| Identification | More | [Name]
2-Phenoxyethylbromide | [CAS]
589-10-6 | [Synonyms]
1-(2-BROMOETHOXY)BENZENE
1-BROMO-2-PHENOXYETHANE
(2-BROMETHOXY)BENZENE
(2-BROMOETHOXY)BENZENE
2-BROMOETHYL PHENYL ETHER
2-PHENOXYETHYL BROMIDE
AKOS BBS-00006631
AKOS BC-2647
B-BROMOETHYL PHENYL ETHER
B-BROMOPHENETOLE
BETA-BROMOPHENETOL
BETA-BROMOPHENETOLE
BETA-BROMOPHENYLETHYL ETHER
BETA-PHENOXYETHYL BROMIDE
B-PHENOXYETHYL BROMIDE
PHENOXYETHYLBROMIDE
(2-bromoethoxy)-benzen
Benzene,(2-bromoethoxy)-
-Bromophenetole
Phenetole, beta-bromo- | [EINECS(EC#)]
209-634-4 | [Molecular Formula]
C8H9BrO | [MDL Number]
MFCD00000234 | [Molecular Weight]
201.06 | [MOL File]
589-10-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
31-34 °C(lit.) | [Boiling point ]
144 °C40 mm Hg(lit.) | [density ]
1.45 | [refractive index ]
1.555-1.557
| [Fp ]
150 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Solubility in methanol is almost transparent. Soluble in chloroform and ethyl acetate. | [form ]
Liquid After Melting | [color ]
Clear colorless | [Water Solubility ]
Insoluble in water. Solubility in methanol is almost transparent. Soluble in chloroform and ethyl acetate. | [BRN ]
508290 | [CAS DataBase Reference]
589-10-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzene, (2-bromoethoxy)-(589-10-6) | [EPA Substance Registry System]
589-10-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
1325 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
4.1 | [PackingGroup ]
II | [HS Code ]
29093038 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
It is used in the synthesis and antihypertensive activity of 4'-substituted spiro[4H-3,1-benzoxazine-4,4'-piperidin]-2(1H)-ones. | [Application]
2-Phenoxyethyl bromide can be used as a pharmaceutical intermediate for the synthesis of nafazodone and oxiperomide. | [Preparation]
2-Phenoxyethyl bromide is synthesized by the reaction of phenol and dibromoethane. Put phenol, dibromoethane and sodium hydroxide in a reaction pot and stir and mix, react at 110 °C for 6 hours, recover dibromoethane, the recovery amount is about 60%, wash with 5% sodium hydroxide solution and water, and divide Take the oil layer, distill under reduced pressure, and collect the fractions at 130-150°C (6.7kPa) to obtain (2-bromoethoxy)benzene. | [Synthesis]
The general procedure for the synthesis of 2-phenoxyethyl bromide from phenol and 1,2-dibromoethane was as follows: phenol (10 mmol), 1,2-dibromoethane (50 mmol) and anhydrous potassium carbonate (30 mmol) were suspended in anhydrous acetonitrile (50 mL) under nitrogen protection. The reaction mixture was stirred at 80 °C for 6 hours. Upon completion of the reaction, the mixture was filtered to recover potassium carbonate, which could be dried under vacuum at 120 °C for 5 h to reactivate. The filtrate was concentrated under reduced pressure to remove the solvent and the resulting crude product was purified by silica gel column chromatography using petroleum ether as eluent to give the target compound 2-phenoxyethyl bromide (Scheme 1, Table 4, Entry 1). The product was a solid with a melting point of 33-34 °C. Its structure was confirmed by 1H NMR (400 MHz, CDCl3), 13C NMR (100 MHz, CDCl3) and mass spectrometry (MS).1H NMR data: δ 7.29-7.26 (m, 2H), 6.95-6.92 (m, 3H), 4.26-4.23 (t, J = 3.6 Hz, 2H), 3.61- 3.58 (t, J = 3.6 Hz, 2H).13C NMR data: δ 158, 129.5, 121.4, 114.8, 67.8, 29.1. Mass spectrometry data: m/z 202 (50, M+2), 200 (48, M+), 109 (97), 107 (100), 94 (60), 77 (29), 65 (38), 51 (22), 39 (52). | [References]
[1] Journal of Chemistry, 2017, vol. 2017,
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1244 - 1251
[3] Patent: US4474964, 1984, A
[4] Patent: US4533731, 1985, A
[5] Russian Journal of Organic Chemistry, 2009, vol. 45, # 5, p. 681 - 686 |
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