144284-25-3

Basic information

• Product Name: 2,4,5-Trifluorobenzyl alcohol
• Synonyms: 2,4,5-tifluorobenzenecarbinol;2,4,5-TrifluorobenzeneMethanol;RARECHEM AL BD 0314;2,4,5-TRIFLUOROBENZYL ALCOHOL;(2,4,5-TRIFLUORO-PHENYL)-METHANOL;2,4,5-Trifluorobenzyl alcohol 97%;2,4,5-Trifluorobenzylalcohol97%;2,4,5-Trifluorobenzyl alcohole
• CAS NO: 144284-25-3
• Molecular Formula: C₇H₅F₃O
• Molecular Weight: 162.11
• EINECS: 1312995-182-4
• Product Categories: Alcohols;C7 to C8;Oxygen Compounds;Benzhydrols, Benzyl & Special Alcohols;Alcohol;Miscellaneous
• Mol File: 144284-25-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 24 °C
• Boiling Point: 201-204 °C(lit.)
• Flash Point: 230 °F
• Appearance: /
• Density: 1.4 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.113mmHg at 25°C
• Refractive Index: n20/D 1.472(lit.)
• Storage Temp.: 2-8°C
• PKA: 13.17±0.10(Predicted)
• CAS DataBase Reference: 2,4,5-Trifluorobenzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-Trifluorobenzyl alcohol(144284-25-3)
• EPA Substance Registry System: 2,4,5-Trifluorobenzyl alcohol(144284-25-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36/37/39-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 144284-25-3(Hazardous Substances Data)

Usage

Chemical Properties

White solid

General Description

2,4,5-Trifluorobenzyl alcohol is an aryl fluorinated building block. It is also referred to as (2,4,5-trifluorophenyl)methanol [IUPAC name].

InChI:InChI=1/C6H3BrF2O/c7-3-1-2-4(10)6(9)5(3)8/h1-2,10H

Upstream product

• 165047-24-5 2,4,5-trifluorobenzaldehyde 

Downstream Products

• 1269260-23-2 ethyl (2E,4E,6E,8E)-3,7-dimethyl-9-(2 4 5-trifluorophenyl)nona-2 4 6 8-tetraenoate 
• 1269259-73-5 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,4,5-trifluorophenyl)nona-2,4,6,8-tetraenoic acid 
• 1269260-21-0 triphenyl(2,4,5-trifluorobenzyl)phosphonium bromide 
• 157911-56-3 2,4,5-trifluorobenzyl bromide 
• 654671-78-0 sitagliptin phosphate 
• 486460-32-6 sitagliptin 
• 486460-25-7 [3-diazo-2-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester 
• 486460-23-5 (R)-tert-butyl 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-ylcarbamate 
• 486460-00-8 (3R)-3-[(1,1-dimethylethoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid 
• 486460-09-7 (R)-2-(tert-butoxycarbonylamino)-3-(2,4,5-trifluorophenyl)propanoic acid 

Relevant articles and documents

Biocatalytic retrosynthesis approaches to d-(2,4,5-trifluorophenyl)alanine, key precursor of the antidiabetic sitagliptin

The integration of biocatalytic steps in retrosynthetic analysis of a target molecule offers multiple advantages, such as reduction of the environmental footprint of the process, viability of milder and safer reaction conditions, and accessibility of transformations that are challenging with traditional chemical synthesis. Herein, six chemo-enzymatic routes are described for the synthesis of a fluorinated d-phenylalanine derivative, precursor of the blockbuster antidiabetic drug sitagliptin. All routes start from the same aldehyde precursor and involve at least one biocatalytic step, including reductive amination, transamination, deracemisation, hydroamination, and alkene reduction. The target molecule was obtained in 2-5 steps from the aldehyde, with ee up to >99% and in 36-62% isolated yield. Furthermore, as part of one of the routes, the first example of a fully biocatalytic conversion of a cinnamic acid derivative to the corresponding d-phenylalanine (formal d-selective hydroamination) is reported.

Electrophilicity and nucleophilicity of commonly used aldehydes

The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.

Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 μM. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability.