61203-01-8

Basic information

• Product Name: 3-bromobut-3-en-2-one
• Synonyms: 3-bromobut-3-en-2-one
• CAS NO: 61203-01-8
• Molecular Formula: C₄H₅BrO
• Molecular Weight: 148.9859
• Mol File: 61203-01-8.mol

Chemical Properties

• Boiling Point: 165.9°C at 760 mmHg
• Flash Point: 86.6°C
• Density: 1.493g/cm³
• Vapor Pressure: 1.83mmHg at 25°C
• Refractive Index: 1.471
• CAS DataBase Reference: 3-bromobut-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromobut-3-en-2-one(61203-01-8)
• EPA Substance Registry System: 3-bromobut-3-en-2-one(61203-01-8)

Safety Data

• Hazardous Substances Data: 61203-01-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 60, p. 2268, 1982 DOI: 10.1139/v82-322

Upstream product

• 854258-70-1 (2-bromo-1-methylen-allyl)-methyl ether 
• 78-94-4 methyl vinyl ketone 
• 67-56-1 methanol 
• 61203-07-4 3-acetyl-2-oxo-γ-butyrolactone 
• 7726-95-6 bromine 
• 83769-09-9 (2-Bromo-3-oxo-butyl)-dimethyl-sulfonium; bromide 
• 104023-23-6 3-bromo-3-phenylselenobutan-2-one 
• 25109-57-3 3,4-dibromobutan-2-one 

Downstream Products

• 726147-66-6 1-[1-bromo-4-(4-methyl-3-pentenyl)-3-cyclohexenyl]ethan-1-one 
• 1359843-45-0 1-(1-cyclohexylaziridin-2-yl)ethanone 
• 31907-94-5 1-(1-benzylaziridin-2-yl)ethan-1-one 
• 83280-65-3 2-acetylnaphtho[2,3-b]furan-4,9-quinone 
• 147568-55-6 2-acetyl-2,3,4,9-tetrahydronaphtho[2,3-b]furan-4,9-dione 
• 41850-71-9 4-(p-Anisoxy)-3-buten-2-on 
• 2048-69-3 5-acetyl-3-phenylisoxazole 
• 161402-83-1 1-(2,3-dihydroimidazo<2,1-b>thiazol-6-yl)ethanone 

Relevant articles and documents

Captodative Formyl- and Acyl(amino)alkenes Containing a Terminal Double Bond or a Weakly Basic Tertiary Amino Group

Piperidine reacts with 3-bromo-3-buten-2-one to give a mixture of 3,4-dipiperidinobutan-2-one and 3-piperidino-3-buten-2-one. The latter is also formed by the action of a strong base (Et3N in THF or MeONa in MeOH) on the dipiperidino derivative. Analogous reaction of 2-bromo-3-phenylpropenal with N-methylaniline affords 2-[methyl(phenyl)amino]-3-phenylpropenal which is the first captodative formyl-(amino)alkene having a weakly basic tertiary amino group.

METHOD FOR PRODUCING 2-ACETYL-4H,9H-NAPHTHO[2,3-B]FURAN-4,9-DIONE

The invention addresses the problem of providing a method for producing 2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione that is suited to industrial production. The invention provides a method for producing 2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione by reacting 3-bromo-3-buten-2-one and 2-hydroxy-1,4-naphthoquinone in the presence of a solvent, then obtaining crystals of 2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione by adding an alcohol-based solvent and/or water to the reaction system, and treating the crystals by using a specific adsorbent in the presence of a solvent.

2-ACETYLNAPHTHO[2,3-B]FURAN -4,9-DIONE FOR USE ON TREATING CANCER

The invention provides naphthofuran compounds, polymorphs of naphthofuran compounds, naphthofuran compounds in particle form, purified compositions that contain one or more naphthofuran compounds, purified compositions that contain one or more naphthofuran compounds in particle form, and methods of using these naphthofuran compounds, polymorphs, purified compositions and/or particle forms to treat subjects in need thereof.

A NOVEL GROUP OF STAT3 PATHWAY INHIBITORS AND CANCER STEM CELL PATHWAY INHIBITORS

The present invention relates to the composition and methods of use of Stat3 pathway inhibitors or cancer stem cell inhibitors in combination treatment of cancer.

Compounds and compositions for targeting cancer stem cells

The invention provides naphthofuran compounds, polymorphs of naphthofuran compounds, naphthofuran compounds in particle form, purified compositions that contain one or more naphthofuran compounds, purified compositions that contain one or more naphthofuran compounds in particle form, methods of producing these naphthofuran compounds, polymorphs, purified compositions and/or particle forms, and methods of using these naphthofuran compounds, polymorphs, purified compositions and/or particle forms to treat subjects in need thereof.

Ruthenium-lewis acid catalyzed asymmetric diels-alder reactions between dienes and α,β-unsaturated ketones

The complex [Ru(Cp)(R,R-BIPHOP-F)(acetone)][SbF6],(R,R)-1a. was used as catalyst for asymmetric Diels-Alder reactions between dienes (cyclopentadiene, methylcyclopentadienc, isoprene, 2,3-dimethylbutadiene) and α,β-unsaturated ketones (methyl vinyl ketone (MVK). ethyl vinyl ketone, divinyl ketone, α-bromovinyl methyl ketone and α-chlorovinyl methyl ketone). The cycloaddition products were obtained in yields of 50-_90% and with enantioselectivities up to 96% ee. Ethyl vinyl ketone, divinyl ketone and the halogenated vinyl ketones worked best and their reactions with acyclic dienes consistently provided products with >90% ee. α-Chlorovinyl methyl ketone performed better than α-bromovinyl methyl ketone. The reaction also provided a [4.3.1]bicyclic ring system in 95% ee through an intramolecular cycloaddition reaction. Crystal structure determinations of [Ru(Cp)((S,S)-BIPHOP-F)(mvk)]-[SbF6], (S,S)-1b, and [Ru(Cp)((R,R)-Me4BIPHOP-F)(acrolein)][SbF6], (R,R)-2b, provided the basis for a rationalization of the asymmetric induction.

Structure-dependent oxidative bromination of unsaturated C-C bonds mediated by selectfluor

A number of olefins were subjected to oxidative bromination using Selectfluor/KBr. For different types of substrates, addition, monobromine-substituted, or Hunsdiecker-Borodin reaction products can be readily afforded.

A radical based addition-elimination route for the preparation of indoles

Indoles, including tricyclic derivatives, are produced by cyclisations of aryl radicals onto vinyl halides followed by elimination of halide radical and tautomerism of the resulting product; the aryl radicals are produced using "clean methodology" either by reaction of iodide ions with arenediazonium salts or by reaction of phosphorus-centred radicals with aryl iodides. The Royal Society of Chemistry 2000.

A new synthesis of indoles

Aryl radical cyclisation onto appropriate vinyl bromides leads to a new route to indoles.

SYNTHESIS OF 2,3,5,6-TETRAHYDROIMIDAZOTHIAZOLES

The reactions of 2-amino-2-thiazoline with alkylating and acylating agents give initial reaction on the endocyclic nitrogen.Acyl groups, however, readily rearrange to the exocyclic nitrogen to give the products usually observed in these reactions.These observations clear up a considerable amount of confusion in the literature and lead to the efficient synthesis of 2,3,5,6-tetrahydroimidazothiazoles.