| Identification | More | [Name]
3-BENZYLOXYBROMOBENZENE | [CAS]
53087-13-1 | [Synonyms]
1-BENZYLOXY-3-BROMOBENZENE
3-BENZYLOXYBROMOBENZENE
3-BROMOPHENYL BENZYL ETHER
BENZYL 3-BROMOPHENYL ETHER
3-Benzyloxybromobenzen
1-Bromo-3-benzyloxybenzene | [EINECS(EC#)]
610-958-7 | [Molecular Formula]
C13H11BrO | [MDL Number]
MFCD00155065 | [Molecular Weight]
263.13 | [MOL File]
53087-13-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Whitetolightyellowcrystalpowde | [Melting point ]
57-60 °C | [Boiling point ]
333.5±17.0 °C(Predicted) | [density ]
1.382±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Solid | [color ]
White | [InChI]
InChI=1S/C13H11BrO/c14-12-7-4-8-13(9-12)15-10-11-5-2-1-3-6-11/h1-9H,10H2 | [InChIKey]
HVWZMGZBJCJDOX-UHFFFAOYSA-N | [SMILES]
C1(Br)=CC=CC(OCC2=CC=CC=C2)=C1 | [CAS DataBase Reference]
53087-13-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,N | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R43:May cause sensitization by skin contact.
R41:Risk of serious damage to eyes. | [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 .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S41:In case of fire and/or explosion do not breathe fumes .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S60:This material and/or its container must be disposed of as hazardous waste . | [RIDADR ]
UN 3077 9/PG 3 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29093090 |
| Hazard Information | Back Directory | [Chemical Properties]
Whitetolightyellowcrystalpowde | [Synthesis]
1. Anhydrous potassium carbonate (37.32 g, 270 mmol) and benzyl chloride (11.50 mL, 99 mmol) were added to a suspension of anhydrous ethanol (300 mL) containing m-bromophenol (15.57 g, 90 mmol) under nitrogen protection. The reaction mixture was heated to reflux for 4 hours. After completion of the reaction, the ethanol was removed by vacuum filtration and evaporation. The residue was extracted with ethyl acetate (EtOAc) and the combined organic layers were washed sequentially with water, 2 M NaOH solution, saturated brine and 2 M HCl solution, dried over anhydrous sodium sulfate (Na2SO4) and concentrated to give the yellow solid product 3-benzyloxybromobenzene (22.02 g, 93%).
2. To a 250 mL two-necked round-bottomed flask, protected by nitrogen, were added dry magnesium chips (2.18 g, 90 mmol) and trace iodine, equipped with two rubber septa and stirred. Anhydrous tetrahydrofuran (THF, 40 mL) solution of 3-benzyloxybromobenzene (15.79 g, 60 mmol) was slowly added through a syringe and kept at reflux. After addition, stirring was continued at reflux for 5 hours. After the reaction mixture was cooled to -30°C, anhydrous THF (60 mL) solution of trimethyl borate (9.36 g, 90 mmol) was slowly added. After addition, the mixture was stirred at room temperature overnight, followed by treatment with saturated ammonium chloride (NH4Cl) solution and continued stirring at room temperature for 1 hour. THF was removed by rotary evaporation, the aqueous layer was extracted with EtOAc, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow crude product. The crude product was purified by recrystallization in water to give white solid target product (7.53 g, 55%). | [References]
[1] Journal of Materials Chemistry, 2010, vol. 20, # 15, p. 3069 - 3078
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 1044 - 1054
[3] Journal of Medicinal and Pharmaceutical Chemistry, 1962, vol. 5, p. 752 - 762
[4] Patent: US5447656, 1995, A
[5] Patent: EP838461, 1998, A2 |
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