27079-92-1

Usage

Uses

Used in Chemical Synthesis:
4-(Bromomethyl)phenol is used as a synthetic intermediate for the production of various chemical compounds. Its reactivity and functional groups make it a valuable building block in the synthesis of a wide range of molecules.
Used in Polymer and Resin Production:
4-(Bromomethyl)phenol is used as a key component in the manufacturing process of certain polymers and resins. Its presence in these materials can influence their properties, such as stability, durability, and reactivity.
Safety Precautions:
Due to its potential hazards, 4-(Bromomethyl)phenol should be handled with care. It may cause skin and eye irritation, as well as respiratory issues if inhaled. Ingestion of this chemical can also lead to adverse health effects. Therefore, it is essential to take necessary safety measures, such as wearing protective gear and working in a well-ventilated area, when working with 4-(Bromomethyl)phenol.

InChI:InChI=1/C7H7BrO/c8-5-6-1-3-7(9)4-2-6/h1-4,9H,5H2

Synthetic route

Conditions	Yield
With sodium perborate In methanol at 25℃; for 0.5h;	80%

→ 4-(bromomethyl)phenol

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine; sodium bromide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h; chemoselective reaction;	59%
With pyridine; phosphorus tribromide In tetrahydrofuran for 18h; Ambient temperature;
With pyridine; phosphorus tribromide In tetrahydrofuran at 20℃; for 12h;

→ 4-(bromomethyl)phenol (27079-92-1)

Conditions	Yield
With perchloric acid; sodium perchlorate; bromide at 25℃; Equilibrium constant;

1,2-dibromomethane (74-95-3) + phenol (108-95-2) → 4-(bromomethyl)phenol (27079-92-1) + 2-hydroxybenzyl bromide (58402-38-3)

Conditions	Yield
Stage #1: phenol With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: 1,2-dibromomethane In N,N-dimethyl-formamide at 60℃; for 2h;

4-hydroxy-benzaldehyde (123-08-0) → 4-(bromomethyl)phenol (27079-92-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol 2: phosphorus tribromide / dichloromethane View Scheme

4-(bromomethyl)phenol (27079-92-1) + phenylacetylene (536-74-3) → 1-(p-hydroxybenzyl)-4-phenyl-1H-1,2,3-triazole (104951-50-0)

Conditions	Yield
With sodium azide In water at 60℃; Inert atmosphere; Green chemistry;	93%

4-(bromomethyl)phenol (27079-92-1) → 4-hydroxy-benzaldehyde (123-08-0)

Conditions	Yield
Stage #1: 4-(bromomethyl)phenol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide In water for 0.0833333h; Reflux; Stage #2: With dihydrogen peroxide In water for 3h;	86%

Upstream product

• 623-05-2 (4-hydroxyphenyl)methanol 
• 439660-38-5 p-hydroxybenzyl cation 
• 52727-95-4 4-acetoxybenzyl bromide 
• 74-95-3 1,1-dibromomethane 
• 108-95-2 phenol 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 140468-02-6 4-(bromomethyl)phenyl phosphorodichloridate 
• 439660-38-5 p-hydroxybenzyl cation 
• 872254-19-8 (S)-1-(4-Hydroxybenzyl)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione 
• 90001-07-3 4-mono(dihydroxy-phosphonyl) methyl phenol 
• 138498-62-1 N-(2(R)-hydroxy-1(S)-indanyl)-5(S)-[1,1-dimethylethoxy-carbonylamino]-4(S)-hydroxy-6-phenyl-2(R)-(4-hydroxyphenylmethyl) hexanamide 
• 140467-84-1 Phosphoric acid 4-bromomethyl-phenyl ester 3-hexadecyloxy-2-methoxy-propyl ester 
• 140467-85-2 Phosphoric acid 4-bromomethyl-phenyl ester 2-methoxy-3-(3-tetradecyl-phenoxy)-propyl ester 
• 478162-98-0 ethyl 3-((4-hydroxyphenyl)methylthio)propionate 
• 1099430-59-7 2-butyl-3-(4-o-cyanobenzyloxybenzyl)-4,5-dihydro-4-oxo-3H-imidazo[4,5-c]pyridine 
• 147876-78-6 6-butyl-1-(4-o-cyanobenzyloxybenzyl)-1,2-dihydro-2-oxopyridine 

Relevant academic research and scientific papers

Synthesis, inhibition properties against xanthine oxidase and molecular docking studies of dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives

This study focused on synthesis various dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives under the conditions of green chemistry without the use of solvent and catalysts. Their inhibition properties were also investigated on xanthine oxidase (XO) activity. All dimethanol and dicarboxylate derivatives exhibited significant inhibition activities with IC50 values ranging from 0.71 to 2.25 μM. Especially, (1-(3-bromobenzyl)-1H-1,2,3-triazole-4,5-diyl)dimethanol (5c) and dimethyl 1-(4-chlorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylate (6 g) compounds were found to be the most promising derivatives on the XO enzyme inhibition with IC50 values 0.71 and 0.73 μM, respectively. Moreover, the double docking procedure was to evaluate compound modes of inhibition and their interactions with the protein (XO) at atomic level. Surprisingly, the docking results showed a good correlation with IC50 [correlation coefficient (R2 = 0.7455)]. Also, the docking results exhibited that the 5c, 6f and 6 g have lowest docking scores ?4.790, ?4.755, and ?4.730, respectively. These data were in agreement with the IC50 values. These results give promising beginning stages to assist in the improvement of novel and powerful inhibitor against XO.

Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides

Direct coupling of unactivated alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a strategy building upon in situ halogenation/reductive coupling of alcohols with aryl halides to forge Csp2-Csp3 bonds. The combination of 2-chloro-3-ethylbenzo[d]oxazol-3-ium salt (CEBO) and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation of alkyl halides. More importantly, the mild and kinetically rapid bromination process has shown good selectivity in the bromination/arylation of symmetric diols and less sterically hindered hydroxyl groups in polyols, thus offering promise for selective functionalization of diols and polyols without laborious protecting/deprotecting operations. The practicality of this work is also evident in the arylation of a number of carbohydrates, drug compounds, and naturally occurring alcohols.

Compounds for the treatment of metabolic disorders

Compounds useful for the treatment of various metabolic disorders, such as insulin resistance syndrome, diabetes, hyperlipidemia, fatty liver disease, cachexia, obesity, atherosclerosis and arteriosclerosis, are disclosed.

Clay-Supported Cu(II) Catalyst: An Efficient, Heterogeneous, and Recyclable Catalyst for Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Alloxan-Derived Terminal Alkyne and Substituted Azides Using Click Chemistry

A novel series of alloxan-derived 1,4-disubstituted 1,2,3-triazoles was synthesized in excellent yields under catalytic conditions using a click reaction strategy through 1,3-dipolar cycloaddition. Their structures have been ascertained on the basis of spectroanalytical and elemental analysis data. Synthesis of hybrid compounds with varying substitutions in the triazole ring was achieved by reaction between alloxan-derived terminal alkyne and a pertinent azide derivative in the presence of clay-Cu(II) as the catalyst in methanolic medium. Also, comparative evaluation of various catalytic systems [viz., CuI, CuSO4, CuI-zeolite, K10Ti, and clay-Cu(II)] was investigated. Of these catalytic systems, clay-Cu(II) was observed to be the best. The catalyst was recyclable for several runs without showing significant loss in its activity. The good selectivity, cost-efficiency, short reaction time, milder reaction conditions, and simple workup procedure are the added salient features of this synthetic protocol.

A chemoselective, easy bromination of (hydroxymethyl)phenols

A simple and chemoselective method for direct bromination of (hydroxymethyl)phenols via reaction with 2,4,6-trichloro[1,3,5]triazine in N,N-dimethylformamide at room temperature is described. The reaction occurs without affecting the phenolic hydroxy group. Georg Thieme Verlag Stuttgart.

Compounds for the treatment of metabolic disorders

Compounds useful for the treatment of various metabolic disorders, such as insulin resistance syndrome, diabetes, hyperlipidemia, fatty liver disease, cachexia, obesity, atherosclerosis and arteriosclerosis, are disclosed.

Flash photolytic generation and study of p-Quinone methide in aqueous solution. An estimate of rate and equilibrium constants for heterolysis of the carbon-bromine bond in p-hydroxybenzyl bromide

Flash photolysis of p-hydroxybenzyl acetate in aqueous perchloric acid solution and formic acid, acetic acid, biphosphate ion, and tris(hydroxymethyl)methylammonium ion buffers produced p-quinone methide as a short-lived species that underwent hydration t

Facile and selective deprotection of aryl acetates using sodium perborate under mild and neutral conditions

A variety of aryl acetates are cleaved to the corresponding phenols using sodium perborate in methanol under mild conditions (25°C). The effectiveness of this protocol is manifested in its tolerance of different functional groups and selectivity of deprotection towards aryl acetates whereas alkyl acetates are found to be unreactive under these reaction conditions.

Rotaxane Assemblies with Dendritic Architecture

Strategies towards the synthesis of well-defined, mechanically interlocked, dendritic assemblies of rotaxanes are developed, one using a divergent, and the other a convergent approach. For the first time covalent bonds are not directly involved in the branching of dendrimers, only mechanical bonds act as unique branching elements.

Analogues of Platelet Activating Factor. 6. Mono- and Bis-Aryl Phosphate Antagonists of Platelet Activating Factor

A series of aryl phosphoglyceride (3, 19-61) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared.A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied.These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets.Selected compounds were also evaluated for their ability to displace PAF from its receptor on rabbit platelets.These in vitro data were compared to similar data obtained for a number of known PAF antagonists.The compounds were evaluated in vivo, in both the mouse and rabbit, for their ability to prevent death induced by a lethal challenge of PAF.The relationships between the biological activity and the nature, lipophilicity, and position of substituents of the aromatic rings were studied.Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.