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a hydrocarbon radical (C4H9)
any of three isomeric hydrocarbons C4H8; all used in making synthetic rubbers (同)butene

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/20 23:32:01」(JST)

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In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C₄H₉, derived from either of the two isomers of butane.

The isomer n-butane can connect either at one of the two terminal carbon atoms or at one of the two internal carbon atoms, giving rise to two "-butyl" groups:

Normal butyl or n-Butyl: CH₃–CH₂–CH₂–CH₂– (fully systematic name: butyl)
Secondary butyl or sec-Butyl: CH₃–CH₂–CH(CH₃)– (fully systematic name: 1-methylpropyl)

The second, branched isomer of butane, isobutane, can connect either at one of the three terminal carbons or at the central carbon, giving rise to another two groups:

Isobutyl: (CH₃)₂CH–CH₂– (fully systematic name: 2-methylpropyl)
Tertiary butyl, tert-Butyl or t-butyl: (CH₃)₃C– (fully systematic name: 1,1-dimethylethyl)

Nomenclature

According to IUPAC nomenclature, "isobutyl", "sec-butyl", and "tert-butyl" are all retained names.

Common name	IUPAC name	Systematic name	Alternate notation
n-butyl	butyl	butyl	butan-1-yl
isobutyl	isobutyl	2-methylpropyl	2-methylpropan-1-yl
sec-butyl	sec-butyl	1-methylpropyl	butan-2-yl
tert-butyl	tert-butyl	1,1-dimethylethyl	2-methylpropan-2-yl

Butyl is the largest substituent for which trivial names are commonly used for all isomers.

The butyl group's carbon that is connected to the rest (R) of the molecule is called the R^I or R-prime carbon^{[citation needed]}. The prefixes sec (from "secondary") and tert (from "tertiary") refer to the number of additional side chains (or carbons) connected to the first butyl carbon. The prefix "iso" (from "isomer") means "equal" while the prefix 'n-' stands for "normal".

Some examples

The following are the four isomers of "butyl acetate":


n-butyl acetate	isobutyl acetate	sec-butyl acetate	tert-butyl acetate

Etymology

As the number of carbons in an alkyl chain increases, butyl is the last to be named historically instead of through Greek numbers. The name is derived from butyric acid, a four-carbon carboxylic acid found in rancid butter. The name of butyric acid, in turn, comes from Latin butyrum, butter.

Tert-butyl effect

The tert-butyl substituent is very bulky and used in chemistry for kinetic stabilisation together with other bulky groups such as the related trimethylsilyl group. The effect that the t-butyl group exerts on the progress of a chemical reaction is called the tert-butyl effect.

This effect is illustrated in the Diels-Alder reaction below, where the tert-butyl substituent causes a reaction rate acceleration by a factor of 240 compared to hydrogen as the substituent.^[1]

References

^ Factors affecting ease of ring formation. The effect of anchoring substitution on the rate of an intramolecular diels-alder reaction with furan-diene Serge Cauwberghs and Pierre J. De Clercq B. Tinant and J. P. Declercq Tetrahedron Letters Volume 29, Issue 20 , 1988, Pages 2493-2496 doi:10.1016/S0040-4039(00)87916-2

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English Journal

Effect of the structure of imidazolium cations in [BF(4)](-)-type ionic liquids on direct electrochemistry and electrocatalysis of horseradish peroxidase in Nafion films.

Lu L, Huang X, Qu Y.SourceKey Laboratory of Colloid & Interface Chemistry of the Education Ministry of China, Shandong University, Jinan 250100, PR China.
Colloids and surfaces. B, Biointerfaces.Colloids Surf B Biointerfaces.2011 Oct 1;87(1):61-6. Epub 2011 May 31.
The direct electrochemistry and bioelectrocatalysis of horseradish peroxidase (HRP) in Nafion films at glassy carbon electrode (GCE) was investigated in three [BF(4)](-)-type room-temperature ionic liquids (ILs) to understand the structural effect of imidazolium cations. The three ILs are 1-ethyl-3-
PMID 21632219

Improved electrochemical immunosensor for myeloperoxidase in human serum based on nanogold/cerium dioxide-BMIMPF(6)/l-Cysteine composite film.

Lu L, Liu B, Li S, Zhang W, Xie G.SourceKey Laboratory of Medical Diagnostics of Ministry of Education, Department of Laboratory Medicine, Chongqing Medical University, Chongqing 400016, PR China.
Colloids and surfaces. B, Biointerfaces.Colloids Surf B Biointerfaces.2011 Sep 1;86(2):339-44. Epub 2011 Apr 17.
An electrochemical immunosensing assay for myeloperoxidase (MPO) determination in human serum has been developed. Firstly, l-Cysteine was initially electropolymerized on an Au electrode to form l-Cysteine film. After that cerium dioxide (CeO(2)) dispersed in 1-butyl-3-methylimidazolium hexafluoropho
PMID 21561744

Japanese Journal

Coordination characteristics of trivalent lanthanides and actinides in molten hydrate salts of Ca(NO3)2 and CaCl2

Fujii Toshiyuki,Okude Genki,Uehara Akihiro,Sekimoto Shun,Hayashi Hirokazu,Akabori Mitsuo,Minato Kazuo,Yamana Hajimu
Journal of Radioanalytical and Nuclear Chemistry 288(1), 181-187, 2011-04
… Distribution behavior of Ce(III), Am(III), and Cm(III) between tri-n-butyl phosphate solution and molten calcium nitrate hydrate Ca(NO3)2·RH2O or molten calcium chloride hydrate CaCl2·RH2O was studied radiochemically. …
NAID 120003087950

Syntheses, crystal structures and electrochemical properties of bis(catechol)s with acetylene group

Suenaga Yusaku,Hirano Yasuhiro,Umehata Yukiko,Kamei Kuniaki,Maekawa Masahiko
理工学総合研究所研究報告 (23), 23-33, 2011-2
… [Abstract] Three bis(catechol) compounds 5,5'-(buta-1,3-diyne-1,4-diyl) bis(3-tert-butylcatechol) (Biscat 1), 5,5'-(2,5-dimethoxy-1,4-phenylene)bis(ethyne-2,1-diyl)bis(3-tert-butyl-catechol) (Biscat 2) and 5,5'-(1,3-phenylene)bis(ethyne-2,1-diyl)bis(3-tert-butylcatechol) (Biscat 3) were obtained from cross-coupling reactions. …
NAID 120003088547

Related Pictures

★リンクテーブル★

リンク元	「GABA」「ブチル」
拡張検索	「p-butylaminobenzoyldiethylaminoethyl hydrochloride」「butyl p-hydroxybenzoate」「dibutylhydroxytoluene」「isobutyl methyl ketone」「methyl isobutyl ketone」
関連記事	「but」