142-04-1 Usage
Chemical Description
Aniline hydrochloride, sodium nitrite, and sodium hydroxide are reagents used in the chemical reactions described in the article.
Description
Aniline hydrochloride, also known as aniline chloride or aniline salt, is a white to greenish crystalline solid that is toxic by ingestion and a skin and eye irritant. It may emit toxic aniline and chloride fumes under exposure to high temperatures or flame. Aniline hydrochloride is used to make dyes and printing ink and is an intermediate in the synthesis of various compounds.
Uses
Used in Chemical Synthesis:
Aniline hydrochloride is used as an intermediate in the synthesis of dyes, printing ink, fentanyl, and its derivatives. It is particularly used in the preparation of polyaniline coated poly(styrene-co-styrene sulfonate) nanoparticles and the imine derivative of NPP.
Used in Research and Forensic Applications:
Aniline hydrochloride serves as an analytical reference standard for research and forensic applications, aiding in the study of various chemical reactions and processes.
Used in Pharmaceutical Applications:
Aniline hydrochloride is 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 exposure.
Used in Dyeing and Printing:
Aniline hydrochloride is used in the dyeing and printing industry as a key component in the production of dyes and printing inks.
Used in Paints and Paint Removers:
Aniline hydrochloride is utilized in the formulation of paints, paint removers, and other related products due to its chemical properties.
Used in Clothing Marking Inks:
It is also used in the production of clothing marking inks, contributing to the color and quality of the final product.
Used in Stove and Shoe Polish:
Aniline hydrochloride is employed as a component in the manufacturing of stove polishers and shoe polishers, enhancing their performance and appearance.
Used in the Synthesis of Crayons and Antioxidants:
Aniline hydrochloride is used in the synthesis of crayons and antioxidants, playing a crucial role in their production process.
Used in the Production of Aniline:
Aniline hydrochloride is used in the production of aniline, a clear, colorless, oily liquid with a characteristic amine-like odor, which darkens on exposure to light. Aniline is an important chemical intermediate with various applications in the chemical industry.
Air & Water Reactions
Aniline hydrochloride is sensitive to air and light (darkens). Soluble in water and denser than water.
Reactivity Profile
Aniline hydrochloride is incompatible with oxidizing materials.
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
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.
Safety Profile
Suspected carcinogen
with experimental carcinogenic and
tumorigenic data. Poison by intraperitoneal
route. Moderately toxic by ingestion.
Experimental teratogenic effects. Human
mutation data reported. A skin and eye
irritant. Combustible when exposed to heat
or flame. When heated to decomposition or
on contact with acid or acid fumes, it emits
highly toxic fumes of aniline and chlorine
compounds. Reacts explosively with aniline at 240℃/7.6 bar. Can react vigorously with
oxidizing materials. To fight fire, use water,
CO2, water mist or spray, dry chemical. See
also ANILINE.
Potential Exposure
Aniline is widely used as an intermediate
in the synthesis of dyestuffs. It is also used in the
manufacture of rubber accelerators and antioxidants, pharmaceuticals,
marking inks; tetryl, optical whitening agents;
photographic developers; resins, varnishes, perfumes, shoe
polishes, and many organic chemicals.
Shipping
UN1547 Aniline, Hazard Class: 6.1; Labels: 6.1-
Poisonous materials. UN1548 Aniline hydrochloride,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification Methods
Purification is as for aniline HBr above. [Beilstein 12 IV 232.]
Incompatibilities
May form explosive mixture with air.
Unless inhibited (usually methanol), aniline is readily able
to polymerize. Fires and explosions may result from contact
with halogens, strong acids; oxidizers, strong base organic
anhydrides; acetic anhydride, isocyanates, aldehydes,
sodium peroxide. Strong reaction with toluene diisocyanate.
Reacts with alkali metals and alkali earth metals. Attacks
some plastics, rubber and coatings; copper and copper
alloys.
Waste Disposal
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing
storage, transportation, treatment, and waste disposal.
Incineration with provision for nitrogen oxides removal from
flue gases by scrubber, catalytic or thermal device.
Check Digit Verification of cas no
The CAS Registry Mumber 142-04-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 142-04:
(5*1)+(4*4)+(3*2)+(2*0)+(1*4)=31
31 % 10 = 1
So 142-04-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H7N.ClH/c7-6-4-2-1-3-5-6;/h1-5H,7H2;1H
142-04-1Relevant articles and documents
Synthesis of N-Aryl-3,5-dichloro-4H-1,2,6-thiadiazin-4-imines from 3,4,4,5-Tetrachloro-4H-1,2,6-thiadiazine
Kalogirou, Andreas S.,Manoli, Maria,Koutentis, Panayiotis A.
, p. 4118 - 4121 (2015)
Condensation of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine with a range of anilines gave 22 N-aryl-3,5-dichloro-4H-1,2,6-thiadiazin-4-imines in 43-96% yields. The scope and limitations of this condensation are briefly investigated. Furthermore, mono- and bis-substitution of the C-3 and C-5 chlorines of 3,5-dichloro-N-phenyl-4H-1,2,6-thiadiazin-4-imine by amine and alkoxide nucleophiles is explored. Finally, Stille coupling chemistry is used to prepare several N-phenyl-3,5-diaryl-4H-1,2,6-thiadiazin-4-imines.
