =CC(CO)(C)C
}}
|Section2={{Chembox Properties
| C =5 | H=12 | O=1
| MolarMass =
| Appearance =
| Density = 0.812 g/mL at 20 °C
| MeltingPtC = 52.5
| BoilingPtC = 113.5
| Solubility = 36 g/L
| SolubleOther = very soluble in ethanol, diethyl ether
}}
|Section4={{Chembox Thermochemistry
| DeltaHf = −399.4 kJ·mol−1
| DeltaHc =
| Entropy =
| HeatCapacity =
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|226|228|319|332|335}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264+265|271|280|303+361+353|304+340|305+351+338|317|319|337+317|370+378|403+233|403+235|405|501}}
| MainHazards =
| FlashPtC = 37
| AutoignitionPtC =
}}
}}
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.{{cite journal |doi=10.15227/orgsyn.040.0076|author=Joseph Hoffman|title=Neopentyl Alcohol|journal=Organic Syntheses|year=1960|volume=40|page=76}}
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.Comptes Rendus, 1891, 112, p. 1065
Neopentyl alcohol can be converted to neopentyl iodide by treatment with triphenylphosphite/methyl iodide:{{cite journal |author=H. N. Rydon|doi=10.15227/orgsyn.051.0044|title=Alkyl Iodides: Neopentyl Iodide and Iodocyclohexane|journal=Organic Syntheses|year=1971|volume=51|page=44}}
:(CH3)3CCH2OH + [CH3(C6H5O)3P]+I− → (CH3)3CCH2I + [CH3(C6H5O)2PO + C6H5OH
See also
References
{{reflist}}
{{alcohols}}