Synthesis of 1-nitronaphthalene

Preparation of 1-nitronaphthalene

Preparation of 1-nitronaphthalene

Preparation of 1-nitronaphthalene

128 g of naphthalene are added to a mixture 103 g of 60% nitric acid, and 300 g of 80% sulphuric acid. The reaction mixture is stirred for 6 hours at 50° C, the temperature being finally, increased to 60° C during 1 hour, after which it is cooled down.  The reaction product 1-nitronaphthalene floats upon the surface of the nitric and sulfuric acids in porous cakes, and consists of about 95 % 1-nitronaphthalene, together with some unchanged naphthalene and a very little dinitro derivative. 2-Nitronaphthalene is either absent or present only in traces. The crude product is melted up several times with boiling water by which means the nitric and sulphuric acid is completely removed and the naphthalene carried off by the steam. The melted product is then poured into cold water, which is kept well agitated, the 1-nitronaphthalene separating out in the form of small spheres. To obtain the compound completely pure, it is dried by melting it at 120° C in an air oven. It is then treated with 10% of its weight of ligroin (b.p. about 150° C), or xylene  may be used instead. It is then filtered hot through a smooth filter and allowed to stand in a closed vessel for some time. A crystalline cake is formed which is well pressed out in a cotton cloth. This purification should be repeated until the 1-nitronaphthalene shows a melting-point of 61° C. It is thus obtained in the form of yellow, glistening crystals. A considerable portion of the 1-nitronaphthalene always remains behind in the mother-liquors and may be recovered by distilling off the solvent.

The fundamental processes of dye chemistry, by F. David, 79-80, 1921

IUPAC Name

1-nitronaphthalene

InChI

InChI=1S/C10H7NO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H

InChI Key

RJKGJBPXVHTNJL-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C=CC=C2[N+](=O)[O-]

MeSH Synonyms

1-nitronaphthalene

Depositor-Supplied Synonyms

1-NITRONAPHTHALENE, Nitrol, 86-57-7, Naphthalene, 1-nitro-, Nitrol (pesticide), alpha-Nitronaphthalene, Mononitronaphthalene, Naphthalene, nitro-, NITRONAPHTHALENE, .alpha.-Nitronaphthalene, 1-Nitronaftalen, NCI-C01956, 1-Nitronaphthaline, Nitrol (VAN), Naphthalene, mononitro-, 1-Nitronaftalen [Czech], Naphthalene, alpha-nitro-, UNII-A51NP1DL2T, CCRIS 450, CHEBI:34104, HSDB 2887, RJKGJBPXVHTNJL-UHFFFAOYSA-N, NSC 9584, EINECS 201-684-5, SBB057510, UN2538, BRN 1867714, AI3-00477, DSSTox_CID_978, ST50406229, DSSTox_RID_75901, DSSTox_GSID_20978, 27254-36-0, CAS-86-57-7, 1-nitronapthalene, 1-Nitro-Naphthalene, alpha-nitro-naphthalene, AC1L1NFV, BCR306_FLUKA, WLN: L66J BNW, A51NP1DL2T, ACMC-1CJ12, SCHEMBL57184, KSC204Q5R, 103594_ALDRICH, AC1Q213P, CHEMBL165373, 73500_FLUKA, CTK1A4858, NSC9584, MolPort-001-757-447, NSC-9584, STR03423, ZINC1700069, Tox21_201407, Tox21_302759, AR-1C4895, ZINC01700069, AKOS000120000, LS-1855, MCULE-5592798733, NE10285, RTR-026964, TRA0050251, NCGC00091715-01, NCGC00091715-02, NCGC00091715-03, NCGC00256373-01, NCGC00258958-01, AN-24104, CJ-28674, KB-13024, LS-94800, OR021509, OR112866, OR251329, DB-056938, TR-026964, FT-0608156, N0212, Nitronaphthalene [UN2538] [Flammable solid], A24106, C14040, Nitronaphthalene [UN2538] [Flammable solid], AE-562/40180003, I14-6812, 3B3-029110, 1-Nitro-4-phenylbenzene;4-nitro-1-biphenyl;4-nitro-bipheny, InChI=1/C10H7NO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7

Removed Synonyms

4-Nitrobiphenyl, CID6849, R278, 4-07-00-01638 (Beilstein Handbook Reference), C016614, 92-93-3

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