Synthesis of isoamyl nitrite

Preparation of isoamyl nitrite (isopentyl nitrite; 3-methylbutyl nitrite; amilnitrite; vaporole)

Preparation of isoamyl nitrite (isopentyl nitrite; 3-methylbutyl nitrite; amilnitrite; vaporole)

Preparation of isoamyl nitrite (isopentyl nitrite; 3-methylbutyl nitrite; amilnitrite; vaporole)

In a 5-liter beaker, 1200 ml (972 g) of isoamyl alcohol are placed and 1000 g of pure sodium nitrite are added. The mixture is cooled to 10° C and while stirring 325 ml of concentrated sulfuric acid are dropwise added very slowly. During this procedure, the nitrite should be kept from settling to the bottom, a process which is easily accomplished by having the stirring so vigorous that a clear layer of alcohol is never visible above the nitrite. During this addition of sulfuric acid, the temperature is an important consideration and should be kept below 25° C. After all of the sulfuric acid has been added (30-60 minutes), the stirring is continued and water gradually added. The obtained solution is poured in a large separatory funnel where isoamyl nitrite rises to the surface. More water is then added to the salt mixture, stirred, allowed to settle, and the nitrite again poured off together with most of the water. The extraction is continued until no more isoamyl nitrite rises to the surface. It is not necessary to dissolve all of the salt but the small lumps must be broken up and the remaining salt should be perfectly white. The yield of crude material amounts to 1300-1350 ml. The isoamyl nitrite is washed once with clean water to remove any acid, dried for a few minutes over calcium chloride and distilled. The fraction which boils from 92-100° C is collected yielding  1250-1300 ml or 1100-1145 g of isoamyl nitrite.

Organic Chemical Reagents, by A. Roger, 49-51, 1919

IUPAC Name

3-methylbutyl nitrite

InChI

InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3

InChI Key

OWFXIOWLTKNBAP-UHFFFAOYSA-N

Canonical SMILES

CC(C)CCON=O

MeSH Synonyms

isoamyl nitrite, isopentyl nitrite

Depositor-Supplied Synonyms

ISOAMYL NITRITE, Isopentyl nitrite, 3-Methylbutyl nitrite, Amilnitrite, Vaporole, 110-46-3, Aspiral, 3-Methylbutanol nitrite, Nitrous acid, 3-methylbutyl ester, Pentanoli nitris, Amyl nitrite I, Nitrous acid, isopentyl ester, Isopentyl alcohol, nitrite, Nitramyl (VAN), Amyl nitrite (VAN), Isoamylnitrite, Amyl nitrosum, Amyl nitrit, Vaporole (TN), Aspiral (TN), Amyl nitrite [USAN], NSC 7903, UNII-5N0U5TUC9Z, CCRIS 1098, CHEBI:2691, HSDB 606, OWFXIOWLTKNBAP-UHFFFAOYSA-N, NCI-C50179, EINECS 203-770-8, BRN 0969510, NCGC00091066-01, AI3-25183, DSSTox_CID_2605, DSSTox_RID_77794, DSSTox_GSID_25455, CAS-110-46-3, Amilnitrit, isoamyInitrite, iso-amylnitrite, isopentylnitrite, iso-pentylnitrite, iso-amyl nitrite, iso-pentyl nitrite, Vaporole amyl nitrite, (3-methylbutyl) nitrite, AC1Q1PHI, Nitrite Isopentyl alcohol, WLN: ONO2Y, AC1L1Q5O, amyl nitrite(mixed isomers), isopentyl ester Nitrous acid, 5N0U5TUC9Z, SCHEMBL23785, Amyl nitrite (JP15/USP), Amyl nitrite (JP16/USP), 3-methyl-1-nitrosooxy-butane, KSC176S6L, C5H11NO3, CHEMBL1535371, CTK0H6965, HMDB01382, Nitrous acid 3-methylbutyl ester, NSC7903, 150495_SIAL, ACMC-209966, ACN-S002434, ACT05198, EBD32335, NSC-7903, Tox21_111074, Tox21_200983, ANW-16156, LS-505, STL264239, ZINC03830220, AKOS009157290, MCULE-5177168468, RP19274, RTR-002157, TRA0169455, Isopentyl nitrite; 3-Methylbutyl nitrite, NCGC00091066-02, NCGC00258536-01, AN-22608, CJ-10786, KB-52714, DB-002757, TR-002157, FT-0627442, I0089, X8940, C07457, D00517, 86685-EP2269993A1, 86685-EP2270006A1, 86685-EP2275404A1, 86685-EP2292622A1, 86685-EP2295411A1, 86685-EP2298312A1, 86685-EP2301918A1, 86685-EP2305640A2, 86685-EP2305675A1, 86685-EP2305684A1, I04-0217, UNII-22T8Z09XAK component OWFXIOWLTKNBAP-UHFFFAOYSA-N, InChI=1/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H

Removed Synonyms

Nitramyl, Amyl nitrite, Pentyl nitrite, Amyl nitrate, ”Amyl nitrite”, mixed isomers, CID8053, 4-01-00-01683 (Beilstein Handbook Reference), IPN

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