D39002
1,2-Dibromobenzene
98%
Synonym(s):
o-Dibromobenzene
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About This Item
Empirical Formula (Hill Notation):
C6H4Br2
CAS Number:
Molecular Weight:
235.90
Beilstein:
970241
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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
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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
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
197.6 °F - closed cup
Flash Point(C)
92 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Regioselectivity in the Aryne Cross-Coupling of Aryllithiums with Functionalized 1, 2-Dibromobenzenes
Vincent D, et al.
European Journal of Organic Chemistry (2011)
Palladium-Catalyzed Double Cross-Coupling Reactions of Organodimetallic Reagents Leading to Polycyclic Aromatic Hydrocarbons
Masaki S, et al.
European Journal of Organic Chemistry, 2013, 8069-8081 (2013)
Efficient and Complementary Methods Offering Access to Synthetically Valuable 1, 2-Dibromobenzenes
Vincent D, et al.
European Journal of Organic Chemistry (2011)
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
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
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