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4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL is a chemical compound with the molecular formula C14H10F6N and a molecular weight of 295.23 g/mol. It is a biphenyl derivative featuring two trifluoromethyl substituents at the 3' and 5' positions, and an amino group at the 4 position. 4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL is characterized by its white solid appearance and its solubility profile, being sparingly soluble in water and more soluble in organic solvents such as acetone, ethyl acetate, and dichloromethane.

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  • 444143-45-7 Structure
  • Basic information

    1. Product Name: 4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL
    2. Synonyms: 4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL;4-[3,5-BIS(TRIFLUOROMETHYL)PHENYL]ANILINE;AKOS BAR-2159;SALOR-INT L446556-1EA;3',5'-Bis(trifluoroMethyl)-[1,1'-biphenyl]-4-aMine;4-[3,5-Bis(trifluoromethyl)phenyl]aniline, 3',5'-Bis(trifluoromethyl)-[1,1'-biphenyl]-4-amine
    3. CAS NO:444143-45-7
    4. Molecular Formula: C14H9F6N
    5. Molecular Weight: 305.22
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 444143-45-7.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. CAS DataBase Reference: 4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL(CAS DataBase Reference)
    10. NIST Chemistry Reference: 4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL(444143-45-7)
    11. EPA Substance Registry System: 4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL(444143-45-7)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 444143-45-7(Hazardous Substances Data)

444143-45-7 Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL is used as a building block in the synthesis of pharmaceuticals for its ability to form carbon-carbon and carbon-nitrogen bonds, which are crucial in creating a variety of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL serves as a key component in the development of agrochemicals, contributing to the creation of effective products for crop protection and enhancement.
Used as a Reagent in Organic Chemistry:
4-AMINO-3',5'-BIS(TRIFLUOROMETHYL)BIPHENYL is utilized as a reagent in organic chemistry reactions, particularly for its role in the formation of essential carbon-carbon and carbon-nitrogen bonds, facilitating the synthesis of complex organic molecules.

Check Digit Verification of cas no

The CAS Registry Mumber 444143-45-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,4,4,1,4 and 3 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 444143-45:
(8*4)+(7*4)+(6*4)+(5*1)+(4*4)+(3*3)+(2*4)+(1*5)=127
127 % 10 = 7
So 444143-45-7 is a valid CAS Registry Number.

444143-45-7Downstream Products

444143-45-7Relevant articles and documents

Bifunctional Naphtho[2,3- d][1,2,3]triazole-4,9-dione Compounds Exhibit Antitumor Effects in Vitro and in Vivo by Inhibiting Dihydroorotate Dehydrogenase and Inducing Reactive Oxygen Species Production

Zuo, Zeping,Liu, Xiaocong,Qian, Xinying,Zeng, Ting,Sang, Na,Liu, Huan,Zhou, Yue,Tao, Lei,Zhou, Xia,Su, Na,Yu, Yamei,Chen, Qiang,Luo, Youfu,Zhao, Yinglan

supporting information, p. 7633 - 7652 (2020/08/21)

Human dihydroorotate dehydrogenase (hDHODH) is an attractive target for cancer therapy. Based on its crystal structure, we designed and synthesized a focused compound library containing the structural moiety of 1,4-benzoquinone, which possesses reactive oxygen species (ROS) induction capacity. Compound 3s with a naphtho[2,3-d][1,2,3]triazole-4,9-dione scaffold exhibited inhibitory activity against hDHODH. Further optimization led to compounds 11k and 11l, which inhibited hDHODH activity with IC50 values of 9 and 4.5 nM, respectively. Protein-ligand cocrystal structures clearly depicted hydrogen bond and hydrophobic interactions of 11k and 11l with hDHODH. Compounds 11k and 11l significantly inhibited leukemia cell and solid tumor cell proliferation and induced ROS production, mitochondrial dysfunction, apoptosis, and cell cycle arrest. Nanocrystallization of compound 11l displayed significant in vivo antitumor effects in the Raji xenograft model. Overall, this study provides a novel bifunctional compound 11l with hDHODH inhibition and ROS induction efficacy, which represents a promising anticancer lead worthy of further exploration.

ω-Phthalimidoalkyl Aryl Ureas as Potent and Selective Inhibitors of Cholesterol Esterase

Dato, Florian M.,Sheikh, Miriam,Uhl, Rocky Z.,Schüller, Alexandra W.,Steinkrüger, Michaela,Koch, Peter,Neud?rfl, J?rg-Martin,Gütschow, Michael,Goldfuss, Bernd,Pietsch, Markus

, p. 1833 - 1847 (2018/09/10)

Cholesterol esterase (CEase), a serine hydrolase thought to be involved in atherogenesis and thus coronary heart disease, is considered as a target for inhibitor development. We investigated recombinant human and murine CEases with a new fluorometric assay in a structure–activity relationship study of a small library of ω-phthalimidoalkyl aryl ureas. The urea motif with an attached 3,5-bis(trifluoromethyl)phenyl group and the aromatic character of the ω-phthalimide residue were most important for inhibitory activity. In addition, an alkyl chain composed of three or four methylene groups, connecting the urea and phthalimide moieties, was found to be an optimal spacer for inhibitors. The so-optimized compounds 2 [1-(3,5-bis(trifluoromethyl)phenyl)-3-(3-(1,3-dioxoisoindolin-2-yl)propyl)urea] and 21 [1-(3,5-bis(trifluoromethyl)phenyl)-3-(4-(1,3-dioxoisoindolin-2-yl)butyl)urea] exhibited dissociation constants (Ki) of 1–19 μm on the two CEases and showed either a competitive (2 on the human enzyme and 21 on the murine enzyme) or a noncompetitive mode of inhibition. Two related serine hydrolases—monoacylglycerol lipase and fatty acid amide hydrolase—were inhibited by ω-phthalimidoalkyl aryl ureas to a lesser extent.

Triazole naphthoquinone connected aromatic (heterocyclic) ring derivative

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Paragraph 0081; 0082; 0083, (2018/10/01)

The invention belongs to the field of chemical medicine, particularly relates to a micromolecule capable of resisting malignant tumor, acute leukemia and arthritis, multiple sclerosis and immunological rejection and a preparation and application of the mi

Catalytic Ester and Amide to Amine Interconversion: Nickel-Catalyzed Decarbonylative Amination of Esters and Amides by C?O and C?C Bond Activation

Yue, Huifeng,Guo, Lin,Liao, Hsuan-Hung,Cai, Yunfei,Zhu, Chen,Rueping, Magnus

supporting information, p. 4282 - 4285 (2017/04/03)

An efficient nickel-catalyzed decarbonylative amination reaction of aryl and heteroaryl esters has been achieved for the first time. The new amination protocol allows the direct interconversion of esters and amides into the corresponding amines and represents a good alternative to classical rearrangements as well as cross coupling reactions.

A terphenyl structure containing between the diamine compound and its synthetic method and application

-

Paragraph 0062; 0063, (2017/04/19)

The invention discloses a diamine compound with a meta-terphenyl structure as well as a synthetic method and application thereof. An amino group is introduced by using an aryl halide through Suzuki reaction, and the functional diamine compound with the meta-terphenyl structure is obtained by virtue of bromination, diazotization, Suzuki coupling and reduction. The synthetic method for the diamine compound is simple and relatively high in yield, and the synthesized compound has certain fluorescence property. The diamine compound can be used for synthesizing high-performance and functional polymers such as polyamide, polyimide, polyamideimide and polyesterimide, and is especially suitable for preparing a soluble, colorless and transparent high-performance functional polyimide material with certain fluorescence property.

Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents: Part II: Alkylation far away from the amino function

Glende, Carsten,Klein, Markus,Schmitt, Heimo,Erdinger, Lothar,Boche, Gernot

, p. 15 - 38 (2007/10/03)

Alkyl and trifluoromethyl derivatives of 4-aminobiphenyl (1) (4ABP) and 2-aminofluorene (7) (2AF) were synthesised and assayed for mutagenicity using Salmonella typhimurium tester strains TA98 and TA100 with and without the addition of S9 mix. Modification of 1 was achieved by attachment of alkyl groups (methyl, ethyl, iso-propyl, n-butyl, tert-butyl) and a trifluoromethyl group (CF3) in the 4′-position, the 3′-position (Me, CF3) and the 3′-, 5′-positions (DiMe, DiCF3). Compound 7 was modified by introduction of alkyl groups (methyl, tert-butyl, adamantyl) and a trifluoromethyl group (CF3) in the 7-position. The derivatives of 1 and 7 show for groups with growing steric demand decreased mutagenic activity. The bulkiest groups (CF3, tert-butyl and adamantyl) induce the strongest effects on the mutagenicity. It was even possible to eliminate the mutagenicity of 1 and 7 by introduction of such substituents. In the last part of the work, we compared the experimental mutagenicities with calculated values derived from QSAR correlations. Our findings show that the predictions for aromatic amines with bulky substituents were generally too high. The strongest deviations were observed in the case of the CF3-, tert-butyl- and the adamantyl-group. Only the parent compounds and derivatives with small alkyl groups were predicted well. These investigations show that "large" substituents have an influence on the mutagenicity caused by their steric demand. To predict the correct mutagenicities of such compounds, it is necessary to introduce steric parameters in the respective QSAR equations which will be done in a forthcoming paper.

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