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133310 Aldrich

Aniline hydrochloride

97%

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Properties

Related Categories Amine Salts, Building Blocks, Chemical Synthesis, Nitrogen Compounds, Organic Building Blocks More...
vapor density   4.46 (vs air)
assay   97%
mp   196-198 °C(lit.)

Description

Biochem/physiol Actions

The acute toxicity of aniline involves its activation in vivo to 4-hydroxyaniline and the formation of adducts with hemoglobin. In erythrocytes, this is associated with the release of iron and the accumulation of methemoglobin and the development of hemolytic anemia and inflammation of the spleen. Tumor formation is often observed in the spleen on prolonged administration.

Application

Aniline hydrochloride was used in the preparation of polyaniline coated poly(styrene-co-styrene sulfonate) nanoparticles1. It was used to study the induction of Nei-like DNA glycosylases (NEIL1/2)-mediated base excision repair(BER) in rat spleen and 8-oxoguanine glycosylase 1-mediated BER due to aniline exposure2.

Other Notes

This product has been replaced by A8524-ALDRICH | Aniline hydrochloride ≥99%

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Safety & Documentation

Safety Information

Signal word 
Danger
RIDADR 
UN 1548 6.1 / PGIII
WGK Germany 
3
RTECS 
CY0875000
Flash Point(F) 
381.2 °F
Flash Point(C) 
194 °C

Protocols & Articles

Peer-Reviewed Papers

References

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1. Preparation of PANI-coated poly (styrene-co-styrene sulfonate) nanoparticles. Kim BJ, et al. Polymer 43(1), 111-116, (2002)

2. Induction of NEIL1 and NEIL2 DNA glycosylases in aniline-induced splenic toxicity. Ma H, Wang J, Abdel-Rahman SZ, et al. Toxicol. Appl. Pharmacol. 251(1), 1-7, (2011)

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Synthesis and application of ionic liquid matrices (ILMs) for effective pathogenic bacteria analysis in matrix assisted laser desorption/ionization (MALDI-MS). Abdelhamid HN, Gopal J, and Wu HF Anal. Chim. Acta 767, 104-11, (2013)

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Gold-catalyzed domino cycloisomerization/Pictet-Spengler reaction of 2-(4-aminobut-1-yn-1-yl)anilines with aldehydes: synthesis of tetrahydropyrido[4,3-b]indole scaffolds. Subba Reddy BV, Swain M, Reddy SM, et al. J. Org. Chem. 77(24), 11355-61, (2012)

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Heterogenized cobalt oxide catalysts for nitroarene reduction by pyrolysis of molecularly defined complexes. Westerhaus FA, Jagadeesh RV, Wienhöfer G, et al. Nature Chemistry 5(6), 537-43, (2013)

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Amperometric detection of dopamine in human serum by electrochemical sensor based on gold nanoparticles doped molecularly imprinted polymers. Xue C, Han Q, Wang Y, et al. Biosens. Bioelectron. 49, 199-203, (2013)

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Copper-catalyzed C-H azidation of anilines under mild conditions. Tang C and Jiao N J. Am. Chem. Soc. 134(46), 18924-7, (2012)

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A highly electron-deficient analogue of aniline, soluble oligomers, and their redox properties. Djukic B, Lough AJ, and Seferos DS J. Org. Chem. 78(18), 9340-4, (2013)

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A novel magnetic poly(aniline-naphthylamine)-based nanocomposite for micro solid phase extraction of rhodamine B. Bagheri H, Daliri R, and Roostaie A Anal. Chim. Acta 794, 38-46, (2013)

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C(sp3)-F bond activation of CF3-substituted anilines with catalytically generated silicon cations: spectroscopic evidence for a hydride-bridged Ru-S dimer in the catalytic cycle. Stahl T, Klare HF, and Oestreich M J. Am. Chem. Soc. 135(4), 1248-51, (2013)

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Organocatalytic asymmetric multicomponent reactions of aromatic aldehydes and anilines with β-ketoesters: facile and atom-economical access to chiral tetrahydropyridines. Li X, Zhao Y, Qu H, et al. Chem. Commun. (Camb.) 49(14), 1401-3, (2013)

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Synthesis of phenanthridinones via palladium-catalyzed C(sp2)-H aminocarbonylation of unprotected o-arylanilines. Liang D, Hu Z, Peng J, et al. Chem. Commun. (Camb.) 49(2), 173-5, (2013)

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Regioselective radical arylation of anilines with arylhydrazines. Jasch H, Scheumann J, and Heinrich MR J. Org. Chem. 77(23), 10699-706, (2012)

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Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of isoindolines. Zhou PX, Luo JY, Zhao LB, et al. Chem. Commun. (Camb.) 49(31), 3254-6, (2013)

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One-pot synthesis of (3-sulfopropyl methacrylate potassium)-silica hybrid monolith via thiol-ene click chemistry for CEC. Yang H, Chen Y, Liu Y, et al. Electrophoresis 34(4), 510-7, (2013)

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Palladium-catalyzed insertion of α-diazocarbonyl compounds for the synthesis of cyclic amino esters. Zhou PX, Zhou ZZ, Chen ZS, et al. Chem. Commun. (Camb.) 49(6), 561-3, (2013)

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One-pot ring-closing metathesis/1,3-dipolar cycloaddition through assisted tandem ruthenium catalysis: synthesis of a dye with isoindolo[2,1-a]quinoline structure. Arisawa M, Fujii Y, Kato H, et al. Angew. Chem. Int. Ed. Engl. 52(3), 1003-7, (2013)

