4-Bromoanisole

Base Information

• Chemical Name: 4-Bromoanisole
• CAS No.: 104-92-7
• Molecular Formula: C7H7BrO
• Molecular Weight: 187.036
• Hs Code.: DERIVATION
• European Community (EC) Number: 203-252-1
• NSC Number: 8042
• UNII: U430F901J9
• DSSTox Substance ID: DTXSID2059308
• Nikkaji Number: J5.038E
• Wikipedia: 4-Bromoanisole
• Wikidata: Q4973725
• Mol file: 104-92-7.mol

Synonyms:4-BROMOANISOLE;1-Bromo-4-methoxybenzene;104-92-7;p-Bromoanisole;4-Methoxybromobenzene;Benzene, 1-bromo-4-methoxy-;Anisyl bromide;p-Anisyl bromide;p-Bromanisole;4-Methoxyphenyl bromide;Anisole, p-bromo-;p-Methoxybromobenzene;p-Methoxyphenyl bromide;4-Methoxy-1-bromobenzene;p-Bromophenyl methyl ether;para-bromoanisole;4-Bromoanisol;C7H7BrO;4-bromo anisole;4-anisyl bromide;1-bromo-4-methoxy-benzene;NSC 8042;4-Bromoanisole-d3;p-Bromomethoxybenzene;4-bromomethoxybenzene;EINECS 203-252-1;AI3-01295;UNII-U430F901J9;NSC-8042;U430F901J9;EC 203-252-1;4-bromo-1-methoxybenzene;4bromoanisole;monobromoanisole;p-bromoanisol;p-bromanisol;p-bromo anisole;p-bromo-anisole;4-bromanisol;parabromo-anisole;4-bromo-anisole;MFCD00000097;4-methoxy-bromobenzene;4-Bromoanisole (Ba);1-methoxy-4-bromobenzene;4-bromophenyl methyl ether;1-bromo-4-methoxy benzene;SCHEMBL9301;1-bromanyl-4-methoxy-benzene;4-Bromoanisole, >=99.0%;DTXSID2059308;CHEBI:47257;NSC8042;BCP24447;STR04213;BR1023;STL453648;AKOS000119001;PS-5119;LS-20206;AM20020130;B0547;BROMOPHENOL P-FORM METHYL ETHER [MI];FT-0612055;FT-0617854;EN300-16110;A801100;Q-200445;Q4973725;F0001-0093

Chemical Property of 4-Bromoanisole

Chemical Property:

• 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
• Storage Temp.: Store below +30°C.
• Water Solubility.: immiscible
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 185.96803
• Heavy Atom Count: 9
• Complexity: 77

Purity/Quality:

99% ^*data from raw suppliers

4-Bromoanisole 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Anisoles
• Canonical SMILES: COC1=CC=C(C=C1)Br
• Uses: 4-Bromoanisole finds application as an intermediate in synthetic chemistry. It is used in the preparation of aryl 1,3-diketones and ethyl 4-methoxycinnamate. It is a used as a brominating reagent. Further, it is used in Suzuki coupling reaction with phenylboronic acid as well as in Heck reaction.

Technology Process of 4-Bromoanisole

There total 153 articles about 4-Bromoanisole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.99%

methoxybenzene (100-66-3) → 1-bromo-4-methoxy-benzene (104-92-7) + 2-bromoanisole (578-57-4) + 2,4-dibromoanisole (21702-84-1)

Guidance literature:

With bromine; tetramethylammonium bromide; In liquid sulphur dioxide; at -23 ℃; Rate constant; Product distribution; Thermodynamic data; in H2O at 25 deg C, NaBr, HClO4; ΔH (excit), -ΔS (excit);

Reference yield: 97.0%

methoxybenzene (100-66-3) → 1-bromo-4-methoxy-benzene (104-92-7) + 2-bromoanisole (578-57-4)

Guidance literature:

With Oxone; potassium bromide; In methanol; at 20 ℃; for 1h;

DOI:10.1081/SCC-120006001

Reference yield: 76.0%

methoxybenzene (100-66-3) + diethylazodicarboxylate (1972-28-7,218603-74-8) → 1-bromo-4-methoxy-benzene (104-92-7) + diethyl hydrazodicarboxylate (4114-28-7)

Guidance literature:

With ZrBr₄; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2008.01.072

upstream raw materials:

methanol

(4-bromophenyl)diazonium chloride

sodium 4-bromophenoxide

phosgene

Downstream raw materials:

4'-(4-methoxyphenoxy)benzoic acid

4-methoxy-4'-ethoxycarbonyl-diphenyl ether

4-bromo-2-chloro-1-methoxybenzene

methoxybenzene

Refernces

• 1、 Zhang, Guangyou,Lv, Guanglei,Li, Liping,Chen, Fan,Cheng, Jiang. "Copper-catalyzed halogenation of arylboronic acids". . p. 1993 - 1995. Retrieved 2011.
• 2、 Adam, Michael J.,Ruth, Thomas J.,Pate, Brian D.,Hall, Laurance D.. "Site-specific Bromination of Aromatic Compounds: a Rapid Method for Radiobromine Labelling". . p. 625 - 626. Retrieved 1982.
• 3、 Tamao, Kohei,Akita, Munetaka,Kato, Hidehito,Kumada, Makoto. "Electrophilic cleavage reactions of carbon-silicon bonds in neutral hexacoordinate silicon compounds: diorgano(phtalocyaninato)silicon". . p. 165 - 180. Retrieved 1988.
• 4、 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.. "Generation of interhalogen fluorides under mild conditions: A comparison of sluggish and reactive interhalogen fluorides". . p. 1094 - 1098. Retrieved 1999.
• 5、 Zhang, Guofu,Liu, Renhua,Xu, Qing,Ma, Lixin,Liang, Xinmiao. "Sodium nitrite-catalyzed oxybromination of aromatic compounds and aryl ketones with a combination of hydrobromic acid and molecular oxygen under mild conditions". . p. 862 - 866. Retrieved 2006.
• 6、 Castellonese, Paul,Villa, Pierre. "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". . p. 1068 - 1077. Retrieved 1983.
• 7、 Raju,Kulangiappar,Anbu Kulandainathan,Uma,Malini,Muthukumaran. "Site directed nuclear bromination of aromatic compounds by an electrochemical method". . p. 4581 - 4584. Retrieved 2006.
• 8、 Arvela, Riina K.,Leadbeater, Nicholas E.. "Fast and easy halide exchange in aryl halides". . p. 1145 - 1148. Retrieved 2003.
• 9、 Li, Bai,Gao, Linfeng,Bian, Fengling,Yu, Wei. "A new recoverable Au(III) catalyst supported on magnetic polymer nanocomposite for aromatic bromination". . p. 1063 - 1066. Retrieved 2013.
• 10、 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. "Predicting the structure of supramolecular dendrimers via the analysis of libraries of AB3 and constitutional isomeric AB2 biphenylpropyl ether self-assembling dendrons". . p. 17500 - 17521. Retrieved 2009.