29922-56-3

Usage

Chemical Properties

off-white crystalline

InChI:InChI=1/C7H7BrO2/c8-6-3-5(4-9)1-2-7(6)10/h1-3,9-10H,4H2

Upstream product

• 623-05-2 (4-hydroxyphenyl)methanol 
• 2973-78-6 3-bromo-4-hydroxybenzylaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 14348-41-5 3-bromo-4-hydroxy-benzoic acid 
• 29415-97-2 methyl 3-bromo-4-hydroxybenzoate 
• 6627-55-0 2-bromo-p-cresol 
• 107-21-1 ethylene glycol 
• 67-56-1 methanol 

Downstream Products

• 1276113-33-7 2-bromo-4-(((tert-butyldimethylsilyl)oxy)-methyl)phenol 
• 1276113-32-6 (2-bromo-4-(((tert-butyldimethylsilyl)oxy)methyl)phenoxy)(tert-butyl)dimethylsilane 
• 1326774-95-1 (3S)-3-((tert-butyldimethylsilyl)oxy)-3,7-dimethyl-1-[2'-((2''-(trimethylsilyl)ethoxy)methoxy)-5'-(((2''-(trimethylsilyl)ethoxy)methoxy)methyl)phenyl]oct-6-en-1-ol 
• 1326774-96-2 (3S)-1-(2'-hydroxy-5'-(hydroxymethyl)phenyl)-3,7-dimethyloct-6-ene-1,3-diol 
• 1326774-97-3 (3'S)-4-hydroxy-3-(3'-hydroxy-3',7'-dimethyloct-6'-enoyl)benzaldehyde 
• 809281-21-8 (3'S)-4-hydroxy-3-(3'-hydroxy-3',7'-dimethyloct-6'-enoyl)benzoic acid 
• 1326775-04-5 (2-((2'-bromo-4'-(((2''-(trimethylsilyl)ethoxy)methoxy)methyl)phenoxy)methoxy)ethyl)trimethylsilane 
• 71119-01-2 2-bromo-4-(methoxymethyl)phenol 
• 1554857-70-3 2-bromo-4-(bromomethyl)phenol 
• 1547399-58-5 2-bromo-4-(bromomethyl)phenol 
• 1580053-71-9 C₂₆H₂₇BrFN₃O₂ 
• 1580053-70-8 C₂₃H₂₉BrFN₃O₂ 
• 1580053-69-5 C₂₂H₂₇BrFN₃O₂ 
• 1580053-68-4 C₂₂H₂₇BrFN₃O₂ 

Relevant academic research and scientific papers

Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates

Benzothieno[60]fullerenes were synthesized using fullerenyl cations as key intermediates. The reaction proceeded through a nucleophilic attack of the sulfur atom as a weak nucleophile to the fullerenyl cation electrophile. A monoarylated fullerene, (2-methylthiophenyl)hydro[60]fullerene, C60ArH (Ar = C6H4-SMe-2 and so on; four derivatives) was subjected to deprotonation with KOtBu to form a fullerenyl anion ArC60-, followed by oxidation using I2 to generate a fullerenyl cation ArC60+, leading to intramolecular demethylative cyclization via fullerene cation-S interaction to the product. Electrochemical and computational studies revealed slightly narrower band gap of this compound than usual fullerene derivatives because of the relatively high-lying HOMO of the fused thieno moiety.

Synthesis of Benzothieno[60]fullerenes through Fullerenyl Cation Intermediates

Benzothieno[60]fullerenes were synthesized using fullerenyl cations as key intermediates. The reaction proceeded through a nucleophilic attack of the sulfur atom as a weak nucleophile to the fullerenyl cation electrophile. A monoarylated fullerene, (2-methylthiophenyl)hydro[60]fullerene, C60ArH (Ar = C6H4-SMe-2 and so on; four derivatives) was subjected to deprotonation with KOtBu to form a fullerenyl anion ArC60-, followed by oxidation using I2 to generate a fullerenyl cation ArC60+, leading to intramolecular demethylative cyclization via fullerene cation-S interaction to the product. Electrochemical and computational studies revealed slightly narrower band gap of this compound than usual fullerene derivatives because of the relatively high-lying HOMO of the fused thieno moiety.

A Quantitative Assay of Sodium Triacetoxyborohydride

Sodium triacetoxyborohydride (STAB) is a common reducing agent with potency that degrades over time and is not uniformly assigned. A simple assay based on an aldehyde reduction has been developed to determine the active borohydride content of this reagent. The HPLC assay yield of a salicylaldehyde reduction has been shown to accurately determine this potency and has been validated against the H2 evolution method as well as yields obtained from a reductive amination. The use of these assay data to adjust the STAB charge as well to optimize a reductive amination has been demonstrated.

