1766-28-5

Usage

Classification

Primary alcohol

Physical state

Colorless liquid

Odor

Slightly sweet and floral

Uses

a. Synthesis of pharmaceuticals
b. Synthesis of other organic compounds
c. Building block for various chemicals
d. Chiral auxiliary in asymmetric synthesis
e. Potential intermediate in the manufacture of agrochemicals and fragrances

Upstream product

• 920-39-8 isopropylmagnesium bromide 
• 459-57-4 4-fluorobenzaldehyde 
• 67-56-1 methanol 
• 403-41-8 1-(4-Fluorophenyl)ethanol 
• 75-26-3 isopropyl bromide 
• 78-84-2 isobutyraldehyde 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 75-30-9 2-iodo-propane 
• 352-13-6 4-flourophenylmagnesium bromide 

Downstream Products

• 702-09-0 1-fluoro-4-(2-methylprop-1-en-1-yl)benzene 
• 26393-91-9 1-(4-fluorophenyl)-2-methylpropan-1-one 
• 335287-91-7 1-(4-fluorophenyl)-2-hydroxy-2-methylpropan-1-one 
• 36758-12-0 2-methyl-1-(4-phenoxyphenyl)propan-1-one 

Relevant academic research and scientific papers

Manganese(I)-Catalyzed β-Methylation of Alcohols Using Methanol as C1 Source

Highly selective β-methylation of alcohols was achieved using an earth-abundant first row transition metal in the air stable molecular manganese complex [Mn(CO)2Br[HN(C2H4PiPr2)2]] 1 ([HN(C2H4PiPr2)2]=MACHO-iPr). The reaction requires only low loadings of 1 (0.5 mol %), methanolate as base and MeOH as methylation reagent as well as solvent. Various alcohols were β-methylated with very good selectivity (>99 %) and excellent yield (up to 94 %). Biomass derived aliphatic alcohols and diols were also selectively methylated on the β-position, opening a pathway to “biohybrid” molecules constructed entirely from non-fossil carbon. Mechanistic studies indicate that the reaction proceeds through a borrowing hydrogen pathway involving metal–ligand cooperation at the Mn-pincer complex. This transformation provides a convenient, economical, and environmentally benign pathway for the selective C?C bond formation with potential applications for the preparation of advanced biofuels, fine chemicals, and biologically active molecules.

Synthesis of Halomethyl Isoxazoles/Cyclic Nitrones via Cascade Sequence: 1,2-Halogen Radical Shift as a Key Link

A novel iminoxyl radical-promoted dichotomous regioselective 5-exo-trig cyclization onto vinylic halogen/1,2-halogen radical shift sequence is developed for the synthesis of halomethyl isoxazoles/cyclic nitrones using β-halo-β,?- and ?-halo-?,?-unsaturated ketoximes as the substrates and PhI(OAc)2/TEMPO as the oxidation system. DFT calculations reveal that a halogen-bridged three-membered ring transition state is involved in the 1,2-Cl-/Br-atom shift, while the 1,2-I atom migration can be taken into account with an elimination/readdition mechanism. The migration ability was indicated to be ranked in the following order: I > Br > Cl.

Halogen-bonded iodonium ion catalysis: A route to α-hydroxy ketones: Via domino oxidations of secondary alcohols and aliphatic C-H bonds with high selectivity and control

A domino synthesis of α-hydroxy ketones has been developed from benzylic secondary alcohols employing catalytic iodonium ions stabilized by DMSO. The reaction proceeds through an unprecedented sequential oxidation of alcohols to ketone and its α-hydroxylation in a controlled manner. The spectroscopic evidence establishes the possibility of formation of a stable halogen-bonded adduct between DMSO and iodonium ions.

Reaction of secondary and tertiary aliphatic halides with aromatic aldehydes mediated by chromium(II): a selective cross-coupling of alkyl and ketyl radicals

Takai-Utimoto reactions with secondary and tertiary aliphatic halides usually failed according to previous reports. Now, significant improvements could be achieved, and especially secondary aliphatic halides can be coupled to aromatic aldehydes in yields of up to >95%. A variety of processes are competing with the desired one, and thus conditions must be adapted to the nature of the aldehyde as well as the aliphatic halide used, as the outcome of these reactions is strongly affected by the putative radical intermediates.

Acetamide and substituted acetamide-containing thiourea inhibitors of herpes viruses

Compounds of the formula: are useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and -7, and Kaposi herpesvirus.

Diaminopuridine-containing thiourea inhibitors of herpes viruses

Compounds of the formula STR1 are useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and -7, and Kaposi herpesvirus.