Aromatic hydrocarbons

Aromatic hydrocarbon refers to the closed-chain hydrocarbon containing a benzene ring or having the basic characteristics of the aromatic compound. It can be divided into mono-cyclic aromatic hydrocarbon, polycyclic aromatic hydrocarbon and non-benzene aromatic hydrocarbons. For monocyclic aromatic hydrocarbon, its molecule contains only one benzene ring, such as toluene, xylene, ethylbenzene, styrene, benzene and acetylene.

Polycyclic aromatic hydrocarbon contains two or more benzene rings. According to the interconnected ways of benzene ring, it can be divided into:
1 polybenzo-aliphatic hydrocarbons including diphenylmethane, triphenylmethane, stilbene, styrene and so on;
2 Biphenyl and polybenzene, such as biphenyl, terphenyl and tetraphenyl, etc;
3 polycyclic aromatic hydrocarbons such as naphthalene, anthracene, phenanthrene, indene, fluorene, acenaphthene, pyrene, coronene and so on;

Non-aromatic hydrocarbon is the hydrocarbon containing certain aromatic property but containing no benzene ring such as azulene and annulene. It is easy to have substitution reaction while being not easy to have addition reaction with the ring being not easy to be broken.
The natural existing aromatic hydrocarbon is mainly is mainly obtained through from the distillate of coal tar and the aromatization product of oil. The main component of coal tar is aromatic hydrocarbon; the main component of various kinds of crude oil of petroleum is aliphatic hydrocarbons with aromatic hydrocarbons only accounting for only 0.2% to 7.4%, but the acute and chronic toxicity of oil is mainly aromatic hydrocarbons, in particular caused by the soluble aromatic hydrocarbons such as naphthalene, phenanthrene contained in it. It can be used as solvent and chemical raw materials.

Benzene is the basic structure of aromatic hydrocarbon, usually using the structure formula of six-membered ring containing three conjugated double bonds, which was proposed at 1865 by the German chemist F.A. Kekule, being called as Kekule formula. From the composition point of view, benzene is an unsaturated hydrocarbon, but it is not easy to be subject to oxidation and addition reaction while being easy to participate in substitution reaction, and there is also special toughness (see "aromatic"). According to the hybrid orbital theory, each carbon atoms contained in the benzene molecule is sp2 hybridized with each of them having two sp2 hybrid orbitals overlapped with the sp2 hybrid orbitals from two adjacent carbon atoms, forming a C-Cσ bond (see Fig. 1), and with a sp2 hybrid orbital overlapping with the 1s orbital of the hydrogen atom, forming a C-Hσ bond.

The simplest aromatic hydrocarbon is benzene. People originally discovered benzene and other aromatic compounds from coal tar, and thereby, coal tar, for quite a long time, had been the major source of aromatics. But the yield from coal tar is only 3% of that of the coal; moreover, the content of various kinds of aromatic compound contained in coal tar is only about 0.3% of that of the coal. Therefore, people have mainly manufactured aromatics from petroleum processing system since the 1940s. Aromatics are all liquid or solid. It is insoluble in water but soluble in organic solvents. It has aromaticity and is not easy to participate in the addition reaction, but is easily subject to substitution reaction, and is relatively stable to heat and oxidant. Aromatic hydrocarbons (especially single-ring aromatic hydrocarbon) are important chemical raw materials (for example, xylene is the raw material for the manufacturing of polyester), many kinds of liquid aromatic hydrocarbon can be used as solvents (for example, paint is easily soluble in aromatic hydrocarbons). However, when the liquid aromatic hydrocarbon has been in contact with the skin for several times, due to dehydration and degreasing, can cause dermatitis. The steam of the aromatic hydrocarbons has a stronger stimulation effect on the mucosa than the aliphatic hydrocarbon. In particular, benzene vapor has a special destroying effect on the hematopoietic function. However, animal tests have shown that alkylbenzene has no such damaging effects.