The synthesis of 4,7-disubstituted-2H-benzo[b][1,4]-oxazin-3(4H)-ones using Smiles rearrangement and their in vitro evaluation as platelet aggregation inhibitors

A series of novel benzo[b][1,4]oxazin-3(4H)-one derivatives were synthesized as platelet aggregation inhibitors for structure-activity relationships (SAR) analysis. The synthetic pattern, involved Smiles rearrangement for the preparation of benzoxazine, was proven to be more efficient than the conventional methods. Biological evaluation demonstrated that among all the synthesized compounds, compound 9u (IC50 = 9.20 μM) exhibited the most potent inhibition activity compared with aspirin, the positive control (IC50 = 7.07 μM). Molecular docking revealed that these set of compounds could be the GPIIb/IIIa antagonist for that they could be situated in the binding site of GPIIb/IIIa receptor quite well.

A highly efficient approach to vanillin starting from 4-cresol

A highly efficient approach to the famous flavor and fragrance compound vanillin has been developed starting from 4-cresol with the attention focused on improving the sustainability of all the reactions. The approach involves a three-step sequence of the quasi-quantitative selective clean oxybromination of 4-cresol, the high-yield selective aerobic oxidation of 2-bromo-4-cresol, and the quantitative methoxylation of 3-bromo-4-hydroxybenzaldehyde with the recovery of pure methanol. Herein, the pivotal oxidation and methoxylation reactions are logically investigated and developed into two concise methodologies. As a green alternative, the approach holds significant value for the sustainable manufacturing of vanillin. the Partner Organisations 2014.

A domino process for benzyne preparation: Dual activation of o-(trimethylsilyl)phenols by nonafluorobutanesulfonyl fluoride

Benzynes were generated from o-(trimethylsilyl)phenols using nonafluorobutanesulfonyl fluoride (NfF) by a domino process, i.e., the nonaflation of the phenolic hydroxyl group of o-(trimethylsilyl)phenols by NfF followed by the attack of the produced fluoride ion on the trimethylsilyl group. The generated benzyne immediately underwent various reactions to give polysubstituted benzenes.

Enantioselective total synthesis and absolute configuration of the alleged structure of crassinervic acid

An enantioselective synthesis of the structure reported for the natural antifungal compound, (-)-crassinervic acid (1), has been achieved starting from geraniol and p-hydroxybenzoic acid. The key chirality-inducing step is a Sharpless asymmetric epoxidation of an allylic alcohol, on the basis of which the S configuration can be assigned to the (-) natural enantiomer. The discrepancies between the spectroscopic data for synthetic and natural crassinervic acid cast some doubts on the structure assigned to the natural compound. A possible revised structure is discussed.

A convenient method to reduce hydroxyl-substituted aromatic carboxylic acid with NaBH4/Me2SO4/B(OMe)3

The reduction of hydroxyl-substituted aromatic carboxylic acid with NaBH4/Me2SO4/B(OMe)3 is described. Borane is generated by the reaction of NaBH4 with Me2SO4 in THF, which is as efficient as the commercial one. B(OMe)3 has been successfully applied to increase the reactivity and selectivity of this reaction. The optimum ratio of borane/B(OMe)3/acid is studied, and a variety of hydroxyl-substituted aromatic acids are reduced in good yields.

Dual aromatase-steroid sulfatase inhibitors

By introducting the steroid sulfatase inhibitory pharmacophore into aromatase inhibitor 1 (YM511), two series of single agent dual aromatase-sulfatase inhibitors (DASIs) were generated. The best DASIs in'vitro (JEG-3 cells) are 5, (IC50(aromatase) = 0.82 nM; IC 50(sulfatase) = 39 nM), and 14, (IC50(aromatase) = 0.77 nM; IC50(sulfatase) = 590 nM). X-ray crystallography of 5, and docking studies of selected compounds into an aromatase homology model and the steroid sulfatase crystal structure are presented. Both 5 and 14 inhibit aromatase and sulfatase in PMSG pretreated adult female Wistar rats potently 3 h after a single oral 10 mg/kg dose. Almost complete dual inhibition is observed for 5 but the levels were reduced to 85% (aromatase) and 72% (sulfatase) after 24 h. DASI 5 did not inhibit aldosterone synthesis. The development of a potent and selective DASI should allow the therapeutic potential of dual aromatase-sulfatase inhibition in hormone-dependent breast cancer to be assessed.