The biosynthesis of ephedrine
Grue-Sorensen,Spenser
, p. 998 - 1009 (1989)
-
Ethoxydeamination of α-phenylaminobenzylphosphonate derivatives [4]
Ismagilov,Moskva,Ofitserov,Shamsutdinova
, p. 818 - 819 (2002)
-
Iron-catalyzed selective reduction of nitro compounds to amines
Pehlivan, Leyla,Métay, Estelle,Laval, Stéphane,Dayoub, Wissam,Demonchaux, Patrice,Mignani, Gérard,Lemaire, Marc
, p. 1939 - 1941 (2010)
An efficient reduction of the nitro group with a catalytic amount of Fe(acac)3 and TMDS in THF at 60 °C affording the corresponding amine is described.
Synthesis and experimental and theoretical characterization of m-fluorosulfinylaniline
Páez Jerez, Ana L.,Chemes, Doly M.,Cutin, Edgardo H.,Oberhammer, Heinz,Robles, Norma L.
, p. 4445 - 4451 (2015)
The synthesis of m-fluorosulfinylaniline together with a tentative assignment of the vibrational, NMR and mass spectra are reported. Quantum chemical calculations predict two stable conformers, with very similar energies, both of which possess in the liquid phase syn structure of the -NSO moiety (syn of the SO double bond relative to the C-N single bond). Both conformers belong to the CS symmetry group and differ by the relative orientation of the fluorine atom and the NSO group. However, the FT-IR, FT-Raman and NMR spectra do not allow a distinction between these two conformers. The experimentally observed spectral data (FT-IR, FT-Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with the spectral data obtained by quantum chemical calculations and the gauge including atomic orbital (GIAO) method (DFT/B3LYP approximation using 6-311+G(df), 6-311++G(df,pd) and cc-pVTZ basis sets). Moreover, natural bond orbital (NBO) analysis is applied for studying the stability of the molecule upon charge delocalization in order to provide an explanation of its electronic properties.
Solvent-freeN-Boc deprotection byex situgeneration of hydrogen chloride gas
De Borggraeve, Wim M.,Gilles, Philippe,Van Mileghem, Seger,Verschueren, Rik H.
, p. 5782 - 5787 (2021/07/12)
An efficient, scalable and sustainable method for the quantitative deprotection of thetert-butyl carbamate (N-Boc) protecting group is described, using down to near-stoichiometric amounts of hydrogen chloride gas in solvent-free conditions. We demonstrate theex situgeneration of hydrogen chloride gas from sodium chloride and sulfuric acid in a two-chamber reactor, introducing a straightforward method for controlled and stoichiometric release of HCl gas. The solvent-free conditions allow deprotection of a wide variety ofN-Boc derivatives to obtain the hydrochloride salts in quantitative yields. The procedure obviates the need for any work-up or purification steps providing an uncomplicated green alternative to standard methods. Due to the solvent-free, anhydrous conditions, this method shows high tolerance towards acid sensitive functional groups and furnishes expanded functional group orthogonality.
Selective and Additive-Free Hydrogenation of Nitroarenes Mediated by a DMSO-Tagged Molecular Cobalt Corrole Catalyst
Sch?fberger, Wolfgang,Timelthaler, Daniel,Topf, Christoph
supporting information, p. 2114 - 2120 (2021/07/22)
We report on the first cobalt corrole that effectively mediates the homogeneous hydrogenation of structurally diverse nitroarenes to afford the corresponding amines. The given catalyst is easily assembled prior to use from 4-tert-butylbenzaldehyde and pyrrole followed by metalation of the resulting corrole macrocycle with cobalt(II) acetate. The thus-prepared complex is self-contained in that the hydrogenation protocol is free from the requirement for adding any auxiliary reagent to elicit the catalytic activity of the applied metal complex. Moreover, a containment system is not required for the assembly of the hydrogenation reaction set-up as both the autoclave and the reaction vessels are readily charged under a regular laboratory atmosphere.
Synthesis, characterization and electropolymerization of functionalized organic salt–anilinium saccharinate and electrochemically controlled release of saccharinate anions
Shen, Lanbo,Gao, Na,Huang, Xirong
, (2019/11/03)
In this work, a novel functionalized organic salt ? anilinium saccharinate ([HANI][Sac]) was synthesized by the ion exchange method, and its composition and properties were characterized by 1H NMR, 13C NMR, ESI/MS and TG-DSC techniques. [HANI][Sac] can be used as both monomer and supporting electrolyte for efficient electrosynthesis of polyaniline (PANI) in acetonitrile. The obtained PANI has hierarchical porous structure and its doping degree with saccharinate anion ([Sac]-) is as high as 33.5%. The resulting [Sac]--doped-PANI (PANI-[Sac]) can be used as an electrochemically controlled drug delivery system. The in vitro release kinetics of [Sac]- under different potential stimuli conditions showed that, at a given time, the release rate of [Sac]- and its release percentage (ratio of the amount released to that loaded) increase with the negative shift of the applied potential. The amount of [Sac]- loaded and/or released can also be regulated by varying the charge for PANI electropolymerization. The present work provides a new strategy for the facile construction of conducting polymer-based electrochemically controlled drug release system.