(R)-(+)-N-(1-Phenylethyl)maleimide

Base Information

• Chemical Name: (R)-(+)-N-(1-Phenylethyl)maleimide
• CAS No.: 6129-15-3
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.225
• European Community (EC) Number: 622-320-5
• DSSTox Substance ID: DTXSID50350027
• Nikkaji Number: J74.427A
• Wikidata: Q82125723
• Mol file: 6129-15-3.mol

Synonyms:(R)-(+)-N-(1-Phenylethyl)maleimide;6129-15-3;1-[(1R)-1-phenylethyl]pyrrole-2,5-dione;(R)-1-(1-Phenylethyl)-1H-pyrrole-2,5-dione;SCHEMBL1795649;DTXSID50350027;(1r)-N-(1-phenylethyl)maleimide;N-[(R)-alpha-Methylbenzyl]maleimide;AKOS024281350;(R)-(+)-N-(1-Phenylethyl)maleimide, 97%;E79360;1-[(1R)-1-phenylethyl]-2,5-dihydro-1H-pyrrole-2,5-dione

Chemical Property of (R)-(+)-N-(1-Phenylethyl)maleimide

Chemical Property:

• Vapor Pressure: 0.000116mmHg at 25°C
• Refractive Index: n20/D 1.556(lit.)
• Boiling Point: 110-115 °C/0.004 mmHg(lit.)
• PKA: -2.37±0.20(Predicted)
• Flash Point: 113 °C
• PSA: 37.38000
• Density: 1.138 g/mL at 25 °C(lit.)
• LogP: 1.61050
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 285

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(+)-N-(1-Phenylethyl)maleimide 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)N2C(=O)C=CC2=O
• Isomeric SMILES: C[C@H](C1=CC=CC=C1)N2C(=O)C=CC2=O
• Uses: This optically active maleimide undergoes radical copolymerization with styrene to yield a ~1:1 copolymer (~98%). Vinyl copolymers with asymmetric main chains can be used as nonlinear optical materials. Dienophile for diastereoselective Diels-Alder reactions.

Technology Process of (R)-(+)-N-(1-Phenylethyl)maleimide

There total 10 articles about (R)-(+)-N-(1-Phenylethyl)maleimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

C12H13NO3 (108088-06-8) → N-(S)-(-)-α-Methylbenzylmaleimide (6129-15-3,60925-76-0,94132-27-1,89143-10-2)

Guidance literature:

With tetrabutylammomium bromide; sodium carbonate; dimethyl sulfate; In water; 1,2-dichloro-ethane; at 20 ℃; for 8h;

Reference yield: 85.0%

maleic anhydride (108-31-6) + (R)-1-phenyl-ethyl-amine (3886-69-9) → (R)-1-(1-phenylethyl)-1H-pyrrole-2,5-dione (60925-76-0,89143-10-2,94132-27-1,6129-15-3)

Guidance literature:

With 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide; In toluene; at 80 ℃; for 4h;

DOI:10.1055/s-0028-1087672

Reference yield: 78.0%

N-(1-phenylethyl)maleamidic acid (33139-83-2,33139-84-3,108088-06-8,62561-81-3) → N-(S)-(-)-α-Methylbenzylmaleimide (6129-15-3,60925-76-0,94132-27-1,89143-10-2)

Guidance literature:

With sodium acetate; acetic anhydride; at 90 ℃;

upstream raw materials:

N-(1-phenylethyl)maleamidic acid

rac-methylbenzylamine

C₁₂H₁₃NO₃

N-(R)-(+)-1-phenylethylmaleamic acid

Downstream raw materials:

4-Methyl-2-(1-phenyl-ethyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

5-Phenyl-2-(1-phenyl-ethyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

2-(1-Phenyl-ethyl)-5-trimethylsilanyloxy-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

6-Methoxy-2-(1-phenyl-ethyl)-4-trimethylsilanyloxy-3a,4,7,7a-tetrahydro-isoindole-1,3-dione

Refernces

Synthesis and stereochemistry of some novel dihydropyrrolo[3,4-c]pyrazoles

10.1007/s00706-011-0618-z

The research presents the synthesis and stereochemistry of eleven novel dihydropyrrolo[3,4-c]pyrazole derivatives, which were obtained through the 1,3-dipolar cycloaddition reaction of chiral (1R)-N(1-phenylethyl)maleimide with C,N-aryl-substituted nitrilimines. The reaction yielded a regioisomeric mixture of cycloadducts, which were separable in some instances. The experiments involved the preparation of hydrazones and hydrazonyl chlorides from para-substituted aromatic aldehydes and hydrazines, followed by the cycloaddition reaction with the chiral maleimide in dry acetonitrile at room temperature. The structures and stereochemistry of the resulting cycloadducts were elucidated using infrared (IR) spectroscopy, proton and carbon-13 nuclear magnetic resonance (NMR), mass spectrometry, X-ray diffraction, and elemental analysis, providing comprehensive characterization of the novel compounds.

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