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Structure Chemical Name CAS MF
2-Methoxybenzonitrile 2-Methoxybenzonitrile 6609-56-9 C8H7NO
4-Chlorostyrene 4-Chlorostyrene 1073-67-2 C8H7Cl
2-Cyano-4'-methylbiphenyl 2-Cyano-4'-methylbiphenyl 93717-55-6 C14H11N
Piperonyl chloride Piperonyl chloride 20850-43-5 C8H7ClO2
1,3,5-Trimethoxybenzene 1,3,5-Trimethoxybenzene 621-23-8 C9H12O3
1-Iado-4-(trifluoromethoxy)benzene 1-Iado-4-(trifluoromethoxy)benzene 103962-05-6 C7H4F3IO
tert-Amylbenzene tert-Amylbenzene 2049-95-8 C11H16
4,4'-Diacetylbiphenyl 4,4'-Diacetylbiphenyl 787-69-9 C16H14O2
1-Bromo-4-chloro-2-fluorobenzene 1-Bromo-4-chloro-2-fluorobenzene 1996-29-8 C6H3BrClF
3,4-(Methylenedioxy)phenylacetonitrile 3,4-(Methylenedioxy)phenylacetonitrile 4439-02-5 C9H7NO2
3,4-Dimethoxytoluene 3,4-Dimethoxytoluene 494-99-5 C9H12O2
1-Bromo-2,4,6-trifluorobenzene 1-Bromo-2,4,6-trifluorobenzene 2367-76-2 C6H2BrF3
Orcinol Orcinol 504-15-4 C7H8O2
o-Xylene o-Xylene 95-47-6 C8H10
4-tert-Butyltoluene 4-tert-Butyltoluene 98-51-1 C11H16
1-Iodo-3,5-dimethylbenzene 1-Iodo-3,5-dimethylbenzene 22445-41-6 C8H9I
1,3-Diethylbenzene 1,3-Diethylbenzene 141-93-5 C10H14
2,2'-Biphenol 2,2'-Biphenol 1806-29-7 C12H10O2
1,5-Dihydroxy naphthalene 1,5-Dihydroxy naphthalene 83-56-7 C10H8O2
4-Bromomethyl-2-cyanobiphenyl 4-Bromomethyl-2-cyanobiphenyl 114772-54-2 C14H10BrN
1-Bromo-4-fluoro-2-iodobenzene 1-Bromo-4-fluoro-2-iodobenzene 202865-72-3 C6H3BrFI
2,3,4-Trifluorobromobenzene 2,3,4-Trifluorobromobenzene 176317-02-5 C6H2BrF3
Phthalonitrile Phthalonitrile 91-15-6 C8H4N2
1-Bromo-2-(1-methylethyl)benzene 1-Bromo-2-(1-methylethyl)benzene 7073-94-1 C9H11Br
1-Bromo-2,4-dimethoxybenzene 1-Bromo-2,4-dimethoxybenzene 17715-69-4 C8H9BrO2
1,2-Dichloro-4-fluorobenzene 1,2-Dichloro-4-fluorobenzene 1435-49-0 C6H3Cl2F
3-(Trifluoromethoxy)fluorobenzene 3-(Trifluoromethoxy)fluorobenzene 1077-01-6 C7H4F4O
3-(Trifluoromethoxy)iodobenzene 3-(Trifluoromethoxy)iodobenzene 198206-33-6 C7H4F3IO
1-Methylnaphthalene 1-Methylnaphthalene 90-12-0 C11H10
Poly(styrene) Poly(styrene) 9003-53-6 H2
1,8-Bis(dimethylamino)naphtalene 1,8-Bis(dimethylamino)naphtalene 20734-58-1 C14H18N2
1,3-Benzodioxole 1,3-Benzodioxole 274-09-9 C7H6O2
Butylbenzene Butylbenzene 104-51-8 C10H14
1,4-Diethoxybenzene 1,4-Diethoxybenzene 122-95-2 C10H14O2
2-Methylhydroquinone 2-Methylhydroquinone 95-71-6 C7H8O2
1,2,4-Trimethoxybenzene 1,2,4-Trimethoxybenzene 135-77-3 C9H12O3
N-Phenyl-1-naphthylamine N-Phenyl-1-naphthylamine 90-30-2 C16H13N
3,5-Dimethylaniline 3,5-Dimethylaniline 108-69-0 C8H11N
1,2,3-Trimethoxybenzene 1,2,3-Trimethoxybenzene 634-36-6 C9H12O3
2-Bromo-1,4-dichlorobenzene 2-Bromo-1,4-dichlorobenzene 1435-50-3 C6H3BrCl2
m-Xylene m-Xylene 108-38-3 C8H10
5-Amino-o-cresol 5-Amino-o-cresol 2835-95-2 C7H9NO
3-Phenyltoluene 3-Phenyltoluene 643-93-6 C13H12
4-Trifluoromethoxytoluene 4-Trifluoromethoxytoluene 706-27-4 C8H7F3O
4-Methoxystyrene 4-Methoxystyrene 637-69-4 C9H10O
