1138-47-2

Basic information

• Product Name: (trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene
• Synonyms: Einecs 214-511-3;Nsc 86504;(trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene;diphenylcyclopropane;1,2-Diphenylcyclopropane, trans-;Benzene, 1,1'-(1,2-cyclopropanediyl)bis-, trans- (9ci);Cyclopropane, 1,2-diphenyl-, trans- (8ci)
• CAS NO: 1138-47-2
• Molecular Formula: C₁₅H₁₄
• Molecular Weight: 194.27166
• EINECS: 214-511-3
• Mol File: 1138-47-2.mol
• Article Data: 50

Chemical Properties

• Boiling Point: 285.73°C (rough estimate)
• Appearance: /
• Density: 1.0200 (estimate)
• Refractive Index: 1.5960
• CAS DataBase Reference: (trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene(1138-47-2)
• EPA Substance Registry System: (trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene(1138-47-2)

Safety Data

• Hazardous Substances Data: 1138-47-2(Hazardous Substances Data)

Usage

Description

(trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene, a cycloalkane with the molecular formula C18H16, is a unique chemical compound featuring two benzene rings connected by a cyclopropane group. This structure endows the molecule with distinctive reactivity and properties, positioning it as a valuable building block in organic chemistry and material science for the synthesis of a range of organic compounds and polymers.

Uses

Used in Organic Chemistry:
(trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene serves as a key intermediate in the synthesis of various organic compounds due to its reactive cyclopropane group and the stability provided by the benzene rings. Its unique structure facilitates multiple types of chemical reactions, making it a versatile component in organic synthesis.
Used in Material Science:
In the field of material science, (trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene is utilized as a precursor for developing new materials with specific properties. The cyclopropane group's reactivity allows for the creation of polymers and other materials with tailored characteristics, such as enhanced stability or specific interactions with other molecules.
Used in Pharmaceutical Development:
The unique structure and properties of (trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene also make it a promising candidate in pharmaceutical research. Its potential applications include the development of new drugs and drug delivery systems, where its reactivity and molecular interactions can be harnessed to improve therapeutic efficacy and targeting.
Used in the Synthesis of Advanced Polymers:
(trans)-1,1'-(1,2-cyclopropanediyl)bisbenzene is employed as a monomer in the synthesis of advanced polymers with specific properties. The cyclopropane group can be manipulated to create polymers with unique mechanical, thermal, or chemical characteristics, suitable for various high-performance applications.

Upstream product

• 100-42-5 styrene 
• 908094-04-2 phenyldiazomethane 
• 16619-60-6 3,5-diphenyl-4,5-dihydro-1H-pyrazole 
• 1138-48-3 cis-1,2-diphenylcyclopropane 
• 10514-16-6 trans-3,5-Diphenyl-1-pyrazoline 
• 84064-86-8 C₁₅H₁₃Li 
• 61608-79-5 ((1R*,2R*)-3-bromocyclopropane-1,2-diyl)dibenzene 
• 34462-03-8 cis-N-nitroso-2,4-diphenylazetidine 
• 34462-03-8 trans-N-nitroso-2,4-diphenylazetidine 
• 145134-43-6 Benzenesulfonic acid 3-methylselanyl-2,3-diphenyl-propyl ester 
• 145134-42-5 Benzenesulfonic acid (1R,3S)-3-methylselanyl-1,3-diphenyl-propyl ester 
• 145134-42-5 Benzenesulfonic acid (1R,3R)-3-methylselanyl-1,3-diphenyl-propyl ester 
• 145134-45-8 Benzenesulfonic acid (1R,3R)-1,3-diphenyl-3-tributylstannanyl-propyl ester 
• 53422-72-3 3,5-Diphenyl-Δ²-pyrazolin 

Downstream Products

• 1250938-61-4 trans-1,2-Di-(p-bromphenyl)-cyclopropan 
• 65662-64-8 C₁₅H₁₄BrCl 
• 65662-65-9 C₁₅H₁₂Br₃Cl 
• 26278-69-3 1,3-diphenyl-1,3-dimethoxy propane 
• 109423-45-2 C₃₁H₂₂N₂ 
• 109423-45-2 C₃₁H₂₂N₂ 
• 109423-45-2 6,7:8,9-dibenzo-1,5-dicyano-cis-2,4-diphenylbicyclo<3.2.2>nona-6,8-diene 
• 109423-45-2 6,7:8,9-dibenzo-1,5-dicyano-trans-2,4-diphenylbicyclo<3.2.2>nona-6,8-diene 
• 90095-72-0 (+/-)-trans-1,2-di(p-iodophenyl)cyclopropane 
• 90095-71-9 (+/-)-1,3-bis(trifluoroacetoxy)-1,3-diphenylpropane 
• 4894-23-9 3,5-diphenyl-4,5-dihydro-isoxazole 
• 1138-48-3 cis-1,2-diphenylcyclopropane 
• 3471-09-8 (1R,2R)-1,2-diphenylcyclopropane 
• 3412-44-0 1,3-diphenylpropene 

