2308-38-5

Basic information

• Product Name: tert-butyl butanoate
• Synonyms: tert-butyl butanoate
• CAS NO: 2308-38-5
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.21
• Mol File: 2308-38-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: -88.07°C (estimate)
• Boiling Point: 136.25°C
• Flash Point: 39.1°C
• Appearance: /
• Density: 0.8836 (estimate)
• Vapor Pressure: 5.3mmHg at 25°C
• Refractive Index: 1.3790 (estimate)
• CAS DataBase Reference: tert-butyl butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl butanoate(2308-38-5)
• EPA Substance Registry System: tert-butyl butanoate(2308-38-5)

Safety Data

• Hazardous Substances Data: 2308-38-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 26, p. 2715, 1996 DOI: 10.1080/00397919608004588

InChI:InChI=1/C8H16O2/c1-5-6-7(9)10-8(2,3)4/h5-6H2,1-4H3

Upstream product

• 3246-27-3 tert-butyl crotonate 
• 540-88-5 acetic acid tert-butyl ester 
• 623-42-7 butanoic acid methyl ester 

Downstream Products

• 2531-81-9 ethyl 2-nitrobutanoate 
• 112197-23-6 2-(Methyl-diphenyl-silanyl)-butyric acid tert-butyl ester 
• 115500-73-7 2(S)-benzyloxycarbonylamino-5-keto-6-t-butyloxycarbonyl octanoic acid benzylester 
• 135560-63-3 (3R,4S)-3-ethyl-4-<(S)-1-<(tert-butyldimethylsilyl)oxy>-phenylmethyl>-2-azetidinone 
• 177540-39-5 2-(p-Tolyl-hydrazono)-butyric acid tert-butyl ester 
• 867150-92-3 (R)-4-Chloro-2-ethyl-3,3-dimethyl-4-((R)-toluene-4-sulfinyl)-butyric acid tert-butyl ester 
• 867150-93-4 tert-butyl 2-{1-[chloro(p-tolylsulfinyl)methyl]cyclohexyl}butanoate 
• 867150-94-5 tert-butyl 2-{1-[chloro(p-tolylsulfinyl)methyl]cyclopentadecyl}butanoate 

Relevant articles and documents

'New' catalysts for the ester-interchange reaction: The role of alkali-metal alkoxide clusters in achieving unprecedented reaction rates

The catalytic effect of alkali-metal tert-butoxide clusters on the rate of ester interchange for several pairs of esters has been determined in nonpolar and weakly polar solvents. Reactivities increase in the order (Li+ + + + +) with the fastest rates reaching 107 catalytic turnovers per hour (TO/h). Ester interchange rates were sensitive to the size of both the transferring OR groups and the ester substituent. Phenyl esters did not exchange with aliphatic esters due to nonstatistical breakdown patterns in the tetrahedral intermediate. A first-order equilibration analysis on the interchange between tert-butyl acetate (tBuAc) and methyl benzoate (MeBz) (5 mol % NaOtBu) indicated enhanced reaction rates as the reaction proceeded. Isolation and quenching (DCl/D2O) of precipitated catalyst points to a mechanism whereby sequential methoxy incorporation into the catalyst cluster increases activity, but eventually precipitates out of solution as a 3:1 OMe:OtBu cluster. The rate law was determined to be k(obs)[MeBz]1[tBuAc]0[NaOtBu](x), where x = 1.2(1), 1.4(1), and 0.85(1) in hexane, ether, and THF, respectively, under conditions where tetrameric catalyst aggregates are expected. Reaction rates were generally observed to be higher in nonpolar solvents (hexane > toluene, ether > THF). Eyring analysis over a 40°C range yielded ΔH(≠) = 10.0(1) kcal mol-1 and ΔS(≠) = -32(3) eu. A Hammett (σ) plot generated with para-substituted methyl benzoates gave ρ +2.35 (R 0.996). These results are interpreted in terms of a catalytic cycle composed of two coupled transesterification reactions with a turnover-limiting addition of a tert-butoxy-containing cluster (tetramer) to methyl benzoate. Catalyst relative reactivities (Cs+ > Rb+ > K+ > Na+ > Li+) are interpreted in terms of competitive electrostatic interactions between the alkali-metal and ground-state and transition-state anions. This analysis predicts the observed linear dependence between log(k(obs)) and l/r(ionic).