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4-(Trifluoromethyl)phenylglycine, an aromatic amino acid derivative with the molecular formula C9H8F3NO2, features a trifluoromethyl group attached to the phenyl ring. This unique structure and properties make it a versatile and important chemical in both organic and medicinal chemistry.

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  • 144789-75-3 Structure
  • Basic information

    1. Product Name: 4-(TRIFLUOROMETHYL)PHENYLGLYCINE
    2. Synonyms: (2S)-amino[4-(trifluoromethyl)phenyl]acetic acid;(2S)-2-AMINO-2-[4-(TRIFLUOROMETHYL)PHENYL]ACETIC ACID;4-(Trifluoromethyl)-L-phenylglycine >=98.0%;4-(TRIFLUOROMETHYL)-L-PHENYLGLYCINE;4-(TRIFLUOROMETHYL)PHENYLGLYCINE;(S)-AMINO-(4-TRIFLUOROMETHYL-PHENYL)-ACETIC ACID;(S)-2-AMINO-2-[4-(TRIFLUOROMETHYL)PHENYL]ACETIC ACID
    3. CAS NO:144789-75-3
    4. Molecular Formula: C9H8F3NO2
    5. Molecular Weight: 219.16
    6. EINECS: N/A
    7. Product Categories: pharmacetical
    8. Mol File: 144789-75-3.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 297.2 °C at 760 mmHg
    3. Flash Point: 133.6 °C
    4. Appearance: /
    5. Density: 1.415 g/cm3
    6. Vapor Pressure: 0.000614mmHg at 25°C
    7. Refractive Index: 1.504
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 4-(TRIFLUOROMETHYL)PHENYLGLYCINE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4-(TRIFLUOROMETHYL)PHENYLGLYCINE(144789-75-3)
    12. EPA Substance Registry System: 4-(TRIFLUOROMETHYL)PHENYLGLYCINE(144789-75-3)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 144789-75-3(Hazardous Substances Data)

144789-75-3 Usage

Uses

Used in Pharmaceutical Synthesis:
4-(Trifluoromethyl)phenylglycine is used as a building block for the synthesis of various pharmaceuticals and organic compounds, leveraging its distinctive structural features to create novel and effective medications.
Used as a Chiral Auxiliary:
In the field of asymmetric synthesis reactions, 4-(Trifluoromethyl)phenylglycine serves as a chiral auxiliary, playing a crucial role in enhancing the selectivity and yield of enantioselective reactions, which is vital for the production of enantiomerically pure compounds.
Used as a Ligand in Metal-Catalyzed Reactions:
4-(Trifluoromethyl)phenylglycine also functions as a ligand in metal-catalyzed reactions, facilitating the formation of desired products with improved efficiency and selectivity, which is essential in the synthesis of complex organic molecules.
Used in Antiviral and Antibacterial Drug Development:
With its potential pharmaceutical applications, 4-(Trifluoromethyl)phenylglycine is utilized in the research and development of antiviral and antibacterial drugs, contributing to the discovery of new therapeutic agents to combat infectious diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 144789-75-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,4,7,8 and 9 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 144789-75:
(8*1)+(7*4)+(6*4)+(5*7)+(4*8)+(3*9)+(2*7)+(1*5)=173
173 % 10 = 3
So 144789-75-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H8F3NO2/c10-9(11,12)6-3-1-5(2-4-6)7(13)8(14)15/h1-4,7H,13H2,(H,14,15)/t7-/m0/s1

144789-75-3 Well-known Company Product Price

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  • Aldrich

  • (16599)  4-(Trifluoromethyl)-L-phenylglycine  ≥98.0%

  • 144789-75-3

  • 16599-1G-F

  • 2,792.79CNY

  • Detail

144789-75-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(TRIFLUOROMETHYL)PHENYLGLYCINE

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:144789-75-3 SDS

144789-75-3Relevant articles and documents

Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction

Das, Braja Gopal,Nallagonda, Rajender,Dey, Dhananjay,Ghorai, Prasanta

, p. 12601 - 12605 (2015/09/01)

Air-/moisture-stable, crystalline, and storable chiral salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α-amino esters, γ- and δ-lactams, and isoindolinones have also been carried out using this methodology. Finally, the method has been applied to synthetic targets of pharmaceutical relevance, such as R-(+)-salsolidine and R-(+)-crispine A.

CATALYST COMPOUNDS

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Paragraph 0314; 0324, (2015/03/28)

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

Primary amines by transfer hydrogenative reductive amination of ketones by using cyclometalated IrIII catalysts

Talwar, Dinesh,Salguero, Noemi Poyatos,Robertson, Craig M.,Xiao, Jianliang

supporting information, p. 245 - 252 (2014/01/17)

Cyclometalated iridium complexes are found to be versatile catalysts for the direct reductive amination (DRA) of carbonyls to give primary amines under transfer-hydrogenation conditions with ammonium formate as both the nitrogen and hydrogen source. These complexes are easy to synthesise and their ligands can be easily tuned. The activity and chemoselectivity of the catalyst towards primary amines is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Both aromatic and aliphatic primary amines were obtained in high yields. Moreover, a first example of homogeneously catalysed transfer-hydrogenative DRA has been realised for β-keto ethers, leading to the corresponding β-amino ethers. In addition, non-natural α-amino acids could also be obtained in excellent yields with this method. Reduce the work! A broad range of ketones have been successfully aminated to afford primary amines under transfer-hydrogenation conditions by using ammonium formate as the amine source and 0.1 mol % of a cyclometalated IrIII catalyst (see scheme). Copyright

CATALYST COMPOUNDS

-

Paragraph 00163; 00173, (2013/11/05)

The present invention relates to an iridium-based catalyst compound for hydrogenating reducible moieties, especially imines and iminiums, the catalyst compounds being defined by the formulas: where ring B is either itself polycyclic, or ring B together with R is polycyclic. The catalysts of the invention are particularly effective in reductive amination procedures 10 which involve the in situ generation of the imine or iminium under reductive hydrogenative conditions.

Highly enantioselective titanium-catalyzed cyanation of imines at room temperature

Seayad, Abdul Majeed,Ramalingam, Balamurugan,Yoshinaga, Kazuhiko,Nagata, Takushi,Chai, Christina L. L.

supporting information; experimental part, p. 264 - 267 (2010/03/24)

(Figure presented) A highly active and enantioselective titanium-catalyzed cyanatlon of imines at room temperature Is described. The catalyst used Is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields In 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.

Reaction of organolead triacetates with 4-ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one. The synthesis of α-aryl- and α-vinyl-N-acetylglycines and their ethyl esters and their enzymic resolution

Morgan, Jacqueline,Pinhey, John T.,Sherry, Christopher J.

, p. 613 - 619 (2007/10/03)

4-Ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one 7, which may be readily obtained from diethyl acetamidomalonate, undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which may be hydrolysed to give either the α-aryl- or α-vinyl-N-acetylglycine or the corresponding ethyl ester. The kinetic resolution of a number of these derivatives by enzymic hydrolysis of either the amide or ester function has been demonstrated.

Synthesis of Optically Active Arylglycines by Photolysis of Optically Active (β-Hydroxyamino) Carbene-Chromium(0) Complexes

Vernier, Jean-Michel,Hegedus, Louis S.,Miller, David B.

, p. 6914 - 6920 (2007/10/02)

Photolysis of chromium complexes having the optically active amino alcohol (1R,2S)-(-)- or (1S,2R)-(+)-2-amino-1,2-diphenylethanol as the amino group produced aryl-substituted oxazinones in good yield with reasonable diastereoselectivity.Facile separation of diastereoisomers followed by mild reductive cleavage produced several arylglycines, having either electron-donating or withdrawing groups on the aromatic ring, in good overall yield and with excellent enantiomeric excess.

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