| Identification | More | [Name]
4-Bromo-3-methylphenol | [CAS]
14472-14-1 | [Synonyms]
4-BROMO-3-METHYLPHENOL
4-BROMO-M-CRESOL
AKOS BBS-00008110
AURORA 4271
4-BROMO-3-METHYLPHENOLBRO7H7C
Phenol, 4-bromo-3-methyl- | [EINECS(EC#)]
238-464-3 | [Molecular Formula]
C7H7BrO | [MDL Number]
MFCD00079723 | [Molecular Weight]
187.03 | [MOL File]
14472-14-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white crystalline powder or chunks | [Melting point ]
59-61 °C (lit.) | [Boiling point ]
142-145 °C/23 mmHg (lit.) | [density ]
1.3839 (rough estimate) | [refractive index ]
1.5772 (estimate) | [Fp ]
142-145°C/23mm | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder or Chunks | [pka]
9.51±0.18(Predicted) | [color ]
White to off-white | [BRN ]
1859122 | [InChI]
InChI=1S/C7H7BrO/c1-5-4-6(9)2-3-7(5)8/h2-4,9H,1H3 | [InChIKey]
GPOQODYGMUTOQL-UHFFFAOYSA-N | [SMILES]
C1(O)=CC=C(Br)C(C)=C1 | [CAS DataBase Reference]
14472-14-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [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:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [PackingGroup ]
III | [HS Code ]
29081990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
white to off-white crystalline powder or chunks | [Uses]
4-Bromo-3-methylphenol may be used in the synthesis of bromo[2-methyl-4-[2-(t-butyldimethylsilyloxy)ethyloxy]phenyl]bis(triphenylphopshine)nickel(II) (protected alcohol-functionalized initiator) and bromo-[2-methyl-4-[6-(t-butyldimethylsilyloxy)hexyloxy]phenyl] bis(triphenylphosphine) nickel. | [General Description]
4-Bromo-3-methylphenol is a brominated phenol. It participates in the total synthesis of 3-methylcalix[4]arene. | [Synthesis]
General procedure for the synthesis of 4-bromo-3-methylphenol from m-cresol:
(a) Preparation of 4-bromo-3-methylphenol: 80.0 g (740 mmol) of m-cresol and 400 mL of glacial acetic acid were added to a 2 L three-neck flask under nitrogen protection. The reaction mixture was cooled to 15 °C, 38 mL (742 mmol) of bromine was added slowly dropwise, and the reaction was stirred for 3 h at 15 °C maintaining the temperature. After completion of the reaction, the reaction solution was poured into 1 L of water and extracted with ether. The organic phase was separated and washed with water to neutral pH and subsequently dried with magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was ground in heptane, filtered and dried to give 70 g (50% yield) of a white powdery product with a melting point of 55-56 °C. | [References]
[1] Letters in Organic Chemistry, 2018, vol. 15, # 8, p. 682 - 687
[2] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 11, p. 4187 - 4189
[3] Journal of Organic Chemistry, 2005, vol. 70, # 11, p. 4267 - 4271
[4] Synlett, 2011, # 15, p. 2265 - 2269
[5] Journal of Chemical Research - Part S, 2003, # 9, p. 597 - 598 |
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