15951-99-2

Basic information

• Product Name: (1R,2S)-1,2-Dichloro-1,2-diphenylethane
• Synonyms: (1R,2S)-1,2-Dichloro-1,2-diphenylethane;Nsc405531
• CAS NO: 15951-99-2
• Molecular Formula: C₁₄H₁₂Cl₂
• Molecular Weight: 251.1511
• Mol File: 15951-99-2.mol

Chemical Properties

• Boiling Point: 325.7°Cat760mmHg
• Flash Point: 163.6°C
• Appearance: /
• Density: 1.212g/cm³
• CAS DataBase Reference: (1R,2S)-1,2-Dichloro-1,2-diphenylethane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-1,2-Dichloro-1,2-diphenylethane(15951-99-2)
• EPA Substance Registry System: (1R,2S)-1,2-Dichloro-1,2-diphenylethane(15951-99-2)

Safety Data

• Hazardous Substances Data: 15951-99-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,2S)-1,2-Dichloro-1,2-diphenylethane is used as a reagent in organic synthesis for the formation of chiral molecules. Its unique chiral properties allow for the creation of complex organic compounds with specific stereochemistry.
Used in Pharmaceutical Production:
(1R,2S)-1,2-Dichloro-1,2-diphenylethane serves as a building block in the production of pharmaceuticals. Its ability to form chiral molecules is crucial in the development of drugs with desired biological activities and reduced side effects.
Used in Agrochemical Production:
(1R,2S)-1,2-Dichloro-1,2-diphenylethane is also used as a building block in the production of agrochemicals, where chiral molecules can be essential for the effectiveness and selectivity of these products.
Used in Material Development:
(1R,2S)-1,2-Dichloro-1,2-diphenylethane has been studied for its potential use in the development of new materials, leveraging its unique properties to create innovative substances with specific applications.
Used in Catalysis Reactions:
As a ligand in catalysis reactions, (1R,2S)-1,2-Dichloro-1,2-diphenylethane can enhance the efficiency and selectivity of various chemical processes, contributing to the advancement of synthetic chemistry.
It is important to handle (1R,2S)-1,2-Dichloro-1,2-diphenylethane with caution, as it is toxic if ingested or inhaled and can cause skin and eye irritation. Proper safety measures should be taken during its use in research and industrial applications.

Upstream product

• 98-87-3 benzylidene dichloride 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 7791-25-5 sulfuryl dichloride 
• 512-85-6 ascaridole 
• 100-52-7 benzaldehyde 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 107-06-2 1,2-dichloro-ethane 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 13440-24-9 anti-1,2-dibromo-1,2-diphenylethane 
• 579-43-1 (1S,2R)-1,2-diphenylethane-1,2-diol 
• 645-49-8 cis-stilben 

Downstream Products

• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 655-48-1 DL-1,2-diphenylethane-1,2-diol 
• 3682-07-3 anti-acetic acid 2-acetoxy-1,2-diphenyl-ethyl ester 
• 3682-07-3 syn-acetic acid 2-acetoxy-1,2-diphenyl-ethyl ester 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 948-99-2 α-chloro-(Z)-stilbene 
• 501-65-5 diphenyl acetylene 
• 17547-17-0 1,1,2-trichloro-1,2-diphenyl ethane 
• 948-98-1 (E)-α-chlorostilbene 
• 98-07-7 Benzotrichlorid 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 13027-48-0 rac-1,2-dibromo-1,2-diphenylethane 
• 13440-24-9 anti-1,2-dibromo-1,2-diphenylethane 
• 588-59-0 stilbene 

Relevant articles and documents

Chlorination of trans-1,2-diarylethenes in chloroform and acetic acid

When chlorinated in chloroform, (E)-stilbenes bearing electron-donor substituents in the para position of the benzene ring give threo-1,2-diaryl-1,2-dichloroethanes, while meta-substituted (E)-stilbenes, predominantly erythro isomers, irrespective of the

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand

Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

Visible-Light-Induced Vicinal Dichlorination of Alkenes through LMCT Excitation of CuCl2

This work demonstrates photoredox vicinal dichlorination of alkenes, based on the homolysis of CuCl2 in response to irradiation with visible light. This catalysis proceeds via a ligand to metal charge transfer process and provides an exciting opportunity for the synthesis of 1,2-dichloride compounds using an inexpensive, low-molecular-weight chlorine source. This new process exhibits a wide substrate scope, excellent functional group tolerance, extraordinarily mild conditions and does not require external ligands. Mechanistic studies show that the ready formation of chlorine atom radicals is responsible for the facile formation of C?Cl bonds in this synthetic process.

Preparation method of dichloro addition product of aromatic olefin under visible light catalysis

The invention relates to a preparation method of a dichloro addition product of aromatic olefin under visible light catalysis. The preparation method comprises the following step: by taking aromatic olefin as a substrate and copper chloride with visible light absorption capability as a chlorine source, reacting in an organic solvent under the irradiation of visible light in an inert atmosphere toobtain a dichloro addition product of the aromatic olefin after the reaction is completed. The aromatic olefin comprises a carbon-carbon double bond and an aryl group connected with the carbon-carbondouble bond through a covalent bond. Visible light is used for providing energy required by the reaction, copper chloride with visible light absorption capacity and a reaction substrate are used for photoinduction of chlorine atom transfer and initiation of an addition reaction to obtain a dichloro addition product, and the method is mild in reaction condition, simple and convenient to operate andwide in universality of the reaction substrate.

