1680-73-5

Basic information

• Product Name: 2-Chloro-1-formyl-1-cyclohexene
• Synonyms: 2-Chloro-1-formyl-1-cyclohexene;2-Chlorocyclohex-1-enecarbaldehyde;1-Cyclohexene-1-carboxaldehyde, 2-chloro-;(2-chlorocyclohex-1-enyl)carboxaldehyde;2-chlorocyclohex-1-enylcarboxaldehyd...;2-Chloro-1-cyclohexene-1-carboxaldehyde;2-Chloro-1-cyclohexenecarboxaldehyde;2-Chloro-1-formylcyclohexene
• CAS NO: 1680-73-5
• Molecular Formula: C₇H₉ClO
• Molecular Weight: 144.59876
• Mol File: 1680-73-5.mol

Chemical Properties

• Boiling Point: 88-90℃ (11 Torr)
• Flash Point: 91.781 °C
• Appearance: /
• Density: 1.134 g/cm³
• Refractive Index: 1.5198 (589.3 nm 20℃)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 2-Chloro-1-formyl-1-cyclohexene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-1-formyl-1-cyclohexene(1680-73-5)
• EPA Substance Registry System: 2-Chloro-1-formyl-1-cyclohexene(1680-73-5)

Safety Data

• Hazardous Substances Data: 1680-73-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Production:
2-Chloro-1-formyl-1-cyclohexene is utilized as a key building block in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Organic Synthesis:
2-Chloro-1-formyl-1-cyclohexene serves as a reagent in organic reactions, particularly in the synthesis of heterocyclic compounds, which are important in the creation of a wide range of chemical products.
Used in Research and Development:
2-Chloro-1-formyl-1-cyclohexene is under investigation for its potential therapeutic applications, especially as an inhibitor of monoamine oxidase A (MAO-A), which could lead to treatments for neurological and mood disorders.
Used in Chemical Research:
Due to its unique chemical properties, 2-Chloro-1-formyl-1-cyclohexene is also used in chemical research to explore new synthetic pathways and understand the reactivity of similar compounds.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 4065-81-0 cyclohexen-1-ol 
• 108-94-1 cyclohexanone 
• 79-01-6 Trichloroethylene 
• 50-00-0 formaldehyd 
• 822-87-7 2-Chlorocyclohexanone 

Downstream Products

• 5632-33-7 5,6,7,8-tetrahydroquinazoline 
• 55338-89-1 [(2-Chloro-cyclohex-1-enyl)-hydroxy-methyl]-phosphonic acid dimethyl ester 
• 55338-78-8 [(2-Chloro-cyclohex-1-enyl)-hydroxy-methyl]-phosphonic acid diethyl ester 
• 42057-99-8 2-methylselanyl-cyclohex-1-enecarbaldehyde 
• 39831-18-0 2-((Z)-3-Oxo-1,2-diphenyl-propenylsulfanyl)-cyclohex-1-enecarbaldehyde 
• 42141-25-3 2-thiocyanato-cyclohex-1-enecarbaldehyde 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 35811-99-5 1,2-Di-(1-cyclohexenyl)aethylenplycol 
• 19809-85-9 di(2-formylcyclohex-1-ene)sulfide 
• 85103-22-6 3-Methyl-10-phenyl-6,8,9,10-tetrahydro-7H-pyrimido[4,5-b]quinoline-2,4-dione 
• 113684-03-0 1-Chlor-2-(1'-hydroxy-ethyl)-cyclohexen 
• 138826-05-8 1-chloro-1-(2-chloro-1-cyclohexenyl)-2,2-dimethylcyclopropane 
• 138826-06-9 1-chloro-1-(2-chloro-1-cyclohexenyl)-2,2,3,3-tetramethylcyclopropane 
• 1262835-66-4 C₁₅H₁₈ClN 

Relevant articles and documents

Vilsmeier Formylation of O-Silylated Enolates of Carboxylic Esters. A New Method for the Synthesis of α-Formylcarboxylic Esters

The Vilsmeier formylation of ketene O-alkyl O'-silyl acetals (O-silylated enolates of carboxylic esters) provides α-formylcarboxylic esters in moderate yields.

