78008-15-8

Basic information

• Product Name: 3-(TRIFLUOROACETYLAMINO)-1-PROPANOL
• Synonyms: 3-(TRIFLUOROACETAMIDO)PROPAN-1-OL;3-(TRIFLUOROACETYLAMINO)-1-PROPANOL;N-TRIFLUOROACETYL-3-AMINO-1-PROPANOL;N-TRIFLUOROACETYL-BETA-ALANINOL;N-(3-HYDROXYPROPYL)TRIFLUOROACETAMIDE;TFA-NH-(CH2)3-OH;TFA-B-ALA-OL;TFA-BETA-ALA-OL
• CAS NO: 78008-15-8
• Molecular Formula: C₅H₈F₃NO₂
• Molecular Weight: 171.12
• Product Categories: Amino Alcohols;Bifunctional Crosslinkers;Building Blocks;Chemical Biology;Chemical Synthesis;Linkers;Organic Building Blocks;Oxygen Compounds;Peptide Chemistry
• Mol File: 78008-15-8.mol

Chemical Properties

• Boiling Point: 120-121 °C0.03 mm Hg(lit.)
• Flash Point: 105 °C
• Appearance: /
• Density: 1.355 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00353mmHg at 25°C
• Refractive Index: n20/D 1.406
• BRN: 4969338
• CAS DataBase Reference: 3-(TRIFLUOROACETYLAMINO)-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(TRIFLUOROACETYLAMINO)-1-PROPANOL(78008-15-8)
• EPA Substance Registry System: 3-(TRIFLUOROACETYLAMINO)-1-PROPANOL(78008-15-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 78008-15-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(TRIFLUOROACETYLAMINO)-1-PROPANOL is used as a pharmaceutical intermediate for its critical role in the synthesis of various drugs and active pharmaceutical ingredients. Its unique properties allow for the development of new and innovative medications.
Used in Organic Chemistry:
In the realm of organic chemistry, 3-(TRIFLUOROACETYLAMINO)-1-PROPANOL is utilized as a reagent, particularly in the production of fluorinated compounds. Its fluorinated nature contributes to the advancement of chemical research and the creation of novel chemical entities.
Used in Agrochemical Development:
3-(TRIFLUOROACETYLAMINO)-1-PROPANOL is employed in the field of agrochemicals, where it may contribute to the development of new pesticides or other agricultural chemicals, enhancing crop protection and yield.
Used in Material Science:
Within material science, 3-(TRIFLUOROACETYLAMINO)-1-PROPANOL has potential applications in the development of new materials, possibly due to its unique structural and chemical properties that could influence material characteristics.
Used in Fluorescent Probes Production:
3-(TRIFLUOROACETYLAMINO)-1-PROPANOL is used in the production of fluorescent probes, which are essential tools in scientific research, particularly in the fields of biochemistry and molecular biology, for visualizing and tracking specific molecules within complex biological systems.

InChI:InChI=1/C5H8F3NO2/c6-5(7,8)4(11)9-2-1-3-10/h10H,1-3H2,(H,9,11)

Upstream product

• 38182-16-0 N-methyl N-cyclohexyl trifluoroacetamide 
• 156-87-6 propan-1-ol-3-amine 
• 383-63-1 ethyl trifluoroacetate, 
• 1415392-93-6 N,N′-[ethane-1,1-diylbis(oxypropane-3,1-diyl)]bis(2,2,2-trifluoroacetamide) 
• 407-25-0 trifluoroacetic anhydride 
• 354-32-5 trifluoracetyl chloride 
• 1339837-81-8 2,2,2-trifluoro-N-[3-(vinyloxy)propyl]acetamide 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 109317-75-1 4-trifluoroacetyl-2,3-dihydrofuran 

Downstream Products

• 181943-85-1 (1R,5S,7R)-3-Ethyl-2-oxo-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-7-carboxylic acid (R)-12-acetoxy-2-acetyl-5-[3-(2,2,2-trifluoro-acetylamino)-propoxymethyl]-1,2,3,4-tetrahydro-naphthacen-2-yl ester 
• 196951-49-2 methyl [(3-trifluoroacetamidopropyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-pyranoside]-2-nonulosonate 
• 196951-45-8 methyl [(3-trifluoroacetamidopropyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-pyranoside]-2-nonulosonate 
• 197795-16-7 3-trifluoroacetamidopropyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside 
• 100496-17-1 3-trifluoroacetamidopropyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside 
• 196951-56-1 methyl [(3-trifluoroacetamidopropyl)-5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-pyranoside]-2-nonulosonate 
• 196951-52-7 methyl [(3-trifluoroacetamidopropyl)-5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-pyranoside]-2-nonulosonate 
• 497869-65-5 3-trifluoroacetamidopropyl (2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 497869-75-7 3-trifluoroacetamidopropyl (2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-(1->4)-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-β-L-rhamnopyranoside 
• 896730-22-6 8-nitro-4-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-quinoline-2-carboxylic acid methyl ester 
• 1015252-19-3 3-trifluoroacetamidopropyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 
• 1007115-73-2 3-trifluoroacetamidoprop-1-yl 2-acetamido-6-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-4-O-[2-O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-3,4,6-tri-O-acetyl-β-D-galactopyranosyl]-2-deoxy-β-D-glucopyranoside 
• 1000780-45-9 3-(trifluoroacetamido)propyl 3-O-acetyl-2,4-di-O-benzyl-α-D-xylopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-glucopyranoside 
• 896730-24-8 8-amino-4-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-quinoline-2-carboxylic acid methyl ester 

Relevant articles and documents

Phosphine-Catalyzed Synthesis of Chiral N-Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling

Phosphine-catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1H-pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.

Rapid Synthesis of Bicyclic N-Heterocyclic Cores from N-Terminal α,β-Unsaturated Diazoketones

A method for the synthesis of bicyclic N-heterocyclic cores from N-terminal α,β-unsaturated diazoketones has been developed. The transformation involves three sequential steps that include N-deprotection, an intramolecular aza-Michael, and a photochemical Wolff rearrangement as a one-pot protocol. By using this strategy, a series of substituted bicyclic N-heterocycles, particularly, indolizidines and pyrrolizidines, were synthesize in good yields.

Naphthalene diimide-polyamine hybrids as antiproliferative agents: Focus on the architecture of the polyamine chains

Naphthalene diimides (NDIs) have been widely used as scaffold to design DNA-directed agents able to target peculiar DNA secondary arrangements endowed with relevant biochemical roles. Recently, we have reported disubstituted linear- and macrocyclic-NDIs that bind telomeric and non-telomeric G-quadruplex with high degree of affinity and selectivity. Herein, the synthesis, biological evaluation and molecular modelling studies of a series of asymmetrically substituted NDIs are reported. Among these, compound 9 emerges as the most interesting of the series being able to bind telomeric G-quadruplex (ΔTm = 29 °C at 2.5 μM), to inhibit the activity of DNA processing enzymes, such as topoisomerase II and TAQ-polymerase, and to exert antiproliferative effects in the NCI panel of cancer cell lines with GI50values in the micro-to nanomolar concentration range (i.e. SR cell line, GI50= 76 nM). Molecular mechanisms of cell death have been investigated and molecular modelling studies have been performed in order to shed light on the antiproliferative and DNA-recognition processes.

Novel Polyamine-Naphthalene Diimide Conjugates Targeting Histone Deacetylases and DNA for Cancer Phenotype Reprogramming

A series of hybrid compounds was designed to target histone deacetylases and ds-/G-quadruplex DNAs by merging structural features deriving from Scriptaid and compound 1. Compound 6 binds different DNA arrangements, inhibits HDACs both in vitro and in cells, and is able to induce a reduction of cell proliferation. Moreover, compound 6 displays cell phenotype-reprogramming properties since it prevents the epithelial to mesenchymal transition in cancer cells, inducing a less aggressive and migratory phenotype, which is one of the goals of present innovative strategies in cancer therapies.

