17951-22-3

Basic information

• Product Name: 1,2-ETHANEDIOL, 1-(P-FLUOROPHENYL)-
• Synonyms: 1,2-ETHANEDIOL, 1-(P-FLUOROPHENYL)-;1-(4-fluorophenyl)-1,2-ethanediol
• CAS NO: 17951-22-3
• Molecular Formula: C₈H₉FO₂
• Molecular Weight: 0
• Mol File: 17951-22-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-ETHANEDIOL, 1-(P-FLUOROPHENYL)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-ETHANEDIOL, 1-(P-FLUOROPHENYL)-(17951-22-3)
• EPA Substance Registry System: 1,2-ETHANEDIOL, 1-(P-FLUOROPHENYL)-(17951-22-3)

Safety Data

• Hazardous Substances Data: 17951-22-3(Hazardous Substances Data)

Upstream product

• 18511-62-1 4-fluorostyrene oxide 
• 405-99-2 para-fluorostyrene 
• 32222-45-0 4-fluoromandelic acid 
• 403-32-7 (4-fluorophenyl)glyoxal 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 403-31-6 4-fluoro-2-hydroxy-acetophenone 
• 156276-23-2 methyl (p-fluorobenzoyl)formate 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 124-38-9 carbon dioxide 
• 62-53-3 aniline 

Downstream Products

• 1580-83-2 paraflutizide 
• 14471-83-1 3-(4-fluoro-benzyl)-1,1-dioxo-6-trifluoromethyl-1,2,3,4-tetrahydro-1λ⁶-benzo[1,2,4]thiadiazine-7-sulfonic acid amide 
• 14331-42-1 6-bromo-3-(4-fluoro-benzyl)-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-benzo[1,2,4]thiadiazine-7-sulfonic acid amide 
• 59363-31-4 1-[2-(4-chloro-phenyl)-4-(4-fluoro-phenyl)-[1,3]dioxolan-2-ylmethyl]-1H-imidazole 
• 59363-63-2 1-[2-(4-bromo-phenyl)-4-(4-fluoro-phenyl)-[1,3]dioxolan-2-ylmethyl]-1H-imidazole 
• 59365-43-4 2-Bromomethyl-2-(4-chloro-phenyl)-4-(4-fluoro-phenyl)-[1,3]dioxolane 
• 59365-39-8 2-Bromomethyl-2-(4-bromo-phenyl)-4-(4-fluoro-phenyl)-[1,3]dioxolane 
• 387337-81-7 4-(4-fluoro-phenyl)-2-phenyl-[1,3]dioxolane 
• 449-46-7 2-(4-fluorophenyl)quinoxaline 
• 213479-90-4 (S)-(+)-1-(4-fluorophenyl)-1,2-ethanediol 
• 179694-35-0 (R)-(-)-1-(4-fluorophenyl)-1,2-ethanediol 

Relevant articles and documents

Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system

A novel one-pot epoxide hydrolase/alcohol dehydrogenase/transaminase cascade process for the asymmetric ring opening of racemic epoxides to enantiopure β-amino alcohols is reported. The product (S)-β-amino alcohols were obtained in 97-99% ee and 79-99% conversion from readily available racemic epoxides.

Lewis Base Catalyzed Dioxygenation of Olefins with Hypervalent Iodine Reagents

1,2-Diols are extremely useful building blocks in organic synthesis. Hypervalent iodine reagents are useful for the vicinal dihydroxylation of olefins to give 1,2-diols under metal-free conditions, but strongly acidic promoters are often required. Herein, we report a catalytic vicinal dioxygenation of olefins with hypervalent iodine reagents using Lewis bases as catalysts. The conditions are mild and compatible with various functional groups.

Catalytic Diastereo- and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen

We present herein an unprecedented diastereoconvergent synthesis of vicinal diamines from diols through an economical, redox-neutral process. Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1,2-diols (as a mixture of diastereomers) couple to forge two C?N bonds in an efficient and diastereoselective fashion. By identifying an effective chiral iridium/phosphoric acid co-catalyzed procedure, the first enantioconvergent double amination of racemic 1,2-diols has also been achieved, resulting in a practical access to highly valuable enantioenriched vicinal diamines.

Iodine-Initiated Dioxygenation of Aryl Alkenes Using tert-Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides

An environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols has been developed in water with iodine as the catalyst and tert-butylhydroperoxides (TBHPs) as the oxidant. The protocol was efficient, sustainable, and operationally simple. Detailed mechanistic studies indicated that one of the hydroxyl groups is derived from water and the other one is derived from TBHP. Additionally, the bisperoxides could be obtained in good yields with iodine as the catalyst, Na2CO3 as the additive, and propylene carbonate as the solvent, instead.

Visible light induced redox neutral fragmentation of 1,2-diol derivatives

A homogeneous, redox-neutral photo fragmentation of diol derivatives was developed. Under photo/hydrogen atom transfer (HAT) dual catalysis, diol derivatives such as lignin model compounds and diol monoesters undergo selective β C(sp3)-O bond cleavage to afford ketones, phenols and acids effectively.

Bifunctional organocatalysts for the conversion of CO2, epoxides and aryl amines to 3-aryl-2-oxazolidinones

A route to synthesize 3-aryl-2-oxazolidinones is developed, which is achieved through a three component reaction between CO2, aryl amines, and epoxides with a binary organocatalytic system composed of organocatalysts and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The method allows wide scopes of epoxide and aryl amine substrates with various functional groups under mild reaction conditions. The control experiments indicate that a cyclic carbonate is formed via cycloaddition of epoxides with CO2, which further reacts with the β-amino alcohol originating from epoxides and aryl amines, resulting in the formation of 3-aryl-2-oxazolidinones finally.

Direct, high-yielding, one-step synthesis of vic-diols from aryl alkynes

An unprecedented, high yielding, direct, one-step synthesis of vic-diols from alkynes has been developed via metal-free, open-to-air dihydroboration with ammonia borane. The electronics of the alkyne and the reaction stoichiometry are critical for obtaining optimal yields of the 1,2-diol.

Developing a Bench-Scale Green Diboration Reaction toward Industrial Application

We report a new methodology for the organocatalytic diboration reaction using inexpensive, sustainable, nontoxic, commercially available halogen salts. This is an educative manuscript for the transformation of laboratory scale reactions into a sustainable approach of appeal to industry.

Ru-MACHO-Catalyzed Highly Chemoselective Hydrogenation of α-Keto Esters to 1,2-Diols or α-Hydroxy Esters

A ruthenium pincer catalyst has been shown to be highly effective for the hydrogenation of a wide range of α-keto esters, affording either diols or hydroxy esters depending on the choice of reaction conditions. Strong base, high temperature, and pressure favor the formation of diols whilst the opposite is true for the hydroxy esters.

Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles

We herein report a transition-metal-free cross-coupling between secondary alkyl halides/mesylates and aryl/alkenylboronic acid, providing expedited access to a series of nonchiral/chiral coupling products in moderate to good yields. Stereospecific SN2-type coupling is developed for the first time with alkenylboronic acids as pure nucleophiles, offering an attractive alternative to the stereospecific transition-metal-catalyzed C(sp2)-C(sp3) cross-coupling.