3-Methyl-3-pentanol

3-Methyl-3-pentanol^[1]
Names


Preferred IUPAC name 3-Methylpentan-3-ol
Other names 3-Methyl-3-pentanol Diethyl carbinol
Identifiers
CAS Number	77-74-7^Y[PubChem]=
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL506184^Y
ChemSpider	6248^Y
ECHA InfoCard	100.000.959
EC Number	201-053-4
PubChem CID	6493
UNII	SR4551FEKB
CompTox Dashboard (EPA)	DTXSID0021755
InChI InChI=1S/C6H14O/c1-4-6(3,7)5-2/h7H,4-5H2,1-3H3^Y Key: FRDAATYAJDYRNW-UHFFFAOYSA-N^Y InChI=1/C6H14O/c1-4-6(3,7)5-2/h7H,4-5H2,1-3H3 Key: FRDAATYAJDYRNW-UHFFFAOYAV
SMILES OC(C)(CC)CC
Properties
Chemical formula	C₆H₁₄O
Molar mass	102.174 g/mol
Appearance	colorless liquid
Odor	fruity
Density	0.8286 g/cm³ at 20 °C
Melting point	−23.6 °C (−10.5 °F; 249.6 K)
Boiling point	122.4 °C (252.3 °F; 395.5 K)
Solubility in water	45 g/L
Solubility	miscible with ethanol, diethyl ether
Thermochemistry
Heat capacity (C)	293.4 J·mol⁻¹·K⁻¹ (liquid)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H302
Precautionary statements	P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P312, P303+P361+P353, P330, P370+P378, P403+P235, P501
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	710 mg/kg rat
Safety data sheet (SDS)	http://www.sciencelab.com/msds.php?msdsId=9926087
Related compounds
Related compounds	Hexanol
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

3-Methyl-3-pentanol (IUPAC name: 3-methylpentan-3-ol) is an organic chemical compound and a tertiary hexanol. It is used in the synthesis of the tranquilizer emylcamate,^[2] and has similar sedative and anticonvulsant actions itself.^[3]

Synthesis

It can be prepared by reacting ethylmagnesium bromide with methyl acetate in the so-called Grignard reaction using dried diethyl ether or tetrahydrofuran as solvent.

It can be prepared also by reacting ethylmagnesium bromide with butanone in the same conditions already mentioned.

References

^ Lide DR (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–400, 5–47, 8–106. ISBN 0-8493-0594-2.
^ Sittig M (1988). Pharmaceutical manufacturing encyclopedia. Vol. 2 (2 ed.). William Andrew. pp. 555–556. ISBN 978-0-8155-1144-1. Retrieved 2010-01-22.
^ Brown B, Schaffarzick RW, Dreisbach RH (October 1955). "Anticonvulsant properties of certain secondary and tertiary alcohols". The Journal of Pharmacology and Experimental Therapeutics. 115 (2): 230–9. PMID 13272171.

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