2,6-xylidine
benzenamine, 2,6-dimethyl-
Identification
| Name | 2,6-xylidine |
| IUPAC | 2,6-dimethylaniline |
| CAS Number | 87-62-7 |
| EINECS | 201-758-7 |
| FDA UNII | 4FT62OX08D |
| Molecular Formula | C8 H11 N |
| Molecular Weight | 121.18267000 |
| MDL Number | MFCD00007747 |
| Nikkaji Number | J43.456F |
| Beilstein | 0636332 |
| XlogP3 | 1.80 (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 SDS | View |
| Oral/Parenteral Toxicity | oral-mouse LD50 707 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for 2,6-xylidine usage levels up to | not for fragrance use. |
| Recommendation for 2,6-xylidine flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
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)].