52190-28-0

Basic information

• Product Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one
• Synonyms: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one;2-Bromo-3',4'-(methylenedioxy)propiophenone;1-(1,3-Benzodioxol-5-yl)-2-broMo-1-propanone;3',4'-Methylenedioxy-α-broMopropiophenone;1-(1,3-benzodioxol-5-yl)-2-bromopropan-1-one
• CAS NO: 52190-28-0
• Molecular Formula: C₁₀H₉BrO₃
• Molecular Weight: 257.08066
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 52190-28-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 345.673 °C at 760 mmHg
• Flash Point: 162.857 °C
• Appearance: /
• Density: 1.585 g/cm³
• CAS DataBase Reference: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one(52190-28-0)
• EPA Substance Registry System: 1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one(52190-28-0)

Safety Data

• Hazardous Substances Data: 52190-28-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

1-(benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one can be used in the preparation of antifungal agents and MDMA analogs.

Upstream product

• 28281-49-4 3,4-methylenedioxypropiophenone 
• 63740-97-6 1-(2H-benzo[3,4-d]1,3-dioxolen-5-yl)butan-1-one 
• 7451-98-1 3',4'-dihydroxypropiophenone 

Downstream Products

• 161096-64-6 methyl 3-hydroxy-4-α-piperonyloylethoxy-5-methoxybenzoate 
• 528-64-3 5,5'-(3,4-dimethyltetrahydrofuran-2,5-diyl)bis(benzo[d][1,3]dioxole) 
• 1206768-27-5 (S)-1-(3,4-(methylenedioxy)phenyl)-2-phenylpropan-1-one 
• 857953-22-1 N-acetyl-sulfanilic acid-(4-benzo[1,3]dioxol-5-yl-5-methyl-thiazol-2-ylamide) 
• 161096-65-7 methyl 3-hydroxy-4-α-methyl-β-hydroxy-β-(3,4-methylenedioxyphenyl)ethoxy-5-methoxybenzoate 
• 186028-79-5 1-(1,3-benzodioxol-5-yl)-2-(methylamino)propan-1-one 
• 850852-86-7 4-benzo[1,3]dioxol-5-yl-5-methyl-thiazol-2-ylamine 

Relevant articles and documents

α-PPP and its derivatives are selective partial releasers at the human norepinephrine transporter: A pharmacological characterization of interactions between pyrrolidinopropiophenones and uptake1 and uptake2 monoamine transporters

While classical cathinones, such as methcathinone, have been shown to be monoamine releasing agents at human monoamine transporters, the subgroup of α-pyrrolidinophenones has thus far solely been characterized as monoamine transporter reuptake inhibitors. Herein, we report data from previously undescribed α-pyrrolidinopropiophenone (α-PPP) derivatives and compare them with the pharmacologically well-researched α-PVP (α-pyrrolidinovalerophenone). Radiotracer-based in vitro uptake inhibition assays in HEK293 cells show that the investigated α-PPP derivatives inhibit the human high-affinity transporters of dopamine (hDAT) and norepinephrine (hNET) in the low micromolar range, with α-PVP being ten times more potent. Similar to α-PVP, no relevant pharmacological activity was found at the human serotonin transporter (hSERT). Unexpectedly, radiotracer-based in vitro release assays reveal α-PPP, MDPPP and 3Br-PPP, but not α-PVP, to be partial releasing agents at hNET (EC50 values in the low micromolar range). Furthermore, uptake inhibition assays at low-affinity monoamine transporters, i.e., the human organic cation transporters (hOCT) 1–3 and human plasma membrane monoamine transporter (hPMAT), bring to light that all compounds inhibit hOCT1 and 2 (IC50 values in the low micromolar range) while less potently interacting with hPMAT and hOCT3. In conclusion, this study describes (i) three new hybrid compounds that efficaciously block hDAT while being partial releasers at hNET, and (ii) highlights the interactions of α-PPP-derivatives with low-affinity monoamine transporters, giving impetus to further studies investigating the interaction of drugs of abuse with OCT1-3 and PMAT.

Formal Total Synthesis of Hybocarpone Enabled by Visible-Light-Promoted Benzannulation

The formal total synthesis of hybocarpone was achieved in eight steps from commercially available 1,2,4-trimethoxybenzene. Key transformations include a visible-light-promoted benzannulation to construct the key α-naphthol intermediate and a modified CAN-mediated dimerization/hydration cascade sequence to generate the vicinal all-carbon quaternary centers in a stereocontrolled manner. The total synthesis of boryquinone was also achieved in seven steps.

Nickel/bis(oxazoline)-catalyzed asymmetric Kumada reactions of alkyl electrophiles: Cross-couplings of racemic α-bromoketones

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