Pharmaceutical intermediates & materials

Home - Products - Pharmaceutical intermediates & materials

4-Bromoanisole

  • Product Name: 4-Bromoanisole
  • CasNo: 104-92-7
  • Purity:
  • Appearance: colourless liquid

Mobile/Wechat/WhatsApp: Chen Shihuai +86-13961989018  Yang Zhengquan +86-13921613169   Chen Yi +86-13962066393

Email:

Inquiry

CasNo: 104-92-7

Molecular Formula: C7H7BrO

Appearance: colourless liquid

Factory supply 4-Bromoanisole 104-92-7 with sufficient production capacity

  • Molecular Formula:C7H7BrO
  • Molecular Weight:187.036
  • Appearance/Colour:colourless liquid 
  • Vapor Pressure:0.147mmHg at 25°C 
  • Melting Point:9-10 °C(lit.) 
  • Refractive Index:1.563 
  • Boiling Point:222.999 °C at 760 mmHg 
  • Flash Point:96.648 °C 
  • PSA:9.23000 
  • Density:1.443 g/cm3 
  • LogP:2.45770 

4-Bromoanisole(Cas 104-92-7) Usage

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 7429, 1994 DOI: 10.1016/0040-4039(94)85333-9Synthesis, p. 868, 1986 DOI: 10.1055/s-1986-31813

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. When heated to decomposition itemits toxic vapors of Br-.

Purification Methods

Crystallise the anisole by repeated partial freezing, then distil it under reduced pressure. [Beilstein 6 III 741, 6 IV 1044.]

Definition

ChEBI: A monomethoxybenzene carrying a bromo substituent at position 4.

General Description

4-Bromoanisole is a useful brominating reagent. It is formed as reaction product in the reaction between HOBr and anisole. Suzuki coupling of 4-bromoanisole with phenylboronic acid catalyzed by palladium pincer complexes has been studied. Heck Reaction of 4-bromoanisole with ethyl acrylates in room-temperature ionic liquids is reported to afford ethyl 4-methoxycinnamate.

InChI:InChI=1/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3

104-92-7 Relevant articles

Dehydroxymethyl Bromination of Alkoxybenzyl Alcohols by Using a Hypervalent Iodine Reagent and Lithium Bromide

Shibata, Ayako,Kitamoto, Sara,Fujimura, Kazuma,Hirose, Yuuka,Hamamoto, Hiromi,Nakamura, Akira,Miki, Yasuyoshi,Maegawa, Tomohiro

, p. 2275 - 2278 (2018)

We describe the dehydroxymethylbrominati...

Copper-catalyzed halogenation of arylboronic acids

Zhang, Guangyou,Lv, Guanglei,Li, Liping,Chen, Fan,Cheng, Jiang

, p. 1993 - 1995 (2011)

In this Letter, a copper-catalyzed halog...

Gold-catalyzed halogenation of aromatics by N-halosuccinimides

Mo, Fanyang,Yan, Jerry Mingtao,Qiu, Di,Li, Fei,Zhang, Yan,Wang, Jianbo

, p. 2028 - 2032 (2010)

(Chemical Equation Presented) Golden bro...

Site-specific Bromination of Aromatic Compounds: a Rapid Method for Radiobromine Labelling

Adam, Michael J.,Ruth, Thomas J.,Pate, Brian D.,Hall, Laurance D.

, p. 625 - 626 (1982)

Bromobenzene and -p-bromoanisole have be...

Applications of Selenonium Cations as Lewis Acids in Organocatalytic Reactions

He, Xinxin,Wang, Xinyan,Tse, Ying-Lung (Steve),Ke, Zhihai,Yeung, Ying-Yeung

, p. 12869 - 12873 (2018)

The use of trisubstituted selenonium sal...

Electrophilic cleavage reactions of carbon-silicon bonds in neutral hexacoordinate silicon compounds: diorgano(phtalocyaninato)silicon

Tamao, Kohei,Akita, Munetaka,Kato, Hidehito,Kumada, Makoto

, p. 165 - 180 (1988)

Preparations of diorgano(phtalocyaninato...

-

Uemura et al.

, p. 147 (1974)

-

Generation of interhalogen fluorides under mild conditions: A comparison of sluggish and reactive interhalogen fluorides

Shellhamer, Dale F.,Horney, Mark J.,Pettus, Benjamin J.,Pettus, Tobiah L.,Stringer, Joy Merry,Heasley, Victor L.,Syvret, Robert G.,Dobrolsky Jr., John M.

, p. 1094 - 1098 (1999)

Interhalogen fluorides (XF; X = I, Br, o...

Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ

Baik, Woonphil,Luan, Wanqiang,Lee, Hyun Joo,Yoon, Cheol Hun,Koo, Sangho,Kim, Byeong Hyo

, p. 213 - 219 (2005)

Halodimethylsulfonium halide 1, which is...

Sodium nitrite-catalyzed oxybromination of aromatic compounds and aryl ketones with a combination of hydrobromic acid and molecular oxygen under mild conditions

Zhang, Guofu,Liu, Renhua,Xu, Qing,Ma, Lixin,Liang, Xinmiao

, p. 862 - 866 (2006)

A novel and efficient catalytic system f...

An efficient, rapid and regioselective nuclear bromination of aromatics and heteroaromatics with NBS using sulfonic-acid-functionalized silica as a heterogeneous recyclable catalyst

Das, Biswanath,Venkateswarlu, Katta,Krishnaiah, Maddeboina,Holla, Harish

, p. 8693 - 8697 (2006)

A simple, efficient and rapid method has...

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

Castellonese, Paul,Villa, Pierre

, p. 1068 - 1077 (1983)

Reactivity-structure correlations for an...

Solvent effect in the free-radical oxidation and electrophilic ipso and hydrogen displacement of p-methoxybenzyl alcohol and N-(p-methoxybenzyl)acetamide by Br2

Bravo, Anna,Fontana, Francesca,Dordi, Barbara,Minisci, Francesco

, p. 3880 - 3881 (2000)

-

Site directed nuclear bromination of aromatic compounds by an electrochemical method

Raju,Kulangiappar,Anbu Kulandainathan,Uma,Malini,Muthukumaran

, p. 4581 - 4584 (2006)

Direct bromination of a wide range of ar...

Green halogenation reactions for (hetero)aromatic ring systems in alcohol, water, or no solvent

Kajorinne, Jessie K.,Steers, Jennifer C.M.,Merchant, Marnie E.,MacKinnon, Craig D.

, p. 1087 - 1091 (2018)

A new method of brominating aromatic and...

Fast and easy halide exchange in aryl halides

Arvela, Riina K.,Leadbeater, Nicholas E.

, p. 1145 - 1148 (2003)

We report here the rapid halide exchange...

Catalytic Sandmeyer bromination

Beletskaya, Irina P.,Sigeev, Alexander S.,Peregudov, Alexander S.,Petrovskii, Pavel V.

, p. 2534 - 2538 (2007)

An efficient catalyst system for Sandmey...

A new recoverable Au(III) catalyst supported on magnetic polymer nanocomposite for aromatic bromination

Li, Bai,Gao, Linfeng,Bian, Fengling,Yu, Wei

, p. 1063 - 1066 (2013)

This Letter presents a facile alternativ...

Bis(sym-collidine)bromine(I) hexafluorophosphate as oxidant

Rousseau,Robin

, p. 8881 - 8885 (2000)

Primary and secondary alcohols in soluti...

Predicting the structure of supramolecular dendrimers via the analysis of libraries of AB3 and constitutional isomeric AB2 biphenylpropyl ether self-assembling dendrons

Rosen, Brad M.,Wilson, Daniela A.,Wilson, Christopher J.,Peterca, Mihai,Won, Betty C.,Huang, Chenghong,Lipski, Linda R.,Zeng, Xiangbing,Ungar, Goran,Heiney, Paul A.,Percec, Virgil

, p. 17500 - 17521 (2009)

The synthesis of 4′-hydroxy-4-biphenylpr...

One-pot synthesis of 4-aryl-2-aminothiazoles from styrenes and thioureas promoted by tribromoisocyanuric acid

de Andrade, Vitor S.C.,de Mattos, Marcio C.S.

, (2020)

A simple and efficient one-pot protocol ...

In situ acidic carbon dioxide/water system for selective oxybromination of electron-rich aromatics catalyzed by copper bromide

Liu, An-Hua,Ma, Ran,Zhang, Meng,He, Liang-Nian

, p. 38 - 43 (2012)

Carbon dioxide, being one of the major g...

Brominations with Pr4NBr9 as a solid reagent with high reactivity and selectivity

Beck, Thorsten M.,Haller, Heike,Streuff, Jan,Riedel, Sebastian

, p. 740 - 747 (2014)

Tetrapropylammonium nonabromide (Pr4NBr9...

-

Beringer,Mausner

, p. 4535 (1958)

-

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe3 or PhSSPh

Hirose, Yuuka,Yamazaki, Mirai,Nogata, Misa,Nakamura, Akira,Maegawa, Tomohiro

, p. 7405 - 7410 (2019)

We developed a mild aromatic halogenatio...

-

Forrest,J.

, p. 589 - 592 (1960)

-

Iodine(I) reagents in hydrochloric acid-catalyzed oxidative iodination of aromatic compounds by hydrogen peroxide and iodine

Bedrac, Leon,Iskra, Jernej

, p. 1243 - 1248 (2013)

Hydrochloric acid activates the oxidativ...

ELECTROPHILIC BROMINATION OF PHENOL ETHERS IN SUPERACID SOLUTION USING ALKALI BROMIDE

Cherry, Ghassan,Culmann, Jean-Christophe,Sommer, Jean

, p. 2007 - 2010 (1990)

Electrophilic aromatic bromination of ph...

Selective halogenation of aromatics by dimethyldioxirane and halogen ions

Bovicelli,Mincione,Antonioletti,Bernini,Colombari

, p. 2955 - 2963 (2001)

The oxidation of halogen anions by dimet...

Vanadium-catalysed oxidative bromination using dilute mineral acids and hydrogen peroxide: An option for recycling waste acid streams

Rothenberg, Gadi,Clark, James H.

, p. 270 - 274 (2000)

Vanadium pentoxide, V2O5, catalyses the ...

Direct halogenation of organic compounds with halides using oxone in water - A green protocol

Firouzabadi,Iranpoor,Kazemi

, p. 1675 - 1681 (2009)

Direct bromination and iodination of var...

-

Korzeniowski,Gokel

, p. 3519 (1977)

-

RADICAL DECARBOXYLATIVE BROMINATION OF AROMATIC ACIDS

Barton, Derek H.R.,Lacher, Brigitte,Zard, Samir Z.

, p. 5939 - 5942 (1985)

Thiohydroxamic esters (mixed anhydrides)...

(Diacetoxyiodo)benzene-Lithium Bromide as a Convenient Electrophilic Br+ Source

Braddock, D. Christopher,Cansell, Gemma,Hermitage, Stephen A.

, p. 461 - 464 (2004)

A mild and versatile procedure for the b...

Oxidative bromination reaction using vanadium catalyst and aluminum halide under molecular oxygen

Kikushima, Kotaro,Moriuchi, Toshiyuki,Hirao, Toshikazu

, p. 340 - 342 (2010)

The vanadium-catalyzed oxidative bromina...

A Mild Selective Monobromination Reagent System for Alkoxybenzenes; N-Bromosuccinimide-Silica Gel

Konishi, Hisatoshi,Aritomi, Katsutomo,Okano, Tamon,Kiji, Jitsuo

, p. 591 - 593 (1989)

The monobromination of alkoxybenzenes wi...

An efficient regioselective NBS aromatic bromination in the presence of an ionic liquid

Pingali, Subramanya R.K.,Madhav, Monika,Jursic, Branko S.

, p. 1383 - 1385 (2010)

A simple, efficient, and rapid method wa...

The oxidative halogenations of arenes in water using hydrogen peroxide and halide salts over an ionic catalyst containing sulfo group and hexafluorotitanate

Wang, Ling,Wang, Sa-Sa,Vo-Thanh, Giang,Liu, Ye

, p. 56 - 62 (2013)

An ionic compound, bis[1-methyl-3-(3′-su...

An efficient vanadium-catalyzed bromination reaction

Moriuchi, Toshiyuki,Yamaguchi, Mitsuaki,Kikushima, Kotaro,Hirao, Toshikazu

, p. 2667 - 2670 (2007)

An efficient catalytic oxidative bromina...

Highly efficient halogenation of organic compounds with halides catalyzed by cerium(III) chloride heptahydrate using hydrogen peroxide as the terminal oxidant in water

Firouzabadi, Habib,Iranpoor, Nasser,Kazemi, Somayeh,Ghaderi, Arash,Garzan, Atefeh

, p. 1925 - 1932 (2009)

In this article a new environmentally fr...

Metal- and base-free synthesis of aryl bromides from arylhydrazines

Phuc Tran, Dat,Nomoto, Akihiro,Mita, Soichiro,Dong, Chun-ping,Kodama, Shintaro,Mizuno, Takumi,Ogawa, Akiya

, (2020)

An efficient method was developed to syn...

Poly-N-bromosulfonamide-melamine as a novel brominating reagent for regioselective ipso-bromination of arylboronic acids

Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin

, p. 1269 - 1276 (2021)

A practical synthetic method for the syn...

An intriguing effect of lithium perchlorate dispersed on silica gel in the bromination of aromatic compounds by N-bromosuccinimide

Bagheri, Mojtaba,Azizi, Najmedin,Saidi, Mohammad R.

, p. 146 - 149 (2005)

A convenient and efficient procedure for...

