597-93-3

Basic information

• Product Name: 5-BUTYL-5-NONANOL
• Synonyms: 5-BUTYL-5-NONANOL;Tributylcarbinol;1,1-Dibutyl-1-pentanol;1,1-Dibutylpentyl alcohol;5-Butylnonane-5-ol;Tributylmethanol
• CAS NO: 597-93-3
• Molecular Formula: C₁₃H₂₈O
• Molecular Weight: 200.36082
• Mol File: 597-93-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 20°C
• Boiling Point: 268.11°C (estimate)
• Flash Point: 107.8°C
• Appearance: /
• Density: 0.8408
• Vapor Pressure: 0.00345mmHg at 25°C
• Refractive Index: 1.4445
• PKA: 15.38±0.29(Predicted)
• CAS DataBase Reference: 5-BUTYL-5-NONANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BUTYL-5-NONANOL(597-93-3)
• EPA Substance Registry System: 5-BUTYL-5-NONANOL(597-93-3)

Safety Data

• Hazardous Substances Data: 597-93-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 2070, 1971 DOI: 10.1021/ja00737a050Tetrahedron Letters, 18, p. 3383, 1977 DOI: 10.1016/S0040-4039(01)83245-7

InChI:InChI=1/C13H28O/c1-4-7-10-13(14,11-8-5-2)12-9-6-3/h14H,4-12H2,1-3H3

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 109-87-5 Dimethoxymethane 
• 110-59-8 pentanonitrile 
• 693-04-9 butyl magnesium bromide 
• 826-29-9 4-allyloxymethyl-1,3-dioxolan-2-one 
• 108-32-7 1,2-propylene cyclic carbonate 
• 96-49-1 [1,3]-dioxolan-2-one 
• 109-72-8 n-butyllithium 
• 122-56-5 tributyl borane 
• 541-41-3 chloroformic acid ethyl ester 
• 109-52-4 valeric acid 
• 62485-87-4 butyl-iodo-manganese 
• 638-29-9 n-valeryl chloride 
• 539-82-2 ethyl n-valerate 

Downstream Products

• 7367-38-6 5-butyl-4-nonene 
• 1138320-53-2 N'-phenylhydrazinecarbodithioic acid 1,1-dibutylpentyl ester 
• 1092840-19-1 N'-phenylhydrazine carboxylic acid 1,1-dibutylpentyl ester 

Relevant articles and documents

Fast Addition of s-Block Organometallic Reagents to CO2-Derived Cyclic Carbonates at Room Temperature, Under Air, and in 2-Methyltetrahydrofuran

Fast addition of highly polar organometallic reagents (RMgX/RLi) to cyclic carbonates (derived from CO2 as a sustainable C1 synthon) has been studied in 2-methyltetrahydrofuran as a green reaction medium or in the absence of external volatile organic solvents, at room temperature, and in the presence of air/moisture. These reaction conditions are generally forbidden with these highly reactive main-group organometallic compounds. The correct stoichiometry and nature of the polar organometallic alkylating or arylating reagent allows straightforward synthesis of: highly substituted tertiary alcohols, β-hydroxy esters, or symmetric ketones, working always under air and at room temperature. Finally, an unprecedented one-pot/two-step hybrid protocol is developed through combination of an Al-catalyzed cycloaddition of CO2 and propylene oxide with the concomitant fast addition of RLi reagents to the in situ and transiently formed cyclic carbonate, thus allowing indirect conversion of CO2 into the desired highly substituted tertiary alcohols without need for isolation or purification of any reaction intermediates.

Reactivity of mixed organozinc and mixed organocopper reagents: 12. Three component reaction of mixed (n-alkyl)(diaryl)zincates, chloroformates and phosphines for the synthesis of esters

The reaction of mixed n-butyldiphenylzincate, n-BuPh2ZnMgBr with ethyl chloroformate, ClCOOEt in the presence n-Bu3P in THF takes place with quantitative yield and phenyl group transfer to give PhCOOEt. Ethoxycarbonylation of n-BuPh2ZnMgBr is preferable to the reaction of PhMgBr forming ester and triphenylcarbinol and also to the reaction of triphenylzincate, Ph3ZnMgBr for atom economy. Group selectivity in the phosphine catalyzed C-COOR coupling of n-BuPh2ZnMgBr and n-Bu2PhZnMgBr can be controlled by changing reaction parameters. n-Bu3P catalyzed reaction of n-BuPh2ZnMgBr with ClCOOEt takes place with phenyl selectivity whereas reaction of n-Bu2PhZnMgBr with ClCOOPh results in n-butyl transfer. Catalysis by Ph3P increases n-butyl group:phenyl group transfer ratio in the ethoxycarbonylation of both zincates. Selective transfer of aryl groups in n-Bu3P catalyzed reaction of n-butyl(aryl)2ZnMgBr reagents with ClCOOEt in THF provides a new procedure for the organometallic synthesis of arenecarboxylic acid ethyl esters at room temperature.

Salt effects on the reactivity and the stability of organomanganese reagents

The reactivity and the stability of organomanganese reagents prepared from the ate complexes MnX2·2LiBr (X= Br,I) and MnCl2·R4NX (X= Br, Cl) were studied. The preparation and the use for synthetic applications of stable sec- and tert-alkylmanganese bromides in ether as well as the acylation of RMnCl by R'COOCOOEt in THF were successfully achieved for the first time.