Category: 421-49-8

Raasch, Maynard S. published the artcileChemistry of sulfur tetrafluoride. IX. Reaction with amino acids in hydrogen fluoride, Name: 1,1,1-Trifluoropropan-2-amine, the publication is Journal of Organic Chemistry (1962), 1406-9, database is CAplus.

cf. Smith, CA 55, 6419i. SF₄ (I) converted the CO group in amino acids to a trifluoromethyl group when the reaction was carried out in HF. When an optically active amino acid was used, optical activity was retained in the resulting fluoro amine. Picolinic, nicotinic, and isonicotinic acids were converted into the Na salts of pipecolic, nipecotic, and isonipecotic acids by dissolving 100 g. of the acid in 300 ml. H₂O containing 33 g. NaOH and charging the solution and 3 g. Ru-C into a bomb, hydrogenating 9 hrs. at 120¡ã, filtering, evaporating, and drying the Na salt 16 hrs. at 90¡ã. Heating 95 g. dodecylamine and 18.5 g. 2-chloropropionic acid 15 hrs. at 100¡ã gave 19 g. N-dodecyl-DL-alanine, m. 210-13¡ã (AcOH-H₂O). The general procedure was to heat 8 hrs. at 120¡ã 0.4 equivalent of the amino acid, 50 g. HF, and 100 g. I in a shaker tube. p-Aminobenzoic acid (14 g.), 100 g. HF, and 30 g. I heated 4 hrs. to 125¡ã then maintained 6 hrs. gave 37% p-aminobenzotrifluoride. With 2-aminobutyric acid, addnl. HF did not raise the low yield. In the absence of HF, I converted nicotinic acid to nicotinoyl fluoride in 50% yield, b₆ 50-2¡ã. This was easily hydrolyzed by H₂O. Except for the picolines, the reaction products were poured into a dish and heated to expel HF. The residue may be transferred to a steam distillation apparatus and steam distilled For the lower amines it was best to isolate as the hydrochloride. In the case of the products from simple aliphatic amino acids, the residue remaining after evaporation of HF stirred with H₂O, filtered, and the filtrate evaporated gave the solid amine-HF. The amine was liberated by addition of 40% KOH. The trifluoromethylpicolines were volatile and such weak bases that evaporation of the reaction mixture, unless carefully done, gave the free picoline. Hence, it was diluted with 75 ml. H₂O, made basic, the mixture steam distilled, and the oil separated The product obtained from quinaldie acid was warmed to expel most of the HF, the residue stirred with H₂O, crystalline 2-(trifluoromethyl)quinoline collected, and recrystallized from hexane. The product from 4,5-imidazoledicarboxylic acid was similarly treated. The following fluoro amines were thus obtained (product, starting amino acid, % yield, b.p., n²⁵_D, and pK_a given): CF₃CH₂NH₂, glycine, 24, 36¡ã, 1.3004, 5.6; CF₃(CH₂)₂NH₂, ¦Â-alanine, 41, 67.5-8.0¡ã, 1.3270, 8.6; CF₃(CH₂)₃NH₂, 4-H₂N(CH₂)₃CO₂H, 7.1, 90-1¡ã, 1.3452, 9.6; MeCH(CF₃)NH₂, DL-alanine, 29, 46-7¡ã, 1.3180, 5.8; EtCH(CF₃)NH₂, DL-2-aminobutyric acid, 3.5, 65-6¡ã, -, 5.7; PrCH(CF₃)NH₂, DL-norvaline, 2.5, 87-8¡ã, 1.3568, 5.7; BuCH(CF₃)NH₂, DL-norleucine, 14, 113-16¡ã, 1.3635, 5.7; Me(CH₂)₅CH(CF₃)NH₂, DL-2-aminooctanoic acid, 39, 158-60¡ã, 1,3825, -; Me₂C(CF₃)NH₂, 2-methylalanine, 35, 54¡ã, 1.3305, 5.8; iso-PrCH(CF₃)NH₂, DL-valine, 4.2, 83-4¡ã, 1.3540, 5.6; iso-PrCH₂CH(CF₃)NH₂, L-leucine, 22, 103-4¡ã, 1.3610, 5.6; CF₃(CH₂)₂CH(CF₃)NH₂, L-glutamic acid, 12, 106¡ã, 1.3222, 4.7; MeS(CH₂)₂CH(CF₃)NH₂, DL-methionine, 1.5, 160-2¡ã, 1.4260, 4.8; MeCH(CF₃)NH(CH₂)₁₁Me, N-dodecyl-DL-alanine, 61, 74-6¡ã/0.18 mm., 1.4119, -; PhCH₂CH(CF₃)NH₂, DL-phenylalanine, 3.6, 53-5¡ã/1 mm., 1.4613, -; p-CF₃C₆H₄NH₂, p-H₂NC₆H₄CO₂H, 37, 85¡ã/14 mm., -, -; 2-CF₃C₅H₁₀N, Na DL-pipecolate, 9.6, 122-4¡ã, 1.3905, 6.4; 3-CF₃C₅H₁₀N, Na DL-nipecotate, 40, 128-30¡ã, 1.3910, 8.7; 4-CF₃C₅H₁₀N, Na isonipecotate, 34, 133¡ã, 1.3920, 9.4; 2-CF₃C₅H₄N, picolinic acid, 53, 139-40¡ã, 1.4166, -; 3-CF₃C₅H₄N, nicotinic acid, 25, 113-15¡ã, 1.4150, -; 4-CF₃C₅H₄N, isonicotinic acid, 57, 108-10¡ã, 1.4155, -; 2-(trifluoromethyl)quinoline, quinaldic acid, 72, 233¡ã (m. 61.5-2.5¡ã), -, -; 4,5-bis(trifluoromethyl)imidazole, 4,5-imidazoledicarboxylic acid, 80, -(m. 167.5-8.0¡ã), -, -.

