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6025-60-1

6025-60-1

Identification

Synonyms:2-(1H-Pyrrol-1-yl)phenylamine;o-(1-Pyrrolyl)aniline;N-(2-Aminophenyl)pyrrole;NSC 130753;Pyrrole,1-(o-aminophenyl)- (7CI);1-(2-Aminophenyl)pyrrole;1-(o-Aminophenyl)pyrrole;2-(1-Pyrrolyl)aniline;2-(1H-Pyrrol-1-yl)benzenamine;2-Pyrrol-1-ylaniline;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH312 Harmful in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H332 Harmful if inhaled 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.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. 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

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:2-(1H-Pyrrol-1-yl)aniline
  • Packaging:100mg
  • Price:$ 60
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:1-(2-Aminophenyl)pyrrole 95%
  • Packaging:1 g
  • Price:$ 120
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:1-(2-Aminophenyl)pyrrole 95%
  • Packaging:5 g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1-(2-Aminophenyl)pyrrole ≥98%
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  • Price:$ 44.4
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1-(2-Aminophenyl)pyrrole ≥98%
  • Packaging:10g
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:[2-(1H-Pyrrol-1-yl)phenyl]amine
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:[2-(1H-Pyrrol-1-yl)phenyl]amine
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:[2-(1H-Pyrrol-1-yl)phenyl]amine
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  • Manufacture/Brand:Crysdot
  • Product Description:2-(1H-Pyrrol-1-yl)aniline 95+%
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  • Manufacture/Brand:Chemenu
  • Product Description:[2-(1H-Pyrrol-1-yl)phenyl]amine 95%+
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Relevant articles and documentsAll total 50 Articles be found

N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones

Ding, Chengcheng,Li, Shichen,Ma, Chen,Ren, Jianing,Wang, Yishou

, p. 16848 - 16857 (2021/12/06)

N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.

Synthesis of 4-Aryl Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Oxidative Coupling from an Unactivated Methyl Arene

Ahn, Jiwon,Lee, Seok Beom,Song, Injae,Chun, Simin,Oh, Dong-Chan,Hong, Suckchang

, p. 7390 - 7402 (2021/06/21)

Herein, we describe the direct synthesis of pyrrolo[1,2-α]quinoxaline via oxidative coupling between methyl arene and 1-(2-aminophenyl) pyrroles. Oxidation of the benzylic carbon of the methyl arene was achieved by di-t-butyl peroxide in the presence of an iron catalyst, followed by conversion to an activated aldehyde in situ. Oxygen played a crucial role in the oxidation process to accelerate benzaldehyde formation. Subsequent Pictet-Spengler-type annulation completed the quinoxaline structure. The protocol tolerated various kinds of functional groups and provided 22 4-aryl pyrrolo[1,2-α]quinoxalines when various methyl arene derivatives were used. The developed method proceeded in air, and all catalysts, reagents, and solvents were easily accessible.

Simple and green synthesis of benzimidazoles and pyrrolo[1,2-: A] quinoxalines via Mamedov heterocycle rearrangement

Li, Shichen,Feng, Lei,Ma, Chen

supporting information, p. 9320 - 9323 (2021/06/14)

A method for the synthesis of coupling compounds of benzimidazoles and pyrrolo[1,2-a]quinoxalines via Mamedov Heterocycle Rearrangement is reported here. This method was conducted at room temperature and only solvent (HOAc) was required. A series of 4-(1H-benzo[d]imidazol-2-yl)pyrrolo[1,2-a]quinoxaline derivatives were obtained in moderate to good yields.

PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions

Ding, Chengcheng,Feng, Kaili,Li, Shichen,Ma, Chen

supporting information, p. 5542 - 5548 (2021/08/16)

A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is

Synthesis of oxazolidinones through ring-opening and annulation of vinylene carbonate with 2-pyrrolyl/indolylanilines under Rh(iii) catalysis

Hu, Fang-Peng,Zhang, Xue-Guo,Wang, Meng,Wang, He-Song,Huang, Guo-Sheng

supporting information, p. 11980 - 11983 (2021/12/01)

Herein, we have developed a rhodium-catalyzed C-H functionalization and subsequent intramolecular ring-opening/cyclization of vinylene carbonate with 2-pyrrolyl/indolylanilines, which leads to oxazolidinones in moderate to good yields. In this transformation, vinylene carbonate only eliminates one oxygen atom rather than -CO3 or CO2. Furthermore, some control experiments are conducted to elucidate the reaction mechanism. This journal is

Process route upstream and downstream products

Process route

cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

2-nitro-aniline
88-74-4

2-nitro-aniline

2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

Conditions
Conditions Yield
With hydrogen; In neat (no solvent); at 120 ℃; for 36h; under 30003 Torr; Autoclave; Green chemistry;
60%
With acetic acid; for 2h; Reflux;
cis,trans-2,5-dimethoxytetrahydrofuran; 2-nitro-aniline; With acetic acid; for 2h; Reflux;
With iron; ammonium chloride; In water; for 4h; Reflux;
cis,trans-2,5-dimethoxytetrahydrofuran; 2-nitro-aniline; With acetic acid; for 2h; Reflux;
With iron; ammonium chloride; In water; for 4h; Reflux;
cis,trans-2,5-dimethoxytetrahydrofuran; 2-nitro-aniline; With acetic acid; for 3h; Reflux;
With iron; ammonium chloride; In water; for 5h; Reflux;
In acetic acid; Reflux;
2-bromoaniline
615-36-1

2-bromoaniline

2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

Conditions
Conditions Yield
With potassium phosphate; copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; In toluene; at 110 ℃; for 24h;
82%
2-nitro-aniline
88-74-4

2-nitro-aniline

2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: AcOH
2: BiCl3; NaBH4 / ethanol
With bismuth(III) chloride; sodium tetrahydroborate; acetic acid; In ethanol; 1: Clauson-Kaas reaction;
Multi-step reaction with 2 steps
1: acetic acid / Heating
2: BiCl3-NaBH4 / ethanol
With bismuth(III) chloride; sodium tetrahydroborate; acetic acid; In ethanol; 1: Clauson-Kaas reaction;
Multi-step reaction with 2 steps
1: AcOH / Heating
2: BiCl3; NaBH4 / ethanol
With bismuth(III) chloride; sodium tetrahydroborate; acetic acid; In ethanol; 1: Clauson-Kaas reaction;
Multi-step reaction with 2 steps
1: acetic acid
2: NaBH4-BiCl3 / ethanol
With bismuth(III) chloride; sodium tetrahydroborate; In ethanol; acetic acid; 1: Condensation / 2: Reduction;
Multi-step reaction with 2 steps
1: 82 percent / acetic acid / 0.13 h / Heating; Irradiation
2: 70 percent / BiCl3, NaBH4 / ethanol / 2 h / Ambient temperature
With bismuth(III) chloride; sodium tetrahydroborate; In ethanol; acetic acid;
Multi-step reaction with 2 steps
1: acetic acid / Microwave irradiation; Heating
2: copper(II) sulfate; sodium tetrahydroborate / ethanol / 20 °C
With sodium tetrahydroborate; copper(II) sulfate; acetic acid; In ethanol; 1: |Clauson-Kaas Synthesis;
Multi-step reaction with 2 steps
1: acetic acid / Reflux
2: bismuth(III) chloride; sodium tetrahydroborate / ethanol
With bismuth(III) chloride; sodium tetrahydroborate; acetic acid; In ethanol;
Multi-step reaction with 2 steps
1: acetic acid / 1 h / 120 °C / Inert atmosphere
2: bismuth(III) chloride; sodium tetrahydroborate / ethanol / 3 h / 0 - 20 °C / Inert atmosphere
With bismuth(III) chloride; sodium tetrahydroborate; acetic acid; In ethanol;
Multi-step reaction with 2 steps
1: hydrogenchloride / water; 1,4-dioxane / 0.08 h / 110 °C
2: tin(II) chloride dihdyrate / ethyl acetate / 2 h / Reflux
With hydrogenchloride; tin(II) chloride dihdyrate; In 1,4-dioxane; water; ethyl acetate;
Multi-step reaction with 2 steps
1: acetic acid / Heating
2: copper(II) sulfate; sodium tetrahydroborate / ethanol / 20 °C
With sodium tetrahydroborate; copper(II) sulfate; acetic acid; In ethanol; 1: |Clauson-Kaas Synthesis;
Multi-step reaction with 2 steps
1: acetic acid / 2 h / 120 °C
2: ammonium chloride / water / 4 h / Reflux
With ammonium chloride; acetic acid; In water;
Multi-step reaction with 2 steps
1: acetic acid / Microwave irradiation; Heating
2: copper(II) sulfate; sodium tetrahydroborate / ethanol / 20 °C
With sodium tetrahydroborate; copper(II) sulfate; acetic acid; In ethanol; 1: |Clauson-Kaas Synthesis;
Multi-step reaction with 2 steps
1: acetic acid / Microwave irradiation; Heating
2: copper(II) sulfate; sodium tetrahydroborate / ethanol / 20 °C
With sodium tetrahydroborate; copper(II) sulfate; acetic acid; In ethanol; 1: |Clauson-Kaas Synthesis;
Multi-step reaction with 2 steps
1: acetic acid / 24 h / Reflux
2: sodium tetrahydroborate; bismuth(III) chloride / ethanol / 3 h / 0 - 20 °C
With bismuth(III) chloride; sodium tetrahydroborate; acetic acid; In ethanol; 1: |Clauson-Kaas Synthesis;
Multi-step reaction with 2 steps
1: acetic acid / 1 h / Reflux
2: copper(ll) sulfate pentahydrate; sodium tetrahydroborate / ethanol / 1 h / 0 - 20 °C
With sodium tetrahydroborate; copper(ll) sulfate pentahydrate; acetic acid; In ethanol;
Multi-step reaction with 2 steps
1: acetic acid / 4.7 h / Inert atmosphere; Reflux
2: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 4 h / 20 °C / 750.08 Torr
With 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid; In methanol;
Multi-step reaction with 2 steps
1: acetic acid / Microwave irradiation
2: copper(II) sulfate; sodium tetrahydroborate / ethanol / 20 °C
With sodium tetrahydroborate; copper(II) sulfate; acetic acid; In ethanol; 1: |Clauson-Kaas Synthesis;
Multi-step reaction with 2 steps
1: acetic acid / 1.5 h / Reflux
2: hydrazine hydrate; hydrogenchloride; palladium 10% on activated carbon / ethanol; water / 5.5 h / 20 °C
With hydrogenchloride; palladium 10% on activated carbon; hydrazine hydrate; acetic acid; In ethanol; water;
Multi-step reaction with 2 steps
1: acetic acid / Reflux
2: iron; ammonium chloride / water / Reflux
With iron; ammonium chloride; acetic acid; In water;
Multi-step reaction with 2 steps
1: acetic acid / 2 h / 120 °C
2: iron; ammonium chloride / water / 4 h / 100 °C
With iron; ammonium chloride; acetic acid; In water;
Multi-step reaction with 2 steps
1: acetic acid / 2 h / 120 °C
2: ammonium chloride; iron / water / 4 h / Reflux
With iron; ammonium chloride; In water; acetic acid;
1-(2-nitrophenyl)-1H-pyrrole
33265-60-0

1-(2-nitrophenyl)-1H-pyrrole

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

Conditions
Conditions Yield
With acetic acid; In ethanol; ethyl acetate;
2-iodophenylamine
615-43-0

2-iodophenylamine

2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

Conditions
Conditions Yield
With potassium phosphate; copper(l) iodide; N,N-dimethylethylenediamine; In toluene; at 110 ℃; for 24h; Inert atmosphere;
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In toluene; at 110 ℃; for 2h; Inert atmosphere;
C<sub>4</sub>H<sub>6</sub>BNO<sub>2</sub>

C4H6BNO2

2-iodophenylamine
615-43-0

2-iodophenylamine

2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

Conditions
Conditions Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate; In 1,4-dioxane; water; at 65 ℃; Schlenk technique; Inert atmosphere;
C4H6BNO2; 2-iodophenylamine; With potassium carbonate; In 1,2-dimethoxyethane; water; at 20 ℃; for 0.5h; Inert atmosphere;
With bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 80 ℃; Inert atmosphere;
(2S,4EZ)-1-(tert-butoxycarbonyl)-4-(ethoxyimino)-2-pyrrolidinecarboxylic acid

(2S,4EZ)-1-(tert-butoxycarbonyl)-4-(ethoxyimino)-2-pyrrolidinecarboxylic acid

2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

4-(ethoxyimino)-N1-pentyl-N2-[2(1H-pyrrol-1-yl)phenyl]-1,2-pyrrolidinedicarboxamide

4-(ethoxyimino)-N1-pentyl-N2-[2(1H-pyrrol-1-yl)phenyl]-1,2-pyrrolidinedicarboxamide

Conditions
Conditions Yield
2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

Conditions
Conditions Yield
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In toluene; at 110 ℃; for 24h; Inert atmosphere; Sealed tube;
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: potassium carbonate; hexamethylenetetramine; copper(l) iodide / N,N-dimethyl-formamide / 24 h / 130 °C
2: hydrazine hydrate; 5%-palladium/activated carbon / ethanol / 8.5 h / Reflux
With copper(l) iodide; hexamethylenetetramine; 5%-palladium/activated carbon; potassium carbonate; hydrazine hydrate; In ethanol; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: copper(l) iodide; caesium carbonate; hexamethylenetetramine / N,N-dimethyl-formamide / 20 h
2: palladium on activated charcoal; hydrazine hydrate / ethanol / 8 h / Reflux; Heating
With copper(l) iodide; hexamethylenetetramine; palladium on activated charcoal; caesium carbonate; hydrazine hydrate; In ethanol; N,N-dimethyl-formamide;
2-(1H-pyrrol-1-yl)aniline
6025-60-1

2-(1H-pyrrol-1-yl)aniline

Conditions
Conditions Yield
pyrrole; 1-fluoro(chloro)-2-nitrobenzene; With sodium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 1.5h;
With tin(II) chloride dihdyrate; In ethyl acetate; at 20 ℃; for 18h;

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