Sec-Butylbenzene

Last updated
sec-Butylbenzene
Sec-Butylbenzene.svg
Names
Preferred IUPAC name
(Butan-2-yl)benzene
Other names
  • sec-butylbenzene
  • s-butylbenzene
  • 1-methylpropylbenzene
Identifiers
3D model (JSmol)
1903902
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.752 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-227-0
261109
KEGG
PubChem CID
UNII
  • InChI=1S/C10H14/c1-3-9(2)10-7-5-4-6-8-10/h4-9H,3H2,1-2H3
    Key: ZJMWRROPUADPEA-UHFFFAOYSA-N
  • CCC(C)C1=CC=CC=C1
Properties
C10H14
Molar mass 134.22
Appearancecolorless liquid
Density 0.863 g/cm3
Melting point −75.5 °C (−103.9 °F; 197.7 K)
Boiling point 174 °C (345 °F; 447 K)
insoluble
Solubility in organic solventsmiscible
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H226, H304, H315, H319, H411
P210, P233, P240, P241, P242, P243, P264, P273, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P313, P337+P313, P362, P370+P378, P391, P403+P235, P405, P501
Flash point 52.0 °C (125.6 °F; 325.1 K)
418 °C (784 °F; 691 K)
Related compounds
Related compounds
iso-Butylbenzene, n-Butylbenzene, tert-Butylbenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

sec-Butylbenzene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring substituted with a sec-butyl group. It is a flammable colorless liquid which is nearly insoluble in water but miscible with organic solvents. [1]

Production

sec-Butylbenzene can be produced by the reaction of benzene with either n-butyl alcohol or sec-butyl alcohol in presence of anhydrous aluminium chloride and hydrochloric acid. [2]

Related Research Articles

<span class="mw-page-title-main">Aromatic compound</span> Compound containing rings with delocalized pi electrons

Aromatic compounds or arenes usually refers to organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying Hückel's Rule. Aromatic compounds have the following general properties:

<span class="mw-page-title-main">Hydrocarbon</span> Organic compound consisting entirely of hydrogen and carbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic; their odor is usually faint, and may be similar to that of gasoline or lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases, liquids, low melting solids or polymers.

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.

<span class="mw-page-title-main">Aromaticity</span> Chemical property

In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected by the stabilization of conjugation alone. The earliest use of the term was in an article by August Wilhelm Hofmann in 1855. There is no general relationship between aromaticity as a chemical property and the olfactory properties of such compounds.

<span class="mw-page-title-main">Aryl group</span> Molecular groups or substituents derived from an aromatic ring

In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as a placeholder for the aryl group in chemical structure diagrams, analogous to “R” used for any organic substituent. “Ar” is not to be confused with the elemental symbol for argon.

<span class="mw-page-title-main">Nitration</span> Chemical reaction which adds a nitro (–NO₂) group onto a molecule

In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.

<span class="mw-page-title-main">Annulene</span> Completely conjugated monocyclic hydrocarbons

Annulenes are monocyclic hydrocarbons that contain the maximum number of non-cumulated or conjugated double bonds ('mancude'). They have the general formula CnHn (when n is an even number) or CnHn+1 (when n is an odd number). The IUPAC accepts the use of 'annulene nomenclature' in naming carbocyclic ring systems with 7 or more carbon atoms, using the name '[n]annulene' for the mancude hydrocarbon with n carbon atoms in its ring, though in certain contexts (e.g., discussions of aromaticity for different ring sizes), smaller rings (n = 3 to 6) can also be informally referred to as annulenes. Using this form of nomenclature 1,3,5,7-cyclooctatetraene is [8]annulene and benzene is [6]annulene (and occasionally referred to as just 'annulene').

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<span class="mw-page-title-main">Mellitic acid</span> Chemical compound

Mellitic acid, also called graphitic acid or benzenehexacarboxylic acid, is an acid first discovered in 1799 by Martin Heinrich Klaproth in the mineral mellite (honeystone), which is the aluminium salt of the acid. It crystallizes in fine silky needles and is soluble in water and alcohol.

<span class="mw-page-title-main">Fluoranthene</span> Chemical compound

Fluoranthene is a polycyclic aromatic hydrocarbon (PAH). The molecule can be viewed as the fusion of naphthalene and benzene unit connected by a five-membered ring. Although samples are often pale yellow, the compound is colorless. It is soluble in nonpolar organic solvents. It is a member of the class of PAHs known as non-alternant PAHs because it has rings other than those with six carbon atoms. It is a structural isomer of the alternant PAH pyrene. It is not as thermodynamically stable as pyrene. Its name is derived from its fluorescence under UV light.

In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular H2. It is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols, and imines to amines. It avoids the need for high-pressure molecular H2 used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts, many of which are chiral, allowing efficient asymmetric synthesis. It uses hydrogen donor compounds such as formic acid, isopropanol or dihydroanthracene, dehydrogenating them to CO2, acetone, or anthracene respectively. Often, the donor molecules also function as solvents for the reaction. A large scale application of transfer hydrogenation is coal liquefaction using "donor solvents" such as tetralin.

The kauri-butanol value is an international, standardized measure of solvent power for a hydrocarbon solvent, and is governed by an ASTM standardized test, ASTM D1133. The result of this test is a scaleless index, usually referred to as the "Kb value". A higher Kb value means the solvent is more aggressive or active in the ability to dissolve certain materials. Mild solvents have low scores in the tens and twenties; powerful solvents like chlorinated solvents and naphthenic aromatic solvents have ratings that are in the low hundreds.

<span class="mw-page-title-main">Benzene</span> Hydrocarbon compound consisting of a 6-sided ring

Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

<span class="mw-page-title-main">Thermal rearrangement of aromatic hydrocarbons</span>

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<i>tert</i>-Butyl peroxybenzoate Chemical compound

tert-Butyl peroxybenzoate (TBPB) an organic compound with the formula C6H5CO3CMe3 (Me = CH3). It is the most widely produced perester; it is an ester of peroxybenzoic acid (C6H5CO3H). It is often used as a radical initiator in polymerization reactions, such as the production of LDPE from ethylene, and for crosslinking, such as for unsaturated polyester resins.

C<sub>4</sub>-Benzenes Index of articles associated with the same name

The C4-benzenes are a class of organic aromatic compounds which contain a benzene ring and four other carbon atoms. There are three tetramethylbenzenes, six dimethylethylbenzenes, three diethylbenzenes, three isopropylmethylbenzenes, three n-propylmethylbenzenes and four butylbenzenes. The saturated compounds have formula C10H14 and molecular weight 134.22 g/mol. C4-benzenes are found in petroleum. Petrol (gasoline) can contain 5-8% C4-benzenes.

<i>n</i>-Butylbenzene Chemical compound

n-Butylbenzene is the organic compound with the formula C6H5C4H9. Of two isomers of butylbenzene, n-butylbenzene consists of a phenyl group attached to the 1 position of a butyl group. It is a slightly greasy, colorless liquid.

Fulvio Cacace was an Italian chemist.

<i>tert</i>-Butylbenzene Organic compound

tert-Butylbenzene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring substituted with a tert-butyl group. It is a flammable colorless liquid which is nearly insoluble in water but miscible with organic solvents.

References

  1. "sec-butylbenzene - Substance Information - ECHA". echa.europa.eu. Retrieved 2020-01-22.
  2. Buess, C. M.; Karabinos, S. V.; Kunz, P. V.; Gibbons, L. C. (1946), The synthesis and purification of aromatic hydrocarbons III : isobutylbenzene, sec-butylebenzene and tert-butylbenzene, National Advisory Committee for Aeronautics, Technical Note No. 1021