Journal of Organic Chemistry published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C3H6F3N, Name: 1,1,1-Trifluoropropan-2-amine.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Xu, Guanghui published the artcileStudy on process for producing ¦Á-trifluoromethyl ethylamine, COA of Formula: C3H6F3N, the publication is Guangdong Huagong (2012), 39(1), 194-195, database is CAplus.

¦Á-Trifluoromethyl ethylamine was prepared under pressure by using L-alanine and sulfur tetrafluoride as raw materials for one step fluorination reaction. The optimal operating conditions for the process were investigated exptl. These conditions obtained are as follows: 100 g of L-alanine as raw material and molar ratio of sulfur tetrafluoride to L-alanine at 1: 2, the reaction at temperature of 55¡ãC and pressure of 18 ? 19 kgf/cm² for 12 h. The yield of the product is above 55% and the m.p. of the hydrochloride of the product is above 218.5¡ãC.

Guangdong Huagong published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C25H21N3O4, COA of Formula: C3H6F3N.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Cheng, Guilin published the artcileChemoenzymatic dynamic kinetic resolution of ¦Á-trifluoromethylated amines: influence of substitutions on the reversed stereoselectivity, Product Details of C3H6F3N, the publication is RSC Advances (2013), 3(25), 9820-9828, database is CAplus.

Enzymic resolution of ¦Á-trifluoromethylated amines via kinetic resolution (KR), dynamic kinetic resolution (DKR) employing Candida antarctica lipase B (CALB)-Pd/Al₂O₃, and a one-pot sequential process of KR/DKR/KR was investigated comparatively for the first time. Although CALB-catalyzed KR of ¦Á-trifluoromethylated amines with substituents of Me (1a), iso-Pr (1c), Ph (1d) and benzyl group (1e) can provide good stereoselectivity factors E from 31 to >200, resp., DKR and sequential process of KR/DKR/KR possess better practical application potential because of the higher conversion (62%-84%) and the similar enantiomeric excesses (90%-99%). The enantio-preference and inversion for the ¦Á-trifluoromethylated amines displayed by CALB were observed and explained by docking modes. Namely, for 1,1,1-trifluoro-2-propylamine (1a), the product amide with R-configuration was obtained, and the enantio-preference was converted to S for the amines (1b-1e) with substituents larger than Me group. The catalysts recycle, and scale-up experiments were demonstrated successfully. All these results indicated the high efficiency and green feature of this enzymic process, and its application significance.

RSC Advances published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C3H6F3N, Product Details of C3H6F3N.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Cheng, Guilin published the artcileSynthesis of highly active enzyme-metal nanohybrids and uncovering the design rules, Formula: C3H6F3N, the publication is Enzyme and Microbial Technology (2022), 109962, database is CAplus and MEDLINE.

Nanobiohybrid CAL-B/MNPs were synthesized through enzyme in situ reduction of metal ions, including noble and non-noble metals. Lipase CAL-B acted as multifunctional reagents (reducing and supporting agents). The hybrid catalysts were systematically characterized by HRTEM, EDX, MALDI-TOF-MS, and XPS anal., confirming that highly dispersed 3-5 nm nanoparticles were evenly dispersed on lipase matrix without agglomeration. The mechanism of CAL-B reducing metal ions was investigated, revealing that AGLFFSSKDL in the amino acid sequence of CAL-B from 111 to 128 formed a stable spatial structure through hydrogen bonding, which was the key factor for enzyme in situ reduction of metal ions into highly dispersed nanoparticles.

