1012-72-2

Basic information

• Product Name: 1,4-Di-tert-butylbenzene
• Synonyms: P-DI-TERT-BUTYL BENZENE;1,4-bis(1,1-dimethylethyl)-benzen;1,4-tert-dibutylbenzene;Benzene, p-di-tert-butyl-;benzene,1,4-di-tert-butyl-;bis(1,1-dimethylethyl)-benzen;bis(1,1-dimethylethyl)benzene;p-di-tert-butyl-benzen
• CAS NO: 1012-72-2
• Molecular Formula: C₁₄H₂₂
• Molecular Weight: 190.32
• EINECS: 213-790-9
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Benzene derivates;Arenes;Building Blocks;Organic Building Blocks
• Mol File: 1012-72-2.mol

Chemical Properties

• Melting Point: 76-78 °C(lit.)
• Boiling Point: 236 °C(lit.)
• Flash Point: 236°C
• Appearance: white/crystalline
• Density: 0.985
• Vapor Pressure: 0.0744mmHg at 25°C
• Refractive Index: 1.4955 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water. Soluble in ethanol, benzene, carbon tetrachloride.
• BRN: 1617000
• CAS DataBase Reference: 1,4-Di-tert-butylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Di-tert-butylbenzene(1012-72-2)
• EPA Substance Registry System: 1,4-Di-tert-butylbenzene(1012-72-2)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 22-24/25-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: CY8444000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 1012-72-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystals or crystalline powder

Uses

Different sources of media describe the Uses of 1012-72-2 differently. You can refer to the following data:
1. 1,4-di-tert-butylbenzene (DTBB) is used as a crystallized form from several organic solvents to study the effect of solvents and crystallization conditions on its habit. It is also used as a solvent and an intermediate in the manufacture of other organic compounds for the finished products of such as curing agents, engineering plastics and cross-linking agents.
2. 1,4-di-tert-butylbenzene (DTBB) is crystallized from several organic solvents to study the effect of solvents and crystallization conditions on its habit.

Purification Methods

Crystallise it from Et2O or EtOH and dry it under vacuum over P2O5 at 55o. [Tanner et al. J Org Chem 52 2142 1987, Beilstein 5 II 344.]

InChI:InChI=1/C14H22/c1-13(2,3)11-7-9-12(10-8-11)14(4,5)6/h7-10H,1-6H3

Upstream product

• 253185-03-4 tert-butylbenzene 
• 78-83-1 2-methyl-propan-1-ol 
• 75-66-1 2-methylpropan-2-thiol 
• 98-82-8 Isopropylbenzene 
• 513-36-0 isobutyryl chloride 
• 71-43-2 benzene 
• 78-77-3 Isobutyl bromide 
• 108-88-3 toluene 
• 115-11-7 isobutene 
• 507-20-0 tertiary butyl chloride 
• 75-65-0 tert-butyl alcohol 
• 540-84-1 2,2,4-trimethylpentane 
• 6223-78-5 2,5-dichloro-2,5-dimethyl hexane 
• 1460-02-2 1,3,5-Tri-tert-butylbenzene 

Downstream Products

• 29685-73-2 (E)-4-(4-(tert-butyl)phenyl)-4-oxobut-2-enoic acid 
• 1460-02-2 1,3,5-Tri-tert-butylbenzene 
• 15084-51-2 4-tert-butylbenzenesulfonyl chloride 
• 3463-35-2 2,5-di-tert-butylnitrobenzene 
• 3282-56-2 4-tert-butylnitrobenzene 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 1014-60-4 1,3-di-tert-butylbenzene 
• 1075-38-3 m-t-butyltoluene 
• 1133-17-1 4-(tert-butyl)benzenesulfonic acid 
• 22875-47-4 2,5-dibromo-1,4-di-tert-butylbenzene 
• 10472-70-5 2,5-di-tert-butyl-p-dinitrobenzene 
• 10565-39-6 1,4-di-tert-butyl-2-chloro-benzene 
• 6683-74-5 2-bromo-1,4-di-tert-butylbenzene 
• 10472-73-8 2,5-di-tert-butyl-1,3-dinitro-benzene 

Relevant articles and documents

Effect of solvent on the lithium-bromine exchange of aryl bromides: Reactions of n-butyllithium and tert-butyllithium with 1-bromo-4-tert- butylbenzene at 0 °C

The outcome of reactions of 1-bromo-4-tert-butylbenzene (1), a representative aryl bromide, with n-BuLi or t-BuLi at 0 °C in a variety of solvent systems has been investigated. The products of reactions of 1 with n-BuLi vary significantly with changes in solvent composition: 1 does not react with n-BuLi in pure heptane; the exchange reaction to give (4-tert-butylphenyl) lithium, which is slow in pure diethyl ether, is virtually quantitative in heptane containing a small quantity of THF; and the reaction of 1 with n-BuLi in THF leads to considerable coupling. Lithium-bromine exchange is the virtually exclusive outcome of reactions of 1 with t-BuLi in every solvent studied except pure heptane: the presence of a small quantity of any of a variety of structurally diverse ethers (Et2O, THF, THP, MTBE) in the predominantly hydrocarbon medium affords (4-tert-butylphenyl)lithium, assayed as tert-butylbenzene, in yields exceeding 97%. The only side products observed from reactions of 1 with t-BuLi are small amounts of benzyne-derived hydrocarbons.

Perfluorooctanesulfonic acid catalyzed Friedel-Crafts alkylation with alkyl halides

A new procedure to prepare superacid perfluorooctanesulfonic acid (POSA) is reported. POSA catalyzed Friedel-Crafts alkylation of aromatic compounds with alkyl halides in liquid-phase reactions. Alkylation gave higher total yields than the corresponding reactions with Nafion-H, without the need of any complex decomposition or work-up. The reactions do not need to be carried out under absolutely anhydrous condition. The catalyst POSA can be easily separated from the reaction mixture and reused or recovered. The reactivity of the alkylation reagents and the mechanism of the reaction are discussed.

Determination of critical temperatures for mixtures of alkylbenzenes

The liquid-vapor critical temperatures of benzene mixtures with 1,3-di-tert-butylbenzene, 1,4-di-tert-butylbenzene, and 1,3,5-tri-tert- butylbenzene; a mixture of di-tert-butylbenzene isomers; and a toluene mixture with 3,5-di-tert-butyltoluene were determined over the entire range of composition by means of the amouule method. It was found that the excess critical temperature of the mixtures is related to the critical volumes of the substances. The capabilities of several calculation methods for predicting the critical temperature of mixtures were analyzed on the basis of published data and the obtained results. The Lee-Kesler rules of mixtures were refined by introducing binary interaction parameters.

Radical aromatic substitution with benzene chromiumtricarbonyl

Radical aromatic substitution of tert-butyl groups for hydrogen on simple arene chromiumtricarbonyl complexes was accomplished. Preexisting tert-butyl groups and methoxy groups directed incoming radicals primarily to the meta-position, and methoxy groups diminished the rate of substitution by roughly tenfold.

Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines

We report a method to activate α-3° amines for deaminative arylation via condensation with an electron-rich aldehyde and merge this reactivity with nickel metallaphotoredox to generate benzylic quaternary centers, a common motif in pharmaceuticals and natural products. The reaction is accelerated by added ammonium salts. Evidence is provided in support of two roles for the additive: inhibition of nickel black formation and acceleration of the overall reaction rate. We demonstrate a robust scope of amine and haloarene coupling partners and show an expedited synthesis of ALK2 inhibitors.

