2,6-xylidine

benzenamine, 2,6-dimethyl-

CAS: 87-62-7 C8 H11 N MW: 121.18267000

Identification

Name2,6-xylidine
IUPAC2,6-dimethylaniline
CAS Number87-62-7
EINECS201-758-7
FDA UNII4FT62OX08D
Molecular FormulaC8 H11 N
Molecular Weight121.18267000
MDL NumberMFCD00007747
Nikkaji NumberJ43.456F
Beilstein0636332
XlogP31.80 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 0.98400 @ 25.00 °C.
Melting Point 11.20 °C. @ 760.00 mm Hg
Boiling Point 215.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.130000 mmHg @ 25.00 °C. (est)
Flash Point 196.00 °F. TCC ( 91.11 °C. )
logP (o/w) 1.840
Soluble in water, 2666 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-mouse LD50 707 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorypharmaceuticals / chemical synthisis
Recommendation for 2,6-xylidine usage levels up tonot for fragrance use.
Recommendation for 2,6-xylidine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

2- amino-1,3-dimethylbenzene 2- amino-1,3-xylene 1- amino-2,6-dimethylbenzene 2- amino-m-xylene aniline, 2,6-dimethyl- benzenamine, 2,6-dimethyl- benzene, 2-amino-1,3-dimethyl- 2,6- dimethyl aniline 2,6- dimethylanilin 2,6- dimethylaniline 2,6- dimethylphenylamine o- xylidine 2,6- xylylamine PubMed: Formation of N-nitrosamines by chloramination or ozonation of amines listed in Pollutant Release and Transfer Registers (PRTRs). PubMed: Determination of xylazine and 2,6-xylidine in animal tissues by liquid chromatography-tandem mass spectrometry. PubMed: Elevated 4-aminobiphenyl and 2,6-dimethylaniline hemoglobin adducts and increased risk of bladder cancer among lifelong nonsmokers--The Shanghai Bladder Cancer Study. PubMed: Prilocaine- and lidocaine-induced methemoglobinemia is caused by human carboxylesterase-, CYP2E1-, and CYP3A4-mediated metabolic activation. PubMed: Genotoxicity of 2,6- and 3,5-dimethylaniline in cultured mammalian cells: the role of reactive oxygen species. PubMed: Effect of carrier composition on 2,6-dimethylaniline degradation in aqueous solution by fluidized-bed Fenton process. PubMed: Further investigations into the genotoxicity of 2,6-xylidine and one of its key metabolites. PubMed: Occurrence and removal of lidocaine, tramadol, venlafaxine, and their metabolites in German wastewater treatment plants. PubMed: Oxidation of 2,6-dimethylaniline by the Fenton, electro-Fenton and photoelectro-Fenton processes. PubMed: Kinetics of 2,6-dimethylaniline oxidation by various Fenton processes. PubMed: Third-order nonlinear optical properties and structures of (E)-N-(4-nitrobenzylidene)-2,6-dimethylaniline and (E)-N-(4-nitrobenzylidene)-2,3-dimethylaniline. PubMed: Chemical oxidation of 2,6-dimethylaniline in the fenton process. PubMed: Chemical oxidation of 2,6-dimethylaniline by electrochemically generated Fenton's reagent. PubMed: Iron-catalyzed dehydrogenative phosphonation of N,N-dimethylanilines. PubMed: Separation and analysis of dimethylaniline isomers by supercritical fluid chromatography--electrospray ionization tandem mass spectrometry. PubMed: Kinetics and mechanism of 2,6-dimethyl-aniline degradation by hydroxyl radicals. PubMed: Retention time prediction of compounds in Grob standard mixture for apolar capillary columns in temperature-programmed gas chromatography. PubMed: Kinetics of 2,6-dimethylaniline degradation by electro-Fenton process. PubMed: Assessment of the medicines lidocaine, prilocaine, and their metabolites, 2,6-dimethylaniline and 2-methylaniline, for DNA adduct formation in rat tissues. PubMed: Temperature investigations of E/Z isomers in ketimines based of p-dibenzoylobenzene with aniline and 2,6-dimethylaniline by infrared spectroscopy. PubMed: DNA adduct formation by 2,6-dimethyl-, 3,5-dimethyl-, and 3-ethylaniline in vivo in mice. PubMed: Amine mediated proton transfer reaction and C-Cl bond activation of solvent chloroform by a trinuclear copper(II) complex of a glucopyranosylamine derived ligand. PubMed: Changes in production of lignin degrading enzymes during interactions between mycelia of the tropical decomposer basidiomycetes Marasmiellus troyanus and Marasmius pallescens. PubMed: Mechanisms of cytotoxicity of selected organogold(III) compounds. PubMed: Solution chemistry and cytotoxic properties of novel organogold(III) compounds. PubMed: Synthesis, structure and pharmacology of acyl-2,6-xylidines. PubMed: Gold complexes inhibit mitochondrial thioredoxin reductase: consequences on mitochondrial functions. PubMed: Metabolic activation of 2,6-xylidine in the nasal olfactory mucosa and the mucosa of the upper alimentary and respiratory tracts in rats. PubMed: Liquid phase overtone spectral investigations of 2,6-dimethylaniline and 2,4-dimethylaniline-evidence for steric nature of the ortho effect and the consequent base weakening. PubMed: Pharmacokinetics of xylazine, 2,6-dimethylaniline, and tolazoline in tissues from yearling cattle and milk from mature dairy cows after sedation with xylazine hydrochloride and reversal with tolazoline hydrochloride. PubMed: Determination of 2,6-dimethylaniline and o-toluidine impurities in preparations for local anaesthesia by the HPLC method with amperometric detection. PubMed: The effect of deuterium and fluorine substitution upon the mutagenicity of N-hydroxy-2,6-dimethylaniline. PubMed: Involvement of liver carboxylesterases in the in vitro metabolism of lidocaine. PubMed: Lack of DNA binding in the rat nasal mucosa and other tissues of the nasal toxicants roflumilast, a phosphodiesterase 4 inhibitor, and a metabolite, 4-amino-3,5-dichloropyridine, in contrast to the nasal carcinogen 2,6-dimethylaniline. PubMed: Analysis of the lidocaine metabolite 2,6-dimethylaniline in bovine and human milk. PubMed: Immunohistochemical and ultrastructural studies of 2,6-dimethylaniline-induced nasal proliferative lesions in a rat two-stage nasal carcinogenesis model initiated with N-bis(2-hydroxypropyl)nitrosamine. PubMed: Oxidation of 2,6-dimethylaniline by recombinant human cytochrome P450s and human liver microsomes. PubMed: Plasma levels of lidocaine and prilocaine after application of Oraqix, a new intrapocket anesthetic, in patients with advanced periodontitis. PubMed: Synthesis, characterization, and comparative 32P-postlabeling efficiencies of 2,6-dimethylaniline-DNA adducts. PubMed: Identification of impurities in technical metalaxyl. PubMed: Sequential observation of 2,6-dimethylaniline-induced nasal lesions in a rat two-stage nasal carcinogenesis model after initiation with N-bis(2-hydroxypropyl) nitrosamine. PubMed: High-performance liquid chromatography-tandem electrospray mass spectrometry for the determination of lidocaine and its metabolites in human plasma and urine. PubMed: Toxicity and blood concentrations of xylazine and its metabolite, 2,6-dimethylaniline, in rats after single or continuous oral administrations. PubMed: Tumor-promoting activity of 2,6-dimethylaniline in a two-stage nasal carcinogenesis model in N-bis(2-hydroxypropyl)nitrosamine-treated rats. PubMed: Studies on sulfation of synthesized metabolites from the local anesthetics ropivacaine and lidocaine using human cloned sulfotransferases. PubMed: The regulatory status of xylazine for use in food-producing animals in the United States. PubMed: An update of the National Toxicology Program database on nasal carcinogens. PubMed: Pharmacokinetics and metabolism of the novel anticonvulsant agent N-(2,6-dimethylphenyl)-5-methyl-3-isoxazolecarboxamide (D2624) in rats and humans. PubMed: Identification of 2,6-xylidine as a major lidocaine metabolite in human liver slices. PubMed: Metabolism and excretion of ropivacaine in humans. PubMed: Validation of high-performance liquid chromatographic methods on two silica base-deactivated reversed phases for the determination of chloroprocaine and bupivacaine. PubMed: Determination of combined residues of metalaxyl and 2,6-dimethylaniline metabolites in urine by gas chromatography/mass spectrometry. PubMed: 2,6-Dimethylaniline--hemoglobin adducts from lidocaine in humans. PubMed: Take the pain? Lidocaine comes under suspicion as a carcinogen. PubMed: Simultaneous determination of xylazine and its major metabolite, 2,6-dimethylaniline, in bovine and swine kidney by liquid chromatography. PubMed: Transformation of BALB/c-3T3 cells: IV. Rank-ordered potency of 24 chemical responses detected in a sensitive new assay procedure. PubMed: 2,6-Dimethylaniline (2,6-xylidine). PubMed: Fluorescence polarization immunoassay and HPLC assays compared for measuring monoethylglycinexylidide in liver-transplant patients. PubMed: Effects of parenteral nutrition on hepatic elimination of lidocaine: a study using the isolated perfused rat liver. PubMed: The evaluation of a multiple dosing protocol for the mouse bone-marrow micronucleus assay using benzidine and 2,6-xylidine. PubMed: Quantification of three lidocaine metabolites and their conjugates. PubMed: NTP Toxicology and Carcinogenesis Studies of 2,6-Xylidine (2,6-Dimethylaniline) (CAS No. 87-62-7) in Charles River CD Rats (Feed Studies). PubMed: The in vivo oxidative metabolism of 2,4- and 2,6-dimethylaniline in the dog and rat. PubMed: Measurement of unscheduled DNA synthesis and S-phase synthesis in rodent hepatocytes following in vivo treatment: testing of 24 compounds. PubMed: Covalent binding of [14C]-2,6-dimethylaniline to DNA of rat liver and ethmoid turbinate. PubMed: [Amino acid derivatives of 2,6-xylidine and p-aminobenzoic acid. II. Synthesis of derivatives of N-(p-aminobenzoylaminoalkylacyl)-2,6-xylidines and study of their resistance to proteolytic factors]. PubMed: [Amino acid derivatives of 2,6 and p-aminobenzoic acid. I. Synthesis of derivatives of 2,6-xylidine and various derivatives of PAB]. PubMed: The in vivo effect of 2,6-xylidine on induction of micronuclei in mouse bone marrow cells. PubMed: In vivo metabolism of lidocaine in the rat. Isolation of urinary metabolites as pentafluorobenzoyl derivatives and their identification by combined gas chromatography-mass spectrometry. PubMed: New antiarrhythmic agents. 6. Quantitative structure-activity relationships of aminoxylidides. PubMed: Determination and temperature effects of lidocaine (lignocaine) hydrochloride, epinephrine, methylparaben, 2,6-dimethylaniline, and p-hydroxybenzoic acid in USP lidocaine injection by ion-pair reversed-phase high pressure liquid chromatography. PubMed: New antiarrhythmic agents. 5. alpha-Aminoaceto-2,6-xylidides with functionalized amide alkyl substituents. PubMed: New antiarrhythmic agents. 2. Amide alkyl alpha-amino xylidides. PubMed: Hepatic effects of xylidine isomers in rats. PubMed: Micromethod for determination of meperidine in plasma. PubMed: [Studies on Xipamide (4-chloro-5-sulfamoyl-2',6'-salicyloxylidide). Part 1: Physico-chemical and chemical properties (author's transl)].