22289-05-0

Basic information

• Product Name: 3-METHYLENE-2,6-HEPTANEDIONE, TECH. 85
• Synonyms: 3-METHYLENE-2,6-HEPTANEDIONE, TECH. 85;3-METHYLENE-2,6-HEPTANEDIONE TECH. 85%;3-Methyleneheptane-2,6-dione
• CAS NO: 22289-05-0
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.17968
• Mol File: 22289-05-0.mol

Chemical Properties

• Appearance: /
• Density: 86
• CAS DataBase Reference: 3-METHYLENE-2,6-HEPTANEDIONE, TECH. 85(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLENE-2,6-HEPTANEDIONE, TECH. 85(22289-05-0)
• EPA Substance Registry System: 3-METHYLENE-2,6-HEPTANEDIONE, TECH. 85(22289-05-0)

Safety Data

• Hazardous Substances Data: 22289-05-0(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 78-94-4 methyl vinyl ketone 
• 123-38-6 propionaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 104-53-0 3-phenyl-propionaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 851867-22-6 3-[(pentafluorophenyl)(pentafluorophenylamino)methyl]but-3-en-2-one 
• 105-07-7 4-cyanobenzaldehyde 
• 75-07-0 acetaldehyde 
• 2043-61-0 cyclohexanecarbaldehyde 
• 915712-34-4 (4-bromo-phenylimino)-acetic acid ethyl ester 
• 915712-37-7 C₁₁H₁₀F₃NO₂ 
• 1097223-19-2 ethyl 2-((3-bromophenyl)imino)acetate 

Downstream Products

• 95-87-4 2,5-Dimethylphenol 
• 95-65-8 3,4-Dimethylphenol 
• 42723-25-1 3-methyl-4-methylenecyclohex-2-enone 
• 60123-43-5 3-methyl-6-methylene-cyclohex-2-en-1-one 
• 15329-10-9 3,6-dimethylcyclohex-2-enone 
• 10463-42-0 3,4-dimethyl-cyclohex-2-enone 

Relevant articles and documents

Elucidation of the complex Baylis-Hillman reaction of 3-methoxy-2- nitrobenzaldehyde with methyl vinyl ketone

DABCO-catalyzed reaction of 3-methoxy-2-nitrobenzaldehyde with methyl vinyl ketone (MVK) affords a mixture of products, comprising the 'normal' Baylis-Hillman adduct, theMVKdimer and a pair of diastereomeric bis-(MVK)Baylis-Hillman adducts. 1H NMRspectroscopy-based kinetic studies have provided clear insights into the competing pathways and product distribution in this complex reaction.

Baylis-Hillman reaction under solvent-free conditions - Remarkable rate acceleration and yield enhancement

A simple and efficient method has been developed for remarkable rate acceleration and yield enhancement of the Baylis-Hillman reaction under solvent-free "neat conditions" and solvent-less isolation of products. Reaction of equimolar quantities of aldehyd

Phosphine-catalyzed annulation of ethyl (arylimino)acetates: Synthesis of highly functionalized oxoimidazolidines

This paper describes an unexpected and novel nucleophilic phosphine-catalyzed annulation of ethyl (arylimino)acetates to give polysubstituted oxoimidazolidine derivatives in moderate to good yields from simple and easily available starting materials under

Octanol-accelerated Baylis-Hillman reaction

The Baylis-Hillman reaction was greatly accelerated by use of octanol as an additive. Under the octanol-accelerated Baylis-Hillman conditions, unactivated aldehydes such as aliphatic aldehydes and aromatic aldehydes with electron-withdrawing substituents

1,3,5-triaza-7-phosphaadamantane (PTA): A practical and versatile nucleophilic phosphine organocatalyst

In this paper, the air-stable and readily available 1,3,5-triaza-7- phosphaadmantane (PTA) is reported as a practical and versatile nucleophilic phosphine organocatalyst. Under the mediation of 15-30 mol% of PTA, various electrophiles like aldehydes and i

An unexpected highly diastereoselective double Baylis-Hillman reaction of per- (or poly)fluorophenyl aromatic aldimines with methyl vinyl ketone

Aza-Baylis-Hillman reaction of per- (or poly)fluorophenyl aromatic aldimines 1 with methyl vinyl ketone (MVK) was studied. It was found that both the used Lewis base and solvent can significantly affect the reaction. Using triphenylphosphine as a Lewis ba

Reexamination of the traditional Baylis-Hillman reaction

In the Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone (MVK), we found that, besides the normal Baylis-Hillman adduct 1, the diadduct 2 can also be formed at the same time and the yield of 2 can reach to 55% if increasing the amount of methyl vinyl ketone. But for ethyl vinyl ketone (EVK), methyl acrylate or acrylonitrile, only the normal Baylis-Hillman adduct 4, 7 or 8 was obtained, respectively. The substituent's effects and Lewis base effects were also examined and a plausible reaction mechanism was proposed for the formation of 2.

The Baylis-Hillman Reaction: A Novel Method for the Synthesis of α-Methylene-β-hydroxy Ketones and 2-Methylene-1,5-diketones

A variety of α-methylene-β-hydroxyalkanones and 2-methylene-1,5-diketones were synthesized via the BAYLIS-HILLMAN reaction, i.e., the DABCO-catalyzed coupling of methyl vinyl ketone with aldehydes and dimerization of vinylic ketones respectively.

Rhodium(I)- or ruthenium(II)-catalyzed direct coupling of vinyl ketones with aldehydes and the subsequent reduction to give aldol derivatives anti-selectively

A vinyl ketone reacts with an aldehyde to give an α-methylene-β-hydroxyalkanone with the concomitant formation of the vinyl ketone dimer in the presence of catalytic amount of RhH(PPh3)4 or RuH2(PPh3)4 under almost neutral conditions.The selectivity of th

A selective synthesis of α-methylene-β-hydroxyalkanones catalyzed by RuH2(PPh3)4

The RuH2(PPh3)4-catalyzed coupling of vinylketones with aldehydes accomplishes the selective synthesis of α-methylene-β-hydroxyalkanones under neutral conditions.A plausible pathway involving possible intermediacy of a ruthenium enolate is proposed.