D39002

1,2-Dibromobenzene

98%

• Synonym(s): o-Dibromobenzene
• Empirical Formula (Hill Notation): C₆H₄Br₂
• CAS Number: 583-53-9
• Molecular Weight: 235.90
• Beilstein/REAXYS Number: 970241
• EC Number: 209-507-3
• MDL number: MFCD00000057
• UNSPSC Code: 12352100
• PubChem Substance ID: 24893794
• NACRES: NA.22

Properties

• vapor density: 8.2 (vs air)
• assay: 98%
• form: liquid
• refractive index: n20/D 1.611 (lit.)
• bp: 224 °C (lit.)
• mp: 4-6 °C (lit.)
• density: 1.956 g/mL at 25 °C (lit.)
• SMILES string: Brc1ccccc1Br
• InChI: 1S/C6H4Br2/c7-5-3-1-2-4-6(5)8/h1-4H
• InChI key: WQONPSCCEXUXTQ-UHFFFAOYSA-N

Description

General description

1,2-Dibromobenzene, also known as o-Dibromobenzene, is an aromatic halogenated hydrocarbon commonly used as a precursor in various organic synthesis reactions based on the intermediate formation of benzynes.

Application

• Selective Covalent Capture of Collagen Triple Helices with Minimal Protecting Group Strategy: This study details the use of Rink Amide MBHA resin for capturing collagen triple helices, highlighting its efficiency in solid-phase synthesis (JDH Le Tracy Yu, 2020).


• Solid phase peptide synthesis: new resin and new protecting group: Introduction of a novel resin, Fmoc-Rink-Amide PEG Octagel, showcasing its application in peptide synthesis (S Ramkisson, 2018).


• Development of a novel, automated, robotic system for rapid, high-throughput, parallel, solid-phase peptide synthesis: This paper discusses the utilization of Rink Amide MBHA resin in developing an automated system for peptide synthesis (K Kiss et al., 2023).


• Synthesis of Peptoids Containing Multiple Nhtrp and Ntrp Residues: A Comparative Study of Resin, Cleavage Conditions and Submonomer Protection: The study compares different resins including Rink Amide MBHA, analyzing their efficacy in peptoid synthesis (A Lone et al., 2020).

It is also used as a key reactant in the synthesis of:

• diborylbenzenes via palladium-catalyzed borylation of bromobenzenes
• o,o′-tri- and -tetrasubstituted biphenyls via aryne cross-coupling reaction

Safety Information

• pictograms: GHS07,GHS09
• signalword: Warning
• hcodes: H315,H319,H335,H411
• pcodes: P273 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 197.6 °F - closed cup
• flash_point_c: 92 °C - closed cup
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter