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

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

Uses

Used in Organic Synthesis:
2,2'-DIBROMODIPHENYLACETYLENE is used as a reagent in organic synthesis for its ability to facilitate the creation of various organic compounds. Its unique molecular structure allows it to be a powerful acetylenic building block, contributing to the versatility of the synthesized products.
Used in Chemical Production:
In the Chemical Production Industry, 2,2'-DIBROMODIPHENYLACETYLENE is used as a starting material for the production of a variety of other chemicals. Its role as a foundational component enables the development of a broad spectrum of chemical products, highlighting its importance in the industry.

Upstream product

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

Downstream Products

• 18887-52-0 2,2'-(ethyne-1,2-diyl)dibenzaldehyde 
• 27714-56-3 2,2'-Bis-(α-chlor-diphenylmethyl)-diphenylacetylen 
• 1246065-47-3 1,2-bis[2-(dimesitylboranyl)phenyl]ethyne 
• 1334165-73-9 2-(2-benzoylphenyl)-3-phenylindenone 
• 1687-94-1 5,10-diphenyldibenzopentalene 
• 1593270-21-3 (Z)-2-(1,2-bis(2-bromophenyl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1616754-77-8 C₂₈H₂₂ 
• 1058722-57-8 (2-bromophenyl){2'-(dimesitylboryl)phenyl}acetylene 
• 1029146-79-9 [(1,2-bis(diphenylphosphino)benzene)(η2-2,2'-dibromotolane)Pt(0)] 
• 4281-16-7 2-[2-(2-carboxyphenyl)acetyl]benzoic acid 
• 973-77-3 Desoxybenzoin-2,2'-dicarbonsaeure-dimethylester 
• 895-04-5 2-(3-oxo-3H-isobenzofuran-1-ylidenemethyl)-benzoic acid 
• 970-93-4 dimethyl 2,2'-(ethyne-1,2-diyl)dibenzoate 
• 35324-44-8 3,3,3',3'-Tetrabromo-2,2'-diphenyl-3H,3'H-[1,1']biindenyl 

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

A Simple One-Pot Synthesis of [1]Benzotelluro[3,2-b][1]-benzotellurophenes and its Selenium and Sulfur Analogues from 2,2′-Dibromodiphenylacetylene [1]

Treatment of 2, 2′-dibromodiphenylacetylene 7 with tert-butyllithium followed by tellurium insertion resulted in intramolecular ring closure to afford [1]benzotelluro[3,2-b][1]benzotellurophene 8a. Similarly, [1]benzoseleno-[3,2-b][1]benzoselenophene 8b a

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

Synthesis of Polycyclic Aromatic Hydrocarbons Decorated by Fluorinated Carbon Acids/Carbanions

The carboarylation reaction of biphenyl-alkynes was successfully triggered by electrophilic attack of 1,1-bis(triflyl)ethylene on the alkyne moiety to give polycyclic aromatic hydrocarbons (PAHs) decorated by superacidic carbon acid functionality. Neutralisation of thus obtained acids with NaHCO3 yielded the corresponding sodium salts, which showed improved solubility in both aqueous and organic solvents.

Highly phosphorescent organopalladium(ii) complexes with metal-metal-to-ligand charge-transfer excited states in fluid solutions

Dinuclear pincer-type cyclometalated Pd(ii) complexes with foldable diacetylide ligands show crystallographically determined intramolecular Pd?Pd contacts of 3.203-3.380 ?. In deoxygenated fluid solutions, these Pd(ii) complexes are highly phosphorescent

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.

Preparation method of diaryl acetylene compounds

The invention relates to preparation of an organic compound, and aims to provide a preparation method of diaryl acetylene compounds. The preparation method includes steps of adding associated tribromomethylarene compound and copper in a reactor to perform deoxidizing treatment; dissolving polyamine in a proper amount of anhydrous and oxygen-free solvent, and then adding to the reactor; performingcoupling reaction at 30-80DEG C for 3-12 hours; separating and purifying to obtain diaryl acetylene compounds. The preparation is gentle in synthesis condition and the reaction has good compatibilityto different functional groups; the raw material associated tribromomethylarene compound is convenient to compound and has different substituent groups and variable structure; by adopting one raw material, high-quality product can be obtained through simple treatment, and the output is high; by adopting two different raw materials, the asymmetrical diaryl acetylene compound can be prepared.

Sulfoxide-Induced Homochiral Folding of ortho-Phenylene Ethynylenes (o-OPEs) by Silver(I) Templating: Structure and Chiroptical Properties

A new family of homochiral silver complexes based on carbophilic interactions with ortho-phenylene ethynylene (o-OPE) scaffolds containing up to two silver atoms are described. These compounds represent a unique class of complexes with chirality at the me

Preparation and Reactions of Mono- and Bis-Pivaloyloxyzinc Acetylides

Mono-pivaloyloxyzinc acetylide and bis-pivaloyloxyzinc acetylide were selectively prepared from ethynylmagnesium bromide in quantitative yields. These zinc reagents readily underwent Negishi cross-couplings with (hetero)aryl iodides or bromides as well as subsequent Sonogashira cross-couplings. 1,3-Dipolar cycloadditions of these zinc acetylides with benzylic azides produced zincated and bis-zincated triazoles which were trapped with several electrophiles. An opposite regioselectivity compared to the Cu-catalyzed click-reactions was observed.