Synthesis of phenylhydrazine

Preparation of phenylhydrazine

Preparation of phenylhydrazine

Preparation of phenylhydrazine

10 g. freshly distilled aniline are added to a solution of 30 g. conc. hydrochloric acid in 75 ml water and diazotized with 8 g. sodium nitrite in 30 ml water, the temperature being kept about 0 ° C 30 g. common salt are added with shaking, and the solution cooled in a freezing mixture. 60 g. stannous chloride in 25 g. conc. hydrochloric acid are then added, and after standing for some hours the hydrochloride of phenylhydrazine separates, is filtered off and washed with a little saturated salt solution. It is transferred to a flask and treated with excess of caustic sodium carbonate solution, when the free base is extracted several times with ether. The ethereal solution is dried with potassium hydroxide, and the ether removed by evaporation. The phenylhydrazine may be purified, if desired, by freezing or by distilling in vacuo. Yield 90% theoretical (10 g.).

By the second method 10 g. aniline are dissolved in hydrochloric acid and water and diazotised as before. The diazonium solution is poured into a saturated solution of sodium sulfite containing 34 g. sodium sulfite. The liquid is now heated with zinc dust and a little acetic acid till it becomes colorless, when it is filtered hot. Sodium phenylhydrazine sulfonate passes into the filtrate, and is immediately mixed with one-third of its volume of fuming hydrochloric acid which converts it into phenylhydrazine hydrochloride, which is thrown out of solution, filtered, and well pressed. The free base is liberated as before. Yeld 75% theoretical (8 g.). Colourless crystals; m.p. 23° C; b.p. 243.5 °C (dec.) ; b.p. 120 °C/12mmHg ; soluble in alcohol, ether, benzene.

Systematic organic chemistry, by W. M. Cumming, 370-371, 1937.

IUPAC Name

phenylhydrazine;hydrochloride

InChI

InChI=1S/C6H8N2.ClH/c7-8-6-4-2-1-3-5-6;/h1-5,8H,7H2;1H

InChI Key

JOVOSQBPPZZESK-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)NN.Cl

MeSH Synonyms

phenylhydrazide, phenylhydrazine, phenylhydrazine hydrochloride, phenylhydrazine monohydrochloride, phenylhydrazine monosulfate

Depositor-Supplied Synonyms

PHENYLHYDRAZINE HYDROCHLORIDE, 59-88-1, Phenylhydrazinium chloride, Phenylhydrazine-HCl, Phenylhydrazine monohydrochloride, Phenylhydrazine.HCl, PHENYLHYDRAZINE HCL, MFCD00012924, Hydrazine, phenyl-, monohydrochloride, Phenylhydrazine hydrochlorid, CCRIS 5707, Hydrazine, phenyl-, hydrochloride, NSC 5710, Phenylhydrazine hydrochloride (VAN), EINECS 200-444-7, Phenylhydrazin hydrochlorid [German], Hydrazine, phenyl-, hydrochloride (1:1), AI3-17266, ST51037414, DSSTox_CID_1148, DSSTox_RID_75976, DSSTox_GSID_21148, phenylhydrazine, chloride, 100-63-0 (Parent), 1-phenylhydrazine hydrochloride, CAS-59-88-1, NCGC00159378-02, NCGC00159378-04, phenyl hydrazine HCl, phenyl-hydrazine HCl, PubChem22925, AC1Q3DGQ, UNII-H7QFK49SVD, phenyldiazane hydrochloride, Phenylhydrazin hydrochlorid, H7QFK49SVD, Phenylhydrazine.cntdot.HCl, phenylhydrazinehydrochloride, WLN: ZMR &GH, AC1L1U8R, phenyl hydrazine hydrochloride, P6926_SIGMA, SCHEMBL304025, N-phenylhydrazine hydrochloride, 114715_ALDRICH, CHEMBL3182475, DTXSID3021148, 78690_FLUKA, CTK3J0749, NSC5710, JOVOSQBPPZZESK-UHFFFAOYSA-N, NSC-5710, EINECS 248-259-0, Tox21_111618, Tox21_202198, Tox21_302936, ANW-75214, AKOS015890451, Tox21_111618_1, CS15210, LS-7656, RP20965, TRA0048753, TRA0173743, NCGC00256328-01, NCGC00259747-01, AK-72992, BR-72992, KB-59583, OR039385, AB0010984, ST2413667, FT-0657380, P0184, M-6035, A800248, I01-6579, J-610042, F1908-0075, 27140-08-5

Removed Synonyms

PHENYLHYDRAZINE, Hydrazine, monohydrochloride, HYDRAZINE, HYDROCHLORIDE, Cyclohexylhydrazine hydrochloride, MolPort-003-925-976, CID60962, RTC-072452, 100-63-0

IUPAC Name

phenylhydrazine

InChI

InChI=1S/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2

InChI Key

HKOOXMFOFWEVGF-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)NN

MeSH Synonyms

phenylhydrazide, phenylhydrazine, phenylhydrazine hydrochloride, phenylhydrazine monohydrochloride, phenylhydrazine monosulfate

Depositor-Supplied Synonyms

PHENYLHYDRAZINE, Hydrazinobenzene, 100-63-0, Hydrazine, phenyl-, 1-Phenylhydrazine, Monophenylhydrazine, Phenylhydrazin, Hydrazine-benzene, Fenilidrazina, Fenylhydrazine, Phenyldiazane, phenyl hydrazine, phenyl-hydrazine, CHEBI:27924, Fenylhydrazine [Dutch], Fenilidrazina [Italian], Phenylhydrazin [German], Phenylhydrazine and its salts, CCRIS 511, UNII-064F424C9K, HSDB 1117, HKOOXMFOFWEVGF-UHFFFAOYSA-N, EINECS 202-873-5, UN2572, BRN 0606080, AI3-15399, DSSTox_CID_1147, DSSTox_RID_75975, DSSTox_GSID_21147, 1-phenylhydrazine hydrochloride, CAS-100-63-0, PHZ, NCGC00159378-02, NCGC00159378-04, aminoaniline, N-phenylhydrazine, 2-phenylhydrazine, HYDRAZINE,PHENYL, AC1L1OXS, ACMC-2097re, SCHEMBL7099, P26252_ALDRICH, KSC174S7D, BIDD:ER0251, SCHEMBL491697, CHEMBL456807, 2545-79-1 (monosulfate), DTXSID8021147, 78670_FLUKA, 78672_FLUKA, CTK0H4971, 59-88-1 (mono-hydrochloride), 27140-08-5 (hydrochloride), BB_SC-6741, ZINC388099, AC1Q5536, Tox21_201977, Tox21_303018, ANW-14328, BBL011601, BDBM50444455, MFCD00007573, SBB040886, STL163333, ZINC00388099, Phenylhydrazine [UN2572] [Poison], AKOS000268993, 064F424C9K, LS-7655, MCULE-1663221893, Phenylhydrazine [UN2572] [Poison], RP18905, TRA0076845, UN 2572, NCGC00159378-03, NCGC00159378-05, NCGC00159378-06, NCGC00256354-01, NCGC00259526-01, PHENYL-D5-HYDRAZINE HYDROCHLORIDE, AJ-20430, AK-48492, AN-23624, AN-24558, BP-13438, CJ-03116, OR000319, OR192768, OR210895, S662, ZB011287, AB0018724, KB-160362, ST2407522, TC-064096, FT-0645290, P0183, ST50214481, A23856, C02304, 67098-EP2269989A1, 67098-EP2284172A1, 67098-EP2289876A1, 67098-EP2292597A1, 67098-EP2295406A1, 67098-EP2308839A1, 4-15-00-00050 (Beilstein Handbook Reference), I01-1976, F2121-0389, InChI=1/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H, 1057722-40-3

Removed Synonyms

Hydrazobenzene, phenylhydrazide, Lead(II) iodide, phenylhydrazine monosulfate, Hydrazine, 1,2-diphenyl-, PHENYLHYDRAZINE HYDROCHLORIDE, C6H8N2, Phenylhydrazine monohydrochloride, CID7516, MolPort-000-872-047, RTC-064096, C1523, C030299, 59-88-1, 10101-63-0

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *