The ambident reactivity of aromatic amines in their reactions with N-2-(2,4,6-trinitrophenyl)-4,6-dinitrobenzotriazole-1-oxide, a new heterocyclic super-electrophile

1983 ◽  
Vol 61 (7) ◽  
pp. 1690-1691 ◽  
Author(s):  
Erwin Buncel ◽  
Richard A. Renfrow ◽  
Michael J. Strauss
Keyword(s):  
Aromatic Amine ◽  
Title Compound ◽  
Aromatic Amines

Reaction between the title compound 2 and 2,6-dimethylaniline, or N,N-dimethylaniline, gives rise to spectrally observable Meisenheimer type σ-complexes in which bonding has occurred between the para carbon of the aromatic amine and the benzotriazole moiety of 2; however, aniline reacts at the picryl moiety to give the product of displacement 5, via the aniline nitrogen as the nucleophilic atom.

scholarly journals P.2.20 Epidemic of bladder cancer in japanese male workers exposed mainly to ortho-toluidine

2019 ◽  
Vol 76 (Suppl 1) ◽  
pp. A93.1-A93
Author(s):  
Makiko Nakano ◽  
Kazuyuki Omae ◽  
Yoko Eitaki ◽  
Satoko Iwasawa ◽  
Kota Fukai ◽  
...  
Keyword(s):  
Bladder Cancer ◽  
Aromatic Amine ◽  
Aromatic Amines ◽  
Organic Dyes ◽  
Cross Sectional Study ◽  
International Agency ◽  
Gross Hematuria ◽  
Cross Sectional ◽  
Exposed Workers ◽  
Medical Histories

BackgroundIn 2012, ortho-toluidine (OT) was listed as a Group 1 carcinogen by the International Agency for Research on Cancer, based on epidemiologic observations in workers co-exposed to OT and aromatic amines. Between 2014 and 2017, 10 cases of bladder cancer (BC) were identified in Japanese males working at two plants of the same company manufacturing intermediates of organic dyes and pigments.ObjectiveTo describe the features of the BC epidemic at the plants.MethodsWe conducted a cross-sectional study of 76 OT and/or aromatic amine-exposed workers including the 10 BC cases at the plants in 2017. The co-exposed aromatic amines were para-toluidine, ortho-anisidine, aniline, 2,4-dimethylaniline, and/or ortho-chloroaniline. Details of each worker’s job-site histories were obtained from the company records. Past medical symptoms and histories were checked in physician interviews. The subjects were divided into the BC group (n=10) and the non-BC group (n=66) and compared. No quantitative exposure data were available. The surrogate level of exposure to each aromatic amine was calculated as the summed job-weight-month in each process in each job-year.ResultsThe mean ages of the non-BC and BC groups were 50 and 56 years and the durations of employment were 23 and 20 years, respectively. The smoking rate in both groups was 80%. Significantly higher rates of gross hematuria (70%) and cystitis (70%) were identified in the BC group’s past medical histories. In the BC group, the surrogate levels of exposure to OT were higher than those of exposures to other aromatic amines. The surrogate levels were high in the job processes of filtering, rinsing, drying and packing products.ConclusionsThe subjects with BC were associated with a high surrogate level of exposure to OT. OT-exposed workers with past histories of gross hematuria and cystitis need a careful follow-up.

Synthesis of aromatic amine phosphonato ester derivatives from the stereoselective reaction between triphenyl phosphite and dimethyl acetylenedicarboxylate in the presence of derivatives of aromatic amines

2009 ◽  
Vol 20 (4) ◽  
pp. 240-245 ◽  
Author(s):  
Malek Taher Maghsoodlou ◽  
Reza Heydari ◽  
Nourallah Hazeri ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Mahmoud Nassiri ◽  
...  
Keyword(s):  
Aromatic Amine ◽  
Aromatic Amines ◽  
Triphenyl Phosphite ◽  
Dimethyl Acetylenedicarboxylate ◽  
Stereoselective Reaction ◽  
Derivatives Of

scholarly journals Predicting Aromatic Amine Mutagenicity with Confidence: A Case Study Using Conformal Prediction

Biomolecules ◽  
2018 ◽  
Vol 8 (3) ◽  
pp. 85 ◽  
Author(s):  
Ulf Norinder ◽  
Glenn Myatt ◽  
Ernst Ahlberg
Keyword(s):  
Aromatic Amine ◽  
Aromatic Amines ◽  
Conformal Prediction ◽  
Additional Information ◽  
Primary Aromatic Amines

The occurrence of mutagenicity in primary aromatic amines has been investigated using conformal prediction. The results of the investigation show that it is possible to develop mathematically proven valid models using conformal prediction and that the existence of uncertain classes of prediction, such as both (both classes assigned to a compound) and empty (no class assigned to a compound), provides the user with additional information on how to use, further develop, and possibly improve future models. The study also indicates that the use of different sets of fingerprints results in models, for which the ability to discriminate varies with respect to the set level of acceptable errors.

Meisenheimer complex formation between 4,6-dinitrobenzofurazan 1-oxide and primary, secondary and tertiary aromatic amines

1984 ◽  
Vol 37 (5) ◽  
pp. 985 ◽  
Author(s):  
RW Read ◽  
RJ Spear ◽  
WP Norris
Keyword(s):  
Complex Formation ◽  
Aromatic Amine ◽  
Aromatic Amines ◽  
Carbonate Solution ◽  
Complexation Reaction ◽  
Amino Group ◽  
Aromatic Carbon ◽  
Potassium Hydrogen Carbonate ◽  
Hydrogen Carbonate ◽  
Potassium Hydrogen

The uncatalysed formation of stable 1 : 1 Meisenheimer complexes between primary, secondary and tertiary aromatic amines and 4,6-dinitrobenzofurazan 1-oxide has been investigated. The thermodynamic product is derived from reaction through the aromatic carbon para or, if this position is substituted, ortho to the amino group of the aromatic amine. The complexes are stable to acid but react in aqueous potassium hydrogen carbonate solution or with aliphatic or aromatic amines to give crystalline salts of the complexes. In the presence of 1,4-diazabicyclo[2.2.2]octane, aniline reacts with 4,6-dinitrobenzofurazan 1-oxide to give an unstable nitrogen-bonded complex which is slowly converted into the carbon-bonded complex. The scope of the complexation reaction has been investigated and some of the mechanistic implications of the results are discussed.

Tertiary Aromatic Amine Accelerators with Molecular Weights Above 400

1972 ◽  
Vol 51 (2) ◽  
pp. 473-482 ◽  
Author(s):  
R.L. Bowen ◽  
H. Argentar
Keyword(s):  
Free Radical ◽  
Nitrogen Atom ◽  
Radical Polymerization ◽  
Aromatic Ring ◽  
Aromatic Amine ◽  
Aromatic Amines ◽  
Free Radical Polymerization ◽  
Molecular Weights ◽  
Rate Of Polymerization

With the proper ring substituents, tertiary aromatic amines with large substituents on the nitrogen atom can be effective accelerators in free radical polymerization. Resistance to discoloration appears to be primarily a function of the substituents on the aromatic ring of the amine, whereas the rate of polymerization is dependent on both the alkyl substituents on the ring and the groups attached to the nitrogen atom.

scholarly journals Efficient extraction of aromatic amines in the air by the needle trap device packed with the zirconium based metal–organic framework sorbent

RSC Advances ◽  
2020 ◽  
Vol 10 (23) ◽  
pp. 13562-13572 ◽  
Author(s):  
Ali Akbar Alinaghi Langari ◽  
Ali Firoozichahak ◽  
Saber Alizadeh ◽  
Davood Nematollahi ◽  
Maryam Farhadian
Keyword(s):  
Gas Chromatography ◽  
Aromatic Amine ◽  
Aromatic Amines ◽  
Metal Organic Framework ◽  
Flame Ionization Detector ◽  
Ionization Detector ◽  
Flame Ionization ◽  
Metal Organic ◽  
Efficient Extraction ◽  
Amine Compounds

Development of a needle trap device (NTD) packed with UiO-66 adsorbent was used for the sampling of the aromatic amine compounds (including aniline, N,N-dimethylaniline and o-toluidine) followed by gas chromatography (GC) with flame-ionization detector (FID) analysis.

Mass resolved IR spectroscopy of aniline–water aggregates

2016 ◽  
Vol 18 (39) ◽  
pp. 27336-27341 ◽  
Author(s):  
I. León ◽  
P. F. Arnáiz ◽  
I. Usabiaga ◽  
J. A. Fernández
Keyword(s):  
Excited State ◽  
Ir Spectroscopy ◽  
Aromatic Amine ◽  
Aromatic Amines ◽  
Excited State Dynamics

Aniline is the simplest aromatic amine and therefore it is a prototypical system to study the microhydration and excited state dynamics of aromatic amines.

Reversible anion intercalation in a layered aromatic amine: a high-voltage host structure for organic batteries

2016 ◽  
Vol 4 (16) ◽  
pp. 6131-6139 ◽  
Author(s):  
Élise Deunf ◽  
Philippe Moreau ◽  
Éric Quarez ◽  
Dominique Guyomard ◽  
Franck Dolhem ◽  
...  
Keyword(s):  
Aromatic Amine ◽  
High Voltage ◽  
Aromatic Amines ◽  
Host Structure ◽  
Organic Batteries

Discovery of a novel organic intercalation material belonging to the class of aromatic amines (dilithium 2,5-dianilinoterephthalate) able to reversibly accommodate anions for organic batteries.

scholarly journals Determination of Aromatic Amines in Cigarette Mainstream Smoke - The CORESTA 2007 Joint Experiment

2010 ◽  
Vol 24 (2) ◽  
pp. 78-92 ◽  
Author(s):  
M Intorp ◽  
S Purkis
Keyword(s):  
Aromatic Amine ◽  
Aromatic Amines ◽  
Collaborative Study ◽  
Internal Standard ◽  
Mainstream Smoke ◽  
Total Particulate Matter ◽  
Wide Range ◽  
Cigarette Mainstream Smoke ◽  
Joint Experiment

AbstractCORESTA joint experiment work in 2006 had compared data on a wide range of smoke constituents obtained from Kentucky reference cigarettes (1R5F and 2R4F), according to the existing methods used by participants. This work had identified that the methods used to determine aromatic amine yields in mainstream smoke would particularly benefit from further study to investigate the main weaknesses and influencing factors in their yield variability before progressing to full method standardisation. This report describes the output from a 2007 joint experiment to address these issues. Participating laboratories carried out experiments to investigate several factors that had been identified in the methodology as potential sources of variability. These were the amine derivative type, the derivatisation time and the point at which the addition of the internal standard for calibration occurred. A statistical assessment was made of their possible influence on aromatic amine smoke yields and yield reproducibility across different laboratories. Results showed that aromatic amines again had poor between-laboratory yield reproducibility. The stage at which the internal standard was added to the smoke sample had the most significant effect on yields. The least variable data were obtained when it was added directly after extraction from the filter pad rather than later in the process. It also appeared beneficial to use at least two calibration standards (i.e., an aminonaphthalene and an aminobiphenyl) to minimise yield differences although this recommendation was not supported by statistically significant data. Large differences in yields were not found when comparing the two studied derivatising agents especially when compared against the greater overall between-laboratory variability. Any differences between laboratories in total particulate matter and puff count at the smoke collection stage did not appear to significantly contribute to betweenlaboratory differences in yields. It appeared that some laboratories had significantly improved their methodology since the last study although high values for the between-laboratory reproducibility in this study were still found. It may be that significant improvements in reproducibility may not be forthcoming for compounds such as the aromatic amines measured at low nanogram smoke yields. Some important features that need to be controlled to minimise variability were identified in this study and will be incorporated within a collaborative study leading to a recommended method. Also, a wider range of product styles will need to be investigated, to determine the effects of differences in tobacco blends and product styles and the potential of greater product variability of commercial products. This should provide more robust estimates of within-laboratory repeatability and between-laboratory reproducibility.

ChemInform Abstract: Synthesis of Aromatic Amine Phosphonato Ester Derivatives from the Stereoselective Reaction Between Triphenyl Phosphite and Dimethyl Acetylenedicaboxylate in the Presence of Derivatives of Aromatic Amines.

ChemInform ◽  
2009 ◽  
Vol 40 (45) ◽  
Author(s):  
Malek Taher Maghsoodlou ◽  
Reza Heydari ◽  
Nourallah Hazeri ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Mahmoud Nassiri ◽  
...  
Keyword(s):  
Aromatic Amine ◽  
Aromatic Amines ◽  
Triphenyl Phosphite ◽  
Stereoselective Reaction ◽  
Derivatives Of
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