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Cas Database

4338-06-1

4338-06-1

Identification

  • Molecular Formula:C10H6N2O4

  • EINECS:

Synonyms:Maleimide,N-(p-nitrophenyl)- (6CI,7CI,8CI);1-(4-Nitrophenyl)-1H-pyrrole-2,5-dione;N-(4-Nitrophenyl) maleimide;N-(p-Nitrophenyl)maleimide;NSC 39726;NSC 55656;p-Nitrophenylmaleimide;

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Safety information and MSDS

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:

  • Hazard Statement:

  • 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

  • Manufacture/Brand
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  • Manufacture/Brand:AHH
  • Product Description:1-(4-Nitrophenyl)-pyrrole-2,5-dione 96%
  • Packaging:250g
  • Price:$ 788
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:1-(4-Nitrophenyl)-2,5-dihydro-1H-pyrrole-2,5-dione
  • Packaging:50mg
  • Price:$ 75
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:1-(4-Nitrophenyl)-2,5-dihydro-1H-pyrrole-2,5-dione
  • Packaging:10mg
  • Price:$ 60
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-(4-Nitrophenyl)maleimide >98.0%(HPLC)
  • Packaging:5g
  • Price:$ 173
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1-(4-Nitrophenyl)-1H-pyrrole-2,5-dione
  • Packaging:5g
  • Price:$ 238
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1-(4-Nitrophenyl)-1H-pyrrole-2,5-dione
  • Packaging:1g
  • Price:$ 80
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1-(4-Nitrophenyl)-1H-pyrrole-2,5-dione
  • Packaging:25g
  • Price:$ 430
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  • Manufacture/Brand:Crysdot
  • Product Description:1-(4-Nitrophenyl)-1H-pyrrole-2,5-dione 97%
  • Packaging:25g
  • Price:$ 424
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:1-(4-NITROPHENYL)-1H-PYRROLE-2,5-DIONE 95.00%
  • Packaging:5G
  • Price:$ 1016.4
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:1-(4-NITROPHENYL)-1H-PYRROLE-2,5-DIONE 95.00%
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Relevant articles and documentsAll total 44 Articles be found

Total synthesis of (±)-dysibetaine CPa and analogs

Oikawa, Masato,Sasaki, Shota,Sakai, Michihiro,Ishikawa, Yuichi,Sakai, Ryuichi

, p. 5789 - 5802,14 (2020/09/15)

The syntheses of the marine sponge-derived γ-amino carboxylic acid dysibetaine CPa and five analogs in their racemic forms were successfully performed by taking advantage of an electron-withdrawing N-(4-nitrophenyl) group in the cyclopropanation reaction,

Thermally Sensitive Protecting Groups for Cysteine, and Manufacture and Use Thereof

-

Paragraph 0086; 0089-0090, (2021/02/12)

In a preferred embodiment, there is provided a protecting group for protecting the thiol side chain of a cysteine residue, the protecting group comprising a Diels-Alder cycloadduct of a furan and a maleimide, and optionally, a linker interposed between the thiol side chain and the Diels-Alder cycloadduct.

Functional Porphyrinic Metal–Organic Framework as a New Class of Heterogeneous Halogen-Bond-Donor Catalyst

Chen, Yu-Sheng,Cheng, Qigan,Ma, Shengqian,Nafady, Ayman,Shan, Chuan,Wojtas, Lukasz,Zhang, Weijie,Zhang, X. Peter

supporting information, p. 24312 - 24317 (2021/10/04)

Biomimetic metal-organic frameworks have attracted great attention as they can be used as bio-inspired models, allowing us to gain important insights into how large biological molecules function as catalysts. In this work, we report the synthesis and utilization of such a metal-metalloporphyrin framework (MMPF) that is constructed from a custom-designed ligand as an efficient halogen bond donor catalyst for Diels–Alder reactions under ambient conditions. The implementation of fabricated halogen bonding capsule as binding pocket with high-density C?Br bonds enabled the use of halogen bonding to facilitate organic transformations in their three-dimensional cavities. Through combined experimental and computational studies, we showed that the substrate molecules diffuse through the pores of the MMPF, establishing a host-guest system via the C?Br???π interaction. The formation of halogen bonds is a plausible explanation for the observed boosted catalytic efficiency in Diels–Alder reactions. Moreover, the unique capability of MMPF highlights new opportunities in using artificial non-covalent binding pockets as highly tunable and selective catalytic materials.

Exploiting: Exo and endo furan-maleimide Diels-Alder linkages for the functionalization of organoruthenium complexes

Castonguay, Annie,Haghdoost, Mohammad Mehdi,Poulet, Sylvain,Tcherkawsky, Paul,Tran, Hoang-Van

, p. 2214 - 2218 (2022/02/17)

Diels-Alder cycloadditions involving furans and maleimides are extensively used in organic chemistry and materials synthesis. Given the promising advances of organoruthenium complexes in therapy, we explored the possibility of exploiting such Diels-Alder linkages as a mean to modulate their biological properties. This journal is

Dual organic dyes as a pseudo-redox mediation system to promotion of tandem oxidation /[3+2] cycloaddition reactions under visible light

Koohgard, Mehdi,Hosseinpour, Zeinab,Hosseini-Sarvari, Mona

, (2021/05/10)

An atom- and step-economy protocol has been developed to synthesize some new biologically active pyrrolo[2,1-a]isoquinoline alkaloids via redox mediation system under visible light irradiation. A vast variety of double and triple bonds, as dipolarophiles, treated with in situ generated azomethine ylides to prepare corresponding products in good to excellent yields. This metal-free method effectively promoted oxidation/[3 + 2] cycloaddition/oxidative/aromatization domino reaction without further oxidant using dual organic dyes as pseudo-redox mediation system. Besides, for most of the products, product precipitate was readily separated from reaction media. To the best of our knowledge, this is the first report of dual dyes as a pseudo-redox mediation system.

Process route upstream and downstream products

Process route

1-(4-nitrophenyl)pyrrole-2-carbaldehyde
30186-41-5

1-(4-nitrophenyl)pyrrole-2-carbaldehyde

N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

Conditions
ConditionsYield
Withchromium(VI) oxide;Inacetic acid;at 75 ℃; for 1.5h;
66%
4-(4-nitrophenylamino)-4-oxobut-2-enoic acid
36342-10-6,36847-91-3,37904-21-5

4-(4-nitrophenylamino)-4-oxobut-2-enoic acid

N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

Conditions
ConditionsYield
70%
70%
at 180 ℃;
at 160 ℃; Geschwindigkeit;
at 180 ℃; Geschwindigkeit;
Withsulfuric acid; at 60 ℃;
With1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide;Intetrahydrofuran;at 40 - 70 ℃; for 4.5h; Inert atmosphere;
Withsodium acetate; acetic anhydride; at 100 ℃; for 2h;
Withsodium acetate; acetic anhydride; at 80 ℃; for 1h;
Withsodium acetate; acetic anhydride; at 100 ℃; for 4h;
581.1 mg
(Z)-3-(4-nitro-phenylcarbamoyl)-acrylic acid
36342-10-6

(Z)-3-(4-nitro-phenylcarbamoyl)-acrylic acid

N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

Conditions
ConditionsYield
95%
74%
62%
Withsodium acetate; acetic anhydride; for 8h; Heating;
Multi-step reaction with 2 steps
1: 85 percent / thionyl chloride / CH2Cl2 / Heating
2: 89 percent / Et3N / acetone / 3 h
Withsodium acetate; acetic anhydride; at 60 ℃; for 2h;
Withsulfuric acid; acetic acid; at 60 ℃; for 0.75h;
Withsodium acetate; acetic anhydride; at 80 ℃; for 10h;
3.44 g
3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione
37904-11-3

3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione

N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

Conditions
ConditionsYield
Withtriethylamine;Inacetone;for 3h;
89%
(Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid
80818-24-2

(Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid

N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione
37904-11-3

3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 24 h / Reflux
2: tetrahydrofuran / 2 h / Reflux
3: triethylamine; thionyl chloride / tetrahydrofuran / 6.5 h / 20 °C / Reflux
(Z)-3-(4-nitro-phenylcarbamoyl)-acrylic acid
36342-10-6

(Z)-3-(4-nitro-phenylcarbamoyl)-acrylic acid

N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione
37904-11-3

3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione

Conditions
ConditionsYield
Withthionyl chloride; triethylamine;Intetrahydrofuran;at 20 ℃; for 6.5h; Reflux;
0.611 g
4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione
37904-11-3

3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 2 h / Reflux
2: triethylamine; thionyl chloride / tetrahydrofuran / 6.5 h / 20 °C / Reflux
N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

N-(2-nitrophenyl)maleimide
2973-15-1

N-(2-nitrophenyl)maleimide

N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

Conditions
ConditionsYield
37%
62%
Withbismuth (III) nitrate pentahydrate; acetic anhydride;Indichloromethane;at 23 ℃; regioselective reaction;
40%
maleic anhydride
108-31-6

maleic anhydride

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

Conditions
ConditionsYield
Withacetic acid; at 140 ℃;
81%
Withsodium acetate; acetic anhydride; at 120 ℃; for 0.5h; Microwave irradiation;
62.1%
WithPPA; at 80 ℃; for 15h;
54%
Withsodium acetate; acetic anhydride; at 100 ℃; for 2h;
50%
Withsodium acetate; acetic anhydride;Intetrahydrofuran;at 120 ℃; for 0.5h; Microwave irradiation;
Inert atmosphere;
maleic anhydride; 4-nitro-aniline;Withacetic acid; at 125 ℃; Inert atmosphere;
Withsodium hydrogencarbonate;Inwater;Inert atmosphere;
Withsodium acetate; acetic anhydride; at 80 ℃; for 1h;
Indiethyl ether;at 0 ℃; for 1h;
N-(4-nitrophenyl)maleimide
4338-06-1

N-(4-nitrophenyl)maleimide

Conditions
ConditionsYield

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