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O-TERPHENYL, also known as ortho-terphenyl, is an organic compound consisting of three benzene rings connected in a chain. It is a colorless, crystalline solid with a melting point of 66-68°C and a boiling point of 340°C. O-TERPHENYL exhibits low toxicity and has a high thermal stability, making it suitable for various industrial applications.

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  • 84-15-1 Structure
  • Basic information

    1. Product Name: O-TERPHENYL
    2. Synonyms: O-DIPHENYLBENZENE;O-TERPHENYL;1,1':2',1 -Terphenyl;1,1':2',1''-Terphenyl;1,1’:2’,1’’-Terphenyl;1,1'-Biphenyl, 2-phenyl-;1,2-terphenyl;2-phenyl-1’-biphenyl
    3. CAS NO:84-15-1
    4. Molecular Formula: C18H14
    5. Molecular Weight: 230.3
    6. EINECS: 201-517-6
    7. Product Categories: Arenes;Building Blocks;Chemical Synthesis;Organic Building Blocks
    8. Mol File: 84-15-1.mol
    9. Article Data: 161
  • Chemical Properties

    1. Melting Point: 56-59 °C(lit.)
    2. Boiling Point: 337 °C(lit.)
    3. Flash Point: >230 °F
    4. Appearance: /Fluid
    5. Density: 1,1 g/cm3
    6. Vapor Pressure: 0.00029mmHg at 25°C
    7. Refractive Index: 1.5500 (estimate)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: 1.24mg/l
    10. Water Solubility: Insoluble in water. Solubility in toluene is almost transparent. Sparingly soluble in lower alcohols and glycols; very soluble i
    11. BRN: 1908446
    12. CAS DataBase Reference: O-TERPHENYL(CAS DataBase Reference)
    13. NIST Chemistry Reference: O-TERPHENYL(84-15-1)
    14. EPA Substance Registry System: O-TERPHENYL(84-15-1)
  • Safety Data

    1. Hazard Codes: Xn,T,Xi,F,N
    2. Statements: 22-36/37/38-50/53-40-36/38-21/22-67-66-11-52/53-36-51/53
    3. Safety Statements: 26-61-60-36/37-24/25-23-16-9
    4. RIDADR: UN 3077 9/PG 3
    5. WGK Germany: 3
    6. RTECS: WZ6472000
    7. TSCA: Yes
    8. HazardClass: 9
    9. PackingGroup: III
    10. Hazardous Substances Data: 84-15-1(Hazardous Substances Data)

84-15-1 Usage

Uses

Used in Heat Storage and Transfer Applications:
O-TERPHENYL is used as a heat storage and transfer agent in industrial processes. Its high thermal stability and low toxicity make it an ideal choice for these applications.
Used in Textile Industry:
In the textile industry, O-TERPHENYL is used as a carrier for textile dyes. Its ability to dissolve dyes effectively and its low toxicity make it a preferred choice for dye carriers.
Used in Lubricant Production:
O-TERPHENYL serves as an intermediate in the production of nonspreading lubricants. Its chemical properties contribute to the development of high-quality lubricants with specific performance characteristics.
Used in Solar-Heating Systems:
In contemporary applications, O-TERPHENYL is utilized in solar-heating systems. Its high thermal stability and ability to store and transfer heat efficiently make it a suitable component for these systems.
Used in Plasticizer Industry:
O-TERPHENYL is used as a plasticizer for polystyrene in thermoplastic recording. Its compatibility with polystyrene and ability to enhance the material's flexibility make it a valuable additive in this application.

Reactivity Profile

O-TERPHENYL is non-flammable but combustible (flash point 339°F). Extremely stable thermally. Incompatible with strong oxidizing agents but not very reactive at room conditions.

Hazard

Combustible. Eye and upper respiratory tract irritant.

Safety Profile

Moderately toxic by ingestion. Combustible when exposed to heat or flame. To fight fire, use water, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise o-terphenyl from EtOH. Also purify it by chromatography of CCl4 solution on alumina, with pet ether as eluent, followed by crystallisation from pet ether (b 40-60o) or pet ether/*C6H6. It also distils under vacuum. [Beilstein 5 III 2292, 5 IV 2478.]

Check Digit Verification of cas no

The CAS Registry Mumber 84-15-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 4 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 84-15:
(4*8)+(3*4)+(2*1)+(1*5)=51
51 % 10 = 1
So 84-15-1 is a valid CAS Registry Number.
InChI:InChI=1/C18H14/c1-3-9-15(10-4-1)17-13-7-8-14-18(17)16-11-5-2-6-12-16/h1-14H

84-15-1 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (A19680)  o-Terphenyl, 98%   

  • 84-15-1

  • 25g

  • 355.0CNY

  • Detail
  • Alfa Aesar

  • (A19680)  o-Terphenyl, 98%   

  • 84-15-1

  • 100g

  • 1001.0CNY

  • Detail
  • Supelco

  • (48169)  o-Terphenylsolution  certified reference material, 2000 μg/mL in acetone

  • 84-15-1

  • 000000000000048169

  • 449.28CNY

  • Detail
  • Supelco

  • (47580-U)  o-Terphenylsolution  certified reference material, 10000 μg/mL in methylene chloride

  • 84-15-1

  • 47580-U

  • 622.44CNY

  • Detail
  • Aldrich

  • (T2800)  o-Terphenyl  99%

  • 84-15-1

  • T2800-25G

  • 479.70CNY

  • Detail
  • Aldrich

  • (T2800)  o-Terphenyl  99%

  • 84-15-1

  • T2800-100G

  • 1,272.96CNY

  • Detail

84-15-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name O-TERPHENYL

1.2 Other means of identification

Product number -
Other names 1,1‘:2‘,1‘‘-Terphenyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:84-15-1 SDS

84-15-1Relevant articles and documents

Comparison of the Oxidative Coupling Reactions of Benzene with Those of Methane of Rare Earth Oxide Catalysts

Sugiyama, Shigeru,Ookubo, Takashi,Shimodan, Kazuaki,Hayashi, Hiromu,Moffat, John B.

, p. 3339 - 3345 (1994)

The oxidative coupling of benzene has been compared with that of methane on La2O3, CeO2, Pr6O11, and Sm2O3. At temperatures greater than 1048 K, the gas phase oxidative coupling of benzene appears to be predominant, while the oxidation occurs catalytically at 873 K. The conversion of benzene and of methane at 873 K follows the order of Sm2O3>La2O3>Pr6O11>CeO2, suggesting that the abstraction of hydrogen from the aromatic and the saturated compounds depends primarily on the nature of the catalyst but not the reactant. Ancillary information has also been obtained from the results of XPS analyses of both fresh catalysts and those previously used in one of the reactions.

Understanding enediyne-protein interactions: Diyl atom transfer results in generation of aminoacyl radicals

Jones, Graham B.,Plourde II, Gary W.,Wright, Justin M.

, p. 811 - 813 (2000)

Formula Presented The origin of the protein modulating capacity of enediynes has been probed. A series of synthetic enediyne-derived diyls participated in atom transfer chemistry with a labeled amino acid. Subsequent experiments suggest that diyl radicals may modulate protein architecture via formation of captodatively stabilized radicals.

Suzuki cross-coupling of hexachlorobenzene promoted by the Buchwald ligands

Burukin, A. S.,Vasil’ev, A. A.,Zhdankina, G. M.,Zlotin, S. G.

, p. 169 - 172 (2022/02/17)

The study of cross-coupling between hexachlorobenzene and phenylboronic acid comprised five Buchwald ligands, from which 2-dicyclohexylphosphino-2′-(dimethylamino)biphenyl (DavePHOS) provided the best conversion. When excess of phenylboronic acid was used, a mixture of isomeric tri-, tetra- and pentaphenyl-substituted derivatives in the ~10:70:20 ratio was obtained, along with minor amounts of hydrodechlorination products.

Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate

Sekiguchi, Yoshiya,Lee, Yan Ying,Yoshikai, Naohiko

, p. 5993 - 5997 (2021/08/16)

We report herein a nickel-catalyzed ring-opening allylation of cyclopropanols with allylic carbonates that occurs under mild and neutral conditions. The reaction displays linear selectivity for both linear and branched acyclic allylic carbonates and is also applicable to cyclic allylic carbonates, affording a variety of δ,?-unsaturated ketones in moderate to good yields. Mechanistic experiments are in accord with a catalytic cycle involving decarboxylative oxidative addition of allylic carbonate to Ni(0), alkoxide exchange with cyclopropanol, cyclopropoxide-to-homoenolate conversion on Ni(II), and C-C reductive elimination.

Buchwald ligand-assisted Suzuki cross-coupling of polychlorobenzenes

Burukin, Alexander S.,Vasil'ev, Andrei A.,Zhdankina, Galina M.,Zlotin, Sergei G.

, p. 400 - 402 (2021/06/07)

Screening of four Buchwald ligands for the cross-coupling of isomeric di-, tri- and tetrachlorobenzenes with arylboronic acids revealed that good yields of exhaustive substitution can be best provided by 2-dicyclohexylphosphino-2′-(dimethylamino) biphenyl (DavePHOS).

Experimental and Computational Studies towards Chemoselective C?F over C?Cl Functionalisation: Reversible Oxidative Addition is the Key

Jacobs, Emily,Keaveney, Sinead T.

, p. 637 - 645 (2020/12/07)

Catalytic cross-coupling is a valuable tool for forming new carbon-carbon and carbon-heteroatom bonds, allowing access to a variety of structurally diverse compounds. However, for this methodology to reach its full potential, precise control over all competing cross-coupling sites in poly-functionalised building blocks is required. Carbon-fluorine bonds are one of the most stable bonds in organic chemistry, with oxidative addition at C?F being much more difficult than at other C-halide bonds. As such, the development of methods to chemoselectively functionalise the C?F position in poly-halogenated arenes would be very challenging if selectivity was to be induced at the oxidative addition step. However, metal-halide complexes exhibit different trends in reactivity to the parent haloarenes, with metal-fluoride complexes known to be very reactive towards transmetalation. In this current work we sought to exploit the divergent reactivity of Ni?Cl and Ni?F intermediates to develop a chemoselective C?F functionalisation protocol, where selectivity is controlled by the transmetalation step. Our experimental studies highlight that such an approach is feasible, with a number of nickel catalysts shown to facilitate Hiyama cross-coupling of 1-fluoronapthalene under base free conditions, while no cross-coupling with 1-chloronapthalene occurred. Computational and experimental studies revealed the importance of reversible C?Cl oxidative addition for the development of selective C?F functionalisation, with ligand effects on the potential for reversibility also presented.

Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization

Choudhury, Joyanta,Dutta, Tapas Kumar,Mandal, Tanmoy,Mohanty, Sunit

supporting information, p. 10182 - 10185 (2021/10/12)

Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.

Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance

Bunda, Szilvia,Joó, Ferenc,Kathó, ágnes,Udvardy, Antal,Voronova, Krisztina

supporting information, (2020/09/18)

Water-soluble salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N’-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were obtained in reactions of sulfosalans and [PdCl4]2?. Characterization of the ligands and complexes included extensive X-ray diffraction studies, too. The Pd (II) complexes proved highly active catalysts of the Suzuki–Miyaura reaction of aryl halides and arylboronic acid derivatives at 80 ?C in water and air. A comparative study of the Pd (II)–sulfosalan catalysts showed that the catalytic activity largely increased with increasing linker length and with increasing steric congestion around the N donor atoms of the ligands; the highest specific activity was 40,000 (mol substrate) (mol catalyst × h)?1. The substrate scope was explored with the use of the two most active catalysts, containing 1,4-butylene and 1,2-diphenylethylene linkers, respectively.

Organocatalyst in Direct C(sp2)-H Arylation of Unactivated Arenes: [1-(2-Hydroxyethyl)-piperazine]-Catalyzed Inter-/Intra-molecular C-H Bond Activation

Yadav, Lalit,Tiwari, Mohit K.,Shyamlal, Bharti Rajesh Kumar,Chaudhary, Sandeep

, p. 8121 - 8141 (2020/07/16)

This article describes the identification of 1-(2-hydroxyethyl)-piperazine as a new, cost-effective, highly efficient organocatalyst, which promotes both inter- A nd intra-molecular direct C(sp2)-H arylations of unactivated arenes in the presence of potassium tert-butoxide. While the inter-molecular C-H arylation of unactivated benzenes with aryl halides (Ar-X; X = I, Br, Cl) toward biaryl syntheses underwent smoothly in the presence of only 10 mol percent organocatalyst, the intra-molecular C-H arylation catalytic system composed of 40 mol percent each of the catalyst and the additive (4-dimethylaminopyridine (DMAP)). The novel catalyst was also able to perform both inter- A nd intra-molecular direct arylations simultaneously in a single pot. The mechanistic studies confirmed the involvement of aryl radical anions and proceeded via a single-electron-transfer (SET) mechanism. The large substrate scope, high functional group tolerance, competition experiments, gram-scale synthesis, and kinetic studies further highlight the importance and versatile nature of the methodology as well as the compatibility of the new catalyst. To the best of our knowledge, this is the first report on any organocatalyst that reported detailed investigations of both inter- A nd intra-molecular direct C(sp2)-H arylations of unactivated arenes in a single representation.

Palladium-catalysed room-temperature Suzuki–Miyaura coupling in water extract of pomegranate ash, a bio-derived sustainable and renewable medium

Appa, Rama Moorhy,Prasad, S. Siva,Lakshmidevi, Jangam,Naidu, Bandameeda Ramesh,Narasimhulu, Manchala,Venkateswarlu, Katta

, (2019/08/12)

An agro waste-derived, ‘water extract of pomegranate ash’ (WEPA), has been utilized for the first time as a renewable medium for Pd(OAc)2-catalysed Suzuki–Miyaura cross-coupling at room temperature. This method offers a simple and sustainable synthesis of biaryls from aryl halides and arylboronic acids under ligand- and external base-free aerobic and ambient conditions. This method has been found effective for both activated and unactivated aryl halides in the production of biaryls with moderate to nearly quantitative yields. The protocol shows high chemoselectivity over identical/similar reactive sites in aryl halides (i.e. selectivity over identical halogens or different halogens of aryl halides). This method exhibits high regioselectivity, i.e. the selective reactivity of a halogen over other identical halogens at different positions on the aromatic nucleus. Therefore, we disclose here a clean, benign, substantial chemo- and regioselective and highly economic alternative method for the palladium-assisted synthesis of biaryls using an agro waste-derived medium.

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