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MilliporeSigma

D39002

Sigma-Aldrich

1,2-Dibromobenzene

98%

Sinónimos:

o-Dibromobenzene

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About This Item

Fórmula empírica (notación de Hill):
C6H4Br2
Número de CAS:
Peso molecular:
235.90
Beilstein/REAXYS Number:
970241
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

8.2 (vs air)

Quality Level

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

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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

pictograms

Exclamation markEnvironment

signalword

Warning

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


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Holger F Bettinger et al.
The Journal of organic chemistry, 72(25), 9750-9752 (2007-11-08)
The one-step high-yield synthesis of 1,2-bis(trimethylsilyl)benzene from 1,2-dibromobenzene using tert-butyllithium and trimethylsilyltriflate is reported. A mechanistic investigation shows that 1,2-dilithiobenzene is not an intermediate in this reaction; the coexistence of trimethylsilyltriflate and tert-butyllithium at very low temperatures allows a sequence
G Shakila et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 86, 449-455 (2011-11-25)
The FT-IR and FT-Raman spectra of the compound 1,2-dibromobenzene have been recorded in the region 4000-100cm(-1). The vibrational analysis has been made using HF and DFT (B3LYP and LSDA) level of theory by employing 6-31 +G (d, p) and 6-311
Jadwiga A Szymańska et al.
International journal of occupational medicine and environmental health, 15(4), 375-383 (2003-03-01)
The distribution, excretion and metabolism of 1,4-dibromobenzene (1,4-DBB) and 1,2-dibromobenzene (1,2-DBB), following a single intraperitoneal administration to female Wistar rats, were investigated using radiotracer 3H and GC-MS technique. The maximum level of 3H after 1,4-DBB administration was detected in all
J A Szymańska et al.
Journal of applied toxicology : JAT, 16(1), 35-41 (1996-01-01)
Various doses of dibromobenzene isomers (1,2-dBB, 1,3-dBB, 1,4-dBB) were administered (i.p.) to BALB mice. The levels of reduced glutathione (GSH) and malondialdehyde (MDA) in the liver, and glutamate-pyruvate transaminase (GPT) (EC.2.6.1.2) gamma-glutamyltransferase (gamma-GT) (EC.2.3.2.2) and triglycerides (TG) in the serum
Mónica Carril et al.
Organic letters, 7(22), 4787-4789 (2005-10-21)
[reaction: see text] A new route to oxcarbazepine (Trileptal), the most widely prescribed antiepileptic drug, starting from commercially available 2'-aminoacetophenone and 1,2-dibromobenzene, is reported. The sequentially accomplished key steps are palladium-catalyzed intermolecular alpha-arylation of ketone enolates and intramolecular N-arylation reactions.

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