400747-98-0

Basic information

• Product Name: 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE
• Synonyms: AKOS BAR-0123;4'-(TRIFLUOROMETHYL)[1,1'-BIPHENYL]-3-AMINE;4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE;3-[4-(Trifluoromethyl)phenyl]aniline;4'-(Trifluoromethyl)-biphenyl-3-amine
• CAS NO: 400747-98-0
• Molecular Formula: C₁₃H₁₀F₃N
• Molecular Weight: 237.22
• Mol File: 400747-98-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 330.9 °C at 760 mmHg
• Flash Point: 147.9 °C
• Appearance: /
• Density: 1.245 g/cm³
• CAS DataBase Reference: 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE(400747-98-0)
• EPA Substance Registry System: 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE(400747-98-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 400747-98-0(Hazardous Substances Data)

Usage

General Description

4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE, also known as 3-Amino-4'-trifluoromethylbiphenyl, is a chemical compound with the molecular formula C13H10F3N. It is a derivative of biphenyl and contains a trifluoromethyl group attached to the 4' position of one of the phenyl rings. 4'-TRIFLUOROMETHYL-BIPHENYL-3-YLAMINE is commonly used in the pharmaceutical and agrochemical industries as a building block for the synthesis of various biologically active compounds and molecules. Its unique molecular structure and properties make it a valuable intermediate in the production of a wide range of therapeutic and agricultural products. Additionally, it has potential applications in research and development as a reagent or catalyst for chemical reactions.

Upstream product

• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 591-19-5 m-Bromoaniline 
• 626-01-7 3-Iodoaniline 
• 1453494-27-3 C₁₃H₁₂F₃NO 
• 122924-26-9 3--2-cyclohexen-1-one 

Downstream Products

• 637352-71-7 ethyl [2-methyl-4-({[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate 
• 637353-20-9 ethyl [2-ethyl-4-({[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate 
• 637352-64-8 methyl [2-methyl-4-({[2-(methylthio)ethyl][4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate 
• 637352-59-1 ethyl [4-({(2-methoxyethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate 
• 637352-58-0 ethyl [4-({butyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate 
• 637352-72-8 ethyl [4-({butyryl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate 
• 637352-60-4 ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate 
• 637352-61-5 ethyl [4-({(2-cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate 
• 637352-73-9 ethyl [2-methyl-4-({(propylsulfonyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate 
• 637352-74-0 ethyl [4-({butyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate 
• 637352-76-2 ethyl [4-({(2-cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate 
• 637352-75-1 ethyl [2-methyl-4-({pentyl[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)phenoxy]acetate 

Relevant articles and documents

Lipid peroxidation inhibition study: A promising case of 1,3-di([1,1′-biphenyl]-3-yl)urea

In the present study eighteen inhibitors of the hydrolytic enzymes of the endocannabinoid system were investigated for antioxidant activity using lipid peroxidation (LP) method. Among the assayed compounds ten belong to carbamates with phenyl [1,1′-biphenyl]-3-ylcarbamate (6), reported for the first time, and eight are retro-amide derivatives of palmitamine. Interestingly, results indicated that most of the tested compounds have good antioxidant properties. In particular, 1,3-di([1,1′-biphenyl]-3-yl)urea (3) shows IC50 = 26 ± 6 μM comparable to ones obtained for standard antioxidants trolox and quercetin (IC50 = 22 ± 6 μM and 23 ± 6 μM, respectively). Compound 3 was investigated further by means of DFT calculations, to clarify a possible mechanism of the antioxidant action. In order to estimate the capability of 3 to act as radical scavenger the structure was optimized at B3LYP/6–311++G** level and the respective bond dissociation enthalpies were calculated. The calculations in non-polar medium predicted as favorable mechanism a donation of a hydrogen atom to the free radical and formation of N-centered radical, while in polar solvents the mechanism of free radical scavenging by SPLET dominates over HAT H-abstraction. The possible radical scavenging mechanisms of another compound with potent antioxidant properties (IC50 = 53 ± 12 μM), the retro-amide derivative of palmitamine (compound 18), was estimated computationally based on the reaction enthalpies of a model compound (structural analogue to 18). The computations indicated that the most favorable mechanisms are hydrogen atom transfer from the hydroxyl group in meta-position of the benzamide fragment in nonpolar medium, and proton transfer from the hydroxyl group in ortho-position of the benzamide fragment in polar medium.

Aromatic amine compound synthesis method

The invention discloses an aromatic amine compound synthesis method which is characterized in that the method is implemented according to any of two methods. The first method includes the steps: mixing an alkyl aromatic compound with a general formula (I) and a nitrogen-containing compound with a general formula (II); performing reaction on mixture under an oxidizing agent and an organic solvent to obtain an aromatic amine compound with a general formula (III). The second method includes the steps: mixing an aromatic alcohol derivative with a general formula (I') and the nitrogen-containing compound with the general formula (II); performing reaction on mixture under an acid additive and an organic solvent to prepare the aromatic amine compound with the general formula (III). According to the method, a lot of alkyl aromatic compounds or aromatic alcohol derivatives firstly serve as raw materials, and the raw materials are reacted to generate the aromatic amine compound without the action of metal catalysis. Compared with a traditional synthesis method, the synthesis method has the advantages that the method is high in yield and simple in condition, waste discharging amount is less,metal participation is omitted, a reaction device is simple, industrial production is easily achieved and the like. The method has a wide application prospect.

Design, synthesis, molecular modelling and in vitro cytotoxicity analysis of novel carbamate derivatives as inhibitors of Monoacylglycerol lipase

Monoacylglycerol lipase (MAGL) has an essential role in the catabolic pathway of the endocannabinoid 2-arachidonoylglycerol, which makes it a potential target for highly specific inhibitors for the treatment of a number of diseases. We designed and synthesized a series of carbamate analogues of URB602. We evaluated their inhibitory activity toward human MAGL in vitro both in cell culture and lysates. The target compounds exhibited moderate to excellent inhibitory activity against MAGL. The most promising compound 2b showed good inhibitory activity with IC50 value of 4.5 ± 0.70 μM reducing MAGL activity to 82% of controls at 10 μM compared to 66% for the parent compound URB602. Interestingly, compounds 2b and 2c induce cell death through the inhibition of MAGL. Molecular modelling approaches and docking studies, used to investigate inhibitory profiles, indicated that trifluoromethyl substitutions of the aryl group and the benzene ring present at the oxygen side of the carbamate molecule had a significant impact on the activity.