A facile and convenient synthesis of (±)-biotin via MgCl2/Et3N-mediated C-C coupling and Mitsunobu reaction

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β-Chloroaldehydes from Trapping Zirconium Enolates Produced in Asymmetric 1,4-Additions

Zirconium enolates, derived from copper-catalyzed asymmetric conjugate additions, are trapped with the Vilsmeier-Haack reagent. Asymmetric additions generate quaternary carbon centers with high enantioselectivity (generally ?90% ee), and the enolates are converted to unsaturated β-chloroaldehydes (41-57% yields). The reaction tolerates changes to the nucleophile, can be used to form five-, six-, or seven-membered ring products, and is scalable to 5 mmol, and the products are readily elaborated by condensation, cross coupling, and addition reactions.

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Cyclization of β-Chlorovinyl Thiohydrazones into Pyridazines: A Mechanistic Study

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Two-Step Synthesis of 3,4-Dihydropyrrolopyrazinones from Ketones and Piperazin-2-ones

An expedient two-step synthesis of 3,4-dihydropyrrolopyrazinones has been achieved via a Vilsmeier-Haack reaction of ketones, followed by an annulation of the corresponding chloroaldehydes with commercially available piperazin-2-ones. A variety of cyclic and acyclic ketones and piperazin-2-ones participated in this two-step chemistry, affording the desired 3,4-dihydropyrrolopyrazinones in up to 78% yield.

Efficient synthesis of 4- And 5-substituted 2-aminopyrimidines by coupling of β-Chlorovinyl Aldehydes and Guanidines

A general, practical, and simple synthesis of functionalized 2-aminopyrimidines starting from β-chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently transformed into the pyrimidine derivatives by a two-step sequence involving the Vilsmeier-Haack reaction followed by a condensation reaction with guanidines. The protocol is distinguished by operational simplicity, inexpensive reagents, and functional-group tolerance. In many cases, pure solid products can be obtained in high to excellent yields without using column chromatography. The synthetic value of the method was demonstrated by the efficient synthesis of steroidal pyrimidines and a precursor of the antitumor agents Imatinib and Mocetinostat.

COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS

A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.

Synthesis, structure and reactivity of β-chalcocyclohexenals: Dichalcogenides and chalcogenides

The present work describes the synthesis and characterization of a series of organochalcogen compounds derived from β-chlorocyclohexenal (27a)/β-bromocyclohexenal (27b) which are stabilized by E...O (E = S, Se, Te) intramolecular secondary bonding interaction (IM-SBI). Di-(2-formylcyclohex-1-ene)sulfide (21) was prepared by treating 27b with disodium sulfide. Di-(2-formylcyclohex-1-ene)diselenide (28) was obtained by reacting 27a with disodium diselenide. The reaction always produced a mixture of di-(2-formylcyclohex-1-ene)diselenide (28) and di-(2-formylcyclohex-1-ene)selenide (29). Attempts to synthesize di-(2-formylcyclohex-1-ene)ditelluride 30 by the reaction of 27b with disodium ditelluride afforded a mixture of monotellurides; 3,4,5,6,7,8-hexahydro-2H-9-telluraanthracene-1-carbaldehyde (26), di-(2-formylcyclohex-1-ene)telluride (22) and 9-hydroxy-2,3,5,6,7,8,9,9a-octahydro-1H-telluroxanthene-4-carbaldehyde (31). Reactions of 28 with halogenating reagents afforded the corresponding organylselenenyl halides; selenenyl chloride 35, selenenyl bromide 36 and selenenyl iodide 37. Tellurides 26 and 22 were used as ligands for metal complexation reactions.

A Straightforward Approach toward Multifunctionalized Pyridazines via Imination/Electrocyclization

A facile synthesis of functionalized 3-carbamide pyridazines starting from readily available chlorovinyl aldehydes and oxamic acid thiohydrazides via cascade imination/electrocyclization is reported. In the presence of p-toluenesulfuric acid, various ketones have been efficiently incorporated into the pyridazine derivatives through a two-step sequence involving a Vilsmeier-Haack reaction and imination. The synthetic value of this method has been demonstrated by efficient synthesis of steroidal pyridazines.