4-Bromotoluene

Base Information

• Chemical Name: 4-Bromotoluene
• CAS No.: 106-38-7
• Molecular Formula: C7H7Br
• Molecular Weight: 171.037
• Hs Code.: 29036990
• European Community (EC) Number: 203-391-8
• NSC Number: 6531
• UNII: 9E349GQ7EU
• DSSTox Substance ID: DTXSID7024661
• Nikkaji Number: J47.007D
• Wikidata: Q27272425
• ChEMBL ID: CHEMBL1377077
• Mol file: 106-38-7.mol

Synonyms:4-bromotoluene;p-bromotoluene

Chemical Property of 4-Bromotoluene

Chemical Property:

• Appearance/Colour: colourless or pale yellow liquid
• Vapor Pressure: 1.04mmHg at 25°C
• Melting Point: 26-29 °C(lit.)
• Refractive Index: 1.549
• Boiling Point: 183.8 °C at 760 mmHg
• Flash Point: 69 °C
• PSA: 0.00000
• Density: 1.39 g/cm³
• LogP: 2.75750
• Storage Temp.: Store below +30°C.
• Solubility.: 0.11g/l insoluble
• Water Solubility.: <0.1 g/100 mL at 24℃
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 169.97311
• Heavy Atom Count: 8
• Complexity: 62.8

Purity/Quality:

99% ^*data from raw suppliers

4-Bromotoluene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,T
• Hazard Codes: Xn:Harmful
• Statements: R22:; R36/37/38:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Brominated Solvents
• Canonical SMILES: CC1=CC=C(C=C1)Br
• Description: 4-Bromotoluene is a p-substituted aryl bromide. As a toluene derivative, it is used as a solvent and starting material for organic synthesis and is found in paints, paint thinners, glues, and other products. 4-Bromotoluene was used in the synthesis of ketones by Cu/Pd-catalyzed decarboxylative cross-coupling reaction. It is also used in manufacturing pharmaceuticals (especially for antihypertensive like losartan, Irbesartan), pesticides and other organic compounds1-3.
• Uses: 4-Bromotoluene was used in the synthesis of ketones by Cu/Pd-catalyzed decarboxylative cross-coupling reaction. 4-Bromotoluene undergoes Heck reaction with styrene in the presence of in situ generated palladium complexes of phosphine-functionalized N-heterocyclic carbene ligands.

Technology Process of 4-Bromotoluene

There total 156 articles about 4-Bromotoluene 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: 43.0%

toluene (108-88-3,15644-74-3,16713-13-6) → para-bromotoluene (106-38-7) + 2-methylphenyl bromide (95-46-5) + benzyl bromide (100-39-0)

Guidance literature:

With K₁₀-montmorillonite clay; bromine; In tetrachloromethane; for 1.5h; Ambient temperature;

DOI:10.1016/S0040-4020(96)01147-7

Reference yield: 5.0%

toluene (108-88-3,15644-74-3,16713-13-6) → para-bromotoluene (106-38-7) + 2-methylphenyl bromide (95-46-5) + benzylidene dibromide (618-31-5) + benzyl bromide (100-39-0)

Guidance literature:

With sodium bromate; sodium hydrogensulfite; In water; acetonitrile; at 20 ℃; for 4h;

DOI:10.1021/jo972263q

Reference yield: 4.0%

4-bromo-benzaldehyde (1122-91-4) → para-bromotoluene (106-38-7) + 4-bromobenzenemethanol (873-75-6) + benzaldehyde (100-52-7) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With hydrogen; platinum(IV) oxide; In water; isopropyl alcohol; at 20 ℃; for 16h; under 724.026 Torr;

DOI:10.1021/jo000867f

upstream raw materials:

1,2-propylene cyclic carbonate

N-Bromosuccinimide

chloranil

toluene

Downstream raw materials:

N-(4-methylphenyl)piperidine

N-(3-methylphenyl)piperidine

(4-methylphenyl)diphenylmethanol

1-p-tolyl-hexadecane

Refernces

• 1、 Ranu,Sarkar,Chakraborty. "A simple and improved procedure for selective ring bromination of alkyl-substituted aromatic hydrocarbons on the surface of alumina". . p. 1095 - 1099. Retrieved 1992.
• 2、 Sadygov,Alimardanov,Chalabiev. "Induced bromination of aromatic hydrocarbons by alkali metals bromides and sodium hypochlorite". . p. 1631 - 1636. Retrieved 2005.
• 3、 Brown,McGary. "-". . p. 2310. Retrieved 1955.
• 4、 Gruzdev,Virzum,Krylov. "Bromination of alkylbenzenes in 1-butyl-3-methylimidazolium bromide and its dibromide complex". . p. 263 - 267. Retrieved 2010.
• 5、 Gnaim, Jallal M.,Sheldon, Roger A.. "Regioselective bromination of aromatic compounds with Br 2/SO2Cl2 over microporous catalysts". . p. 4465 - 4468. Retrieved 2005.
• 6、 Zoratti, Mario,Bunnett, J. F. "Reactivities of Several Nucleophiles toward 4-Methylbenzyne in Very Hot Water". . p. 1776 - 1782. Retrieved 1980.
• 7、 Deshmukh, Anjali P.,Padiya, Kamlesh J.,Jadhav, Vidyadhar K.,Salunkhe, Manikrao M.. "Halogenation of Aromatic Compounds by using Sodium Perborate as an Oxidant". . p. 828 - 829. Retrieved 1998.
• 8、 Robinson, Gary N.,Continetti, Robert E.,Lee, Yuan T.. "Dynamics of endoergic substitution reactions. I. Br+chlorinated aromatic compounds". . p. 6226 - 6237. Retrieved 1988.
• 9、 Vega, Fernando de la,Sasson, Yoel. "Selective para-Bromination of Toluene catalysed by Na-Y Zeolite in the Presence of an Epoxide". . p. 653 - 654. Retrieved 1989.
• 10、 Sadygov,Alimardanov,Chalabiev. "Induced bromination of aromatic hydrocarbons with alkali metal bromides in the presence of oxidants". . p. 949 - 956. Retrieved 2006.