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Cas Database

142-04-1

142-04-1

Identification

  • Product Name:Benzenamine,hydrochloride (1:1)

  • CAS Number: 142-04-1

  • EINECS:205-519-8

  • Molecular Weight:129.589

  • Molecular Formula: C6H7N.HCl

  • HS Code:29214100

  • Mol File:142-04-1.mol

Synonyms:Aniline,hydrochloride (6CI,8CI);Benzenamine, hydrochloride (9CI);Anilinium chloride;C.I. 76001;Phenylamine hydrochloride;Phenylammonium chloride;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT, DangerousN

  • Hazard Codes:T,N

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH311 Toxic in contact with skin H317 May cause an allergic skin reaction H318 Causes serious eye damage H331 Toxic if inhaled H341 Suspected of causing genetic defects H351 Suspected of causing cancer H372 Causes damage to organs through prolonged or repeated exposure H400 Very toxic to aquatic life

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. See Notes. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention . See Notes. Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. (ERG, 2016)

  • Fire-fighting measures: Suitable extinguishing media Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016) Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. 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. (ERG, 2016) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants, strong acids and food and feedstuffs. Dry. Well closed. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:Aniline hydrochloride
  • Packaging:1g
  • Price:$ 85
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Aniline hydrochloride
  • Packaging:2.5 kg
  • Price:$ 317
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Aniline hydrochloride
  • Packaging:100 g
  • Price:$ 100
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Aniline hydrochloride
  • Packaging:500 g
  • Price:$ 138
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Anilinium chloride for synthesis. CAS No. 142-04-1, EC Number 205-519-8., for synthesis
  • Packaging:8200991000
  • Price:$ 112
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Anilinium chloride for synthesis. CAS No. 142-04-1, EC Number 205-519-8., for synthesis
  • Packaging:8200990250
  • Price:$ 80.4
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Aniline hydrochloride purum p.a., for sugar analysis, ≥99.0% (AT)
  • Packaging:50g-f
  • Price:$ 77.3
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Anilinium chloride for synthesis
  • Packaging:250 g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Aniline hydrochloride ≥99%
  • Packaging:50g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Aniline hydrochloride ≥99%
  • Packaging:5g
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Relevant articles and documentsAll total 97 Articles be found

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.

Anilinium dihydrogen phosphate

Kaman, Ondej,Smrcok, Lubomir,Gyepes, Robert,Havlicek, David

, p. o57-o60 (2012)

The triclinic structure of the title compound, C6H 8N+·H2PO4-, with three symmetry-independent structural units (Z′ = 3), is formed of separate organic and inorganic layers alternating along the b axis. The building blocks of the inorganic layer are deformed H2PO4 tetra-hedra assembled into infinite ladders by short and hence strong hydrogen bonds. The anilinium cations forming the organic layer are not hydrogen bonded to one another, but they are anchored by four N-H...O crosslinks between the dihydrogen phosphate chains of adjacent ladders. Two H atoms of each-NH3 group then form one normal and one bifurcated N-H...O hydrogen bond to the P=O oxygens of two tetra-hedra of one chain, while the third H atom is hydrogen bonded to the nearest O atom of an adjacent chain belonging to another dihydrogen phosphate ladder.

The biosynthesis of ephedrine

Grue-Sorensen,Spenser

, p. 998 - 1009 (1989)

-

Effect of Solvents on Acid-Catalyzed Claisen Amino Rearrangement in N-(1-Methyl-2-butenyl)aniline

Abdrakhmanov,Sharafutdinov,Mustafin,Zimin, Yu. S.,Daminev

, p. 23 - 27 (2019)

Abstract: The effect solvents have on the processes of rearrangement and elimination in N-(1-methyl-2-butenyl)aniline (I) in the presence of HCl is studied. It is shown that the dependence of the rearrangement and elimination rate constants of (I) · HCl on the nature of solvents are described perfectly by the Koppel–Palm equation, which considers both nonspecific and specific solvation. The inhibitory effect of solvent nucleophilicity is explained by the complexation between (I) · HCl and solvent molecules. Analysis of the (I) · HCl conversion products obtained in a mixed solvent (m-toluidine + nitrobenzene) demonstrates the intermolecular transfer of the allyl moiety, confirming the formation of allyl cations in the Claisen amino rearrangement.

Ethoxydeamination of α-phenylaminobenzylphosphonate derivatives [4]

Ismagilov,Moskva,Ofitserov,Shamsutdinova

, p. 818 - 819 (2002)

-

Cyclometalated Ruthenium(II) NHC Complexes with Imidazo[1,5-a]pyridine-Based (C^C*) Ligands – Synthesis and Characterization

Schleicher, David,Tronnier, Alexander,Soellner, Johannes,Strassner, Thomas

, p. 1956 - 1965 (2019)

We present the synthesis and characterization of cyclometalated ruthenium(II) NHC complexes with phenyl-substituted imidazo[1,5-a]pyridine C^C* ligands. The corresponding p-cymene complexes can be reacted with bipyridine to form bisheteroleptic ruthenium(II) dyes. The compounds have been characterized by one- and two-dimensional 1H/13C NMR spectroscopy, elemental analysis, cyclic voltammetry, infrared spectroscopy, as well as solid-state structure (X-ray) analysis.

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.

Semi-organic salts of aniline with inorganic acids: Prospective materials for the second harmonic generation

Matulková, Irena,Cihelka, Jaroslav,Fejfarová, Karla,Duek, Michal,Pojarová, Michaela,Vank, Pemysl,Kroupa, Jan,ála, Michal,Krupková, Radmila,Němec, Ivan

, p. 4131 - 4138 (2011)

Three novel inorganic salts of aniline with sulfuric and selenic acids were prepared and characterized by X-ray structural analysis. Anilinium(1+) selenate, (C6H5NH3 +) 2SeO4 2-, and anilinium sulfate, (C 6H5NH3 +)2SO 4 2-, crystallize in the monoclinic space group C2. The crystal structures are based on hydrogen bonded layers of alternating anilinium cations and inorganic anions. Anilinium(1+) selenate dihydrate, (C 6H5NH3 +)2SeO 4 2-·2H2O, crystallizes in the monoclinic space group C2/c. The crystal structure is formed by a network of alternating anilinium cations, selenate anions and water molecules connected by a system of intermolecular hydrogen bonds. The FTIR and Raman spectra of all the compounds have been recorded and discussed as well as their crystal structures. According to the DSC curves and temperature dependence of lattice parameters, anilinium sulfate exhibits phase transitions at 217 and 182 K. The appropriate changes of vibrational spectra were also recorded during cooling of the sample especially in the N-H stretching and sulfate antisymmetric stretching (ν3 SO4 2-) spectral regions. The quantitative measurements of the second harmonic generation at 1064 nm were performed using powdered samples of anilinium sulfate, anilinium chloride and anilinium selenate, and the relative efficiencies deff = 0.05dKDP, deff = 2.33dKDP and deff = 0.05dKDP (KDP; i.e. KH 2PO4) have been observed, respectively.

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.

Amine Catalysis of the Hydrolysis of Trifluoroacetanilide

Huffman, Robert W.

, p. 2675 - 2680 (1980)

Only hydrolysis products could be isolated from the reaction of trifluoroacetanilide I with aqueous n-butylamine buffer at pH 10.5.Kinetic studies of the decomposition of trifluoroacetanilide I in aqueous morpholine, n-butylamine, piperidine and trimethylamine buffers were also conducted.The most reasonable scheme for the reaction mechanism, compatible with all data, is presented in Scheme I and involves the general-base-catalyzed decomposition of the intermediate III which can be formed by hydroxide ion or water addition to I.Utilizing the constants of Table I, eq 6 is capable of predicting observed rate constants with an error of l ess than 9 percent (see Tables II an III).Some variation in values for these constants for trimethylamine buffers is observed and attributed to possible activity changes for the solutions.Deuterium isotope rate effects were determined for these constants in morpholine buffers.A value of k1H2O/k2D2O of 0.39 was obtained and may indicate the presence of a third pathway for the generation of III (eq 9), involving the hydration of the anion II.A value of k4H2O/k4D2O of 1.65 and a Broensted β value of 0.23 for k4 are interpreted to indicate general-base catalysis by the amine buffer.The low values for these quantities are indicative of a transition state involving an early proton transfer.General-base catalysis of proton transfer for the k4 step is also indicated by the fact that trimethylamine appears to behave mechanistically, similar to the other amines used.The value of 8.8 obtained for k3H2O/k3D2O clearly shows proton transfer to be occuring in this step as well.The results of this study thus support those suggested previously in that the hydrolysis of I undergoes a change in rate-determining step in mild alkaline aqueous solutions.This occurs because of the combination of the poor leaving ability of the anilinium ion and acyl activation present in the substrate trifluoroacetanilide.

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.

Direct Amidation of Esters by Ball Milling**

Barreteau, Fabien,Battilocchio, Claudio,Browne, Duncan L.,Godineau, Edouard,Leitch, Jamie A.,Nicholson, William I.,Payne, Riley,Priestley, Ian

supporting information, p. 21868 - 21874 (2021/09/02)

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

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.

Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides

Gudun, Kristina A.,Hayrapetyan, Davit,Khalimon, Andrey Y.,Segizbayev, Medet,Slamova, Ainur,Zakarina, Raikhan

, (2021/11/30)

The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.

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.

Process route upstream and downstream products

Process route

diethyl ether
60-29-7,927820-24-4

diethyl ether

aniline
62-53-3

aniline

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

benzene diazonium chloride
100-34-5

benzene diazonium chloride

Phenyl azide
622-37-7

Phenyl azide

Conditions
Conditions Yield
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

phenyl-phosphonic acid monoanilide

phenyl-phosphonic acid monoanilide

phenylphosphinic acid
1779-48-2

phenylphosphinic acid

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

Conditions
Conditions Yield
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

benzylphenyltriazene
17683-10-2,20667-64-5,20667-65-6

benzylphenyltriazene

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
benzylidene phenylamine
538-51-2

benzylidene phenylamine

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

benzaldehyde
100-52-7

benzaldehyde

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
With chloroform; at 550 ℃;
3 g
2.5 g
water
7732-18-5

water

benzyliden-aniline; bis hydrochloride of benzylidenaniline
1135-34-8,143896-65-5

benzyliden-aniline; bis hydrochloride of benzylidenaniline

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
water
7732-18-5

water

α-anilino-benzyl alcohol; hydrochloride

α-anilino-benzyl alcohol; hydrochloride

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
N-Phenylbenzimidchlorid
143896-65-5

N-Phenylbenzimidchlorid

N-phenyl benzoyl amide
93-98-1,5705-51-1

N-phenyl benzoyl amide

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
Beim Aufbewahren an der Luft;
N-Phenylbenzimidchlorid
143896-65-5

N-Phenylbenzimidchlorid

N-phenyl benzoyl amide
93-98-1,5705-51-1

N-phenyl benzoyl amide

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
diethyl ether
60-29-7,927820-24-4

diethyl ether

acetyl chloride
75-36-5

acetyl chloride

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

benzaldehyde
100-52-7

benzaldehyde

Acetanilid
103-84-4

Acetanilid

Conditions
Conditions Yield
3,3-dimethyl-1-phenyl-triazene
7227-91-0

3,3-dimethyl-1-phenyl-triazene

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

aniline yellow
60-09-3

aniline yellow

Conditions
Conditions Yield

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