1075-77-0

Usage

InChI:InChI=1/C9H7ClO/c10-9-5-3-8(4-6-9)2-1-7-11/h1-7H/b2-1+

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 75-07-0 acetaldehyde 
• 70326-38-4 (Z)-3-(4-Chloro-phenyl)-1-(2-thioxo-thiazolidin-3-yl)-propenone 
• 36382-28-2 1-Chloro-4-(1,3,3-triethoxy-propyl)-benzene 
• 495-48-7 azoxybenzene 
• 24583-70-8 3-(4-chlorophenyl)-2-propene-1-ol 
• 5909-74-0 N-phenyl-C-(4-chlorophenyl)nitrone 
• 603-35-0 triphenylphosphine 
• 637-87-6 1-Chloro-4-iodobenzene 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 107-18-6 allyl alcohol 
• 106485-15-8 p-chlorocinnamaldehyde diethylacetal 
• 35086-79-4 p-chlorocinnamoyl chloride 
• 1615-02-7 p-chlorocinnamic acid 

Downstream Products

• 61712-99-0 1,5-bis-(4-chloro-phenyl)-penta-2,4-dien-1-one 
• 40978-57-2 C₁₀H₁₁ClN₄ 
• 24583-70-8 3-(4-chlorophenyl)-2-propene-1-ol 
• 116016-37-6 5-(p-chlorocinnamylidene)rhodanine 
• 138958-35-7 5-[(1E,3E)-4-(4-Chloro-phenyl)-buta-1,3-dienyl]-2,2-dimethyl-furan-3-one 
• 93626-92-7 (2E)-3-(4-chlorophenyl)acrylaldehyde O-methyl oxime 
• 120360-27-2 1,10-bis(p-chlorophenyl)deca-1,3,5,7,9-pentaene 
• 120360-28-3 1,12-bis(p-chlorophenyl)dodeca-1,3,5,7,9,11-hexaene 
• 75677-02-0 3-(4-chlorophenyl)propionaldehyde 
• 81981-17-1 3-acetoxy-3-cyano-1-(4-chlorophenyl)propene 
• 233760-07-1 p-chlorocinnamaldehyde ethylene acetal 
• 81981-18-2 (E)-4-(4-chlorophenyl)but-3-enenitrile 
• 87639-25-6 2-[(E)-2-(4-Chloro-phenyl)-vinyl]-pent-4-ynenitrile 
• 103979-29-9 para-chlorocinnamyl chloride 

Relevant academic research and scientific papers

Secondary amine-catalyzed [3 + 3] benzannulation to access polysubstituted benzenes through iminium activation

An organocatalytic [3 + 3] benzannulation to access polysubstituted benzenes from readily available α,β-unsaturated aldehydes and 1,3-bis(phenylsulfonyl)propene or 4-sulfonylcrotonates is described. The key reaction step is considered to be the iminium ac

Microwave-assisted InCl3-catalyzed Meyer-Schuster rearrangement of propargylic aryl carbinols in aqueous media: a green approach to α,β-unsaturated carbonyl compounds

A novel, efficient, simple and environmentally benign protocol for the Meyer-Schuster isomerization of propargylic aryl carbinols into α,β-unsaturated carbonyl compounds has been developed using catalytic amounts of InCl3, pure water as the solvent, and microwave irradiation as the heating source.

Modular synthesis of (E)-cinnamaldehydes directly from allylarenes via a metal-free DDQ-mediated oxidative process

An efficient synthesis of (E)-cinnamaldehydes by a metal-free DDQ-mediated oxidative transformation of allylarenes was developed. The protocol provides a practical method to prepare diverse (E)-cinnamaldehydes with broad functional group tolerance in good to excellent yields, including easy access to natural products randainal and geranyloxy sinapyl aldehyde from plant extracts. Finally, the mechanism of a single-electron transfer process was proposed.

Iron-facilitated direct oxidative C-H transformation of allyl arenes to alkenyl aldehydes

A direct oxidative approach to alkenyl aldehydes from allyl arenes via allyl sp3 C-H functionalization was disclosed. An inexpensive iron catalyst was employed to facilitate this transformation. The mechanistic studies indicate that the cleavage of the allyl sp3 C-H bond is involved in the rate-determining step.

Substrate-selective mechanisms in biocatalysis demonstrated with a versatile and efficient aldolase antibody

A structure-activity relationship study with a series of aldol substrates shows that the mechanism of the antibody 38C2-catalyzed retrograde aldol reaction depends on the nature of the substrate with electron-deficient substrates an early deprotonation precedes the C-C bond cleavage while with electron-rich substrates the catalytic mechanism involves an initial C-C bond cleavage leading to a positively charged intermediate.

Br?nsted acid-catalyzed meyer-schuster rearrangement for the synthesis of α, β -unsaturated carbonyl compounds

An efficient and simple protocol for the Meyer-Schuster rearrangement of propargyl alcohols into α,β-unsaturated carbonyl compounds has been developed using catalytic amounts of p-toluenesulfonic acid in 1,2-dichloroethane.

Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions

Arenediazonium o-benzenedisulfonimides can be used as new and efficient reagents for Heck-type arylation reactions of some common substrates containing C-C multiple bonds, namely ethyl acrylate, acrylic acid, acroleyne, styrene and cyclopentene. The reactions were carried out in an organic solvent, in the presence of Pd(OAc)2 as pre-catalyst, and gave rise to arylated products, for example, ethyl cinnamates, cinnamic acids, cinnamic aldehydes and stilbenes, possessing an (E)-configuration, and 1-arylcyclopentenes, in good to excellent yields. It is noteworthy that all the reactions led to the recovery, in greater than 80% yield, of o-benzenedisulfonimide, recyclable for the preparation of other diazonium salts.

Synergistic catalysis: Enantioselective addition of Alkylbenzoxazoles to Enals

A novel catalytic enantioselective methodology based on synergistic catalysis is reported. The strategy involves: 1) the metal-Lewis-acid activation of alkylazaarenes, and 2) the secondary-amine activation of enals. Consequently, highly functionalized chiral alkylazaarenes were obtained in good yields and with reasonable stereoselectivity.

Self pH regulated iron(II) catalyst for radical free oxidation of benzyl alcohols

Selective oxidation of various aromatic benzyl alcohols to benzaldehydes was found to be catalyzed with 90% conversion and 99% selectivity by an iron (II) catalyst herein designated as Fe-DDPA [DDPA = 3′-disulfanediyldipropionic acid]. The Fe-DDPA catalyst was prepared by a small loading of FeCl2 into a 2D sheet formed by the supramolecular assembling of DDPA. From both solid and liquid state nuclear magnetic resonance (NMR) spectroscopic study it was evident for the stabilization of the Fe(II) center through Fe-S interaction with the disulfide (S-S) unit of DDPA. DDPA was found to serve as an excellent support to maintain a pH that was required for a radical free oxidation of benzyl alcohol to aldehydes. The catalytic oxidation of benzyl alcohols was found to occur with excellent conversion and selectivity in acetonitrile (CH3CN) solvent in comparison to various other solvents. From various spectroscopic studies viz UV-vis, FT-IR and ESI-MS it was ascertained that the CH3CN interacted with Fe-DDPA to form a [(DDPA)2Fe(CH3CN)2]2+ species which then reacted with H2O2 to form an intermediate Fe-hydroxoperoxo, FeIII-OOH species. The Fe-OOH further got oxidized to the active FeIV=O species and was responsible for bringing the high selectivity in the oxidation reaction. The generation of highly unstable Fe-OOH species was further confirmed by electrochemical study, UV–vis, Raman and ESR spectroscopic analysis.

Development of a robust reagent for the two-carbon homologation of aldehydes to (E)-α,β-unsaturated aldehydes in water

Synthesis of a new pinacolacetal-phosphonium salt and its reaction with aldehydes to give homologated acetals and two-carbon homologated unsaturated aldehydes is presented. The chemistry takes place in water under mild conditions and the sequence can be performed in one-flask operation.