Metal and H2O2 free aerobic oxidative aromatic halogenation with [RNH3+] [NO3-]/HX and [BMIM(SO3H)][NO3)x(X)y] (X = Br, Cl) as multifunctional ionic liquids

Prebil, Rok,Laali, Kenneth K.,Stavber, Stojan

, p. 2108 - 2111 (2013)

Novel multifunctional ionic liquids (ILs...

The X-ray crystal structures and computational analysis of NH...π hydrogen bonded banana-shaped carbazole derivatives and thermal analysis of higher mesogenic homologues

Belloni, Maura,Manickam,Ashton, Peter R.,Kariuki, Benson M.,Preece, Jon A.,Spencer, Neil,Wilkie, John

, p. 17 - 35 (2001)

The synthesis of a series of banana-shap...

Arenediazonium o-benzenedisulfonimides: Some kinetics of azo coupling reactions with naphthols

Boga, Carla,Degani, Jacopo,Del Vecchio, Erminia,Fochi, Rita,Forlani, Luciano,Todesco, Paolo E.

, p. 3837 - 3843 (2002)

Kinetic investigation of azo coupling re...

Anodically-Generated Br-Cl Composite Halogenating Reagents

Fukui, Kouta,Nonaka, Tsutomu

, p. 943 - 948 (1992)

The halogenating power of Br-Cl composit...

Detection of Aryl Radicals in Hydrodediazoniations

Wassmundt, Frederick W.,Kiesman, William F.

, p. 8304 - 8308 (1997)

Iodoacetic acid, an effective aryl radic...

Methanolysis of 4-bromobenzenediazonium ions. Effects of acidity, [MeOH] and temperature on the formation and decomposition of diazo ethers that initiate homolytic dediazoniation

Fernandez-Alonso, Alejandra,Bravo-Diaz, Carlos

, p. 4004 - 4011 (2008)

We have investigated the effects of solv...

Silver catalyzed bromination of aromatics with N-bromosuccinimide

Zhang, Rui,Huang, Lei,Zhang, Yanfang,Chen, Xiaorong,Xing, Weihong,Huang, Jun

, p. 378 - 383 (2012)

A heterogeneous silver catalyst was prep...

AUTOMATED DIAZOMETHANE GENERATOR, REACTOR AND SOLID PHASE QUENCHER

-

Page/Page column 17-18, (2022/03/09)

An automated apparatus (Diazo-M-pen and ...

Eco-Friendly Methodology for the Formation of Aromatic Carbon–Heteroatom Bonds by Using Green Ionic Liquids

Richards, Kenza,Petit, Eddy,Legrand, Yves-Marie,Grison, Claude

supporting information, p. 809 - 814 (2020/11/30)

A new sustainable method is reported for...

Visible-Light Promoted C–O Bond Formation with an Integrated Carbon Nitride–Nickel Heterogeneous Photocatalyst

Vijeta, Arjun,Casadevall, Carla,Roy, Souvik,Reisner, Erwin

supporting information, p. 8494 - 8499 (2021/03/08)

Ni-deposited mesoporous graphitic carbon...

104-92-7 Process route

rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

3-bromo-4-methoxyacetophenone
35310-75-9

3-bromo-4-methoxyacetophenone

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
With PE-N-oxyl; sodium hydrogencarbonate; sodium bromide; at 5 ℃; Electrolysis;
38%
36%
3%
rac-1-(4-methoxyphenyl)-ethanol
3319-15-1

rac-1-(4-methoxyphenyl)-ethanol

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

3-bromo-4-methoxyacetophenone
35310-75-9

3-bromo-4-methoxyacetophenone

3-bromo-α-methyl-4-methoxybenzenemethanol
94670-25-4

3-bromo-α-methyl-4-methoxybenzenemethanol

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

Conditions
Conditions Yield
Et3N-WS-TEMPO bromide; In water; at 0 ℃; Electrochemical reaction;
49%
4%
8%
6%
With polymer-immobilized TEMPO radical; sodium hydrogencarbonate; sodium bromide; In water; at 0 ℃; Electrochemical reaction;
22%
19%
19%
12%

104-92-7 Upstream products

  • 67-56-1
    67-56-1

    methanol

  • 2028-85-5
    2028-85-5

    (4-bromophenyl)diazonium chloride

  • 7003-65-8
    7003-65-8

    sodium 4-bromophenoxide

  • 75-44-5
    75-44-5

    phosgene

104-92-7 Downstream products

  • 3525-22-2
    3525-22-2

    4'-(4-methoxyphenoxy)benzoic acid

  • 50793-28-7
    50793-28-7

    4-methoxy-4'-ethoxycarbonyl-diphenyl ether

  • 50638-47-6
    50638-47-6

    4-bromo-2-chloro-1-methoxybenzene

  • 100-66-3
    100-66-3

    methoxybenzene

Leave Your Message

Relevant Products