Synonyms:

Group of substances:

Physical appearance:

Empirical formula (Hill's system for organic substances):

Structural formula as text:

Molar/atomic mass: 78.1118

Melting point (°C):

Boiling point (°C):

CAS №: 71-43-2

Solubility (g/100 g of solvent):

Numerical data:

Density:

Synthesis 1:

18,6 gr of aniline is dissolved in a mixture of 60 ml of concentrated hydrochloric acid and 100 ml of water in porcelain beaker, equiped with a stirrer, a dropping funnel and a thermometer. The mixture is cooled on an ice bath until 0 C (small pieces of ice are placed into the beaker if necessary). 14,4 gr of sodium nitrite in 60 ml of water is added slowly from the dropping funnel to the cooled mixture of aniline hydrochloride. After addition of all sodium nitrite the mixture should give the reaction on potassium iodide starch test paper and have the acidic reaction on indicator paper. the solution, which was obtained by mixing 54 gr of SnCl2*2H2O in 60 ml of water and 70 gr of sodium hydroxide in 140 ml of water, is added to the diazosolution with caution and cooling. The rate of addition of this mixture depends on the intensity of releasing of nitrogen. Then the contents of the beaker is placed into a round-bottom flask and formed benzene is distilled with water steam. Water is separated in a separation funnel, benzene is dried with fused calcium chloride and distilled from a Wurtz flask.

The yield is 4,2 gr (27% from theory).

Benzene is a colourless liquid with boiling point at 80 C, d(20/4)=0,8790, n(20 C, D-line)=1,50165

UV-spectrum [λmax (lg e) ]: 184 nm (4,78) (in n-heptane). Spectrum NMR (in CCl4): singlet 7,24 ppm

Synthesis 2:

The yield is 12-14 gr.

Reactions of synthesis:

1. Yeild 80%. [Ref.1]
   3C₂H₂ → C₆H₆
   
2. Yeild 93%. [Ref.1]
   C₆H₅Br + 2NH₄Cl + Zn → C₆H₆ + ZnCl₂ + NH₄Br + NH₃
   

Reactions:

1. Yeild 80-95%. [Ref.1]
   C₆H₆ + NO₂BF₄ → C₆H₅NO₂ + HBF₄
   
2. Yeild 80%. [Ref.1]
   C₆H₆ + (CH₃)₂CHOH → (CH₃)₂CHC₆H₅ + H₂O
   
3. Yeild 70-80%. [Ref.1, Ref.2, Ref.3]
   
   
4. Yeild 48-53%. [Ref.1, Ref.2, Ref.3]
   C₆H₆ + Br₂ → C₆H₅Br + HBr
   
5. Yeild 32%. [Ref.1]
   C₆H₆ + CH₂=CHCH₂Cl → C₆H₅CH₂CHClCH₃
   
6. Yeild 50%. [Ref.1]
   C₆H₆ + C₂H₅Cl → C₆H₅C₂H₅ + HCl
   
7. [Ref.1]
   C₆H₅CH=CH₂ + C₆H₆ → (C₆H₅)₂CHCH₃
   
8. [Ref.1, Ref.2]
   C₆H₆ + CH₃CH=CH₂ → C₆H₅CH(CH₃)₂
   

Refractive index (n_D):

Vapour pressure (Torr):

Dissociation:

Retention indices for gas chromatography:

Permittivity (dielectric constant):

Surface tension (mN/m):

Speed sound (m/s):

Standard molar enthalpy (heat) of formation Δ_fH⁰ (298.15 K, kJ/mol):

Standard molar entropy S⁰ (298.15 K, J/(mol·K)):

Molar heat capacity at constant pressure C_p (298.15 K, J/(mol·K)):

Molar enthalpy (heat) of fusion Δ_fusH (kJ/mol):

Enthalpy (heat) of vaporization Δ_vapH (kJ/mol):

Flash point (°C):

Autoignition temperature (°C):

Heat of combustion (kJ/mol):

Gas phase basicity Δ_baseG (298 K, kJ/mol)

Enthalpy (heat) of solution Δ_solH (J/mol)

LD₅₀ (mg/kg):

Critical temperature (°C):

Critical pressure (MPa):

Critical density (g/cm³):

References:

1. Lewis R.J. Sax's Dangerous Properties of Industrial Materials. - 11ed. - Wiley-interscience, 2004. - pp. 360-361
   
2. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941. - pp. 368-370
   
3. Smallwood I.M. Handbook of organic solvent properties. - 1996. - pp. 35-37
   
4. Yalkowsky S.H., Yan H. Handbook of aqueous solubility data. - CRC Press, 2003. - pp. 238-242
   
5. Воскресенский П.И., Каверина А.А., Парменов К.Я., Цветков Л.А., Эпштейн Д.А. Справочник по химии. - 4 изд. - М.: Просвещение, 1978. - pp. 200 [Russian]
   
6. Вредные вещества в промышленности: Справочник для химиков, инженеров и врачей. - 7-е изд., Т.1. - Л.: Химия, 1976. - pp. 88-97 [Russian]
   
7. Вредные химические вещества: Углеводороды, галогенпроизводные углеводородов. Справочник. - Л.: Химия, 1990. - pp. 115-140 [Russian]
   
8. Гордон А., Форд Р. Спутник химика. - М.: Мир, 1976. - pp. 186, 462 [Russian]
   
9. Гурвич Я.А. Справочник молодого аппаратчика-химика. - М.: Химия, 1991. - pp. 229 [Russian]
   
10. Некрасов Б.В. Основы общей химии. - Т.1. - М.: Химия, 1973. - pp. 550-551 [Russian]
    
11. Новый справочник химика и технолога. Общие сведения. Строение вещества. Физические свойства важнейших веществ. Ароматические соединения. Химия фотографических процессов. Номенклатура органических соединений. Техника лабораторных работ. Основы технологии. Интеллектуальная собственность. - СПб.: НПО Профессионал, 2006. - pp. 557-605 [Russian]
    
12. Огородников С.К., Лестева Т.М., Коган В.Б. Азеотропные смеси: Справочник. - Л.: Химия, 1971. - pp. 282 [Russian]
    
13. Промышленные хлорорганические продукты: Справочник. - М.: Химия, 1978. - pp. 620-622 [Russian]
    
14. Рабинович В.А., Хавин З.Я. Краткий химический справочник. - Л.: Химия, 1977. - pp. 129 [Russian]
    
15. Справочник по растворимости. - Т.1, Кн.1. - М.-Л.: ИАН СССР, 1961. - pp. 432-433 [Russian]
    
16. Справочник по растворимости. - Т.1, Кн.2. - М.-Л.: ИАН СССР, 1962. - pp. 1111, 1263 [Russian]
    
17. Справочник химика. - 2 изд., Т.1. - Л.-М.: Химия, 1966. - pp. 553 [Russian]
    
18. Справочник химика. - Т. 3. - М.-Л.: Химия, 1965. - pp. 634 [Russian]
    
19. Химическая энциклопедия. - Т. 1. - М.: Советская энциклопедия, 1988. - pp. 268-269 [Russian]
    
20. Химия и жизнь. - 1990. - №5. - pp. 82 [Russian]
    
21. Энциклопедия для детей. - Т.17: Химия. - М.: Аванта+, 2004. - pp. 376, 380-381 [Russian]
    
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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru