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242284 Sigma-Aldrich

Aniline

ACS reagent, ≥99.5%

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Properties

grade   ACS reagent
vapor density   3.22 (185 °C, vs air)
vapor pressure   0.7 mmHg ( 25 °C)
assay   ≥99.5%
autoignition temp.   1139 °F
expl. lim.   11 %
impurities   Hydrocarbons, passes test
  Nitrobenzene, passes test (lim. ~0.001%)
  ≤0.01% chlorobenzene
ign. residue   ≤0.005%
color   APHA: ≤250
refractive index   n20/D 1.586(lit.)
bp   184 °C(lit.)
mp   −6 °C(lit.)
density   1.022 g/mL at 25 °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.

Packaging

5, 100, 4×100, 500 mL in glass bottle

Physical properties

Material darkens in storage to reddish-brown with no loss in purity.

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Safety & Documentation

Safety Information

Signal word 
Danger
Precautionary statements 
Target organs 
Blood
RIDADR 
UN 1547 6.1 / PGII
WGK Germany 
3
RTECS 
BW6650000
Flash Point(F) 
158 °F
Flash Point(C) 
70 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Determination of Water Content in Aniline Using Karl Fischer Titration

Nitrogen compounds, acid amides and weakly basic amines (heterocyclenes) give no problems. They can be titrated according to the standard procedures. Strongly basic amines alter the pH value and must...
Keywords: Pharmaceutical, Solvents, Titrations

Determination of Water Content in Aniline Using Karl Fischer Titration

Nitrogen compounds, acid amides and weakly basic amines (heterocyclenes) give no problems. They can be titrated according to the standard procedures. Strongly basic amines alter the pH value and must...
Keywords: Pharmaceutical, Solvents, Titrations

Peer-Reviewed Papers

References

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Biomonitoring of aromatic amines VI: determination of hemoglobin adducts after feeding aniline hydrochloride in the diet of rats for 4 weeks. Zwirner-Baier, I., et al. Arch. Toxicol. 77, 672-67, (2003)

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Hemolytic drugs aniline and dapsone induce iron release in erythrocytes and increase the free iron pool in spleen and liver. Ciccoli, L., et al. Toxicol. Lett. 110, 57-66, (1999)

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Differential 12C-/13C-isotope dansylation labeling and fast liquid chromatography/mass spectrometry for absolute and relative quantification of the metabolome. Guo K and Li L Anal. Chem. 81(10), 3919-32, (2009)

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Variation in enzymes of arylamine procarcinogen biotransformation among bladder cancer patients and control subjects. Vaziri SA, Hughes NC, Sampson H, et al. Pharmacogenetics 11(1), 7-20, (2001)

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QSAR study on permeability of hydrophobic compounds with artificial membranes. Masaaki Fujikawa et al Bioorg. Med. Chem. 15, 3756-67, (2007)

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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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[Aniline modification of the mutagenic activity of cyclophosphamide in a chronic experiment on mice]. Litvinov NN, Sokolovskiĭ VV, and Zhurkov VS Gig. Sanit. (8), 16-8, (1983)

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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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White blood cell DNA adducts and fruit and vegetable consumption in bladder cancer. Peluso M, Airoldi L, Magagnotti C, et al. Carcinogenesis 21(2), 183-7, (2000)

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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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Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Lourdes Santana et al J. Med. Chem. 51, 6740-51, (2008)

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Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk). Giulia Caron et al J. Med. Chem. 48, 3269-79, (2005)

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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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Perspectives on the mechanism of action of the splenic toxicity of aniline and structurally-related compounds. Bus JS and Popp JA Food Chem. Toxicol. 25(8), 619-26, (1987)

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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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Under the skin: Biotransformation of para-aminophenol and para-phenylenediamine in reconstructed human epidermis and human hepatocytes. Nohynek GJ, Duche D, Garrigues A, et al. Toxicol. Lett. 158(3), 196-212, (2005)

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Genotoxic activities of aniline and its metabolites and their relationship to the carcinogenicity of aniline in the spleen of rats. Bomhard EM and Herbold BA Crit. Rev. Toxicol. 35(10), 783-835, (2005)

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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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Simultaneous determination of various aromatic amines and metabolites of aromatic nitro compounds in urine for low level exposure using gas chromatography-mass spectrometry. Weiss T and Angerer J J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 778(1-2), 179-92, (2002)

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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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Identification and quantitative determination of aniline and toluidines in human urine. el-Bayoumy K, Donahue JM, Hecht SS, et al. Cancer Res. 46(12 Pt 1), 6064-7, (1986)

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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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Evaluation of 4-aminobiphenyl-DNA adducts in human breast cancer: the influence of tobacco smoke. Faraglia B, Chen SY, Gammon MD, et al. Carcinogenesis 24(4), 719-25, (2003)

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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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Alkylaniline-hemoglobin adducts and risk of non-smoking-related bladder cancer. Gan J, Skipper PL, Gago-Dominguez M, et al. J. Natl. Cancer Inst. 96(19), 1425-31, (2004)

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Interactions of aniline with soil and groundwater at an industrial spill site. Kosson DS and Byrne SV Environ. Health Perspect. 103 Suppl 5, 71-3, (1995)

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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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Quercetin glucuronides inhibited 2-aminofluorene acetylation in human acute myeloid HL-60 leukemia cells. Kuo HM, Ho HJ, Chao PD, et al. Phytomedicine 9(7), 625-31, (2002)

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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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Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity. Joanna Romanowska et al J. Med. Chem. 54, 6482-91, (2011)

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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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Prostate expression of N-acetyltransferase 1 (NAT1) and 2 (NAT2) in rapid and slow acetylator congenic Syrian hamster. Hein DW, Doll MA, Xiao GH, et al. Pharmacogenetics 13(3), 159-67, (2003)

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Pyrrole versus quinoline formation in the palladium catalyzed reaction of 2-alkynyl-3-bromothiophenes and 2-alkynyl-3-bromofurans with anilines. A combined experimental and computational study. Salman GA, Nisa RU, Iaroshenko VO, et al. Org. Biomol. Chem. 10(47), 9464-73, (2012)

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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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Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins. Alfonso Pérez-Garrido et al Bioorg. Med. Chem. 17, 896-904, (2009)

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Acute intoxication with aniline: detection of acetaminophen as aniline metabolite. Iwersen-Bergmann S and Schmoldt A Int. J. Legal Med. 113(3), 171-4, (2000)

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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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Aniline--a 'historical' contact allergen? Current data from the IVDK and review of the literature. Uter W, Stropp G, Schnuch A, et al. Ann. Occup. Hyg. 51(2), 219-26, (2007)

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QSAR study and synthesis of new phenyltropanes as ligands of the dopamine transporter (DAT). Sylvie Mavel et al Bioorg. Med. Chem. 20, 1388-95, (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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Absorption, metabolism, and disposition of 1,3-diphenyl-1-triazene in rats and mice after oral, i.v., and dermal administration. Mathews JM and De Costa KS Drug Metab. Dispos. 27(12), 1499-504, (1999)

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Immunochemical detection of arylamine N-acetyltransferase in normal and neoplastic bladder. Stanley LA, Coroneos E, Cuff R, et al. J. Histochem. Cytochem. 44(9), 1059-67, (1996)

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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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High-Density Real-Time PCR-Based in vivo Toxicogenomic Screen to Predict Organ-Specific Toxicity. Gabriella Fabian et al Int. J. Mol. Sci. 12, 6116-34, (2011)

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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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The many roles for fluorine in medicinal chemistry. William K Hagmann et al J. Med. Chem. 51, 4359-69, (2008)

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Merck 14,659

Beil. 12,IV,223

Fieser 6,21

Aldrich MSDS 1, 125:D / Corp MSDS 1 (1), 270:A / FT-IR 1 (1), 1189:A / FT-IR 2 (2), 2024:A / FT-NMR 1 (2), 451:A / IR-Spectra (2), 630:A / IR-Spectra (3), 714:A / NMR-Reference 2 (1), 987:A / RegBook 1 (1), 1383:A / Sax 6, 280 / Sigma FT-IR 1 (2), 284:A / Structure Index 1, 214:A:1 / Vapor Phase 3, 1109:A

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