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:

99.9% ^*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
• General Description: **Benzene,1-bromo-4-methyl- (also known as 4-bromotoluene or p-bromotoluene)** is an aryl halide commonly used as a substrate in cross-coupling reactions, such as the Suzuki-Miyaura reaction, where it couples with boronic acids to form carbon-carbon bonds. It also serves as a key intermediate in the synthesis of complex organic structures, including dipeptide mimetics, where it undergoes Cu-catalyzed coupling with amino acids. Its reactivity in these transformations highlights its utility in constructing pharmacologically relevant scaffolds and optimizing catalytic systems.

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

1-(4′-methylphenyl)isoquinoline

p-butyltoluene

Refernces

Phosphorus derivatives of carboranes as ligands for Pd-catalyzed cross-coupling reactions

10.1007/s11172-008-0326-y

This research investigates the use of carborane-containing phosphorus derivatives as ligands in Pd-catalyzed cross-coupling reactions, specifically the Suzuki-Miyaura reaction, which forms carbon-carbon bonds by coupling aryl halides with boronic acids. The purpose is to develop ligands with optimized steric and electronic properties to enhance catalytic activity. The study synthesized various phosphine and phosphite ligands with different substituents and tested their efficiency in the cross-coupling reactions. Key chemicals used include phenylboronic acid, aryl halides like bromobenzene and 4-bromotoluene, and various carborane-containing ligands. The results showed that ligands with electron-withdrawing carboranyl substituents and sterically congested phosphorus centers provided the highest conversion rates. Additionally, anhydrous reaction conditions enabled the use of more synthetically accessible phosphite ligands. The findings suggest that fine-tuning the electronic and steric properties of carborane ligands can significantly improve their performance in cross-coupling reactions, opening new avenues for developing more active catalysts.

Synthesis of 1,5-benzothiazepine dipeptide mimetics via two cul-catalyzed cross coupling reactions

10.1021/ol900943b

This study presents a novel method for the synthesis of 1,5-benzothiazepine dipeptide mimetics using two cuprous iodide-catalyzed cross-coupling reactions. The process begins with the coupling of 4-methylphenyl bromide with amino acids under cuprous iodide catalysis to form N-aryl amino acids. This is then converted to a linear dipeptide by iodination and condensation with an acyl chloride derived from L-cysteine. The final cyclization step is achieved by a cuprous iodide/N,N-dimethylglycine-catalyzed intramolecular coupling of the aryl iodide with the released thiol to afford the 1,5-benzothiazepine dipeptide mimetic. This study also explores the use of benzoyl as an ester protecting group, which can be cleaved to obtain the desired mimetic acid form. This method can introduce a variety of N-substituents by changing the amino acid coupling partner, enabling the development of more diverse peptide mimetics for biological studies.