5-BROMO-2,2-DIMETHYL-1,3-BENZODIOXOLE
- Product Name
- 5-BROMO-2,2-DIMETHYL-1,3-BENZODIOXOLE
- CAS No.
- 73790-19-9
- Chemical Name
- 5-BROMO-2,2-DIMETHYL-1,3-BENZODIOXOLE
- Synonyms
- 5-BROMO-2,2-DIMETHYL-1,3-BENZODIOXOLE;1,3-Benzodioxole, 5-bromo-2,2-dimethyl-;5-BroMo-2,2-diMethylbenzo[d][1,3]dioxole
- CBNumber
- CB9315255
- Molecular Formula
- C9H9BrO2
- Formula Weight
- 229.07
- MOL File
- 73790-19-9.mol
5-BROMO-2,2-DIMETHYL-1,3-BENZODIOXOLE Property
- Boiling point:
- 97-102 °C(Press: 8 Torr)
- Density
- 1.475±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- Appearance
- Colorless to light yellow Liquid
- InChI
- InChI=1S/C9H9BrO2/c1-9(2)11-7-4-3-6(10)5-8(7)12-9/h3-5H,1-2H3
- InChIKey
- DBVCFVNYPVLZKX-UHFFFAOYSA-N
- SMILES
- O1C2=CC=C(Br)C=C2OC1(C)C
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B700833
- Product name
- 5-Bromo-2,2-dimethylbenzo[d][1,3]dioxole
- Packaging
- 500mg
- Price
- $200
- Updated
- 2021/12/16
- Product number
- Z5084
- Product name
- 5-Bromo-2,2-dimethylbenzo[d][1,3]dioxole
- Packaging
- 250mg
- Price
- $144
- Updated
- 2021/12/16
- Product number
- FB11822
- Product name
- 5-Bromo-2,2-dimethyl-1,3-benzodioxole
- Packaging
- 1g
- Price
- $465
- Updated
- 2021/12/16
- Product number
- HCH0316749
- Product name
- 5-BROMO-2,2-DIMETHYL-1,3-BENZODIOXOLE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $500.74
- Updated
- 2021/12/16
- Product number
- FB11822
- Product name
- 5-Bromo-2,2-dimethyl-1,3-benzodioxole
- Packaging
- 2g
- Price
- $744
- Updated
- 2021/12/16
5-BROMO-2,2-DIMETHYL-1,3-BENZODIOXOLE Chemical Properties,Usage,Production
Uses
5-Bromo-2,2-dimethylbenzo[d][1,3]dioxole is used as a reactant in the preparation of phenanthridine-based Bcl-XL inhibitors.
Synthesis
14005-14-2
73790-19-9
General procedure for the synthesis of 5-bromo-2,2-dimethylbenzo[d][1,3]dioxolane from 2,2-dimethylbenzo[d][1,3]dioxolane: 2,2-dimethyl-2H-1,3-benzo[d]dioxolane (1.00 g, 6.66 mmol) was dissolved in anhydrous N,N-dimethylformamide (20 mL). N-bromosuccinimide (1.19 g, 6.66 mmol) was added batchwise at room temperature. The reaction mixture was stirred at the same temperature overnight. Analysis by liquid chromatography-mass spectrometry (LCMS) showed almost complete consumption of the starting material. The reaction process was difficult to monitor by TLC as the starting material and the product had the same Rf value on thin layer chromatography (TLC). Upon completion of the reaction, the mixture was diluted with water, appropriate amount of saturated saline was added, followed by ethyl acetate for extraction. The organic and aqueous phases were separated and the organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated to dryness. The crude product was purified by silica gel column chromatography with the eluent cyclohexane/ethyl acetate (95:5, v/v). The product-containing fraction was collected and concentrated to dryness to afford 5-bromo-2,2-dimethyl-2H-1,3-benzodioxole (1.32 g, 86% yield) as a colorless oil.1H NMR (300 MHz, DMSO-d6, δ/ppm): 1.63 (s, 6H), 6.79 (d, 1H, J = 8.1Hz), 6.95 (dd , 1H, J = 8.1Hz, J = 2.1Hz), 7.06 (d, 1H, J = 2.1Hz).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 22, p. 4133 - 4137
[2] Patent: WO2018/138362, 2018, A1. Location in patent: Page/Page column 68; 130; 131
[3] Heterocycles, 2014, vol. 88, # 2, p. 1121 - 1133
[4] ChemMedChem, 2018, vol. 13, # 21, p. 2332 - 2348
[5] Molecules, 2015, vol. 20, # 5, p. 8654 - 8665
5-BROMO-2,2-DIMETHYL-1,3-BENZODIOXOLE Preparation Products And Raw materials
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