Enzyme and Microbial Technology published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C3H6F3N, Formula: C3H6F3N.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Xu, Yan published the artcileEfficient Z-Selective Olefin-Acrylamide Cross-Metathesis Enabled by Sterically Demanding Cyclometalated Ruthenium Catalysts, Recommanded Product: 1,1,1-Trifluoropropan-2-amine, the publication is Journal of the American Chemical Society (2020), 142(50), 20987-20993, database is CAplus and MEDLINE.

The efficient Z-selective cross-metathesis between acrylamides and common terminal olefins has been developed by the use of novel cyclometalated ruthenium catalysts with bulky N-heterocyclic carbene (NHC) ligands. Superior reactivity and stereoselectivity are realized for the first time in this challenging transformation, allowing streamlined access to an important class of cis-Michael acceptors from readily available feedstocks. The kinetic preference for cross-metathesis is enabled by a pivalate anionic ligand, and the origin of this effect is elucidated by d. functional theory calculations

Journal of the American Chemical Society published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C11H11NO2, Recommanded Product: 1,1,1-Trifluoropropan-2-amine.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Dickey, J. B. published the artcileFluorinated aminoanthraquinone dyes, Safety of 1,1,1-Trifluoropropan-2-amine, the publication is Industrial and Engineering Chemistry (1956), 209-13, database is CAplus.

A new series of pink to violet fluorinated aminoanthraquinone dyes for cellulose acetate, having in some cases enhanced fastness to light and gas, was prepared by replacing one OH group of quinizarin with a fluoroalkylamino group. Fluoroalkylamine intermediates, which were prepared by the reaction of fluoroalkyl halides with NH₄OH, include 2,2,2-trifluoroethylamine, b. 35-6¡ã, 2,2-difluoroethylamine, b. 68-9¡ã, 2,2,2′,2′-tetrafluorodiethylamine, b. 122-3¡ã, 3,3-difluoropropylamine, b. 92-4¡ã, n_D²⁰ 1.3650, 3,3,3′,3′-tetrafluorodipropylamine, b₅₀ 91-4¡ã, n_D²⁰ 1.3744, 2,2-difluoropropylamine, b. 76-7¡ã, n_D²⁵ 1.3622, 2,2,2-trifluoro-1-methylethylamine, b. 46-7¡ã, n_D²⁰ 1.3210, 3,3,3-trifluoropropylamine, b. 67¡ã, n_D²⁰ 1.3316, and 4,4-difluoropentylamine, b. 125-30¡ã, n_D²⁵ 1.3864. The dyes which were prepared include 1-hydroxy-4-(2,2,2-trifluoroethylamino)anthraquinone, m. 158-60¡ã, 1-(2,2-difluoroethylamino)-4-hydroxyanthraquinone, m. 141-2¡ã, 1,4-bis(2,2-difluoroethylamino)anthraquinone, m. 242-3¡ã, 1-(2,2-difluoropropylamino)-4-hydroxyanthraquinone, m. 135-8, 1-hydroxy-4-(2,2,2-trifluoro-1-methylethylamino)anthraquinone, m. 143-5¡ã, 1-(3,3-difluoropropylamino)-4-hydroxyanthraquinone, and 1-(4,4-difluoropentylamino)-4-hydroxyanthraquinone, m. 128-30¡ã. Another series of dyes can be prepared by the reaction of 1-amino-4-bromo-2-trifluoromethylanthraquinone with a series of o-and p-(hydroxypolyethoxy)anilines. These dye cellulose acetate bright-blue shades and have excellent light-fastness and good resistance to gas fading. Intermediates prepared for this series include 1-chloro-2-methylanthraquinone, m. 158-9.5¡ã, 1-chloro-2-trichloromethylanthraquinone, m. 203-5¡ã, 1-chloro-2-trifluoromethylanthraquinone, m. 208¡ã, 1-amino-2-trifluoromethylanthraquinone, m. 144-6¡ã, and 1-amino-4-bromo-2-trifluoromethylanthraquinone, m. 175-7¡ã. The dye which was prepared was 1-amino-4-{p-{2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethoxy}anilino}-2-trifluoro-methylanthraquinone, m. 110-15¡ã.

