96000-21-4

Basic information

• Product Name: (E)-p-methylcinnamyl chloride
• Synonyms: (E)-p-methylcinnamyl chloride
• CAS NO: 96000-21-4
• Molecular Weight: 166.65
• Mol File: 96000-21-4.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (E)-p-methylcinnamyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-p-methylcinnamyl chloride(96000-21-4)
• EPA Substance Registry System: (E)-p-methylcinnamyl chloride(96000-21-4)

Safety Data

• Hazardous Substances Data: 96000-21-4(Hazardous Substances Data)

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 58824-48-9 1-(4-methylphenyl)-2-propen-1-ol 
• 15851-89-5 (E)-p-methylcinnamoyl chloride 
• 1866-39-3 trans-p-methylcinnamic acid 
• 1866-39-3 4-methylcinnamic acid 
• 7560-43-2 methyl 3-(4-methylphenyl)acrylate 
• 1504-75-2 3-(4-methylphenyl)acrylaldehyde 
• 122058-30-4 4-methylcinnamyl alcohol 
• 122058-30-4 p-methylcinnamyl alcohol 
• 2749-96-4 4-methylphenylallene 
• 97585-04-1 ethyl (E)-3-(4-methylphenyl)acrylate 

Downstream Products

• 30779-92-1 (E)-3-(4-methylbenzylidene)-4-chromanone 
• 1338068-67-9 1-methyl-4-((3R,4R)-4-methylhexa-1,5-dien-3-yl)benzene 
• 1464149-41-4 (E)-(3-(p-tolyl)allyl)(trifluoromethyl)sulfane 
• 1616917-70-4 C₂₂H₂₇BO₃ 
• 1427549-02-7 (S)-4,4,5,5-tetramethyl-2-(4-p-tolylhexa-1,5-dien-2-yl)-1,3,2-dioxaborolane 
• 1076239-10-5 (2E,4E)-methyl 2-phenyl-5-p-tolylpenta-2,4-dienoate 

Relevant articles and documents

Lanthanide-Catalyzed Tandem Addition of Amines to Cyanoalkenes: Synthesis of Cyclic Amidines

A tandem insertion of aliphatic nitriles and unactivated alkenes to the N-H bond of secondary aliphatic amines catalyzed by simple trialkyl rare-earth metal complexes was disclosed. This reaction provides a highly atom-economic and stereoselective way to a range of cyclic amidines under mild reaction conditions.

Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. We report a photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes. Quantum mechanical calculations (uM06-2X and DLPNO), including TD-DFT calculations, and experimental studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cla￠ radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. We anticipate that the use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity.

PdII/Novel Chiral Cinchona Alkaloid Oxazoline-Catalyzed Enantioselective Oxidative Cyclization of Aromatic Alkenyl Amides

A highly enantioselective PdII-catalyzed aza-Wacker oxidation tandem cyclization of aromatic nitrogen-containing dienes has been achieved in the presence of novel chiral cinchona alkaloid oxazoline ligands for the first time, affording chiral dihydroindole nitrogen-containing polycyclic compounds with good yields (up to 83 %), high diastereoselectivities (> 95:5 dr), and excellent enantioselectivities (up to 97 % ee).