15181-11-0

Basic information

• Product Name: 3,5-DI-TERT-BUTYLTOLUENE
• Synonyms: 1,3-bis(1,1-dimethylethyl)-5-methylbenzene;1,3-di-tert-butyl-5-methyl-benzene;1,3-Ditert-butyl-5-methylbenzene;Benzene, 1,3-bis(1,1-dimethylethyl)-5-methyl-;Benzene, 1-methyl-3,5-bis-(1,1-dimethylethyl);benzene,1,3-bis(1,1-dimethylethyl)-5-methyl-;Toluene, 3,5-di-tert-butyl-;toluene,3,5-di-tert-butyl-
• CAS NO: 15181-11-0
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 239-230-3
• Product Categories: Arenes;Building Blocks;Organic Building Blocks
• Mol File: 15181-11-0.mol

Chemical Properties

• Melting Point: 31-32 °C(lit.)
• Boiling Point: 244 °C(lit.)
• Flash Point: 196 °F
• Appearance: /
• Density: 0.86 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0486mmHg at 25°C
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• BRN: 2043032
• CAS DataBase Reference: 3,5-DI-TERT-BUTYLTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DI-TERT-BUTYLTOLUENE(15181-11-0)
• EPA Substance Registry System: 3,5-DI-TERT-BUTYLTOLUENE(15181-11-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 15181-11-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3,5-Di-tert-butyltoluene is used as a starting material for the synthesis of various organic compounds, such as 3,5-di-tert-butyl(bromomethyl)benzene and di-tert-butylbenzoic acid. Its unique structure and reactivity make it a valuable intermediate in the production of a range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,5-di-tert-butyltoluene is used as a synthetic intermediate for the production of various drugs and pharmaceutical compounds. Its versatility in chemical reactions allows for the creation of a wide array of molecules with potential therapeutic applications.
Used in Polymer Industry:
3,5-Di-tert-butyltoluene is also utilized in the polymer industry as a component in the synthesis of certain polymers. Its presence in the polymer structure can contribute to improved stability, durability, and other desirable properties.
Used in Material Science:
In the field of material science, 3,5-di-tert-butyltoluene can be employed in the development of novel materials with specific properties. Its incorporation into various materials can lead to enhanced performance characteristics, such as increased resistance to heat, light, or chemical degradation.
Overall, 3,5-di-tert-butyltoluene is a versatile compound with a wide range of applications across different industries, primarily due to its unique chemical structure and reactivity.

InChI:InChI=1/C15H24/c1-11-8-12(14(2,3)4)10-13(9-11)15(5,6)7/h8-10H,1-7H3

Upstream product

• 507-20-0 tertiary butyl chloride 
• 98-51-1 4-tert-butyltoluene 
• 1075-38-3 m-t-butyltoluene 
• 107-39-1 2,4,4-trimethyl-1-pentene 
• 108-88-3 toluene 
• 1012-72-2 1,4-di-tert-butylbenzene 
• 75-28-5 Isobutane 
• 106-42-3 para-xylene 
• 141888-43-9 2,4-di-tert-butyl-6-methylphenylarsine 
• 23288-49-5 (4,4'-isopropylidenedithio)bis[2,6-di-tert-butylphenol] 
• 7664-39-3 hydrogen fluoride 
• 513-36-0 isobutyryl chloride 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 4873-09-0 allyl tosylate 

Downstream Products

• 20444-30-8 1,5-di-tert-butyl-3-methyl-2-nitrobenzene 
• 51625-14-0 3,5-di-tert-butyl-benzoyl chloride 
• 101354-77-2 1,5-di-tert-butyl-3-methyl-2,4-dinitro-benzene 
• 16225-26-6 3,5-di-tert-butylbenzoic acid 
• 62938-08-3 3,5-di-tert-butylbenzyl bromide 
• 31912-89-7 1,5-di-tert-butyl-2-chloro-3-methylbenzene 
• 36393-44-9 (3,5-di-tert-butylbenzyl)triphenylphosphonium bromide 
• 17610-00-3 3,5-Di-tert-butylbenzaldehyde 
• 16358-71-7 2-bromo-1,5-di-tert-butyl-3-methyl-benzene 
• 153474-38-5 3,5-di-tert-butyl(dibromomethyl)benzene 
• 71-43-2 benzene 
• 90-47-1 xanth-9-one 
• 100045-13-4 xanthone ketyl radical 
• 142987-58-4 C₁₅H₂₃ 

Relevant articles and documents

Framework-Substituted Sn-MOR Zeolite Prepared by Multiple pH-Adjusting Сo-Hydrolysis As Efficient Catalyst for tert-Butylation of Toluene

Abstract: A series of Sn-MOR samples with different tin species loadings were prepared via a mutiple pH?adjusting co-hydrolysis method. Their properties were characterized by XRD, XRF, UV–Vis, FT-IR, Py-IR, N2 sorption and SEM techniques. The catalytic performance was evaluated in liquid-phase toluene alkylation with tert-butyl alcohol. The characterization results shows that compared to framework destruction of mordenite for the Sn/MOR sample with floccule prepared by ion exchange method, higher relative crystallinity and larger surface area and pore volume for Sn-MOR samples with walnut morphology can be obtained. The doping with tin species can increase the Lewis acidity and decrease the pore size resulting in both higher toluene conversion and p-tert-butyltoluene (PTBT) selectivity. The Sn-MOR(0.010) sample shows the highest catalytic performance with toluene conversion of 48.0% and PTBT selectivity of 85.6%. It?shows high stability: toluene conversion of 45.3% and PTBT selectivity of 87.2% can be obtained even after 5 consecutive runs.

Tert-Butylation of toluene with tert-butyl alcohol over immobilized titanium species on the Al-MCM-48

A series of Ti-Al-M48 (M48 stand for MCM-48) samples with different titanium species loadings were prepared by immobilization method. Their physical chemical properties were characterized by XRD, liquid N2 adsorption-desorption, Py-IR, NH3-TPD and UV-vis DRS techniques, and their catalytic performances were investigated in the tert-butylation of toluene with tert-butyl alcohol in a 100 ml stainless steel autoclave equipped with a magnetically driven impeller. The Ti-Al-M48 samples have a large BET surface and ordered mesoporous structure. Although the titanium species loading is the same, the 4% Ti-Al-M48 sample has a larger acid amount than the 4% Ti/Al-M48 sample prepared by impregnation. The Py-IR and UV-vis DRS spectra revealed that the isolated TiO4 tetrahedra by isomorphous substitution into the Al-M48 network have Lewis acidity. The 4% Ti-Al-M48 has a higher catalytic performance than other samples and the influence of reaction conditions on the tert-butylation of toluene was discussed. The conversion of toluene is 47.5% and the selectivity of p-tert-butyltoluene is 77.2% at the molar ratio of tert-butyl alcohol to toluene 2, the weight ratio of toluene to catalyst 8, reaction temperature 453K and reaction time 4 h. The 4% Ti-Al-M48 sample shows high stability, and toluene conversion 43.7% and p-tert-butyltoluene selectivity 78.4% can be obtained even though after repeated reaction for 3 times.

Catalytic Asymmetric Hydroalkenylation of Vinylarenes: Electronic Effects of Substrates and Chiral N-Heterocyclic Carbene Ligands

An asymmetric tail-to-tail cross-hydroalkenylation of vinylarenes with terminal olefins was achieved by catalysis with NiH complexes bearing chiral N-heterocyclic carbenes (NHCs). The reaction provides branched gem-disubstituted olefins with high enantioselectivity (up to 94% ee) and chemoselectivity (cross/homo product ratio: up to 99:1). Electronic effects of the substituents on the vinylarenes and on the N-aryl groups of the NHC ligands, but not a π,π-stacking mechanism, assist the steric effect and influence the outcome of the cross-hydroalkenylation.

Nickel-catalyzed hydrodehalogenation of aryl halides

In the present study, the nickel-catalyzed dehalogenation of aryl and alkyl halides with iso-propyl zinc bromide or tert-butylmagnesium chloride has been examined in detail. With a straightforward nickel complex as pre-catalyst good to excellent yields and chemoselectivities were feasible for a variety of aryl and alkyl halides.

PROCESS FOR THE PREPARATION OF M-SUBSTITUTED ALKYLTOLUENES BY ISOMERIZATION WITH IONIC LIQUIDS AS CATALYSTS

The invention relates to a process for the preparation of m-substituted alkyltoluenes of the formula (I) in which R1 is C1-C5-alkyl, wherein a p-substituted alkyltoluene of the formula (II) in which R1 has the meaning given under formula (I), is isomerized in the presence of ionic liquids to give an m-substituted alkyltoluene of the formula (I). The m-substituted alkyltoluenes obtainable according to the invention are starting compounds for the preparation of fragrances and aroma substances.

Easier preparation of 2,6-Di-tert-butylphenyl derivatives 1

Despite steric shielding by the 2,6-di-tert-butylphenyl group (super-2,6-xylyl=xyl*), inexpensive sodium phenolate (xyl*-ONa) reacts with dimethyl sulfate to produce only xyl*-OCH3 (94%) with complete suppression of the alternative 4-methylation. Reductive cleavage of xyl*-OCH3 by elemental lithium with the help of an electron carrier generates xyl*-Li, which in turn yields xyl*-CO2H (63%). The corresponding 4-methyl-derivatives of these compounds were obtained analogously. The acid chloride xyl*-COCl (77% yield) acylates HalMgCH 2R to give only xyl*-COCH3 (86%) or xyl*-COEt (97%). These two ketones react with n-butyllithium (no carbonyl addition) and Cl-PO(OEt)2 to furnish only the enol phosphates xyl*-C(=CH 2)OPO(OEt)2 (84%) or xyl*-C(=CHCH 3)OPO(OEt)2 (up to 70%), respectively. Only 1,2-elimination occurs when the latter two products are treated with tert-butyllithium, affording xyl*-CCH (68%) or xyl*-CCMe (88%), respectively. Georg Thieme Verlag Stuttgart - New York.

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.

Unusual demethylation of O,O′-dimethyl chlorothiophosphate with aryllithiums

The reaction of O,O′-dimethyl chlorothiophosphate with aryllithiums took place easily to afford the corresponding methylated aryl compounds in place of expected O,O′-dimethyl aryl(thiophosphonate)s. Copyright

Palladium-catalyzed benzannulation from alkynes and allylic compounds

Various alkynes reacted with allyl tosylates in the presence of palladium catalysts, giving polysubstituted benzenes with good to high regioselectivity. Pentasubstituted and trisubstituted benzenes were readily prepared by reaction of internal alkynes and

A new synthetic route to donor-acceptor porphyrins

Some new donor-acceptor porphyrins have been prepared based on a metallated bis(ethynyl) porphyrin core. 4-(Dimethylamino)phenyl was used as the donor group and 4-nitrophenyl, 4-cyanophenyl and 5-nitrothiazoyl as the acceptor groups. Dipyrrylmethane was used for large scale porphyrin ring synthesis because the absence of methylene substituents reduces the difficulty of substituent scrambling that occurs during porphyrin synthesis.