Substituent Effects on the pH Sensitivity of Acetals and Ketals and Their Correlation with Encapsulation Stability in Polymeric Nanogels

The effect of structural variations in acetal- and ketal-based linkers upon their degradation kinetics is studied through the design, synthesis, and study of six series of molecules, comprising a total of 18 different molecules. Through this systematic study, we show that the structural fine-tuning of the linkers allows access to variations in kinetics of degradation of more than 6 orders of magnitude. Hammett correlations show that the ρ value for the hydrolysis of benzylidene acetals is about ?4.06, which is comparable to an SN1-like process. This shows that there is a strong, developing positive charge at the benzylic position in the transition state during the degradation of acetals. This positively charged transition state is consistent with the relative degradation rates of acetals vs ketals (correlated to stabilities of 1°, 2°, and 3° carboxonium ion type intermediates) and the observed effect of proximal electron-withdrawing groups upon the degradation rates. Following this, we studied whether the degradation kinetics study correlates with pH-sensitive variations in the host-guest characteristics of polymeric nanogels that contains these acetal or ketal moieties as cross-linking functionalities. Indeed, the trends observed in the small molecule degradation have clear correlations with the encapsulation stability of guest molecules within these polymeric nanogels. The implications of this fundamental study extend to a broad range of applications, well beyond the polymeric nanogel examples studied here.

Synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols or 3-amino alcohols using iodobenzene dichloride and sodium azide

A general and efficient method for the synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols and 3-amino alcohols has been developed using the same reagent combination of iodobenzene dichloride (PhICl2) and sodium azide (NaN3).

Synthesis of Acetals Containing a Primary Amino Group

Amino acetals of the general formula MeCH(OR)(OXNH2) (R = Et, Bu, X = CH2CH2, CH2CH2CH 2, CH2CMe2) were synthesized in 53-91% yield by acid-catalyzed reaction of N-(2-hydroxyethyl)-, N-(3-hydroxypropyl)-, and N-(2-hydroxy-1,1-dimethylethyl)-2,2,2-trifluoroacetamides with vinyl ethers, followed by removal of the trifluoroacetyl protection by alkaline hydrolysis. Pleiades Publishing, Ltd., 2012.

REDUCTIVE RELEASE PROBES CONTAINING A CHEMOSELECTIVELY CLEAVABLE ALPHA-AZIDOETHER LINKER AND METHODS OF USE THEREOF

Probes comprising one or more selectively cleavable α-azidoether moieties are provided; and linkers comprising the one or more selectively cleavable α-azidoether moieties. The α-azidoether moiety will undergo a Staudinger reaction with a suitable reducing agent, resulting in cleavage. The probes find use in a variety of detection assays, e.g. specific polynucleotide binding assays, polypeptide binding assays, etc. The cleavable linkers are suitable for synthetic reactions, e.g. to prepare probes of the invention; in the synthesis of cleavable peptide conjugates; and the like.

Convenient one-pot synthesis of N-substituted 3-trifluoroacetyl pyrroles

A new one-pot strategy for the synthesis of a series of new N-substituted 3-trifluoroacetyl pyrroles is presented. These compounds were obtained by the reaction of 3-trifluoroacetyl-4,5-dihydrofuran with primary amines, which generated 1,1,1-trifluoro-3-(2-hydroxyethyl)-4-alkylaminobut-3-en-2-one intermediates. In most cases these intermediates were not stable enough to be isolated. Thus, in the same reaction vessel they were directly submitted to oxidation with PCC (Corey's reagent) to furnish 1,1,1-trifluoro-3-(2-ethanal)-4- alkylaminobut-3-en-2-ones, which under reflux underwent intramolecular cyclization to give the desired N-substituted 3-trifluoroacetyl pyrroles, in moderate yields. All of these pyrroles were tested against pan-susceptible Mycobacterium tuberculosis H37Rv and clinical isolates INH- and RMP-resistant strain and some of these compounds showed significant in vitro antimicrobial activity. Georg Thieme Verlag Stuttgart.