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Cas Database

4144-22-3

4144-22-3

Identification

Synonyms:Maleimide,N-tert-butyl- (7CI,8CI);1-(1,1-Dimethylethyl)-1H-pyrrole-2,5-dione;N-tert-Butylmaleimide;

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Safety information and MSDS view more

  • Pictogram(s):

  • 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.

  • 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 view more

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:1-(tert-Butyl)-1H-pyrrole-2,5-dione
  • Packaging:100mg
  • Price:$ 60
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-tert-Butylmaleimide >98.0%(GC)
  • Packaging:5g
  • Price:$ 109
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N-tert-Butylmaleimide >98.0%(GC)
  • Packaging:1g
  • Price:$ 36
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:N-tert-Butylmaleimide 97%
  • Packaging:1g
  • Price:$ 52.6
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1-(tert-Butyl)-1H-pyrrole-2,5-dione >95%
  • Packaging:10g
  • Price:$ 450
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1-(tert-Butyl)-1H-pyrrole-2,5-dione >95%
  • Packaging:5g
  • Price:$ 270
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1-(tert-Butyl)-1H-pyrrole-2,5-dione >95%
  • Packaging:1g
  • Price:$ 90
  • Delivery:In stock
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:N-tert-Butylmaleimide 97%
  • Packaging:1g
  • Price:$ 66
  • Delivery:In stock
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:N-tert-Butylmaleimide 97%
  • Packaging:250mg
  • Price:$ 25
  • Delivery:In stock
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:N-tert-Butylmaleimide 97%
  • Packaging:5g
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Relevant articles and documentsAll total 8 Articles be found

The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation

Li, Shanshan,Song, Gao,Wang, Liang-Liang,Weng, Zhiying,Xu, Guowei,Yang, Weimin,Yang, Yanming,Yang, Yaqing,Zhang, Jiajun,Zuo, Zhili

supporting information, (2020/02/27)

Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.

Cavity-promoted Diels - Alder reactions of unsubstituted naphthalene: Fine reactivity tuning by cavity shrinkage

Fang, Yu,Murase, Takashi,Fujita, Makoto

supporting information, p. 1095 - 1097 (2015/09/02)

By finely tuning the cavity volume of a coordination cage, the Diels - Alder reactivity of aromatic compounds was enhanced. Even unsubstituted naphthalene could be made to undergo the Diels - Alder reaction with N-tert-butylmaleimide, with perfectly controlled syn-selectivity. M6L4 cages with standard and contracted cavities had opposite effects on the reaction: the former favored larger Diels - Alder substrates, whereas the latter favored smaller ones.

Chemical reactivity and antimicrobial activity of N-substituted maleimides

Salewska, Natalia,Boros-Majewska, Joanna,Lcka, Izabela,Chylinska, Katarzyna,Sabisz, Michal,Milewski, Slawomir,Milewska, Maria J.

scheme or table, p. 117 - 124 (2012/04/18)

Several N-substituted maleimides containing substituents of varying bulkiness and polarity were synthesised and tested for antimicrobial and cytostatic activity. Neutral maleimides displayed relatively strong antifungal effect minimum inhibitory concentrations (MICs in the 0.54 g ml-1 range); their antibacterial activity was structure dependent and all were highly cytostatic, with IC50 values below 0.1 g ml-1. Low antimicrobial but high cytostatic activity was noted for basic maleimides containing tertiary aminoalkyl substituents. Chemical reactivity and lipophilicity influenced antibacterial activity of neutral maleimides but had little if any effect on their antifungal and cytostatic action. N-substituted maleimides affected biosynthesis of chitin and β(1,3)glucan, components of the fungal cell wall. The membrane enzyme, β(1,3)glucan synthase has been proposed as a putative primary target of N-ethylmaleimide and some of its analogues in Candida albicans cells.

Process route upstream and downstream products

Process route

N-tert-butyl maleamic acid
134276-00-9

N-tert-butyl maleamic acid

N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

Conditions
Conditions Yield
With sodium acetate; acetic anhydride; Heating;
With sodium acetate; acetic anhydride; at 110 ℃; for 4h;
With sodium acetate; In acetic anhydride; at 120 ℃; for 0.5h; Microwave irradiation;
C<sub>8</sub>H<sub>12</sub>ClNO<sub>2</sub>

C8H12ClNO2

N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

Conditions
Conditions Yield
With N,N-dimethyl-aniline; at 50 ℃; for 4.83333h; Temperature;
(Z)-4-(tert-butylamino)-4-oxo-2-butenoic acid
32350-46-2

(Z)-4-(tert-butylamino)-4-oxo-2-butenoic acid

N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

Conditions
Conditions Yield
With acetic anhydride; triethylamine; In butanone; for 6h; Heating;
71.3%
C<sub>10</sub>H<sub>8</sub>*C<sub>8</sub>H<sub>11</sub>NO<sub>2</sub>*4C<sub>18</sub>H<sub>12</sub>N<sub>6</sub>*Pd<sup>(8+)</sup>*C<sub>30</sub>H<sub>28</sub>N<sub>2</sub>*12NO<sub>3</sub><sup>(1-)</sup>

C10H8*C8H11NO2*4C18H12N6*Pd(8+)*C30H28N2*12NO3(1-)

N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

4C<sub>18</sub>H<sub>12</sub>N<sub>6</sub>*Pd<sup>(8+)</sup>*C<sub>30</sub>H<sub>28</sub>N<sub>2</sub>*12NO<sub>3</sub><sup>(1-)</sup>*C<sub>10</sub>H<sub>8</sub>

4C18H12N6*Pd(8+)*C30H28N2*12NO3(1-)*C10H8

Conditions
Conditions Yield
In water;
maleic anhydride
108-31-6

maleic anhydride

<i>tert</i>-butylamine
75-64-9

tert-butylamine

N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

Conditions
Conditions Yield
N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

Conditions
Conditions Yield
3-bromo-2-thiophenecarboxaldehyde
930-96-1

3-bromo-2-thiophenecarboxaldehyde

N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

DL-alanine ethyl ester hydrochloride
617-27-6

DL-alanine ethyl ester hydrochloride

C<sub>18</sub>H<sub>23</sub>BrN<sub>2</sub>O<sub>4</sub>S

C18H23BrN2O4S

Conditions
Conditions Yield
With triethylamine; In acetonitrile; at 110 ℃; for 6h; diastereoselective reaction; Sealed tube;
N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

Ac-Cys-OMe
7652-46-2

Ac-Cys-OMe

trifluoroacetic acid
76-05-1

trifluoroacetic acid

C<sub>13</sub>H<sub>21</sub>N<sub>3</sub>O<sub>4</sub>S*C<sub>2</sub>HF<sub>3</sub>O<sub>2</sub>

C13H21N3O4S*C2HF3O2

Conditions
Conditions Yield
Ac-Cys-OMe; With ammonium hydroxide; In water; toluene; at 20 ℃; for 19h; Inert atmosphere;
With triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
N-tert-butylmaleimide; trifluoroacetic acid; Further stages;
6%
N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

2-chlorophenacyl bromide
5000-66-8

2-chlorophenacyl bromide

2-(tert-butyl)-6-chloro-3a,9b-dihydro-1H-benzo[e]isoindole-1,3,5(2H,4H)-trione

2-(tert-butyl)-6-chloro-3a,9b-dihydro-1H-benzo[e]isoindole-1,3,5(2H,4H)-trione

Conditions
Conditions Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); dipotassium hydrogenphosphate; In acetonitrile; at 20 ℃; for 20h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;
51%
N-tert-butylmaleimide
4144-22-3

N-tert-butylmaleimide

Nitrosobenzene
586-96-9

Nitrosobenzene

1-Bromo-2-phenylacetylene
932-87-6

1-Bromo-2-phenylacetylene

3-(bromo(phenyl)methylene)-5-(tert-butyl)-2-phenyltetrahydro-4H-pyrrolo[3,4-d]isoxazole-4,6(5H)-dione

3-(bromo(phenyl)methylene)-5-(tert-butyl)-2-phenyltetrahydro-4H-pyrrolo[3,4-d]isoxazole-4,6(5H)-dione

3-(bromo(phenyl)methylene)-5-(tert-butyl)-2-phenyltetrahydro-4H-pyrrolo[3,4-d]isoxazole-4,6(5H)-dione

3-(bromo(phenyl)methylene)-5-(tert-butyl)-2-phenyltetrahydro-4H-pyrrolo[3,4-d]isoxazole-4,6(5H)-dione

Conditions
Conditions Yield
In water; ethyl acetate; at 40 ℃; for 11h; Overall yield = 76 percent; Overall yield = 67 mg; stereoselective reaction; Inert atmosphere; Schlenk technique; Green chemistry;
44 % de

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