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Cas Database

102-28-3

102-28-3

Identification

  • Product Name:Acetamide,N-(3-aminophenyl)-

  • CAS Number: 102-28-3

  • EINECS:203-021-5

  • Molecular Weight:150.18

  • Molecular Formula: C8H10N2O

  • HS Code:29214200

  • Mol File:102-28-3.mol

Synonyms:m-Aminoacetanilide;Acetanilide,3'-amino- (6CI,7CI,8CI);1-Acetylamino-3-aminobenzene;1-Amino-3-(acetylamino)benzene;3-(Acetylamino)aniline;3-Acetamidoaniline;3-Acetylaminobenzeneamine;3-Amino-N-acetylaniline;N-(3-Aminophenyl)acetamide;N-Acetyl-1,3-diaminobenzene;N-Acetyl-m-phenylenediamine;NSC 165576;m-(Acetylamino)aniline;m-Acetamidoaniline;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes.

  • Fire-fighting measures: Suitable extinguishing media Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. Flash point data concerning this compound are not available, however, it is probably combustible. 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. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. 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. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • 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

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  • Manufacture/Brand:TRC
  • Product Description:N-(3-Aminophenyl)acetamide
  • Packaging:25g
  • Price:$ 75
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  • Manufacture/Brand:TRC
  • Product Description:N-(3-Aminophenyl)acetamide
  • Packaging:2.5g
  • Price:$ 45
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3'-Aminoacetanilide >98.0%(HPLC)(T)
  • Packaging:25g
  • Price:$ 33
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3′-Aminoacetanilide 97%
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  • Product Description:N-(3-Aminophenyl)acetamide
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  • Product Description:N-(3-Aminophenyl)acetamide
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:3-Aminoacetanilide
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:3-Aminoacetanilide
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  • Manufacture/Brand:Frontier Specialty Chemicals
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  • Manufacture/Brand:Crysdot
  • Product Description:N-(3-Aminophenyl)acetamide 98%
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Relevant articles and documentsAll total 31 Articles be found

Citric acid catalysed Beckmann rearrangement, under solvent free conditions

Thopate, Shankar Ramchandra,Kote, Santosh Rajaram,Rohokale, Sandeep Vasantrao,Thorat, Nitin Madhukar

, p. 124 - 125 (2011)

Citric acid is reported to be a highly efficient and eco-friendly catalyst for the Beckmann rearrangement under solvent free conditions.

In situ generated iron oxide nanocrystals as efficient and selective catalysts for the reduction of nitroarenes using a continuous flow method

Cantillo, David,Baghbanzadeh, Mostafa,Kappe, C. Oliver

, p. 10190 - 10193 (2012)

The best of both worlds: The benefits of homogeneous and heterogeneous nanocatalysis are combined, whereby highly reactive colloidal Fe 3O4 nanocrystals are generated in situ that remain in solution long enough to allow the efficient and selective reduction of nitroarenes to anilines in continuous-flow mode (see scheme). After completion of the reaction, the nanoparticles aggregate and can be recovered by a magnet. Copyright

Radical arylation of triphenyl phosphite catalyzed by salicylic acid: Mechanistic investigations and synthetic applications

Estruch-Blasco, Manel,Felipe-Blanco, Diego,Bosque, Irene,Gonzalez-Gomez, Jose C.

, p. 14473 - 14485 (2020)

A straightforward and scalable methodology to synthesize diphenyl arylphosphonates at 20 °C within 1-2 h is reported using inexpensive SA as the catalytic promoter of the reaction. Mechanistic investigations suggest that the reaction proceeds via radical-radical coupling, consistent with the so-called persistent radical effect. The reaction tolerated a wide range of functional groups and heteroaromatic moieties. The synthetic usefulness and the unique reactivity of the obtained phosphonates were demonstrated in different one-step transformations.

Preparation method of aminoacetanilide

-

Paragraph 0046-0064, (2021/01/29)

The invention belongs to the technical field of dye intermediate production, and particularly relates to a preparation method of aminoacetanilide, which comprises the following steps of 1) adding an acetate compound, phenylenediamine and a catalyst triethylene diamine into a reactor, and uniformly mixing to obtain a mixed solution, 2) under the protection of nitrogen, heating the mixed solution to65-90 DEG C, dropwise adding acetic acid, and reacting for 4-9 hours after dropwise adding is finished, and 3) after the reaction is finished, cooling to 15-25 DEG C, standing for 5-8 hours, filtering, fully washing a filter cake with n-butyl alcohol, and drying in vacuum at 80 DEG C for 6 hours to obtain aminoacetanilide. Aminoacetanilide is synthesized by using an acetate method, acetic anhydride which is high in price and easy to prepare drugs is not used, the production cost is reduced, and the method is suitable for industrial production; the method has the advantages of few reaction steps, no generation of waste acid, waste water and waste salt and no pollution to the environment; the yield (based on the weight of phenylenediamine) of the aminoacetanilide product prepared by the method is up to 97% or above, and the purity is up to 98% or above.

Copper nanoparticles (CuNPs) catalyzed chemoselective reduction of nitroarenes in aqueous medium

Chand, Dillip Kumar,Rai, Randhir

, (2021/08/20)

Abstract: A procedure for practical synthesis of CuNPs from CuSO4·5H2O is established, under appropriate reaction conditions, using rice (Oryza sativa) as an economic source of reducing as well as a stabilizing agent. Optical and microscopic techniques are employed for the characterization of the synthesized CuNPs and the sizes of the particles were found to be in the range of 8 ± 2 nm. The nanoparticles are used as a catalyst for chemoselective reduction of aromatic nitro compounds to corresponding amines under ambient conditions and water as a reaction medium. Graphic abstract: CuNPs are synthesized using hydrolysed rice and used as catalyst for chemoselective reduction of nitroarenes to their corresponding amines in water. [Figure not available: see fulltext.]

Applicability of aluminum amalgam to the reduction of arylnitro groups

Luzzio, Frederick A.,Monsen, Paige J.

supporting information, (2020/11/02)

An array of arylnitro compounds with various functionality were treated with freshly-prepared aluminum amalgam in THF/water solution and resulted in the corresponding arylamines. The Al(Hg)-mediated reductions are relatively rapid with consumption of the amalgam and disappearance of starting material occurring over 20–30 min. The workup of the reductions involves only removal of the insoluble by-products by filtration followed by concentration. Only in some cases is chromatography required to secure the pure product. The desired arylamines are furnished in quantities of 25–100 mg, which in some cases, could be taken on to the next reaction without further purification. Reductions of 4-nitrobenzyl derivatives of carbohydrates or nucleosides were selective in affording the corresponding 4-aminobenzyl products. To show applicability in click chemistry, selected aminobenzyl products are directly azidated to yield products that were then used in click reactions to afford the corresponding 1,2,3-triazoles.

2-Arylamino-6-ethynylpurines are cysteine-targeting irreversible inhibitors of Nek2 kinase

Bayliss, Richard,Boxall, Kathy,Carbain, Benoit,Coxon, Christopher R.,Fry, Andrew M.,Golding, Bernard T.,Griffin, Roger J.,Hardcastle, Ian R.,Harnor, Suzannah J.,Mas-Droux, Corine,Matheson, Christopher J.,Newell, David R.,Richards, Mark W.,Sivaprakasam, Mangaleswaran,Turner, David,Cano, Céline

supporting information, p. 707 - 731 (2020/08/24)

Renewed interest in covalent inhibitors of enzymes implicated in disease states has afforded several agents targeted at protein kinases of relevance to cancers. We now report the design, synthesis and biological evaluation of 6-ethynylpurines that act as covalent inhibitors of Nek2 by capturing a cysteine residue (Cys22) close to the catalytic domain of this protein kinase. Examination of the crystal structure of the non-covalent inhibitor 3-((6-cyclohexylmethoxy-7H-purin-2-yl)amino)benzamide in complex with Nek2 indicated that replacing the alkoxy with an ethynyl group places the terminus of the alkyne close to Cys22 and in a position compatible with the stereoelectronic requirements of a Michael addition. A series of 6-ethynylpurines was prepared and a structure activity relationship (SAR) established for inhibition of Nek2. 6-Ethynyl-N-phenyl-7H-purin-2-amine [IC50 0.15 μM (Nek2)] and 4-((6-ethynyl-7H-purin-2-yl)amino)benzenesulfonamide (IC50 0.14 μM) were selected for determination of the mode of inhibition of Nek2, which was shown to be time-dependent, not reversed by addition of ATP and negated by site directed mutagenesis of Cys22 to alanine. Replacement of the ethynyl group by ethyl or cyano abrogated activity. Variation of substituents on the N-phenyl moiety for 6-ethynylpurines gave further SAR data for Nek2 inhibition. The data showed little correlation of activity with the nature of the substituent, indicating that after sufficient initial competitive binding to Nek2 subsequent covalent modification of Cys22 occurs in all cases. A typical activity profile was that for 2-(3-((6-ethynyl-9H-purin-2-yl)amino)phenyl)acetamide [IC50 0.06 μM (Nek2); GI50 (SKBR3) 2.2 μM] which exhibited >5-10-fold selectivity for Nek2 over other kinases; it also showed > 50% growth inhibition at 10 μM concentration against selected breast and leukaemia cell lines. X-ray crystallographic analysis confirmed that binding of the compound to the Nek2 ATP-binding site resulted in covalent modification of Cys22. Further studies confirmed that 2-(3-((6-ethynyl-9H-purin-2-yl)amino)phenyl)acetamide has the attributes of a drug-like compound with good aqueous solubility, no inhibition of hERG at 25 μM and a good stability profile in human liver microsomes. It is concluded that 6-ethynylpurines are promising agents for cancer treatment by virtue of their selective inhibition of Nek2. This journal is

Process route upstream and downstream products

Process route

N-(3-nitrophenyl)acetanilide
122-28-1

N-(3-nitrophenyl)acetanilide

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
With sodium tetrahydroborate; TPGS-750-M; In tetrahydrofuran; water; at 20 ℃; for 0.5h;
98%
With aluminum amalgam; water; In tetrahydrofuran; at 20 ℃; for 0.5h;
96%
With iron; acetic acid; In neat liquid; at 50 ℃; for 0.25h;
91%
With sodium tetrahydroborate; In water; at 20 ℃; for 4h; chemoselective reaction;
90%
With palladium 10% on activated carbon; hydrazine hydrate; In ethanol;
80%
With sodium tetrahydroborate; palladium 10% on activated carbon; In methanol; at 0 ℃; for 1h;
75%
In water; at 31 - 35 ℃; for 72h; reduction with baker's yeast (Saccharomyces cerevisiae);
59%
With hydrazine hydrate; In ethanol; water; at 150 ℃; for 4h; under 3750.3 - 13501.1 Torr;
59%
With 5% Pd/C; hydrazine; In ethanol; at 95 ℃;
52%
With palladium 10% on activated carbon; ammonium formate; In methanol; at 20 ℃; for 24h; Sealed tube; Inert atmosphere;
48%
With palladium; cyclohexene;
With nickel; ethyl acetate; under 73550.8 Torr; Hydrogenation;
With iron; acetic acid;
With hydrogen; palladium on activated charcoal; In ethanol;
With sodium nitrate; In ethanol; water; at 25 ℃; Product distribution; Mechanism; Kinetics; pH=2.00 (polarographic reduction). Variation of pH.;
With hydrogen; platinum(IV) oxide; In methanol;
With palladium 10% on activated carbon; hydrogen; In methanol; dichloromethane; at 20 ℃; under 760.051 Torr;
With tin(II) chloride dihdyrate; In ethanol; for 16h; Reflux;
acetic acid
64-19-7,77671-22-8

acetic acid

ethyl acetate
141-78-6

ethyl acetate

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
With 1,4-diaza-bicyclo[2.2.2]octane; at 65 - 90 ℃; for 6h; Time; Inert atmosphere;
98.4%
1-(3-aminophenyl)ethanone oxime
6011-18-3

1-(3-aminophenyl)ethanone oxime

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
With chlorosulfonic acid; In toluene; at 90 ℃; for 0.5h;
98%
With tricarallylic acid; at 160 ℃; for 0.0833333h; Inert atmosphere; neat (no solvent);
90%
3-Chloroacetanilide
588-07-8

3-Chloroacetanilide

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate; In 1,4-dioxane; at 80 ℃; for 24h; Inert atmosphere;
48%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
With iron(III)-acetylacetonate; hydrazine hydrate; In methanol; at 150 ℃; Microwave irradiation; Green chemistry;
99%
1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
88.5%
acetic anhydride
108-24-7

acetic anhydride

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
In tetrahydrofuran; at -10 ℃; for 5h;
34.2%
With acetic acid; Reflux;
3-nitro-aniline
99-09-2

3-nitro-aniline

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: palladium on activated charcoal; hydrogen / methanol / 8 h / 20 °C
2: acetic acid / Reflux
With palladium on activated charcoal; hydrogen; acetic acid; In methanol;
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / dichloromethane; methanol / 20 °C / 760.05 Torr
With palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane
2: tin(II) chloride dihdyrate / ethanol / 16 h / Reflux
With tin(II) chloride dihdyrate; triethylamine; In ethanol; dichloromethane;
Multi-step reaction with 2 steps
1: 0.5 h / 20 °C
2: acetic acid; iron / neat liquid / 0.25 h / 50 °C
With iron; acetic acid; In neat liquid;
m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: HCl / H2O / 8 h / pH = 1,5-3,5
2: 20 percent NaCl-solution / pH
With hydrogenchloride; sodium chloride; In water;
N-(3-aminophenyl)-acetamide hydrochloride
621-35-2,59736-00-4

N-(3-aminophenyl)-acetamide hydrochloride

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
Conditions Yield
With sodium chloride; pH ;

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