2-methylenecyclopropane-1-carbaldehyde

Base Information

• Chemical Name: 2-methylenecyclopropane-1-carbaldehyde
• CAS No.: 142423-24-3
• Molecular Formula: C₅H₆O
• Molecular Weight: 82.102

Synonyms:

Chemical Property of 2-methylenecyclopropane-1-carbaldehyde

Chemical Property:

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Technology Process of 2-methylenecyclopropane-1-carbaldehyde

There total 1 articles about 2-methylenecyclopropane-1-carbaldehyde 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:

2-methylene-cyclopropanecarboxylic acid ethyl ester (18941-94-1) → (2-hydroxymethyl)methylenecyclopropane (29279-66-1) + 2-methylenecyclopropane-1-carbaldehyde (142423-24-3)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/j.bmc.2007.11.082

Reference yield: 53.0%

2-methylenecyclopropane-1-carbaldehyde (142423-24-3) → (R*)-<(1S*)-(Methylidenecyclopropyl)>phenylmethanol

Guidance literature:

In diethyl ether; for 2h; Heating;

DOI:10.1021/jo00097a066

Reference yield: 53.0%

potassium cyanide (151-50-8) + ammonium carbonate (506-87-6,6721-33-1,10361-29-2) + 2-methylenecyclopropane-1-carbaldehyde (142423-24-3) → 5-(2-methylenecyclopropyl)imidazolidine-2,4-dione (502150-92-7)

Guidance literature:

In ethanol; at 58 - 60 ℃; for 24h;

DOI:10.1055/s-2006-926320

upstream raw materials:

2-methylene-cyclopropanecarboxylic acid ethyl ester

Downstream raw materials:

(R*)-<(1S*)-(Methylidenecyclopropyl)>cyclohexylmethanol

(R*)-<(1R*)-(Methylidenecyclopropyl)>cyclohexylmethanol

5-(2-methylenecyclopropyl)imidazolidine-2,4-dione

(2-methylenecyclopropyl)glycine

Refernces

Palladium-catalyzed reactions of 3-substituted methylenecyclopropanes

10.1002/ejoc.201001082

The research presents a comprehensive study on the palladium-catalyzed reactions of 3-substituted methylenecyclopropanes (MCPs), focusing on the effects of substituents such as hydroxymethyl or formyl groups on the reaction outcomes. The purpose of the study was to explore the synthetic potential of these MCPs under varying conditions, including the presence or absence of an acid source like acetic acid. The conclusions drawn from the research indicated that Pd-catalyzed reactions of methylenecyclopropylcarbinols (Z)-1 in the presence of acetic acid yielded 2-methylene-but-3-enyl esters 4 in moderate yields, while Pd alone catalyzed the isomerization of (E)-1 to form pent-4-enals 3 in good yields. The reactions of methylenecyclopropanecarbaldehydes (E)-5 and (Z)-5 under Pd catalysis and acetic acid presence resulted in different products, with (E)-5 leading to penta-2,4-dienals 6 and (Z)-5 leading to 2-(3-formylpenta-2,4-dienylidene)cyclopropanecarbaldehydes 7. The study elucidated plausible mechanisms for these transformations based on the results and control experiments. Key chemicals used in the process included Pd(PPh3)4 as the catalyst, AsPh3 as a ligand, and variously substituted MCPs such as methylenecyclopropylcarbinols 1 and methylenecyclopropanecarbaldehydes 5.

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