Synthesis of amyl nitrite

Preparation of amyl nitrite

Preparation of amyl nitrite

Preparation of amyl nitrite

A 1-liter three-necked flask is fitted with a mechanical stirrer, a separatory funnel with a stem extending to the bottom of the flask, and a thermometer. The flask is cooled in a mixture of ice and salt and a solution of 95 grams of sodium nitrite in 375 ml of water is placed. When the temperature has fallen to 0° C slowly from the separatory funnel a mixture of 25 ml of water, 34 ml (62.5 g) of concentrated sulfuric acid and 135 ml (110 g) of n-amyl alcohol are added, which has previously been cooled to 0° C. The addition takes 45-60 minutes and the rate of addition must be controlled so that the temperature is maintained at ± 1° C . When the sulfuric acid and n-amyl alcohol have been added the mixture is left to stand for 1.5 hours and filtered from the precipitated sodium sulfate. The upper yellow n-amyl nitrite layer is separated, washed with a solution containing 1 grams of sodium bicarbonate and 12.5 g of sodium chloride in 50 ml of water, and dried with anhydrous magnesium sulfate. The resulting crude n-amyl nitrite (107 g) is satisfactory for many purposes. Upon distillation, it passes over largely at 104° C with negligible decomposition. The boiling point under reduced pressure is 29°/40 mm. n-Amyl and other alkyl nitrites decompose slowly upon standing and should be kept in a cool place. They must be used within a few days or, at most within two weeks of their preparation. The decomposition products include water, oxides of nitrogen, the alcohol and polymerisation products of the aldehyde.

A text book of practical organic chemistry, by A. I. Vogel, 306, 1974

By another method to the round bottom flask cooled with ice-water 50 g of amyl alcohol and 300 g of cold 20% sulfuric acid are placed. From the funnel, 60 g of sodium nitrite in small portions with constant stirring are added.  During the formation of amyl nitrite, addition each fresh portion of sodium nitrite must be stopped until the reaction from the previous addition is ended and the yellowish-red vapors have disappeared from the flask. About 30 minutes is required for this operation, meanwhile, the reaction is complete after waiting an hour longer. The amyl nitrite is separated in a separatory funnel, washed twice with water without shaking and dried by standing overnight with lumps of fused calcium chloride. Amyl nitrite is very gently distilled yielding 60 grams of final product with boiling point 97° C.

Laboratory methods of inorganic chemistry by H. Biltz, 209, 1928

An alternative method of preparation consist of a concentrated aqueous solution of 35 g of sodium nitrite is treated with 44 g of amyl alcohol, and the mixture cooled to 0° C. With efficient stirring and cooling 43 ml of hydrochloric acid (d=1.19) are added, the temperature being maintained at 0° C. The oil is then separated, washed, dried and distilled, amyl nitrite passing over at 94-98° C yielding 53 g of final product.

Organic medical chemicals, by M. Barrowliff, 225, 1921

IUPAC Name

pentyl nitrite

InChI

InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3

InChI Key

CSDTZUBPSYWZDX-UHFFFAOYSA-N

Canonical SMILES

CCCCCON=O

MeSH Synonyms

Amyl Nitrite, Nitrite, Amyl

Depositor-Supplied Synonyms

Pentyl nitrite, Amyl nitrite, n-Amyl nitrite, 463-04-7, n-Pentyl nitrite, Nitrous acid, pentyl ester, Pentyl alcohol, nitrite, CCRIS 763, CHEBI:55344, CSDTZUBPSYWZDX-UHFFFAOYSA-N, EINECS 207-332-7, BRN 1701241, AI3-25184, Pentylnitrite, AmylNitrite, n-pentylnitrite, ACMC-1ACPW, nitrous acid pentyl ester, DSSTox_CID_4522, UN 1113 (Related), AC1L1UC5, 3-methyl-1-nitrosooxybutane, DSSTox_RID_77442, DSSTox_GSID_24522, SCHEMBL34065, KSC492M8F, CHEMBL3188202, CTK3J2682, Pentyl alcohol nitrite(ambiguous), MolPort-001-783-773, poppers (colloquial, street slang), Tox21_202898, ANW-30428, STL268844, ZINC20230701, Nitrous acid, pentyl ester(ambiguous), AKOS015853631, DB01612, LS-1274, MCULE-8065075083, RP19275, RTX-010823, NCGC00260444-01, AN-45098, CAS-463-04-7, CJ-16578, KB-59504, SC-25603, A0455, FT-0622367, A19477, 54273-EP2298767A1, 54273-EP2301918A1, 54273-EP2308562A2, 4-01-00-01644 (Beilstein Handbook Reference), A802198, I14-16514, 3B3-052145

Removed Synonyms

Nitramyl, 1-Nitropentane, Nitrite, Amyl, ISOAMYL NITRITE, CID10026, D000680, 110-46-3, 8017-89-8

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