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Properties of substance:

isoamyl nitrite

Synonyms:

isopentyl nitrite

Group of substances:

organic

Physical appearance:

yellowish liquid

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

C5H11NO2

Structural formula as text:

(CH3)2CHCH2CH2ONO

Molar/atomic mass: 117.146

Boiling point (°C):

99.2

Solubility (g/100 g of solvent):

benzene: miscible [Ref.]
chloroform: miscible [Ref.]
diethyl ether: miscible [Ref.]
ethanol: miscible [Ref.]
water: very slightly soluble [Ref.]

Density:

0.87 (20°C, g/cm3)

Synthesis 1:

Reference: Голодников Г.В. Практические работы по органическому синтезу. - Л.: ИЛУ, 1966 pp. 85

4,4 gramms of isoamyl alcohol, 3,7 gramms of sodium nitrite and 7 ml. of water is placed into a beaker or a broad-mouth flask. The mixture is cooled until 0 degrees Celsius with mechanical stirring. A thermometre is placed in the mixture, 4,4 ml of concentrated hydrochloric acid (d. 1,19) is added to the mixture from a dropping funnel, the temperature shouldn't rise above +5 degrees Celsius (excess of hydrochloric acid should be avoided). The reaction mixture is then placed into a separatory funnel; the flask is washed several times with 20 ml. of water, which is also poured into the funnel (the work should be done with caution, because isoamyl nitrite is very toxic). Then the mixture is shaked and given time to settle, the water layer is separated and the ester is washed with dilute solution of sodium bicarbonate and water until the neutral reaction of washing solution (by kongo).

3-4 granules of fused calcium chloride is added to the wet ester, which is in the separatory funnel. The mixture is shaked until the end of the collection of saturated solution of calcium chloride at the bottom of the funnel, the solution is then separated.

The ester is drained to a small conical flask, left for the night above calcium chloride (2-3 granules) and then distilled under vacuum (50-60 mm Hg). with strong cooling of the receiver. Under this pressure isoamyl nitrite boils at around 30 degrees Celsius. Yellow oil is obtained.

The yield is 4,6 gr. (80% from theory).

Refractive index (nD):

1.38708 (20.7°C)

Vapour pressure (Torr):

60 (30°C)

References:

  1. CRC Handbook of Chemistry and Physics. - 95ed. - CRC Press, 2014. - pp. 3-330
  2. Clarke's isolation and identification of drugs. - 2ed. - London: Pharmaceutical press, 1986. - pp. 353
  3. Беликов В.Г. Учебное пособие по фармацевтической химии. - М.: Медицина, 1979. - pp. 136 [Russian]
  4. Вредные вещества в промышленности: Справочник для химиков, инженеров и врачей. - 7-е изд., Т.3. - Л.: Химия, 1976. - pp. 116 [Russian]
  5. Рабинович В.А., Хавин З.Я. Краткий химический справочник. - Л.: Химия, 1977. - pp. 122 [Russian]
  6. Химический энциклопедический словарь. - Под ред. Кнунянц И.Л. - М.: Советская энциклопедия, 1983. - pp. 33 [Russian]

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru