37629-90-6

Usage

Yellow crystalline solid

This describes the physical appearance of the compound, which is a yellow solid with a crystalline structure.

Molecular weight

269.3 g/mol This is the mass of one mole of the compound, measured in grams.

Uses

Organic synthesis, building block for pharmaceuticals and agrochemicals, intermediate in the synthesis of fine chemicals, and intermediate in the production of polymer additives This lists some of the common uses of the compound in various industries.

Photoluminescent properties

This describes the compound's ability to emit light when exposed to certain types of radiation, which may make it useful in optoelectronic applications.

Skin and eye irritant

This indicates that the compound can cause irritation to the skin and eyes, and that appropriate safety precautions should be taken when handling it.

Harmful if ingested or inhaled

This warns that the compound can be harmful if it is swallowed or breathed in, and that appropriate safety measures should be taken to avoid exposure.

Upstream product

• 50882-23-0 α'-nitro-4-methoxy-trans-stilbene 
• 622-42-4 1-nitro-1-phenylmethane 
• 16928-40-8 2,3,6,7-tetrahydro-2-(4-methoxylphenyl)-3-propylcyclo-penta[e][1,3]oxazin-4(5H)-one 
• 59019-40-8 1-[(1Z)-2-bromo-2-nitroethenyl]-4-methoxybenzene 
• 98-80-6 phenylboronic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 3910-55-2 N-(p-methoxybenzylidene)butylamine 

Downstream Products

• 50882-23-0 α'-nitro-4-methoxy-trans-stilbene 
• 92664-25-0 α-hydroxyimino-α-(p-methoxyphenyl)acetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 874-90-8 4-methoxybenzonitrile 
• 1337927-85-1 3-(4'-methoxyphenyl)-4-phenyl-1H-pyrrole-2-carboxaldehyde 
• 1337927-93-1 3-(4'-methoxyphenyl)-4-phenyl-1H-pyrrol-2(5H)-one 
• 1337927-73-7 N-methoxy-3-(4'-methoxyphenyl)-N-methyl-4-phenyl-1H-pyrrole-2-carboxamide 

Relevant academic research and scientific papers

Synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones utilizing pyrrole weinreb amides

A regiocontrolled synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones has been achieved in three steps from 1,2-diaryl-1-nitroethenes with pyrrole-2-carboxamides (pyrrole Weinreb amides) serving as the key linchpin intermediates. Two different methods for the preparation of the requisite nitroalkenes were investigated: (1) modified Henry reaction between arylnitromethanes and arylimines; and (2) Suzuki-Miyaura cross-coupling reaction of 2-aryl-1-bromo-1-nitroethenes with arylboronic acids. Some difficulty was encountered in the preparation of arylnitromethanes, thus leading to the exploration of a cross-coupling strategy that proved more useful. A Barton-Zard pyrrole cyclocondensation reaction between 1,2-diaryl-1-nitroethenes and N-methoxy-N-methyl-2-isocyanoacetamide gave the corresponding pyrrole Weinreb amides, which were then converted into the desired 3-pyrrolin-2-ones in two steps. Overall, this method allowed for the construction of 3,4-diaryl-3- pyrrolin-2-ones with complete regiocontrol of the substituents with respect to the lactam carbonyl. The utility of this synthetic methodology was demonstrated by the preparation of eight unsymmetrical and symmetrical 3,4-diaryl-3-pyrrolin- 2-ones including the N-H lactam analogue of the selective COX-II inhibitor, rofecoxib.

Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes

(Z)-α-Bromo-β-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)4 as catalyst to afford (E)-α,β-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of α-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful α,β-disubstituted nitroethylenes.