597-49-9

Basic information

• Product Name: 3-Ethyl-3-pentanol
• Synonyms: 3-ETHYL-3-PENTANOL;3-ETHYL-2-PENTANOL;TERT-HEPTANOL;TERT-HEPTYL ALCOHOL;TRIETHYLCARBINOL;TRIETHYLMETHYL ALCOHOL;3-Aethyl-pentanol-(3);3-Ethyl-3-hydroxypentane
• CAS NO: 597-49-9
• Molecular Formula: C₇H₁₆O
• Molecular Weight: 116.2
• EINECS: 209-902-0
• Mol File: 597-49-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: -12.5 °C
• Boiling Point: 141 °C743 mm Hg(lit.)
• Flash Point: 104 °F
• Appearance: clear colorless to slightly yellow liquid
• Density: 0.824 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.81mmHg at 25°C
• Refractive Index: n20/D 1.430(lit.)
• Storage Temp.: Flammables area
• PKA: 15.38±0.29(Predicted)
• Water Solubility: Slightly soluble in water. Soluble in alcohol.
• BRN: 1731643
• CAS DataBase Reference: 3-Ethyl-3-pentanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethyl-3-pentanol(597-49-9)
• EPA Substance Registry System: 3-Ethyl-3-pentanol(597-49-9)

Safety Data

• Hazard Codes: Xn
• Statements: 10-41-37/38-22
• Safety Statements: 16-39-26
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• RTECS: SA6780000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 597-49-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

3-Ethyl-3-pentanol was used to study the effect of alkanols on the micropolarity and microviscosity of the head group region, in the reverse micelles of AOT-heptane-water by fluorescence probing.

Synthesis Reference(s)

Journal of the American Chemical Society, 84, p. 4715, 1962 DOI: 10.1021/ja00883a020Organic Syntheses, Coll. Vol. 2, p. 602, 1943

Safety Profile

Moderately toxic by subcutaneousroute. When heated to decomposition it emits acrid smokeand irritating vapors.

InChI:InChI=1/C7H16O/c1-4-7(8,5-2)6-3/h8H,4-6H2,1-3H3

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 76529-39-0 methyl (phenylseleno)formate 
• 994-51-4 tetrakis-propionyloxy-silane 
• 101970-86-9 methyl 1,1,1-trichloromethyl carbonate 
• 811-49-4 ethyllithium 
• 949015-02-5 4‐((prop‐2‐yn‐1‐yloxy)methyl)‐1,3‐dioxolan‐2‐one 
• 826-29-9 4-allyloxymethyl-1,3-dioxolan-2-one 
• 2463-45-8 4-chloromethyl-[1,3]dioxolan-2-one 
• 108-32-7 1,2-propylene cyclic carbonate 
• 96-49-1 [1,3]-dioxolan-2-one 
• 96-22-0 pentan-3-one 
• 6285-06-9 3-ethyl-1-pentyn-3-ol 
• 1421931-22-7 5,5-dimethyl-2-(3-ethylpent-3-yl)-1,3,2-dioxaborinane 
• 74-95-3 1,1-dibromomethane 

Downstream Products

• 816-79-5 3-ethyl-2-pentene 
• 118-90-1 ortho-methylbenzoic acid 
• 29908-88-1 2,3-Epoxy-3-ethylpentan 
• 96-22-0 pentan-3-one 
• 138109-52-1 bis-(1,1-diethyl-propyl)-peroxide 
• 64-19-7 acetic acid 
• 802294-64-0 propionic acid 
• 612058-37-4 (1,1-diethylpropoxy)di(phenyl)phosphine 
• 1448551-56-1 (2R,3S)-3-ethylpentan-3-yl 3-hydroxy-2-methyl-3-phenylpropanoate 
• 1448551-76-5 (2R,3R)-3-ethylpentan-3-yl 3-hydroxy-2-methyl-3-phenylpropanoate 
• 1448551-57-2 (2R,3R)-3-ethylpentan-3-yl 3-hydroxy-2-methyl-5-phenylpentanoate 
• 1448551-59-4 (2R,3R,E)-3-ethylpentan-3-yl 3-hydroxy-2-methyl-5-phenylpent-4-enoate 
• 1448551-61-8 (2R,3R,4S,5S)-3-ethylpentan-3-yl 5-((tert-butyldimethylsilyl)oxy)-7-((3,4-dimethoxybenzyl)oxy)-3-hydroxy-2,4-dimethylheptanoate 
• 1448551-62-9 (2S,3S,4S,5S)-3-ethylpentan-3-yl 5-((tert-butyldimethylsilyl)oxy)-7-((3,4-dimethoxybenzyl)oxy)-3-hydroxy-2,4-dimethylheptanoate 

Relevant articles and documents

ETHERS AND ESTERS OF TERTIARY ALKANOLS FOR USE AS AROMA CHEMICALS

The present invention relates to the use of an ether or an ester of a tertiary alkanol or of mixtures of two or more ethers or esters of tertiary alkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aromachemicals; to the use thereof for modifying the scent character of a fragranced composition; to an aroma chemical composition containing an ether or an ester of tertiary alkanol or of mixtures of two or more ethers or esters of tertiary alkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition. The invention further relates to specific ethers or esters of tertiary alkanols.

Factors affecting migration of tertiary alkyl groups in reactions of alkylboronic esters with bromomethyllithium

The reactions of bromomethyllithium with tert-alkylboronic esters could be of great potential for the formation of quaternary carbon centers but often give poor yields/conversions. Calculations and experimental evidence show that tert-alkyl groups migrate less effectively than other types of alkyl group in such reactions and that O-migration competes. Furthermore, slow/incomplete capture of the bromomethyl reagent by the boronic ester is a problem in more hindered systems, and an additional competing reaction, possibly Li-Br exchange on the bromomethylborate species, also leads to lower yields of migrated products. Based on this, experimental protocols have been devised in which the competing reactions are largely suppressed, leading to higher conversions to migrated product for several substrates.