38399-13-2

Basic information

• Product Name: 2,2'-DIBROMODIPHENYLACETYLENE
• Synonyms: BIS(2-BROMOPHENYL)ETHYNE;2,2'-DIBROMODIPHENYLACETYLENE;1,2-bis(2-broMophenyl)ethyne;Bis(2-bromophenyl)acetylene
• CAS NO: 38399-13-2
• Molecular Formula: C₁₄H₈Br₂
• Molecular Weight: 336.02
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives
• Mol File: 38399-13-2.mol
• Article Data: 31

Chemical Properties

• Melting Point: 79.0 to 83.0 °C
• Boiling Point: 402.5°Cat760mmHg
• Flash Point: 230.7°C
• Appearance: /
• Density: 1.74g/cm³
• Solubility: soluble in Tetrahydrofuran
• CAS DataBase Reference: 2,2'-DIBROMODIPHENYLACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-DIBROMODIPHENYLACETYLENE(38399-13-2)
• EPA Substance Registry System: 2,2'-DIBROMODIPHENYLACETYLENE(38399-13-2)

Safety Data

• Hazardous Substances Data: 38399-13-2(Hazardous Substances Data)

Usage

General Description

2,2'-Dibromodiphenylacetylene is a chemical compound with the molecular formula C14H8Br2. It is an organic compound that is commonly used as a reagent in organic synthesis and as a starting material for the production of various other chemicals. It appears as a white to light brown solid and is insoluble in water, but soluble in organic solvents. It is known to be a powerful acetylenic building block for the synthesis of various organic compounds, and its unique molecular structure and properties make it a versatile and useful chemical in the field of organic chemistry.

Upstream product

• 108476-09-1 2,α,2',α'-tetrabromo-bibenzyl 
• 583-55-1 1-Bromo-2-iodobenzene 
• 766-46-1 2-bromo-1-ethynylbenzene 
• 74-86-2 acetylene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 92022-50-9 1-bromo-2-((phenylsulfonyl)methyl)benzene 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 38274-16-7 2-bromo-1-(trimethylsilylethynyl)benzene 
• 92672-77-0 1-bromo-2-(prop-1-yn-1-yl)benzene 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 2052-07-5 2-Bromobiphenyl 
• 471-25-0 Propiolic acid 

Downstream Products

• 100542-21-0 2,2'-ethynylenedibenzeneboronic acid 
• 35324-46-0 o,o’-diiodo-diphenylacetylene 
• 27499-64-5 o-bis(ethynyl)tolane 
• 792-60-9 2,2'-(ethyne-1,2-diyl)dibenzoic acid 
• 380240-07-3 C₄₄H₅₀O₂Si₂ 
• 448895-62-3 2,2'-bis-(triisopropylsilyl)ethynyltolan 
• 18887-52-0 2,2'-(ethyne-1,2-diyl)dibenzaldehyde 
• 625389-84-6 bis[2-(dimethylsilyl)phenyl]acetylene 
• 388111-11-3 bis[2-(4-methoxyphenyl)phenyl]acetylene 
• 388111-10-2 bis[2-(3-methoxyphenyl)phenyl]acetylene 
• 388111-09-9 bis[2-(3,4-dimethoxyphenyl)phenyl]acetylene 
• 120651-34-5 2,2'-bis(trimethylsilylethynyl)diphenylacetylene 
• 947546-07-8 2-bis[2-(prop-1-ynyl)phenyl]ethyne 
• 14207-78-4 1,7-Dimethyl-chrysen 

Relevant articles and documents

Synthesis and Structure of a Strained, Cyclic meta-Quaterphenylene Acetylene

A strained, cyclic hydrocarbon comprising a meta-quaterphenyl-based arc that is clamped by an alkyne tether was synthesized via Yamamoto coupling of a dichloro precursor. DFT calculations (B3LYP/6-31G*) indicate that the lowest-energy ground state adopts

Tolanophane revisited-Resolution and racemization mechanism of a twisted chiral aromatic compound

Enantiomers of tolanophane consisting of two tolane units were resolved by chiral HPLC, contrary to the previous attempts by Staab et al. Racemization took place rapidly at room temperature, and the barrier to enantiomerization was determined to be 93.2 kJ mol-1 at 283 K. This energy barrier was rationally deduced with a mechanism involving rotations about the single and triple bond axes, as revealed by DFT calculations. A tetrahedrane intermediate resulting from a transannular reaction between the two adjacent triple bonds was ruled out.

An on-surface Diels–Alder reaction

The Diels–Alder reaction is one of the most popular reactions in organic chemistry. However, its use in the field of on-surface synthesis is hampered by the spatial restrictions of this cycloaddition reaction. Herein we selected a cyclic strained triyne t

Tailoring Diindenochrysene through Intramolecular Multi-Assemblies by C?F Bond Activation on Aluminum Oxide

The unique nature of the alumina-mediated cyclodehydrofluorination gives the opportunity to execute the preprogrammed algorithm of the C?C couplings rationally built into a precursor. Such multi-assemblies facilitate the construction of the carbon-skeleton, superseding the conventional step-by-step by the one-pot intramolecular assembly. In this work, the feasibility of the alumina-mediated C?F bond activation approach for multi-assembly is demonstrated on the example of a fundamental bowl-shaped polycyclic aromatic hydrocarbon (diindenochrysene) through the formation of all “missing” C?C bonds at the last step. Beside valuable insights into the reaction mechanism and the design of the precursors, a facile pathway enabling the two-step synthesis of diindenochrysene was elaborated, in which five C?C bonds form in a single synthetic step. It is shown that the relative positions of fluorine atoms play a crucial role in the outcome of the assembly and that governing the substituent positions enables the design of effective precursor molecules “programmed” for the consecutive C?C bond formations. In general, these findings push the state of the field towards the facile synthesis of sophisticated bowl-shaped carbon-based nanostructures through multi-assembly of fluoroarenes.