Industrial and Engineering Chemistry published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C3H6F3N, Safety of 1,1,1-Trifluoropropan-2-amine.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Abrahami, Renata A. published the artcileA de novo synthetic route to 1,2,3,4-tetrahydroisoquinoline derivatives, Application In Synthesis of 421-49-8, the publication is Synlett (2018), 29(15), 2066-2070, database is CAplus.

A novel synthetic approach was developed for the construction of the 1,2,3,4-tetrahydroisoquinoline framework, e.g. I (R¹ = Et, CHF₂CH₂, CF₃CH₂, CF₃CHMe, PhCH₂, etc.; R² = H, Br), possessing varied functions. The synthetic strategy is based on oxidative ring opening of the corresponding indandiols, e.g. II, followed by double reductive amination of the dicarbonyl intermediates with various primary alkyl- or fluoroalkylamines R¹NH₂.

Synlett published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C3H6F3N, Application In Synthesis of 421-49-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Hock, Katharina J. published the artcileDifluoro- and trifluoro diazoalkanes – complementary approaches in batch and flow and their application in cycloaddition reactions, Computed Properties of 421-49-8, the publication is Green Chemistry (2017), 19(4), 905-909, database is CAplus.

Herein, the applications of fluorinated diazoalkanes in cycloaddition reactions, with the emphasis on studying subtle differences between diverse fluorinated diazo compounds was reported. These differences led to two major synthetic protocols in batch and flow that allow the safe and scalable synthesis of fluoroalkyl-, sulfone-substituted pyrazolines.

Green Chemistry published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C3H6F3N, Computed Properties of 421-49-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Yao, Yuqin published the artcileDesign, synthesis and pharmacological evaluation of 4-(3-chloro-4-(3-cyclopropylthioureido)-2-fluorophenoxy)-7-methoxyquinoline-6-carboxamide (WXFL-152): a novel triple angiokinase inhibitor for cancer therapy, Recommanded Product: 1,1,1-Trifluoropropan-2-amine, the publication is Acta Pharmaceutica Sinica B (2020), 10(8), 1453-1475, database is CAplus and MEDLINE.

In this study, the design, synthesis, target identification, mol. mechanism, pharmacodynamics (PD) and pharmacokinetics (PK) research of a novel triple-angiokinase inhibitor WXFL-152 is reported. WXFL-152, identified from a series of 4-oxyquinoline derivatives based on a structure-activity relationship study, inhibited the proliferation of vascular endothelial cells (ECs) and pericytes by blocking the angiokinase signals VEGF/VEGFR2, FGF/FGFRs and PDGF/PDGFRb simultaneously in vitro. Significant anticancer effects of WXFL-152 were confirmed in multiple preclin. tumor xenograft models, including a patient-derived tumor xenograft (PDX) model. Pharmacokinetic studies of WXFL-152 demonstrated high favorable bioavailability with single-dose and continuous multi-dose by oral administration in rats and beagles. In conclusion, WXFL-152, which is currently in phase Ib clin. trials, is a novel and effective triple-angiokinase inhibitor with clear PD and PK in tumor therapy.

Acta Pharmaceutica Sinica B published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C18H17N5O3, Recommanded Product: 1,1,1-Trifluoropropan-2-amine.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Koehling, Jonas published the artcileOxamates as 1,2-Diketone Equivalents: The Effect of Fluorine, HPLC of Formula: 421-49-8, the publication is ChemistrySelect (2021), 6(8), 1882-1886, database is CAplus.

In this paper, new fluorinated derivatives were presented, which were synthesized from selected fluorinated primary amines R^FNH₂ (R^F=CH₂CF₃, CH₂CHF₂, CH₂CF₂CH₃, CH(CF₃)₂, CH(CH₃)CF₃) or their hydrochlorides and Et oxalylchloride. Since oxamates was considered as 1,2 diketones, their properties, geometries, effective charges at oxygen and nitrogen and the pK_a values for the N-H grouping were investigated . In two cases, the mol. structures was measured by XRD, observing almost planar arrangement of C₂-N₁-C₃-C₄ atoms. The effect of fluorine was discussed and compared with non-fluorinated oxamates. The effective charges were controlled by various alkyl substituents at nitrogen (branched or straight, fluorinated or non-fluorinated) and can open a new field, especially when fluorinated, for multiple applications in material sciences (surfaces) and biochem. systems (enzymes).

ChemistrySelect published new progress about 421-49-8. 421-49-8 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain, name is 1,1,1-Trifluoropropan-2-amine, and the molecular formula is C3H6F3N, HPLC of Formula: 421-49-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia