16251-99-3

Basic information

• Product Name: Benzene, 1-(1,1-dimethylethyl)-4-(phenylmethyl)-
• CAS NO: 16251-99-3
• Molecular Formula: C17H20
• Molecular Weight: 224.346
• Mol File: 16251-99-3.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1-(1,1-dimethylethyl)-4-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(1,1-dimethylethyl)-4-(phenylmethyl)-(16251-99-3)
• EPA Substance Registry System: Benzene, 1-(1,1-dimethylethyl)-4-(phenylmethyl)-(16251-99-3)

Safety Data

• Hazardous Substances Data: 16251-99-3(Hazardous Substances Data)

Upstream product

• 507-20-0 tertiary butyl chloride 
• 101-81-5 Diphenylmethane 
• 22543-74-4 4-tert-butylbenzhydrol 
• 253185-03-4 tert-butylbenzene 
• 100-44-7 benzyl chloride 
• 1012-72-2 1,4-di-tert-butylbenzene 
• 877-65-6 p-tert-butylbenzyl alcohol 
• 71-43-2 benzene 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 100-39-0 benzyl bromide 
• 39895-55-1 4-(1,1-dimethylethyl)-benzenemethanamine 
• 1022339-31-6 N-[(4-tert-butylphenyl)methyl]-4-methylbenzenesulfonamide 
• 1602929-09-8 N,N-ditosyl-4-tert-butylbenzylamine 

Downstream Products

• 22679-54-5 4-tert-butylbenzophenone 
• 1200120-13-3 1-phenyl-3-phenyl-3-(4-tert-butylphenyl)-1-propyne 
• 1326231-77-9 1-((4-tert-butylphenyl)(phenyl)methyl)-1H-benzo[d]imidazole 
• 1334474-85-9 (4-(tert-butyl)phenyl)(phenyl)methyl acetate 
• 19767-95-4 4-tert-butyl-benzhydryl chloride 

Relevant articles and documents

Method for reducing carbonyl reduction to methylene under illumination

The invention belongs to the technical field of organic chemical synthesis. The method comprises the following steps: (1) mixing the carbonyl compound and the amine compound in a solvent, reacting 3 - 6 under the illumination of 380 - 456 nm, the reaction system is low in toxicity, high in atom utilization rate 12 - 24h. and production efficiency, safe and controllable in reaction process and capable of simplifying the operation in the preparation and production process. At the same time, the residue toxicity of the reaction is minimized, the pollution caused by the production process to the environment is reduced, and the steps and operations of removing residues after the reaction are simplified. In addition, the reactant feedstock is readily available. The reactant does not need additional modification before the reaction, can be directly used for preparing production, simplifies the operation steps, and shortens the reaction route. The production cost is obviously reduced.

Borane-catalyzed C(sp3)-F bond arylation and esterification enabled by transborylation

The activation and functionalization of carbon- fluorine bonds represent a significant synthetic challenge, given the high thermodynamic barrier to C-F bond cleavage. Stoichiometric hydridoborane-mediated C-F functionalization has recently emerged, but is yet to be rendered catalytic. Herein, the borane-catalyzed coupling of alkyl fluorides with arenes (carbon-carbon bond formation) and carboxylic acids (carbon-oxygen bond formation) has been developed using transborylation reactions to achieve catalytic turnover. Successful C-C and C-O coupling across a variety of structurally and electronically differentiated arenes and carboxylic acids was achieved using 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) as the catalyst and pinacolborane (HBpin), with broad functional group tolerance. Experimental and computational studies suggest a mechanistic dichotomy for the carbon-carbon and carbon-oxygen coupling reactions. B-F transborylation (B-F/B-H metathesis) between F-B-9-BBN and HBpin enabled catalytic turnover for carbon-carbon bond formation, whereas direct exchange between the alkyl fluoride and acyloxyboronic ester (C-F/B-O metathesis) was proposed for carbon-oxygen coupling, where H-B-9-BBN catalyzed the dehydrocoupling of the carboxylic acid with HBpin.

Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**

Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.

Photoredox Heterobimetallic Dual Catalysis Using Engineered Covalent Organic Frameworks

The functionalization of an imine-based layered covalent organic framework (COF), containing phenanthroline units as ligands, has allowed the obtention of a heterobimetallated material. Photoactive Ir and Ni fragments were immobilized within the porous structure of the COF, enabling heterogeneous light-mediated Csp3-Csp2cross-couplings. As radical precursors, potassium benzyl- and alkoxy-trifluoroborates, organic silicates, and proline derivatives were employed, which brings out the good versatility ofIr,Ni@Phen-COF. Moreover, in all the studied cases, an enhanced activity and stability have been observed in comparison with analogous homogenous systems.

Dual Nickel- And Photoredox-Catalyzed Reductive Cross-Coupling of Aryl Halides with Dichloromethane via a Radical Process

The first catalytic strategy to harness a new chloromethane radical from dichloromethane under dual Ni/photoredox catalytic conditions has been developed. Compared with traditional two-electron reductive process associated with metallic reductants, this method via a single-electron approach can proceed under exceptionally mild conditions (visible light, ambient temperature, no strong base) and exhibits complementary reactivity patterns. It affords a broad scope of many functional groups, including alkenyl, which suffers cyclopropanation in previous routes. The diarylmethane-d2 compounds can be readily available with this transformation.

Visible Light-Catalyzed Benzylic C-H Bond Chlorination by a Combination of Organic Dye (Acr+-Mes) and N-Chlorosuccinimide

By combining "N-chlorosuccinimide (NCS)"as the safe chlorine source with "Acr+-Mes"as the photocatalyst, we successfully achieved benzylic C-H bond chlorination under visible light irradiation. Furthermore, benzylic chlorides could be converted to benzylic ethers smoothly in a one-pot manner by adding sodium methoxide. This mild and scalable chlorination method worked effectively for diverse toluene derivatives, especially for electron-deficient substrates. Careful mechanistic studies supported that NCS provided a hydrogen abstractor "N-centered succinimidyl radical,"which was responsible for the cleavage of the benzylic C-H bond, relying on the reducing ability of Acr?-Mes.

Carbonyl and olefin hydrosilylation mediated by an air-stable phosphorus(iii) dication under mild conditions

The readily-accessible, air-stable Lewis acid [(terpy)PPh][B(C6F5)4]21 is shown to mediate the hydrosilylation of aldehydes, ketones, and olefins. The utility and mechanism of these hydrosilylations are considered.

Preparation and application of blended nickel (II) complex with bisoxazoline derived azacyclo-carbene ligand and phosphite ester ligand

The invention discloses a blended nickel (II) complex with a bisoxazoline derived azacyclo-carbene ligand and a phosphite ester ligand and application of the blended nickel (II) complex. The blended nickel (II) complex has a chemical formula of Ni(NHC)[P(OR)3]X2, in the formula, R is one of ethyl or isopropyl; X is one of bromine atoms or helium atoms; and NHC is the bisoxazoline derived azacyclo-carbene ligand. In the presence of magnesium chips, the blended nickel (II) complex with the bisoxazoline derived azacyclo-carbene ligand and the phosphite ester ligand, which is disclosed by the invention, is capable of catalyzing aromatic hydrocarbon or fluoro-aromatic hydrocarbon with low activity to have a reduction cross coupling reaction with a benzyl chloride type compound at a single temperature, then a diarylmethane compound can be generated at one step, and a novel method is provided for synthesizing diarylmethane compounds.

9-Borabicyclo[3.3.l]nonane-induced Friedel-Crafts benzylation of arenes with benzyl fluorides

Friedel-Crafts benzylation of arenes with benzyl fluorides using 9-borabicyclo[3.3.l]nonane (9-BBN) as a mediator has been developed. This provides a simple and cheap route to the activation of C-F bonds to synthesize 1,1-diarylmethanes in good to excellent yields (up to 98%) under mild conditions. Functional group tolerance and the mechanism are considered.

Construction of Di(hetero)arylmethanes Through Pd-Catalyzed Direct Dehydroxylative Cross-Coupling of Benzylic Alcohols and Aryl Boronic Acids Mediated by Sulfuryl Fluoride (SO2F2)

A practical Pd-catalyzed direct dehydroxylative coupling of (hetero)benzylic alcohols with (hetero)arylboronic acids for the constructions of di(hetero)arylmethane derivatives under SO2F2 was described. This new method provided a strategically distinct approach to di(hetero)arylmethane derivatives from readily available and abundant benzylic alcohols under mild condition.