| Identification | More | [Name]
6-BROMO-1,4-BENZODIOXANE | [CAS]
52287-51-1 | [Synonyms]
3,4-ETHYLENDIOXYBROMOBENZENE
3,4-ETHYLENEDIOXYBROMOBENZENE
4-BROMO-1,2-ETHYLENEDIOXYBENZENE
6-BROMO-1,4-BENZODIOXANE
6-BROMO-2,3-DIHYDRO-1,4-BENZODIOXIN
6-BROMO-2,3-DIHYDRO-1,4-BENZODIOXINE
6-BROMO-2,3-DIHYDROBENZO[B][1,4]DIOXINE
BUTTPARK 95\50-63
TIMTEC-BB SBB003399
6-Bromo-1,4-benzodioxane~3,4-(Ethylenedioxy)bromobenzene
6-Bromo-2,3-dihydro-benzo[1,4]dioxine
6-Bromo-1,4-benzodiaxane
6-Bromo-2,3-dihydro-1,4-benzodioxine, 95+%
3,4-Ethylenedioxybromobenzene 97%
3,4-Ethylenedioxybromobenzene97%
3,4-Ethylenedioxybrombenzene
6-Bromo-1,4-benzodioxane ,97% | [EINECS(EC#)]
257-817-2 | [Molecular Formula]
C8H7BrO2 | [MDL Number]
MFCD00040750 | [Molecular Weight]
215.04 | [MOL File]
52287-51-1.mol |
| Chemical Properties | Back Directory | [Boiling point ]
259-260 °C(lit.)
| [density ]
1.598 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.588(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Liquid | [color ]
Colorless to pale yellow | [Specific Gravity]
1.598 | [Detection Methods]
HPLC | [BRN ]
6223 | [InChI]
InChI=1S/C8H7BrO2/c9-6-1-2-7-8(5-6)11-4-3-10-7/h1-2,5H,3-4H2 | [InChIKey]
LFCURAJBHDNUNG-UHFFFAOYSA-N | [SMILES]
O1C2=CC=C(Br)C=C2OCC1 | [CAS DataBase Reference]
52287-51-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29329990 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Government regulation-->1,4-Benzodioxan-->N,N-Dimethylformamide-->N-Bromosuccinimide | [Preparation Products]
1,4-BENZODIOXAN-6-CARBOXALDEHYDE-->R-(+)-6,6'-BIS(DIPHENYLPHOSPHINO)-2,2',3,3'-TETRAHYDRO-5,5'-BI-1,4-BENZODIOXIN-->3-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-pyridine-->6-vinyl-2,3-dihydrobenzo[b][1,4]dioxine-->6-methyl-2,3-dihydro-1,4-benzodioxine |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless liquid | [Uses]
6-Bromo-1,4-benzodioxane may be used as a starting reagent in the synthesis of chiral diphosphines (SYNPHOS and DIFLUORPHOS). | [General Description]
6-Bromo-1,4-benzodioxane is an aryl halide. It can be synthesized from 1,4-benzodioxane, via bromination with bromine in acetic acid. It undergoes alkoxycarbonylation reaction with sodium tert-butoxide in the presence of CO to yield 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid t-butyl ester. | [Synthesis]
General procedure for the synthesis of 6-bromo-1,4-benzodioxane from 1,4-benzodioxane: 35 g of 1,4-benzodioxane and 200 ml of anhydrous dimethylformamide were added to a reaction flask and cooled to 0 °C under argon protection. Subsequently, 54.9 g of N-bromosuccinimide was added in batches. After the reaction mixture was gradually warmed up to room temperature, stirring was continued for 24 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the white solid obtained was washed with dichloromethane. The filtrates were combined and treated with 50 ml of saturated aqueous sodium sulfate solution, washed with 50 ml of saturated aqueous sodium chloride solution and finally dried with anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, a yellow oily product was obtained (quantitative yield). The product was confirmed by EI mass spectrometry with molecular ion peak M+ = 214. 1H NMR (200 MHz, CDCl3) data were as follows: δ 4.25 (4H, s); 6.74 (1H, d); 6.93 (1H, dd); 7.02 (1H, d). | [References]
[1] Tetrahedron Letters, 2003, vol. 44, # 4, p. 823 - 826
[2] European Journal of Organic Chemistry, 2003, # 10, p. 1931 - 1941
[3] Patent: US2004/260101, 2004, A1. Location in patent: Page 5-6
[4] Organic Process Research and Development, 2003, vol. 7, # 3, p. 399 - 406
[5] Synthetic Communications, 2008, vol. 38, # 16, p. 2814 - 2819 |
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