2,4-Dibromoaniline

Base Information

• Chemical Name: 2,4-Dibromoaniline
• CAS No.: 615-57-6
• Molecular Formula: C6H5Br2N
• Molecular Weight: 250.92
• Hs Code.: 29214210
• European Community (EC) Number: 210-434-4
• NSC Number: 88324
• UNII: 8D6YF8BB75
• DSSTox Substance ID: DTXSID4060654
• Nikkaji Number: J95.568J
• Wikidata: Q72463778
• ChEMBL ID: CHEMBL1710125
• Mol file: 615-57-6.mol

Synonyms:2,4-DIBROMOANILINE;615-57-6;Benzenamine, 2,4-dibromo-;2,4-dibromobenzenamine;Dibromobenzenamine;2.4-Dibromoaniline;NSC 88324;MLS000737163;8D6YF8BB75;EINECS 210-434-4;NSC-88324;2,4-Dibromo-phenylamine;63505-64-6;2,4-Dibromanilin;NSC88324;2,4-di-bromo-aniline;Benzenamine,4-dibromo-;2,4-bis(bromanyl)aniline;NCIOpen2_005148;UNII-8D6YF8BB75;2,4-Dibromoaniline, 98%;SCHEMBL417742;CHEMBL1710125;DTXSID4060654;ANILINE, 2,4-DIBROMO-;HMS2884A04;AMY23964;STR01937;MFCD00007633;STL497388;AKOS000113480;NCGC00246894-01;AC-17039;SMR000528396;D1153;FT-0609985;EN300-20283;A833299;W-105132;Z104477574

Chemical Property of 2,4-Dibromoaniline

Chemical Property:

• Appearance/Colour: White crystal or powder
• Vapor Pressure: 0.0095mmHg at 25°C
• Melting Point: 78-82 °C
• Refractive Index: 1.661
• Boiling Point: 264.8 °C at 760 mmHg
• PKA: 1.83±0.10(Predicted)
• Flash Point: 114 °C
• PSA: 26.02000
• Density: 2.022g/cm³
• LogP: 3.37500
• Storage Temp.: Store below +30°C.
• Water Solubility.: Insoluble in water
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 250.87682
• Heavy Atom Count: 9
• Complexity: 97.1

Purity/Quality:

99% ^*data from raw suppliers

2,4-Dibromoaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi,N,T
• Statements: 36/37/38-33-20/21/22-51/53-25
• Safety Statements: 36/37/39-26-61-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Br)Br)N
• Uses: 2,4-Dibromoaniline is used in preparation of glycopeptides and targeted bifunctional degraders. 2,4-Dibromoaniline can be used as:A starting material to synthesize acetylenic amine by reacting with trimethylsilylacetylene, which is used as a ligand to prepare the bis-amido complex of Ti(IV).A substrate in the Pd-catalyzed ortho-selective cross-coupling reactions of dihaloarenes with Grignard reagents.A reactant to prepare dialkyl-substituted aminoaryl sulfides using a Grignard reagent.A starting material to synthesize substituted 2-mercapto benzimidazoles.

Technology Process of 2,4-Dibromoaniline

There total 74 articles about 2,4-Dibromoaniline 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: 99.0%

4-bromo-aniline (106-40-1) → 2,4-dibromo-aniline (615-57-6)

Guidance literature:

With bromine; In tetrachloromethane; at 20 ℃; Cooling with ice;

DOI:10.1134/S1070427209090122

Reference yield: 98.0%

aniline (62-53-3) → 2,4-dibromo-aniline (615-57-6)

Guidance literature:

With N-Bromosuccinimide; lithium perchlorate; silica gel; In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1139/v05-001

Reference yield: 97.0%

2-bromoaniline (615-36-1) → 2,4-dibromo-aniline (615-57-6)

Guidance literature:

With N-bromosaccharin; In tetrahydrofuran; at 0 ℃; for 0.0333333h; regioselective reaction;

DOI:10.4067/S0717-97072011000400008

upstream raw materials:

N-bromophthalimide

aniline

5,7-Dibromoisatin

N,N'-dichloro-urea

Downstream raw materials:

N,N'-bis-(2,4-dibromo-phenyl)-thiourea

N-(2,4-dibromo-phenyl)-phthalimide

4,5,6,7-tetrabromo-2-(2,4-dibromo-phenyl)-isoindoline-1,3-dione

ethyl (2,4-dibromophenyl)carbamate

Refernces

• 1、 Takahashi, Yusuke,Seki, Masahiko. "A Practical Procedure for Regioselective Bromination of Anilines". . p. 1828 - 1832. Retrieved 2021/04/15.
• 2、 Jiang, Xuefeng,Li, Yiming,Lu, Lingling. "Visible-light-promoted oxidative halogenation of (hetero)arenes". supporting information. p. 5989 - 5994. Retrieved 2020/10/18.