107018-37-1

Basic information

• Product Name: Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)- (9CI)
• Synonyms: Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)- (9CI);4-(2,2,2-trifluoro-1-hydroxyethyl)benzonitrile;Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)-
• CAS NO: 107018-37-1
• Molecular Formula: C₉H₆F₃NO
• Molecular Weight: 201.1452496
• Product Categories: ACETYLHALIDE
• Mol File: 107018-37-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)- (9CI)(107018-37-1)
• EPA Substance Registry System: Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)- (9CI)(107018-37-1)

Safety Data

• Hazardous Substances Data: 107018-37-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)(9CI) is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical structure allows it to be a versatile building block in the development of new pharmaceutical compounds.
Used in Chemical Industry:
Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)(9CI) is used as a chemical intermediate in the synthesis of various organic compounds. Its reactivity and solubility properties make it a valuable component in the production of specialty chemicals.

Upstream product

• 75-63-8 Bromotrifluoromethane 
• 105-07-7 4-cyanobenzaldehyde 
• 844-40-6 diphenylmethanol trifluoroacetate 
• 3058-39-7 4-iodobenzonitrile 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2314-97-8 iodotrifluoromethane 

Downstream Products

• 1135312-09-2 (R)-2,2,2-trifluoro-1-(4'-cyanophenyl)ethanol 
• 1135311-95-3 (S)-2,2,2-trifluoro-1-(4'-cyanophenyl)ethyl isobutyrate 
• 1135312-30-9 2,2,2-trifluoro-1-(4'-cyanophenyl)ethyl isobutyrate 
• 193954-48-2 4-(2,2,2-trifluoro-1,1-dihydroxyethyl)benzonitrile 
• 23516-85-0 4-(2,2,2-trifluoroacetyl)benzonitrile 

Relevant articles and documents

Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

Tertiary alcohols bearing a trifluoromethyl group are of considerable medicinal interest. Using an umpolung strategy, we herein report the first intermolecular reductive cross-coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines with the aid of a Br?nsted acid catalyst upon visible-light irradiation. This metal-free reaction is operationally simple and performed at ambient temperature, allowing access to desired tertiary alcohols with tri-/difluoromethyl groups in moderate to excellent yields. The commercially available and easily handled Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.

Flow trifluoromethylation of carbonyl compounds by Ruppert-Prakash reagent and its application for pharmaceuticals, efavirenz and HSD-016

The Ruppert-Prakash reagent is the most powerful and well-documented reagent for trifluoromethylation. Despite its versatility, no general method exists for its use in a flow system. Here we report the first flow trifluoromethylation of carbonyl compounds

One-Pot and Reducible-Functional-Group-Tolerant Synthesis of α-Aryl- and α-Heteroaryl-α-Trifluoromethyl Alcohols via Tandem Trifluoroacetylation and MPV Type Reduction

We have developed a new one-pot synthesis of α-aryl- and α-heteroaryl-α-trifluoromethyl alcohols carrying not only arenes with electron-withdrawing groups but also electron-deficient nitrogen-containing heteroarenes, which are of increasing interest becau

Borazine-CF3? Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation

A fluoroform-derived borazine CF3? transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for catalytic trifluoromethylation. Organic electrophiles included (hetero)arenes, enabling C?H and C?X trifluoromethylation reactions. Mechanistic analysis supports a dissociative mechanism for CF3? transfer, and cation modification afforded a reagent with enhanced stability.

Nucleophilic trifluoromethylation using trifluoromethyl iodide. A new and simple alternative for the trifluoromethylation of aldehydes and ketones

(Matrix Presented) A novel method for nucleophilic trifluoromethylation of aldehydes and ketones, based on photoinduced reduction of trifluoromethyl iodide by tetrakis(dimethylamino)ethylene (TDAE), is presented.

Design, synthesis, and biological evaluation of furosemide analogs as therapeutics for the proteopathy and immunopathy of Alzheimer's disease

β-Amyloid (Aβ) triggered proteopathic and immunopathic processes are a postulated cause of Alzheimer's disease (AD). Monomeric Aβ is derived from amyloid precursor protein, whereupon it aggregates into various assemblies, including oligomers and fibrils, which disrupt neuronal membrane integrity and induce cellular damage. Aβ is directly neurotoxic/synaptotoxic, but may also induce neuroinflammation through the concomitant activation of microglia. Previously, we have shown that furosemide is a known anthranilate-based drug with the capacity to downregulate the proinflammatory microglial M1 phenotype and upregulate the anti-inflammatory M2 phenotype. To further explore the pharmacologic effects of furosemide, this study reports a series of furosemide analogs that target both Aβ aggregation and neuroinflammation, thereby addressing the combined proteopathic-immunopathic pathogenesis of AD. Forty compounds were synthesized and evaluated. Compounds 3c, 3g, and 20 inhibited Aβ oligomerization; 33 and 34 inhibited Aβ fibrillization. 3g and 34 inhibited the production of TNF-α, IL-6, and nitric oxide, downregulated the expression of COX-2 and iNOS, and promoted microglial phagocytotic activity, suggesting dual activity against Aβ aggregation and neuroinflammation. Our data demonstrate the potential therapeutic utility of the furosemide-like anthranilate platform in the development of drug-like molecules targeting both the proteopathy and immunopathy of AD.

FUROSEMIDE ANALOGUES AND COMPOSITIONS AND USES THEREOF FOR TREATMENT OF ALZHEIMER'S DISEASE

The present application provides furosemide analogues of the general formula Z having activity as anti-Aβ aggregation agents and/or as inhibitors of Aβ induced neuroinflammation. Formula Z These compounds are useful in preventing, delaying and/or treating Alzheimer's Disease. Accordingly, the present application further provides pharmaceutical compositions and method for preventing, delaying and/or treating Alzheimer's Disease.

Oxidation of α-trifluoromethyl and non-fluorinated alcohols: Via the merger of oxoammonium cations and photoredox catalysis

We present an alcohol oxidation strategy to access α-trifluoromethyl ketones (TFMKs) merging catalytic oxoammonium cation oxidation with visible-light photoredox catalysis. This work uses 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl as an organic oxidant capable of generating TFMKs in good yields. The methodology serves as an improvement over previous reports of an analogous oxidation strategy requiring superstoichiometric quantities of oxidant. Both primary and secondary non-fluorinated alcohols can also be oxidised in good yields.

COMPLEXES FOR NUCLEOPHILIC, RADICAL, AND ELECTROPHILIC POLYFLUOROALKYLATION

Disclosed herein are borazine complexes and use of the same in perfluoroalkylation reactions.

FLUOROALKYLATING AGENT

Problem to be Solved It is intended to provide an industrially preferable fluoroalkylating agent and use thereof. Solution The present invention provides a fluoroalkylating agent represented by the general formula (1) wherein R1 is a C1 to C8 fluoroalkyl group; R2 and R3 are each independently a C1 to C12 alkyl group or the like; Y1 to Y4 are each independently a hydrogen atom, a halogen atom, or the like; and X? is a monovalent anion. A compound of the general formula (3): R4—S—R1 having an introduced C1 to C8 fluoroalkyl group is easily obtained by reacting a compound of the general formula (2): R4—S—Z wherein R4 is a hydrocarbon group or the like; and Z is a leaving group, with the compound of the general formula (1).