Cross-Linked Artificial Enzyme Crystals as Heterogeneous Catalysts for Oxidation Reactions

Designing systems that merge the advantages of heterogeneous catalysis, enzymology, and molecular catalysis represents the next major goal for sustainable chemistry. Cross-linked enzyme crystals display most of these essential assets (well-designed mesoporous support, protein selectivity, and molecular recognition of substrates). Nevertheless, a lack of reaction diversity, particularly in the field of oxidation, remains a constraint for their increased use in the field. Here, thanks to the design of cross-linked artificial nonheme iron oxygenase crystals, we filled this gap by developing biobased heterogeneous catalysts capable of oxidizing carbon-carbon double bonds. First, reductive O2 activation induces selective oxidative cleavage, revealing the indestructible character of the solid catalyst (at least 30 000 turnover numbers without any loss of activity). Second, the use of 2-electron oxidants allows selective and high-efficiency hydroxychlorination with thousands of turnover numbers. This new technology by far outperforms catalysis using the inorganic complexes alone, or even the artificial enzymes in solution. The combination of easy catalyst synthesis, the improvement of "omic" technologies, and automation of protein crystallization makes this strategy a real opportunity for the future of (bio)catalysis.

Vicinal dichlorination of olefins using NH4Cl and oxone

A mild and efficient protocol for the preparation of 1,2-dichloroalkane derivatives from olefins using NH4Cl and Oxone at room temperature is described. A variety of terminal, internal, and cyclic alkenes reacted smoothly to give the corresponding dichlorinated products in good to excellent yields. Moreover, 1,2-disubstituted symmetrical and unsymmetrical olefins dichlorinated with moderate to excellent diastereoselectivity. This method precludes the use of acidic additives and transition metals in the synthesis of vicinal dichlorides.

Dichlorination of olefins with NCS/Ph3P

A 2:1 mixture of NCS and Ph3P successfully promoted the anti-dichlorination of olefins to provide corresponding dichlorides, serving as a molecular chlorine surrogate generated in situ.

Convenient chlorination with concentrated hydrochloric acid in the presence of iodosylbenzene

An efficient chlorination of -keto esters, 1,3-diketones, and alkenes was performed conveniently with concentrated HCl in the presence of PhIO, selectively giving -chloro - keto esters, 2-chloro-1,3-diketones, and 1,2-dichloroalkanes, respectively. It was suggested that the chlorination took place with (dichloroiodo)benzene generated in situ. A selective anti-addition was observed in the chlorination of indene. Georg Thieme Verlag Stuttgart New York.

Bis- N -heterocyclic carbene palladium(IV) tetrachloride complexes: Synthesis, reactivity, and mechanisms of direct chlorinations and oxidations of organic substrates

This Article describes the preparation and isolation of novel octahedral CH2-bridged bis-(N-heterocyclic carbene)palladium(IV) tetrachlorides of the general formula LPdIVCl4 [L = (NHC)CH 2(NHC)] from LPdIICl2 and Cl2. In intermolecular, nonchelation-controlled transformations LPdIVCl 4 reacted with alkenes and alkynes to 1,2-dichlorination adducts. Aromatic, benzylic, and aliphatic C-H bonds were converted into C-Cl bonds. Detailed mechanistic investigations in the dichlorinations of alkenes were conducted on the 18VE PdIV complex. Positive solvent effects as well as kinetic measurements probing the impact of cyclohexene and chloride concentrations on the rate of alkene chlorination support a PdIV-Cl ionization in the first step. Product stereochemistry and product distributions from various alkenes also support Cl+-transfer from the pentacoordinated PdIV-intermediate LPdIVCl 3+ to olefins. 1-Hexene/3-hexene competition experiments rule out both the formation of π-complexes along the reaction coordinate as well as in situ generated Cl2 from a reductive elimination process. Instead, a ligand-mediated direct Cl+-transfer from LPd IVCl3+ to the π-system is likely to occur. Similarly, C-H bond chlorinations proceed via an electrophilic process with in situ formed LPdIVCl3+. The presence of a large excess of added Cl- slows cyclohexene chlorination while the presence of stoichiometric amounts of chloride accelerates both PdIV-Cl ionization and Cl+-transfer from LPdIVCl3 +. 1H NMR titrations, T1 relaxation time measurements, binding isotherms, and Job plot analysis point to the formation of a trifurcated Cl-...H-C bond in the NHC-ligand periphery as a supramolecular cause for the accelerated chemical events involving the metal center.

Insights into the reaction of trans-diarylethenes with thionyl chloride: A practical synthesis of chlorobenzo[b]thiophenes

The reactivity of a variety of trans-1,2-diarylethenes with thionyl chloride has been investigated. All the substrates could readily afford 3-chlorobenzo[b]thiophenes in moderate yields and a pair of threo- and erythro-1,2-dichloro-1,2-diarylethanes as th