146952-30-9

Usage

Chemical compound

Benzenemethanol, 2-(acetyloxy)-

Physical form

white, crystalline powder

Function

pain reliever, anti-inflammatory, fever reducer

Mechanism of action

inhibits production of certain chemicals causing pain and inflammation

Specific content

Active ingredient in aspirin
Widely used medication
Available over the counter
Used to treat headaches, muscle aches, arthritis, fevers

Potential side effects

stomach irritation, bleeding in some individuals

Upstream product

• 5663-67-2 2-acetoxybenzaldehyde 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 90-01-7 salicylic alcohol 
• 75-36-5 acetyl chloride 
• 89-95-2 2-methyl-benzyl alcohol 
• 108-24-7 acetic anhydride 

Downstream Products

• 1118974-20-1 2-acetyloxybenzyl diethylphosphate 
• 15068-08-3 o-chloromethylphenyl acetate 

Relevant academic research and scientific papers

Nickel(II) Catalyzed Hydroboration: A Route to Selective Reduction of Aldehydes and N-Allylimines

A cationic [(iminophosphine)nickel(allyl)]+ complex was found to be sufficiently electrophilic to activate aldehydes and N-allylimines to undergo hydroboration with pinacolborane (HBpin) under mild reaction conditions. The catalyst displayed excellent selectivity toward aldehydes in the presence of ketones. A wide variety of functional groups were tolerated, including halogens, NO2, CN, OMe, and alkenes for both aldehydes and imines. Electron-rich substrates were found to be significantly more reactive than their electron poor counterparts, a feature that was correlated to their enhanced ability to coordinate to the Lewis acidic nickel center.

Catalytic hydrosilylation of carbonyl compounds by hydrido thiophenolato iron(II) complexes

The hydrosilylation of aldehydes and ketones under mild conditions with hydrido thiophenolato iron(II) complexes [cis–Fe(H)(SAr)(PMe3)4] (1–4) as catalysts is reported using (EtO)3SiH as an efficient reducing agent in the yields up to 95%. Among them complex 1 is the best catalyst. Complex 1 could also be used as catalyst to reduce the α,β-unsaturated carbonyl compounds selectively to the α,β-unsaturated alcohols in high yields.

Homoleptic iron(II) and cobalt(II) bis(phosphoranimide) complexes for the selective hydrofunctionalization of unsaturated molecules

Low-coordinate homoleptic bulky M2(NPtBu3)4 (M = Fe (A), Co (B)) complexes were synthesized and characterized as dimeric structures by crystallographic studies. The iron complex A can catalyze the hydroboration reaction of aldehydes and ketones. The cobalt complex B outperformed its iron counterpart in hydrogenations of several typical alkenes and alkynes under mild conditions. Poisoning experiments indicate that the Co(ii)/HBpin catalytic system could be homogeneous.

Selective C-F and C-H Activation of Fluoroarenes by Fe(PMe3)4 and Catalytic Performance of Iron Hydride in Hydrosilylation of Carbonyl Compounds

The reactions of perfluorinated toluene (CF3C6F5), pentafluoropyridine (C5NF5), and hexafluorobenzene (C6F6) with the iron(0) complex Fe(PMe3)4 were investigated. The Fe(I) complexes (4-CF3C6F4)Fe(PMe3)4 (1), (4-C5NF4)Fe(PMe3)4 (2), and (C6F5)Fe(PMe3)4 (3) were obtained by selective activation of the C-F bonds. However, under similar reaction conditions, the reaction of Fe(PMe3)4 with perfluoronaphthalene (C10F8) afforded a π-coordinated Fe(0) complex, (η4-1,2,3,4-C10F8)Fe(PMe3)3 (4), and the expected C-F bond activation reaction was not observed. The expected iron hydride (C6F5)FeH(PMe3)4 (6) could be obtained in a yield of 80% by the reaction of bromopentafluorobenzene with Fe(PMe3)4 and subsequent reduction with NaBH4. The molecular structures of complexes 2, 4, and 6 were determined by single-crystal X-ray diffraction. Complexes 1-4 and 6 could be used as catalysts for the hydrosilylation of carbonyl compounds. Among them, complex 6 is the best catalyst. The selective reduction of carbonyl groups of α,β-unsaturated aldehydes and ketones was also realized with 6 as catalyst.

Ruthenium Catalyzed Selective Hydroboration of Carbonyl Compounds

Using the [Ru(p-cymene)Cl2]2 (1) complex, catalytic hydroboration of aldehydes and ketones with pinacolborane under neat and mild conditions is reported. At rt, chemoselective hydroboration of aldehydes over the ketones is also attained. Mechanistic studies confirmed the immediate formation of monohydride bridged dinuclear complex [{(μ6-p-cymene)RuCl}2(μ-H-μ-Cl)] (1b) from the reaction of 1 with pinacolborane, which catalyzed the highly efficient hydroboration reactions. The catalytic cycle containing mononuclear Ru-H species and intramolecular 1,3-hydride transfer is postulated.

Synthesis and biological activity of acetyl-protected hydroxybenzyl diethyl phosphates (EHBP) as potential chemotherapeutic agents

Several acetyl-protected hydroxybenzyl diethyl phosphates (EHBPs) that are capable of forming quinone methide intermediates were synthesized and their cell growth inhibitory properties were evaluated in four different human cancer cell lines. Compounds 1, 1a, and 1b, corresponding to (4-acetyloxybenzyl diethylphosphate), (3-methyl-4-acetyloxybenzyl diethylphosphate), and (3-chloro-4-acetyloxybenzyl diethylphosphate), were significantly more potent than compounds 2 and 3, (2-acetyloxybenzyl diethylphosphate) and (3-acetyloxybenzyl diethylphosphate), respectively. Using HT-29 human colon cancer cells, compounds 1 and 3 increased apoptosis, inhibited proliferation, and caused a G2/M block in the cell cycle. Our data suggest that these compounds merit further investigation as potential anti-cancer agents.

Practical and chemoselective reduction of acyl chloride to alcohol by borohydride in aqueous dichloromethane

A simple methodology for the reduction of acid chlorides to their corresponding alcohols has been developed. Various carboxylic acids were converted to alcohols in excellent yields using NaBH4-K2CO3 in a mixed solvent system of dichloromethane and water (1:1) in the presence of a phase-transfer catalyst at low temperature. The importance of the work is its simplicity, selectivity, excellent yield, and very short reaction time. This new reduction condition has proved to be an excellent chemoselective method for a range of acid chlorides in the presence of various functional groups.

Mn(0)-mediated chemoselective reduction of aldehydes. Application to the synthesis of α-deuterioalcohols

A mild, simple, safe, chemoselective reduction of different kinds of aldehydes to the corresponding alcohols mediated by the Mn dust/water system is described. In addition to this, the use of D2O leads to the synthesis of α-deuterated alcohols and constitutes an efficient, inexpensive alternative for the preparation of these compounds.

Study of different substituted cyclic and acyclic benzylpronucleotides of d4T relative to their hydrolytic stability and antiviral activity

CycloSal-d4TMP and two different bis(benzyl) phosphate triesters of the antivirally active nucleoside analog d4T were studied with regard to their chemical hydrolysis behavior at pH 7.3, in CEM/0 cell extracts, and their anti-HIV activity. In contrast to