62415-74-1

Basic information

• Product Name: 3,4-Dibromoanisole
• Synonyms: 3,4-Dibromoanisole 94%, remainder predominantly isomer;1,2-Dibromo-4-methoxybenzene
• CAS NO: 62415-74-1
• Molecular Formula: C₇H₆Br₂O
• Molecular Weight: 265.93
• Product Categories: Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds
• Mol File: 62415-74-1.mol

Chemical Properties

• Boiling Point: 127℃
• Flash Point: 104.9±20.3℃
• Appearance: /
• Density: 1.823±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0153mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,4-Dibromoanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dibromoanisole(62415-74-1)
• EPA Substance Registry System: 3,4-Dibromoanisole(62415-74-1)

Safety Data

• Hazardous Substances Data: 62415-74-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dibromoanisole is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs, contributing to the advancement of medical treatments.
Used in Agrochemical Industry:
In the agrochemical sector, 3,4-Dibromoanisole serves as an essential intermediate in the production of various agrochemicals. Its properties make it suitable for the synthesis of pesticides and other agricultural chemicals, helping to improve crop protection and yield.
Used in Organic Synthesis:
3,4-Dibromoanisole is utilized as a precursor in organic synthesis, enabling the creation of a wide range of chemical compounds. Its reactivity and functional groups make it a valuable building block for the development of new organic molecules with diverse applications.
Used in Drinking Water Treatment:
Although not intended for this purpose, 3,4-Dibromoanisole has been identified as a potential byproduct of disinfection processes in drinking water treatment. Its presence in drinking water raises concerns about potential health impacts, necessitating further investigation and monitoring to ensure public safety.

InChI:InChI=1/C7H6Br2O/c1-10-5-2-3-6(8)7(9)4-5/h2-4H,1H3

Upstream product

• 615-54-3 1,2,4-tribromobenzene 
• 124-41-4 sodium methylate 
• 104-94-9 4-methoxy-aniline 
• 74317-85-4 2-bromo-4-methoxybenzoic acid 
• 615-56-5 3,4-dibromophenol 
• 74-88-4 methyl iodide 
• 95970-11-9 2-Acetamido-4,5-dibromoanisole 
• 93-26-5 2-methoxyacetanilide 
• 2398-37-0 3-methoxyphenyl bromide 

Downstream Products

• 80323-72-4 4-methoxyphthalonitrile 
• 1427042-51-0 1-methoxy-3,4-bis(trimethylsilyl)benzene 
• 71866-40-5 2-hydroxydibenzo-p-dioxin 
• 97025-36-0 methoxy-4 phtalate d'ethyle 
• 102-51-2 4-methoxy-1,2-phenylenediamine 
• 67929-86-6 methyl 5-methoxyindole-2-carboxylate 
• 98081-83-5 methyl 6-methoxy-1H-indole-2-carboxylate 

Relevant articles and documents

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide

Although iodine-catalyzed reaction has rapid advances in recent years, examples on iodine-catalyzed bromination are rare and the mechanism of these reactions remains unclear. Herein, we reported an I2-catalyzed aromatic bromination of aryl ethers by NBS and presented the details of the mechanistic study including kinetic study and the study of kinetic isotope effects. The study revealed that the reaction was actually catalyzed by IBr formed in the induction period, and the rate-determining step was the HBr-elimination of the Wheland intermediate assisted by IBr.

Regioselectivity in the aryne cross-coupling of aryllithiums with functionalized 1,2-dibromobenzenes

Tri- and tetrasubstituted ortho-bromobiaryls have been synthesized in good-to-excellent yields by aryne cross-coupling reactions starting from 1,3-dimethoxybenzene and functionalized 1,2-dibromobenzenes. This study outlines the influence of the 1,2-dibromobenzene precursor as well as the reaction temperature on the outcome of the aryl-aryl bond formation and indicates, in the case of dissymmetrical benzyne precursors, how structural parameters (electronic effects, steric hindrance, temperature, etc.) control the regioselectivity of the aryne cross-coupling reactions. A wide range of o,o′-tri- and-tetrasubstituted biphenyls have been prepared by a transition-metal-free "aryne" cross-coupling starting from 2,6-dimethoxyphenyllithium and various functionalized 1,2-dibromobenzenes. Mechanistic investigations outline the key parameters that govern both the aryl-aryl bond formation and the regioselectivity of the reaction with dissymmetrical aryne precursors. Copyright

Hydrochloric acid catalysis of N-bromosuccinimide (NBS) mediated nuclear aromatic brominations in acetone

Nuclear bromination of activated aromatic substrates can be achieved quickly and in high yields using N-bromosuccinimide (NBS) in acetone with 1 M HCl catalysis.

POLYBROMINATED AROMATIC COMPOUNDS. IV. METHOXYDEBROMINATION REACTIONS OF POLYBROMOBENZENES IN PYRIDINE

The rates were measured and the orientation was studied for the methoxydebromination of all polybromobenzenes C6HnBr6-n (n = 0-3) in pyridine at 115 deg C.From comparison of the partial rates of substitution of the bromine atom at various positions of the benzene ring it was found that the activating effect of the bromine atom in relation to the point of nucleophilic attack changes in the order o-Br > m-Br > p-Br, and the directing selectivity of the bromine is low (compared with fluorine in the methoxydefluorination of polyfluorobenzenes) and increases with decrease in the number of bromine atoms in the aromatic ring of the substrate.

POLYBROMINATED AROMATIC COMPOUNDS. III. SYNTHESIS OF BROMINE-SUBSTITUTED ANISOLES

Reliable methods were developed for the synthesis of di-, tri-, and tetrabromoanisoles, and all the possible individual isomers were synthesized.The structures of the isomers were proved by alternative synthesis and spectral methods (PMR, IR).It was shown that the published data are incorrect in a number of cases; either the final product was assigned the incorrect structure, or the published methods led to mixture of the various isomers.

107. Substitution electrophile aromatique dans l'anhydride sulfureux liquide. Etude cinetique de la reaction de bromination d'anisoles monosubstitues. Transmission des effets electroniques et caracteristiques de l'etat de transition

Reactivity-structure correlations for anisole and eleven of its substituted derivatives established from bromination rate constants in liquid SO2, unlike observations in water, show the reaction to be highly sensitive to substituent effects, (ρ+H2O = -7.1; ρ+SO2 = -10.51).This result is ascribed to the solvation of the methoxy group which decreases the conjugation of para-substituted (ρ+O = -9.70) compared to that of ortho-substituted derivatives (ρ+p = -8.86).The highly solvated transition state lies far from reactants on the reaction coordinate and the positive charge developed in this state is nearly unity.

ETUDE CINETIQUE DE LA REACTION DE BROMINATION DANS LE SO2 LIQUIDE. REACTIVITES DU BENZENE, DES POLYMETHYLBENZENES ET D'ANISOLES SUBSTITUES. DETERMINATION DES REACTIVITES RELATIVES ET CALCUL DES FACTEURS DE VITESSE PARTIELLE

Absolute rate constants for the bromination of a series of anisoles and polymethylbenzenes, have been measured in liquid sulfur dioxide at -23 +/- 2 deg C.Rate constants for benzene and toluene were determined by extrapolation as: 9.6E-7 and 4.2E-4 l mol-1 mn-1 respectively.Under these conditions, the bromination of anisole provides 0.56percent ortho- and 98.99percent para-bromoanisole, and the rate relative to benzene is 6.98E8/1.00.These date lead to the partial rate factors for the methoxy group: οOMef = 1.1E7 and pOMef = 4.12E9.The value mOMef = 1.4 is calculated from the rate constant for p-dimethoxy benzene, 10 l mol-1 mn-1.Similarly, in the case of bromination of toluene, a relative rate of 443/1.00, and an isomer distribution of 16percent ortho- and 84percent para, permit the calculation of partial rate for the methyl group:οMef = 212 mMef = 6.4 pMef = 2232 > correlations log k = f(Σ?+), established for the bromination of anisoles and polymethylbenzenes, exhibit large values for their slopes (ρAnisoles+ = -10.51; ρ+polymethylbenzenes = -9.5), and indicate satisfactory additivity of substituent effects.It appears that the + M effect of the methoxy group is less strong in this solvent than it is in water or acetic acid.Despite its low dielectric constant, (D = 17.5 at -20 deg C), liquid sulfur dioxide appearars to be quite a favourable medium for electrophilic aromatic substitution.Thus, for identical experimental conditions, the rate constants for bromination are 1E2 to 1E4 lower than those observed in water, but 1E3 to 1E5 larger than those in acetic acid.

Alkyl Nitrite-Metal Halide Deamination Reactions. 7. Synthetic Coupling of Electrophilic Bromination with Substitutive Deamination for Selective Synthesis of Multiply Brominated Aromatic Compounds from Arylamines

Aromatic amines undergo substitution with copper(II)bromide that is in competition with substitutive deamination when these reactions are performed with tert-butyl nitrite.Except for the exceptionally reactive 4-substituted 1-aminonaphthalenes,which undergo selective bromine substitution at the 1- and 2-positions in relatively high isolated yields,rates for oxidative bromination and substitutive deamination are not sufficiently different that selective multiple bromination can be achieved.Oxidative bromination of N,N-dimethylaniline by copper(II)bromide occurs with partial dealkylation,and nitration products are observed from reactions performed with copper(II)bromide and tert-butyl nitrite.Implications of these results for the successful utilization of copper(II)bromide/tert-butyl nitrite combinations in substitutive deamination reactions of aromatic amines are discussed.Multiply brominated aromatic compounds are produced from aromatic amines in high yield through treatment of the aromatic amine with the combination of molecular bromine and catalytic quantities of copper(II)bromide and,following a normally brief time delay,with tert-butyl nitrite.All unsubstituted aromatic ring positions ortho and para to the amino group,as well as the position of the amino group,are substituted by bromine.The only observed byproducts from use of this procedure (usually 2percent yield) are the partially brominated benzene derivatives.