Relevant articles and documents

The nickel and palladium catalyzed stereoselective cross coupling of cyclopropyl nucleophiles with aryl halides

The reaction of 2-phenylcyclopropylzinc chloride with some substituted (het)aryl halides gave the corresponding coupling products with good yields and stereoselectivities under the influence of a catalytic amount of Pd(PPh3)4. Other Ni- and Pd-catalysts were less efficient. Alkyl-substituted cyclopropyl nucleophiles gave lower yields.

Kinetische und mechanistische Untersuchungen von Uebergangsmetall-Komplex-Reactionen.XVII. Untersuchungenen zur Substituentenabhaengigkeit der cis/trans-Cyclopropan-Produktherhaeltnisse bei der Uebertragung von Benzylidenliganden auf Styrole

The benzylidene complexes (CO)5M=C(C6H4R-p)H react with styrenes, H2C=C(C6H4R-p)H (R = F, Cl, Br, H, Me, OMe), α-methylstyrene, vinylcyclohexane and 2-methyl-2-butene, respectively, by transfer of the benzylidene ligand to the C=C bond and formation of cis- and trans-cyclopropanes.From the temperature dependence of the cis/trans isomer ratios the differences in the activation enthalpies ΔΔH* = Δ(Hcis)* - Δ(Htrans)* and activation entropies ΔΔS* = Δ(Scis)* - Δ(Strans)* weredetermined.With all reactions the formation of the cis-isomer is favoured by the lower activation enthalpy.The formation of the trans-isomers, however, is generally favoured by the lower activation entropy.Exceptions are the reactions of 1a with styrene and of 1c with 2-methyl-2-butene.These two opposing influences determine the cis/trans isomer ratio observed.The results are discussed on the basis of stabilizing electronic and destabilizing steric interactions.

On the synthesis of aryl cyclopropanes from γ-benzenesulfonylalkyl tin derivatives and n-butyllithium

γ-Benzenesulfonyloxyalkyl tin derivatives readily available from γ-hydroxyalkyl selenides, n-butyllithium and trialkyl tin chlorides react with n-butyllithium and stereospecifically lead to aryl cyclopropanes. The transformation is quite general and allows the synthesis of α,β-di- and trisubstituted ones.

Cyclopropanation of styrenes and stilbenes using lithiomethyl trimethylammonium triflate as methylene donor

Lithiomethyl trimethylammonium triflate, prepared from tetramethylammonium triflate, cyclopropanates several styrenes and stilbenes with electron-donating and selected electron-withdrawing substituents efficiently. Kinetic data support a stepwise nucleophilic addition-ring closure mechanism for this methylenation. This journal is the Partner Organisations 2014.

The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound

The first α-boryl diazo compound that is capable of engaging in classic synthetic organic diazo reaction chemistry is described. The diazomethyl-1,2-azaborine 1, which is a BN isostere of phenyldiazomethane, is significantly more stable than phenyldiazomethane; its reaction chemistry ranges from C-H activation, O-H activation, [3+2] cycloaddition, and halogenation, to Ru-catalyzed carbonyl olefination. The demonstrated broad range of reactivity of diazomethyl-1,2-azaborine 1 makes it an exceptionally versatile synthetic building block for the 1,2-azaborine heterocyclic motif.

Reductive Ring-Opening 1,3-Difunctionalizations of Arylcyclopropanes with Sodium Metal

Sodium dispersion promotes reductive ring opening of arylcyclopropanes. The presence of a reduction-resistant electrophile, such as methoxypinacolatoborane, epoxide, oxetane, paraformaldehyde, or chlorotrimethylsilane, during the reductive ring opening event leads to the formation of 1,3-difunctionalized 1-arylalkanes by immediate trappings of the resulting two reactive carbanions. In particular, the ring-opening 1,3-diborylations of arylcyclopropanes afford 1,3-diborylalkanes with high syn selectivity.

Iron-catalyzed synthesis of cyclopropanes by in situ generation and decomposition of electronically diversified diazo compounds

The modular synthesis of a variety of trans 1,2-disubstituted cyclopropanes in a safe and user-friendly one-pot iron-catalyzed cyclopropanation reaction is described. Easily synthesized N-nosylhydrazones are used as diazo precursors, allowing the in situ generation of electron-rich diazo compounds under mild reaction conditions and their direct participation in the cyclopropanation reaction.