127292-60-8

Basic information

• Product Name: [1,1'-Biphenyl]-4-MethanaMine, N,N-diMethyl-
• Synonyms: [1,1'-Biphenyl]-4-MethanaMine, N,N-diMethyl-;N,N-dimethyl-[1,1'-Biphenyl]-4-methanamine
• CAS NO: 127292-60-8
• Molecular Formula: C₁₅H₁₇N
• Molecular Weight: 211.30218
• Mol File: 127292-60-8.mol

Chemical Properties

• Boiling Point: 112-114 °C(Press: 0.02 Torr)
• Appearance: /
• Density: 1.000±0.06 g/cm3(Predicted)
• PKA: 8.69±0.28(Predicted)
• CAS DataBase Reference: [1,1'-Biphenyl]-4-MethanaMine, N,N-diMethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1'-Biphenyl]-4-MethanaMine, N,N-diMethyl-(127292-60-8)
• EPA Substance Registry System: [1,1'-Biphenyl]-4-MethanaMine, N,N-diMethyl-(127292-60-8)

Safety Data

• Hazardous Substances Data: 127292-60-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
[1,1'-Biphenyl]-4-MethanaMine, N,N-diMethylis used as a key intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique structure and reactivity make it a valuable component in the development of new medications.
Used in Organic Chemistry:
In the field of organic chemistry, [1,1'-Biphenyl]-4-MethanaMine, N,N-diMethylis utilized as a catalyst to facilitate numerous organic reactions. Its ability to participate in various chemical processes enhances the efficiency and effectiveness of these reactions.
Used in Dye and Pigment Synthesis:
[1,1'-Biphenyl]-4-MethanaMine, N,N-diMethylis also employed as a precursor in the synthesis of dyes, pigments, and optical brighteners. Its versatile nature allows for the creation of a wide range of colorants and additives used in various industries, including textiles, plastics, and printing.
Used in Optical Brighteners:
In the production of optical brighteners, [1,1'-Biphenyl]-4-MethanaMine, N,N-diMethylserves as an essential precursor. These brighteners are used to enhance the appearance of materials by reflecting light more effectively, making them appear brighter and more vivid. This application is particularly relevant in the textile and paper industries.

Upstream product

• 2567-29-5 p-phenylbenzyl bromide 
• 124-40-3 dimethyl amine 
• 506-59-2 N,N-dimethylammonium chloride 
• 33322-67-7 N, N-dimethyl [1,1’-biphenyl]-4-carboxamide 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 15184-98-2 N,N-dimethyl-4-chlorobenzylamine 
• 98-80-6 phenylboronic acid 
• 644-08-6 4-Methylbiphenyl 
• 3218-36-8 4-Phenylbenzaldehyde 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 3597-91-9 biphenyl-4-yl methanol 
• 6274-57-3 (4-bromobenzyl)dimethylamine 

Downstream Products

• 67362-98-5 2-([1,1′-biphenyl]-4-yl)benzo[d]thiazole 
• 3218-36-8 4-Phenylbenzaldehyde 
• 644-08-6 4-Methylbiphenyl 
• 5728-52-9 (4-biphenylyl)acetic acid 
• 27643-99-8 2-([1,1'-biphenyl]-4-yl)-1-phenylethan-1-ol 

Relevant articles and documents

Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1 H)-ones

A palladium-catalyzed straightforward procedure for the synthesis of 3-arylquinolin-2(1H)-ones has been developed. The synthesis proceeds through a palladium-catalyzed reductive aminocarbonylation reaction of benzylic ammonium triflates with o-nitrobenzaldehydes, and a wide range of 3-arylquinolin-2(1H)-ones was obtained in moderate to good yields with very good functional group compatibility.

Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides

New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.

Pd-Catalyzed Suzuki coupling reactions of aryl halides containing basic nitrogen centers with arylboronic acids in water in the absence of added base

The Pd-catalyzed Suzuki coupling reactions of a series of aryl chlorides and aryl bromides containing basic nitrogen centers with arylboronic acids in water in the absence of added base are reported. The reactions proceed either partially or entirely under acidic conditions. After surveying twenty-two phosphorus ligands, high yields of products were obtained with aryl chlorides only when a bulky ligand, 2-(di-tert-butyl-phosphino)-1-phenyl-1H-pyrrole (cataCXiumPtB) was used. In contrast, aryl bromides produced high yields of products in the absence of both added base and added ligand. In order to explore the Suzuki coupling process entirely under acidic conditions, a series of reactions were conducted in buffered acidic media using several model substrates. 4-Chlorobenzylamine, in the presence of cataCXiumPtB, produced high yields of product at buffered pH 6.0; the yields dropped off precipitously at buffered pH 5.0 and lower. The fall-off in yield was attributed to the decomposition of the Pd-ligand complex due to the protonation of the ligand in the more acidic aqueous media. In contrast, in the absence of an added ligand, 4-amino-2-chloropyridine produced quantitative yields at buffered pH 3.5 and 4.5 while 4-amino-2-bromopyridine produced quantitative yields in a series of buffered media ranging from pH 4.5 to 1.5. These substrates are only partially protonated in acidic media and can behave as active Pd ligands in the Suzuki catalytic cycle.

METHODS FOR EXTERNAL BASE-FREE SUZUKI COUPLINGS

The present disclosure describes a method of coupling a first aromatic compound to a second aromatic compound, the method comprising: (a) preparing a reaction mixture comprising the first aromatic compound, the second aromatic compound, a catalyst and water; the reaction mixture does not contain an external base, the reaction mixture having an initial pH of from 11 to 1; the catalyst having at least one group 10 atom; the first aromatic compound having a halogen, triflate or sulfonate substituent; the second aromatic compound having a boron-containing substituent; wherein, at least one of the first aromatic compound or the second aromatic compound includes one or more heteroatom; and (b) reacting the first aromatic compound and the second aromatic compound in the reaction mixture, the reaction mixture having a final pH following reaction of the first aromatic compound and the second aromatic compound.

Aqueous Suzuki Coupling Reactions of Basic Nitrogen-Containing Substrates in the Absence of Added Base and Ligand: Observation of High Yields under Acidic Conditions

A series of aqueous heterogeneous Suzuki coupling reactions of substrates containing basic nitrogen centers with phenylboronic acid in the absence of added base and ligand is presented. High yields of products were obtained by employing aryl bromides containing aliphatic 1°, 2°, and 3° amine substituents, and good to high yields were obtained by employing a variety of substituted bromopyridines. In the former series, the pH of the aqueous phase changed from basic to acidic during the course of the reaction, while in the latter series the aqueous phase was on the acidic side of the pH scale throughout the entire course of reaction. A mechanistic interpretation for these observations, which generally preserves the oxo palladium catalytic cycle widely accepted in the literature, is presented.

Synthesis of 2-aryl benzothiazoles via K2S2O 8-mediated oxidative condensation of benzothiazoles with benzylamines

A novel way to synthesize 2-arylbenzothiazoles is described. Reactions of benzothiazoles with diverse benzylamines in the presence of K2S 2O8 and KOt-Bu in DMSO-H2O afforded the desired 2-arylbenzothiazoles in good yields. It is notable that no transition-metal catalyst is needed in this reaction. Compared with other known methods, this method of synthesizing 2-arylbenzothiazoles can be advantageous in cases where substituted benzothiazoles and benzylamines are readily available. Georg Thieme Verlag Stuttgart. New York.

Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding

It was discovered that the presence of water as a cosolvent enables the reaction of activated alkyl fluorides for bimolecular nucleophilic substitution reactions. DFT calculations show that activation proceeds through stabilization of the transition structure by a stronger F···H 2O interaction and diminishing C-F bond elongation, and not simple transition state electrostatic stabilization. Overall, the findings put forward a distinct strategy for C-F bond activation through H-bonding.

LiCl-Promoted Pd(ii)-catalyzed ortho carbonylation of N,N- dimethylbenzylamines

Palladium-catalyzed highly regioselective carbonylation of substituted N,N-dimethylbenzylamines with the assistance of LiCl was developed. The ortho-functionalized N,N-dimethylbenzylamine was further transformed into ortho-methyl benzoate under mild conditions. These two transformations could be combined into one pot to produce the desired product in moderate yield. Applications of this methodology to synthesize the fragments of variolaric acid were also studied.

Cationic chalcone antibiotics. Design, synthesis, and mechanism of action

This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the B-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the á-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 μM against methicillin resistant Staphylococus aureus.