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A highly enantioselective four-component reaction for the efficient construction of chiral β-hydroxy-α-amino acid derivatives. Qian Y, Jing C, Liu S, et al. Chem. Commun. (Camb.) 49(26), 2700-2, (2013)

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Precise sequence control in linear and cyclic copolymers of 2,5-bis(2-thienyl)pyrrole and aniline by DNA-programmed assembly. Chen W and Schuster GB J. Am. Chem. Soc. 135(11), 4438-49, (2013)

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Ultrafast dynamics of aniline following 269-238 nm excitation and the role of the S2(pi3s/pi sigma) state. Spesyvtsev R, Kirkby OM, and Fielding HH Faraday Discuss. 157, 165-79; discussion 243-84, (2012)

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Ionic matrices pre-spotted matrix-assisted laser desorption/ionization plates for patient maker following in course of treatment, drug titration, and MALDI mass spectrometry imaging. Bonnel D, Franck J, Mériaux C, et al. Anal. Biochem. 434(1), 187-98, (2013)

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Synthesis of N(4)-(substituted phenyl)-N(4)-alkyl/desalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines and identification of new microtubule disrupting compounds that are effective against multidrug resistant cells. Gangjee A, Zaware N, Devambatla RK, et al. Bioorg. Med. Chem. 21(4), 891-902, (2013)

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Indoles synthesized from amines via copper catalysis. Besandre R, Jaimes M, and May JA Org. Lett. 15(7), 1666-9, (2013)

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Reduced and oxidized forms of the Pt-organometallic version of polyaniline. Kenny T, Lamare S, Aly SM, et al. Inorg. Chem. 51(24), 13081-95, (2012)

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Organocatalytic multicomponent reaction for the acquisition of a selective inhibitor of mPTPB, a virulence factor of tuberculosis. He R, Zeng LF, He Y, et al. Chem. Commun. (Camb.) 49(20), 2064-6, (2013)

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Chemical oxidation of aniline and N-methylaniline: a kinetic study by Raman spectroscopy. Mažeikienė R, Niaura G, and Malinauskas A Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 106, 34-40, (2013)

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Simulation of the chromatographic separation process in HPLC employing suspended-state NMR spectroscopy - comparison of interaction behavior for monomeric and hydride-modified C18 stationary phases. Yeman H, Nicholson T, Matyska MT, et al. J. Sep. Sci. 36(1), 173-81, (2013)

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Synthesis, growth, crystalline perfection of 4-bromo-4'dimethylamino benzylideneaniline (BDMABA) and photons absorption of BDMABA crystal. Subashini A, Bhagavannarayana G, and Ramamurthi K Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 104, 403-8, (2013)

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Polyamide nanofiltration membranes to remove aniline in aqueous solutions. Hidalgo AM, León G, Gómez M, et al. Environ. Technol. 35(9-12), 1175-81, (2014)

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Design, synthesis, and evaluation of (E)-N-substituted benzylidene-aniline derivatives as tyrosinase inhibitors. Bae SJ, Ha YM, Park YJ, et al. Eur. J. Med. Chem. 57, 383-90, (2012)

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Ugi multicomponent reaction product: the inhibitive effect on DNA oxidation depends upon the isocyanide moiety. Wang R and Liu ZQ J. Org. Chem. 78(17), 8696-704, (2013)

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Novel amphiphilic polymeric ionic liquid-solid phase micro-extraction membrane for the preconcentration of aniline as degradation product of azo dye Orange G under sonication by liquid chromatography-tandem mass spectrometry. Cai MQ, Wei XQ, Du CH, et al. J. Chromatogr. A 1349, 24-9, (2014)

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Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing. Trmčić M, Chadbourne FL, Brear PM, et al. Org. Biomol. Chem. 11(16), 2660-75, (2013)

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Induction of base excision repair enzymes NTH1 and APE1 in rat spleen following aniline exposure. Ma H, Wang J, Abdel-Rahman SZ, et al. Toxicol. Appl. Pharmacol. 267(3), 276-83, (2013)

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Diverse reactivity in microwave-promoted catalyst-free coupling of substituted anilines with ethyl trifluoropyruvate and biological evaluation. Zhang C, Zhuang DM, Li J, et al. Org. Biomol. Chem. 11(34), 5621-33, (2013)

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Function of a glutamine synthetase-like protein in bacterial aniline oxidation via γ-glutamylanilide. Takeo M, Ohara A, Sakae S, et al. J. Bacteriol. 195(19), 4406-14, (2013)

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Removal of aniline and phenol from water using raw and aluminum hydroxide-modified diatomite. Wu CD, Zhang JY, Wang L, et al. Water Sci. Technol. 67(7), 1620-6, (2013)

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Cultivation of aerobic granules in a novel configuration of sequencing batch airlift reactor. Rezaei LS, Ayati B, and Ganjidoust H Environ. Technol. 33(19-21), 2273-80, (2012)

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Application of Fered-Fenton process for m-phenylenediamine degradation. Su CC, Panopio LV, Peralta GL, et al. J. Environ. Sci. Health. A. Tox. Hazard. Subst. Environ. Eng. 48(9), 1012-8, (2013)

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Merck 14,659

Beil. 12,IV,232

Aldrich MSDS 1, 126:A / Corp MSDS 1 (1), 270:B / FT-IR 2 (2), 2024:B / FT-IR 1 (1), 1189:B / FT-NMR 1 (2), 451:B / IR-Spectra (2), 630:B / IR-Spectra (3), 714:B / RegBook 1 (1), 1383:B / Sax 6, 360 / Sigma FT-IR 1 (2), 284:B / Structure Index 1, 214:B:1

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A8524 Aniline hydrochloride, ≥99%

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