1625-91-8

Basic information

• Product Name: 4,4'-DI-TERT-BUTYLBIPHENYL
• Synonyms: 1,1'-Biphenyl, 4,4'-bis(1,1-dimethylethyl)-;4,4'-Ditert-butyl-1,1'-biphenyl;4,4'-DI-T-BUTYLBIPHENYL;4,4'-DI-TERT-BUTYLBIPHENYL;TIMTEC-BB SBB007812;4,4'-Di-tert-butylbiphenyl, 99+%;4,4'-Di-tert-butylbiphenyl Zone Refined (number of passes:30);4,4'-Di-t-butylbiphenyl
• CAS NO: 1625-91-8
• Molecular Formula: C₂₀H₂₆
• Molecular Weight: 266.42
• EINECS: 216-615-4
• Product Categories: Biphenyl derivatives;Biphenyl & Diphenyl ether;Highly Purified Reagents;Other Categories;Zone Refined Products;Arenes;Building Blocks;Organic Building Blocks;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 1625-91-8.mol

Chemical Properties

• Melting Point: 126-130 °C(lit.)
• Boiling Point: 190-192 °C13 mm Hg(lit.)
• Flash Point: 190-192°C/13mm
• Appearance: Light yellow to yellow-orange/Crystalline Powder
• Density: 0.9463 (estimate)
• Refractive Index: 1.5928 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: dioxane: 0.1 g/mL, clear
• BRN: 2095855
• CAS DataBase Reference: 4,4'-DI-TERT-BUTYLBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DI-TERT-BUTYLBIPHENYL(1625-91-8)
• EPA Substance Registry System: 4,4'-DI-TERT-BUTYLBIPHENYL(1625-91-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1625-91-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4,4'-Di-tert-butylbiphenyl is used as a reagent in the generation of 1,2-di(lithiomethyl)benzene, which is an important intermediate in the synthesis of various organic compounds.
Used in Metalation Reactions:
In the production of homoallylic amine derivatives, 4,4'-di-tert-butylbiphenyl is used as a reagent, contributing to the formation of these valuable building blocks in organic synthesis.
Used in the Preparation of Lithium Di-tert-butylbiphenylide:
4,4'-Di-tert-butylbiphenyl is used in the preparation of lithium di-tert-butylbiphenylide, a radical anion that is considered superior to sodium or lithium naphthalenides for metalation reactions. 4,4'-DI-TERT-BUTYLBIPHENYL is particularly useful in the field of organic chemistry for its ability to facilitate various synthetic transformations.
Used in Catalysis:
4,4'-Di-tert-butylbiphenyl, along with lithium, catalyzes the reaction of chloromethyl ethyl ether with different carbonyl compounds, yielding the corresponding hydroxyethers. This application is significant in the synthesis of complex organic molecules and pharmaceuticals.
Used in the Reductive Opening of N-Phenylazetidine:
4,4'-Di-tert-butylbiphenyl also plays a role in the reductive opening of N-phenylazetidine, a reaction that is important in the synthesis of various nitrogen-containing compounds.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 1655, 1985 DOI: 10.1016/S0040-4039(00)98576-9

Upstream product

• 92-52-4 biphenyl 
• 78-83-1 2-methyl-propan-1-ol 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 253185-03-4 tert-butylbenzene 
• 769-92-6 4-tert-Butylaniline 
• 507-20-0 tertiary butyl chloride 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 53692-25-4 4,3′-di-tert-butylbiphenyl 
• 60705-72-8 bis(4-t-butylphenyl) methylphosphonate 
• 201230-82-2 carbon monoxide 
• 58377-39-2 bis(4-tert-butylphenyl)iodonium bromide 
• 38579-34-9 C₁₄H₁₃F₆O₄Tl 
• 70728-93-7 2,2′-dibromo-4,4′-di-tert-butylbiphenyl 
• 75-78-5 dimethylsilicon dichloride 

Downstream Products

• 69386-34-1 4,4'-di-tert-butyl-2-nitrobiphenyl 
• 70728-93-7 2,2′-dibromo-4,4′-di-tert-butylbiphenyl 
• 132657-11-5 3-(4-tert-Butylphenyl)-3,6,6-trimethoxycyclohexa-1,4-diene 
• 58775-13-6 2,7-di-tert-butylfluorenone 
• 84405-38-9 4,4'-di-tert-butylbiphenyl-2,2'-dicarboxylic acid 
• 70728-89-1 2-bromo-4,4'-di-tert-butylbiphenyl 
• 63992-30-3 2,2'-dihydroxy-4,4'-bis(tert-butyl)biphenyl 
• 439791-57-8 2,7-dibromo-(2',7'-di-tert-butyl)-9,9'-spirobifluorene 
• 32750-01-9 6,6'-dimethyl-2,2'-biphenyldiol 
• 69386-35-2 3,6-di-tert-butyl-9H-carbazole 
• 58775-05-6 2,7-di-tert-butyl-9H-fluorene 
• 351002-33-0 2,2'-dibromo-5,5'-diphenyl-4,4'-di-tert-butylbiphenyl 
• 351002-34-1 2,2'-dibromo-5,5'-bis(4-methoxyphenyl)-4,4'-di-tert-butylbiphenyl 
• 132657-22-8 4-(4-tert-Butylphenyl)-4-methoxycyclohexa-2,5-dienone 