2-Chloro-1,4-dimethoxybenzene 2-Chloro-1,4-dimethoxybenzene 2100-42-7 C8H9ClO2
2-(Trifluoromethoxy)bromobenzene 2-(Trifluoromethoxy)bromobenzene 64115-88-4 C7H4BrF3O
2-Methylresorcinol 2-Methylresorcinol 608-25-3 C7H8O2
1-Methyl-4-(methylsulfonyl)-benzene 1-Methyl-4-(methylsulfonyl)-benzene 3185-99-7 C8H10O2S
3-(Trifluoromethoxy)chlorobenzene 3-(Trifluoromethoxy)chlorobenzene 772-49-6 C7H4ClF3O
4-Methylcatechol 4-Methylcatechol 452-86-8 C7H8O2
4-Bromostyrene 4-Bromostyrene 2039-82-9 C8H7Br
Mesitylene Mesitylene 108-67-8 C9H12
2,6-Diaminotoluene 2,6-Diaminotoluene 823-40-5 C7H10N2
2-Methylnaphthalene 2-Methylnaphthalene 91-57-6 C11H10
tert-Butylbenzene tert-Butylbenzene 98-06-6 C10H14
1-Methoxynaphthalene 1-Methoxynaphthalene 2216-69-5 C11H10O
4-Benzyloxybromobenzene 4-Benzyloxybromobenzene 6793-92-6 C13H11BrO
Cyclohexylbenzene Cyclohexylbenzene 827-52-1 C12H16
1,3,5-Tri-tert-butylbenzene 1,3,5-Tri-tert-butylbenzene 1460-02-2 C18H30
Pentamethylbenzene Pentamethylbenzene 700-12-9 C11H16
1,3,5-Triisopropylbenzene 1,3,5-Triisopropylbenzene 717-74-8 C15H24
2,4-Difluoroiodobenzene 2,4-Difluoroiodobenzene 2265-93-2 C6H3F2I
1,4-Diacetoxybenzene 1,4-Diacetoxybenzene 1205-91-0 C10H10O4
4'-Methyl-2-cyanobiphenyl 4'-Methyl-2-cyanobiphenyl 114772-53-1 C14H11N
4-Cyano-4'-ethylbiphenyl 4-Cyano-4'-ethylbiphenyl 58743-75-2 C15H13N
4,4'-Biphenol 4,4'-Biphenol 92-88-6 C12H10O2
2-(Trifluoromethoxy)aniline 2-(Trifluoromethoxy)aniline 1535-75-7 C7H6F3NO
1,4-Diphenoxybenzene 1,4-Diphenoxybenzene 3061-36-7 C18H14O2
Bis-2,6-N,N-(2-hydroxyethyl)diaminotoluene Bis-2,6-N,N-(2-hydroxyethyl)diaminotoluene 149330-25-6 C11H18N2O2
4-Phenylphenol 4-Phenylphenol 92-69-3 C12H10O
3,4,5-Trimethoxytoluene 3,4,5-Trimethoxytoluene 6443-69-2 C10H14O3
5,6,7,8-Tetrahydro-1-naphthylamine 5,6,7,8-Tetrahydro-1-naphthylamine 2217-41-6 C10H13N
3,4-Diaminotoluene 3,4-Diaminotoluene 496-72-0 C7H10N2
1,3-Diphenylbenzene 1,3-Diphenylbenzene 92-06-8 C18H14
2-Bromo-4-chloro-1-fluorobenzene 2-Bromo-4-chloro-1-fluorobenzene 1996-30-1 C6H3BrClF
2,3-Dihydroxynaphthalene 2,3-Dihydroxynaphthalene 92-44-4 C10H8O2
2-Bromo-1-chloro-4-fluorobenzene 2-Bromo-1-chloro-4-fluorobenzene 201849-15-2 C6H3BrClF
p-Terphenyl p-Terphenyl 92-94-4 C18H14
1-Iodo-2-(trifluoromethoxy)benzene 1-Iodo-2-(trifluoromethoxy)benzene 175278-00-9 C7H4F3IO
3-(Trifluoromethoxy)bromobenzene 3-(Trifluoromethoxy)bromobenzene 2252-44-0 C7H4BrF3O
2,5-Bis(trifluoromethyl)bromobenzene 2,5-Bis(trifluoromethyl)bromobenzene 7617-93-8 C8H3BrF6
Phenylpentane Phenylpentane 538-68-1 C11H16
2-(Trifluoromethoxy)fluorobenzene 2-(Trifluoromethoxy)fluorobenzene 2106-18-5 C7H4F4O
2-Chlorostyrene 2-Chlorostyrene 2039-87-4 C8H7Cl
1-Bromo-3,5-dimethoxybenzene 1-Bromo-3,5-dimethoxybenzene 20469-65-2 C8H9BrO2
2,6-Dibromotoluene 2,6-Dibromotoluene 69321-60-4 C7H6Br2
1'-Acetonaphthone 1'-Acetonaphthone 941-98-0 C12H10O
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