Carbon-based leaving group in substitution reactions: Functionalization of sp3-hybridized quaternary and tertiary benzylic carbon centers

Lewis acid promoted substitution reactions employing Meldrum's acid and 5-methyl Meldrum's acid as carbon-based leaving groups are described which transform unstrained quaternary and tertiary benzylic Csp 3-Csp3 bonds into Csp3-X bonds (X = C, H, N). Importantly, this reaction has a broad scope in terms of both suitable substrates and nucleophiles with good to excellent yields obtained (typically >90%).

Nickel-catalyzed cross-coupling of aryl bromides with tertiary grignard reagents utilizing donor-functionalized N-heterocyclic carbenes (NHCs)

Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis, allowing the efficient construction of complex structures from simpler, readily available building blocks.Many applications in large and small-scale synthesis can be found in different areas such as agrochemicals, pharmaceuticals and supramolecular chemistry. Whereas the coupling of sp2-hybridized carbon atoms in either reaction partner is well established, the use of CACHTUNGTRENUNG(sp3)-hybridized substrates presents some challenges. Catalytic cross-coupling of sterically hindered tertiary alkyl substrates is especially difficult, generally resulting in low yields, and thus, only few reports exist.[27] A big challenge in this field is not only to get the required level of reactivity, but also to overcome competing pathways like β-hydride elimination, hydrodehalogenation or isomerization

Nickel-catalyzed Kumada cross-coupling reactions of tertiary alkylmagnesium halides and aryl bromides/triflates

We report a Ni-catalyzed process for the cross-coupling of tertiary alkyl nucleophiles and aryl bromides. This process is extremely general for a wide range of electrophiles and generally occurs with a ratio of retention to isomerization >30:1. The same procedure also accommodates the use of aryl triflates, vinyl chlorides, and vinyl bromides as the electrophilic component.

Silylium-arene adducts: An experimental and theoretical study

The solvent-coordinated [Me3Si·arene][B(C 6F5)4] salts (arene = benzene, toluene, ethylbenzene, n-propylbenzene, isopropylbenzene, o-xylene, m-xylene, p-xylene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene) are prepared and fully characterized. As an interesting decomposition product the formation of bissilylated fluoronium ion [Me3Si-F-SiMe 3]+ was observed and even cocrystallized with [Me 3Si·arene][B(C6F5)4] (arene = benzene and toluene). Investigation of the degradation of [Me 3Si·arene][B(C6F5)4] reveals the formation of fluoronium salt [Me3Si-F-SiMe3][B(C 6F5)4], B(C6F5) 3, and a reactive "C6F4" species which could be trapped with CS2. Upon addition of CS2, the formation of a formal S-heterocyclic carbene adduct, C6F 4CS2-B(C6F5)3, was observed. The structure and bonding of substituted [Me3Si· arene][B(C6F5)4] with arene = R nC6H6-n (R = H, Me, Et, Pr, and Bu; n = 0-6) is discussed on the basis of experimental and theoretical data. X-ray data of [Me3Si·arene][B(C6F5)4] salts reveal nonplanar arene species with significant cation...anion interactions. As shown by different theoretical approaches (charge transfer, partial charges, trimethylsilyl affinity values) stabilizing inductive effects occur; however, the magnitude of such effects differs depending on the degree of substitution and the substitution pattern.

Alkylation of pyrocatechol in tert-butyl alcohol-sulfuric acid-benzene

Alkylation of pyrocatechol with tert-butyl alcohol in benzene in the presence of sulfuric acid gave 3,5-di-tert-butylbenzene-1,2-diol in a higher yield than in analogous reaction with tert-butyl alcohol. This result was rationalized by reduction of inhibitory effect of liberated water, formation of heterogeneous system, and occurrence of the alkylation process in nonpolar organic phase. Intermediate products were identified and found to undergo intra- and intermolecular tert-butyl group transfer with formation of more stable 3,5-di-tert-butylbenzene-1,2-diol. The formation of p-di-tert-butylbenzene indicated participation of benzene in crossalkylation processes. Pleiades Publishing, Ltd., 2011.