72109-65-0

Basic information

• Product Name: 2,6-Bis(bromomethyl)-4-methylphenol
• Synonyms: 2,6-Bis(bromomethyl)-4-methylphenol
• CAS NO: 72109-65-0
• Molecular Formula: C₉H₁₀Br₂O
• Molecular Weight: 293.9831
• Mol File: 72109-65-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 336.5°Cat760mmHg
• Flash Point: 157.3°C
• Appearance: /
• Density: 1.802g/cm³
• Vapor Pressure: 5.71E-05mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: 2,6-Bis(bromomethyl)-4-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Bis(bromomethyl)-4-methylphenol(72109-65-0)
• EPA Substance Registry System: 2,6-Bis(bromomethyl)-4-methylphenol(72109-65-0)

Safety Data

• Hazardous Substances Data: 72109-65-0(Hazardous Substances Data)

Usage

General Description

2,6-Bis(bromomethyl)-4-methylphenol, also known as 4,4'-methylenediphenol dibromide, is a chemical compound with the formula C9H10Br2O. It is a brominated derivative of 4-methylphenol and is used as a building block in the synthesis of various organic compounds. 2,6-Bis(bromomethyl)-4-methylphenol is a white to off-white crystalline solid and is insoluble in water but soluble in organic solvents. It is commonly used in the production of flame retardants, industrial coatings, and adhesives. Due to its bromine content, it is considered to be potentially harmful to human health and the environment, and proper safety measures should be taken when handling and using this chemical.

InChI:InChI=1/C9H10Br2O/c1-6-2-7(4-10)9(12)8(3-6)5-11/h2-3,12H,4-5H2,1H3

Upstream product

• 153707-56-3 3,5-bis(hydroxymethyl)phenol 
• 106-44-5 p-cresol 
• 91-04-3 2,6-bis(hydroxymethyl)-4-methylphenol 
• 50-00-0 formaldehyd 

Downstream Products

• 121252-88-8 2,6-bis(1,4,7-triazacyclonon-1-ylmethyl)-4-methylphenol hexahydrochloride 
• 1552271-75-6 ((2S,2'S,5R,5’R)-1,1'-((2-hydroxy-5-methyl-1,3-phenylene)-bis-(methylene))-bis-(5-phenylpyrrolidine-2,1-diyl))-bis-(diphenyl-methanol) 
• 1552271-89-2 ((2S,2'S,5S,5'S)-1,1'-((2-hydroxy-5-methyl-1,3-phenylene)-bis-(methylene))-bis-(5-([1,1'-biphenyl]-4-yl)pyrrolidine-2,1-diyl))-bis-(diphenylmethanol) 
• 1552271-87-0 ((2S,2'S,5S,5'S)-1,1'-((2-hydroxy-5-methyl-1,3-phenylene)-bis-(methylene))-bis-(5-(naphthalen-2-yl)pyrrolidine-2,1-diyl))-bis-(diphenylmethanol) 
• 1552271-85-8 ((2S,2'S,5S,5'S)-1,1'-((2-hydroxy-5-methyl-1,3-phenylene)-bis-(methylene))-bis-(5-(naphthalen-1-yl)pyrrolidine-2,1-diyl))-bis-(diphenylmethanol) 
• 1552271-83-6 ((2S,2'S,5S,5’S)-1,1'-((2-hydroxy-5-methyl-1,3-phenylene)-bis-(methylene))-bis-(5-phenylpyrrolidine-2,1-diyl))-bis-(diphenylmethanol) 
• 320714-00-9 ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) 
• 1004960-65-9 (2S,2'S)-1,1'-(2-hydroxy-5-methyl-1,3-phenylene)bis(methylene)bis(N-benzhydrylpyrrolidine-2-carboxamide) 
• 912281-64-2 C₃₉H₅₂N₄O₃ 
• 1004960-66-0 C₃₃H₄₀N₄O₃ 
• 320713-99-3 C₂₁H₃₀N₂O₅ 
• 189561-71-5 2,6-Bis-[(di-tert-butyl-phosphanyl)-methyl]-4-methyl-phenol 
• 651300-76-4 [3-(dimethoxy-phosphorylmethyl)-2-hydroxy-5-methyl-benzyl]phosphonic acid dimethyl ester 
• 108817-13-6 5-phenyl-11-tert-butyl-17-carbethoxy-23-methyl-25,26,27,28-tetrahydrocalix<4>arene 

Relevant articles and documents

A CuII2 Paramagnetic Chemical Exchange Saturation Transfer Contrast Agent Enabled by Magnetic Exchange Coupling

The ability of magnetic exchange coupling to enable observation of paramagnetic chemical exchange saturation transfer (PARACEST) in transition metal ions with long electronic relaxation times (s) is demonstrated. Metalation of the dinucleating, tetra(carboxamide) ligand HL with Cu2+ in the presence of pyrophosphate (P2O7)4- affords the complex [LCuII2(P2O7)]-. Solution-phase variable-temperature magnetic susceptibility data reveal weak ferromagnetic superexchange coupling between the two S = 1/2 CuII centers, with a coupling constant of J = +2.69(5) cm-1, to give an S = 1 ground state. This coupling results in a sharpened NMR line width relative to a GaCu analogue, indicative of a shortening of s. Presaturation of the amide protons in the Cu2 complex at 37 °C leads to a 14% intensity decrease in the bulk water 1H NMR signal through the CEST effect. Conversely, no CEST effect is observed in the GaCu complex. These results provide the first example of a Cu-based PARACEST magnetic resonance contrast agent and demonstrate the potential to expand the metal ion toolbox for PARACEST agents through introduction of magnetic exchange coupling.

PROPARGYL-FUNCTIONALIZED MACROCYCLIC COMPOUNDS

Propargyl-functionalized macrocyclic compounds can include non-aggregating compounds having at least one phthalocyanine (Pc), azaphthalocyanine (AzaPc), or naphthalocyanine (Nc) unit. The compounds can be metal-free or metal-complexed. The metal-complexed

Electronic Effects of Ligand Substitution in a Family of CoII2 PARACEST pH Probes

We report three new Co2-based paramagnetic chemical exchange saturation transfer (PARACEST) probes with the ability to ratiometrically quantitate pH. A CoII2 complex, [LCo2(etidronate)]-, featuring tetra(carboxamide) and OH-substituted etidronate ligands with opposing pH-dependent CEST peak intensities, was previously shown to exhibit a linear correlation between log(CESTOH/CESTNH) and pH in the pH range 6.5-7.6 that provided a sensitivity of 0.99(7) pH unit-1 at 37 °C. Here, we demonstrate through a series of CF3-functionalized CoII2 complexes [(XL′)Co2(etidronate)]- (X = NO2, F, Me), that modest changes in the electronic structure of CoII centers through remote ligand substitution can significantly affect the NMR and CEST properties of Co2-based PARACEST probes. Variable-pH NMR and CEST analyses reveal that the chemical shifts of the ligand protons are highly affected by the nature of the X substituent. The ratios of OH and NH CEST peak intensities at 115 and 88, 93 and 79, and 88 and 76 ppm for X = NO2, F, and Me, respectively, afford pH calibration curves with remarkably high sensitivities of 1.49(9), 1.48(7), and 2.04(5) pH unit-1 across the series. The 1.5-2-fold enhancement in pH sensitivity for the CF3-functionalized Co2 probes stems from the complete separation of the OH and NH CEST peaks. Furthermore, incorporation of electron-withdrawing CF3 groups shifts the detection window to a more acidic range of pH 6.2-7.4. Finally, the CoII2 complexes are found to be extremely robust toward substitution and oxidation in aqueous solutions. Taken together, these results highlight the unique ability of transition metal-based PARACEST probes to provide a highly sensitive concentration-independent measure of pH and demonstrate that modest ligand modifications can be a powerful tool for optimizing the pH sensing performance of these probes.