Relevant articles and documents

Synthesis of unsymmetrical N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)nitroxyl radical, the first stable diarylnitroxyl with vacant para-position

The title compound, first example of a stable diarylnitroxyl with vacant para-position, was best synthesized by CuCl-assisted coupling of o-tert-butylnitrosobenzene and p-tert-butylphenylboronic acid followed by N-xidation of the thus obtained unsymmetrical diarylamine. ESR investigation showed that ortho-substituted aromatic ring is removed from the conjugation plane providing unusual stability of this radical.

tert-Butylated spirobifluorene derivative incorporating triphenylamine groups: A deep-blue emitter with high thermal stability and good hole transport ability for organic light emitting diode applications

Abstract A tert-butylated spirobifluorene derivative incorporating triphenylamine groups was synthesized starting from the readily available reagent biphenyl. Without any hole-transport layer, an unoptimized double-layer device exhibits excellent electroluminescent performances with a radiance of 3013 cd/m2 at 9.8 V, a maximum electroluminescent efficiency of 1.71 cd/A, a maximal external quantum efficiency of 2.58% at a brightness of 4.8 cd/m2, narrow full width at half-maximum (54 nm), and blue emission with Commission Internationale de l'Eclairage coordinates of (0.152, 0.103), which is close to the standard for blue. Compared to the reported organic light emitting diodes materials, the molecule displays very high thermal stability. In addition, the bilayer device showed a greatly improved performance as compared to a trilayer device with NPB as hole-transporting layer, which indicated that the molecule possesses good hole transport ability and can be good candidate for hole-transporting layer in organic light emitting diodes.

Oxidative homocoupling reaction of aryltrimethylsilanes by Pd/o-chloranil catalysis

A practical oxidative homocoupling reaction of aryltri-methylsilanes has been achieved by Pd/o-chloranil catalytic system. The reaction shows the good functional group tolerability toward bromo, fluoro, ester, and methoxy groups to give a series of biaryls bearing electron-withdrawing and -donating groups. The boronate group is also retained on biaryls without any ArB bond cleavage, which is highly advantageous for orthogonal coupling.

Shape-selective alkylation of biphenyl over H-[Al]-SSZ-24 zeolites with AFI topology

H-[Al]-SSZ-24 zeolites with AFI topology were synthesized through the alumination of [B]-SSZ-24 zeolites, and applied for the alkylation of biphenyl (BP). H-[Al]-SSZ-24 zeolites have high activity for the isopropylation. The shape-selective formation of 4,4′-diisopropylbiphenyl (4,40-DIPB) occurred at moderate temperature; however, the selectivity for 4,40-DIPB decreased with an increase in the reaction temperature. Isomerization of 4,4′-DIPB occurred at higher temperatures over internal and external acid sites when there are enough acid sites inside the channels. The channels can discriminate 4,4′-DIPB from the other DIPB isomers in their transition states; however, they can not prevent the isomerization of 4,4′-DIPB at higher temperatures. The selectivity for the least bulky 4,4′-dialkylbiphenyl increased with the bulkiness of alkylating agents in the order: isopropylation s-butylation t-butylation. These results strongly support the shape-selective formation of the least bulky products inside the channels of H-[Al]-SSZ-24 zeolites.

Hydride Transfer to Gold: Yes or No? Exploring the Unexpected Versatility of Au???H?M Bonding in Heterobimetallic Dihydrides

The potential for coordination and H-transfer from Cp2MH2 (M=Zr, W) to gold(I) and gold(III) complexes was explored in a combined experimental and computational study. [(L)Au]+ cations react with Cp2WH2 giving [(L)Au(κ2-H2WCp2)]+ (L=IPr (1), cyclic (alkyl)(amino)carbene (2), PPh3 (3) and Dalphos-Me (4) [IPr=1,3-bis(diisopropylphenyl)imidazolylidene; Dalphos-Me=di(1-adamantyl)-2-(dimethylamino)phenyl-phosphine], while [Au(DMAP)2]+ (DMAP=p-dimethylaminopyridine) affords the C2-symmetric [Au(κ-H2WCp2)2]+ (5). The Dalphos complex 4 can be protonated to give the bicationic adduct 4 H, showing AuI???H+?N hydrogen bonding. The gold(III) Lewis acid [(C^N?CH)Au(C6F5)(OEt2)]+ binds Cp2WH2 to give an Au-H-W σ-complex. By contrast, the pincer species [(C^N^C)Au]+ adds Cp2WH2 by a purely dative W→Au bond, without Au???H interaction. The biphenylyl-based chelate [(C^C)Au]+ forms [(C^C)Au(μ-H)2WCp2]+, with two 2-electron-3-centre W?H???Au interactions and practically no Au?W donor acceptor contribution. In all these complexes, strong but polarized W?H bonds are maintained, without H-transfer to gold. On the other hand, the reactions of Cp2ZrH2 with gold complexes led in all cases to rapid H-transfer and formation of gold hydrides. Relativistic DFT calculations were used to rationalize the striking reactivity and bonding differences in these heterobimetallic hydride complexes along with an analysis of their characteristic NMR parameters and UV/Vis absorption properties.

Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes

An intermolecular, three-component reductive dicarbofunctionalization of alkenes is presented here. The combination of Ni catalysis with TDAE as final reductant enables the direct formation of Csp3-Csp3 and Csp3-Csp2 bonds across a variety of π-systems using two different electrophiles that are sequentially activated with exquisite selectivity under mild reaction conditions.

Rapid Ligand-Free Base-Accelerated Copper-Catalyzed Homocoupling Reaction of Arylboronic Acids

A rapid, ligand-free, base-accelerated, copper-catalyzed homocoupling reaction of (het)arylboronic acids is presented. A -CuCl2·2H2O/Na2CO3-based catalyst enabled the formation of bi(het)aryl compounds by a homocoupling process in moderate to excellent yields (72-97%) within 15 minutes. A mechanism for the copper-catalyzed base-accelerated reaction is proposed.

Homocoupling of arylboronic acids with a catalyst system consisting of a palladium(II) N-heterocyclic carbene complex and p-benzoquinone

In the presence of 1-3 mol% SIPr-ligated Pd(OAc)2 and 0.6 equivalent of p-benzoquinone, various arylboronic acids underwent homocoupling in MeOH at ambient temperature to produce symmetrical biaryls in 38-96% yields. Georg Thieme Verlag Stuttgart.

Kinetically Controlled Reticular Assembly of a Chemically Stable Mesoporous Ni(II)-Pyrazolate Metal-Organic Framework

The application scope of metal-organic frameworks (MOFs) is severely restricted by their weak chemical stability and limited pore size. A robust MOF with large mesopores is highly desired, yet poses a great synthetic challenge. Herein, two chemically stable Ni(II)-pyrazolate MOFs, BUT-32 and -33, were constructed from a conformation-matched elongated pyrazolate ligand through the isoreticular expansion. The two MOFs share the same sodalite-type net, but have different pore sizes due to the network interpenetration in BUT-32. Controlled syntheses of the two MOFs have been achieved through precisely tuning reaction conditions, where the microporous BUT-32 was demonstrated to be a thermodynamically stable product while the mesoporous BUT-33 is kinetically favored. To date, BUT-32 represents the first example of Ni4-pyrazolate MOF whose structure was unambiguously determined by single-crystal X-ray diffraction. Interestingly, the kinetic product BUT-33 integrates 2.6 nm large mesopores with accessible Ni(II) active sites and remarkable chemical stability even in 4 M NaOH aqueous solution and 1 M Grignard reagent. This MOF thus demonstrated an excellent catalytic performance in carbon-carbon coupling reactions, superior to other Ni(II)-MOFs including BUT-32. These findings highlight the importance of kinetic control in the reticular synthesis of mesoporous MOFs, as well as their superiority in heterogeneous catalysis.

The alkylation of biphenyl over fourteen-membered ring zeolites. the influence of zeolite structure and alkylating agent on the selectivity for 4,4′-dialkylbiphenyl

Alkylation, i.e. isopropylation, s-butylation, and t-butylation, of biphenyl (BP) was examined over fourteen-mem-bered ring (14-MR) zeolites, CIT-5, UTD-1, and SSZ-53, in order to elucidate the relationships between structure of zeolites and bulkiness of alkylating agents on the shape-selective catalysis. CIT-5 zeolite (CFI) yielded 4,4′-diisopropyl- biphenyl (4,4′-DIPB) in the level of 50-60% in the isopropylation in the range of 150-300°C. 2,2′-, 2,3′-, and 2,4′-DIPB (2,x′-DIPB) isomers were obtained as the predominant DIPB isomers at lower temperatures, and the formation of 3,4′- and 3,3′-DIPB isomers increased with an increase in the temperature. However, the selectivities were in the level of 10- 15% for UTD-1 (DON) and SSZ-53 (SFH) zeolites in the range of 150-350°C. The s-butylation with 1-butene gave results similar to the isopropylation, although the selectivities for 4,4′-di-s-butylbiphenyl (4,4′-DSBB) were higher than those for 4,4′-DIPB at 250 °C: 80-85% for CFI, 40-50% for DON, and 30-40% for SFH. High selectivity for 4,4′-di-f-butylbiphenyl (4,4′-DTBB) was observed in the f-butylation at 250 °C: 95% for CFI, 90% for DON, and 80% for SFH. These differences are due to the spatial difference in their channels, and also due to bulkiness of alkylating agents, propene, 1-butene, and 2-methylpropene. The selectivity for 4,4′- dialkylbiphenyl (4,4′-DABP) was governed by the exclusion of the bulky DABP isomers at the transition state by steric restriction in the zeolite channels.