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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
2-Hydroxybenzyl alcohol (Salicyl alcohol), which can be found in a number of food items such as red huckleberry, rye, jerusalem artichoke, and ceylon cinnamon, is precursor of salicylic acid and is formed from salicin by enzymatic hydrolysis by Salicyl-alcohol beta-D-glucosyltransferase or by acid hydrolysis.
Synonyms: 2-Hydroxybenzyl alcohol; Saligenin
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 90-01-7 |
Formula : | C7H8O2 |
M.W : | 124.14 |
SMILES Code : | C1=CC=CC(=C1O)CO |
Synonyms : |
2-Hydroxybenzyl alcohol; Saligenin
|
MDL No. : | MFCD00004617 |
InChI Key : | CQRYARSYNCAZFO-UHFFFAOYSA-N |
Pubchem ID : | 5146 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | at 150℃; for 1.0h;Pyrex pressure bottle; | 1. Synthesis of 2-methoxymethyl-phenol Il-a 2-Hydroxybenzyl alcohol (10 g, 80.55 mmol) is dissolved in dry methanol (150 mL) and transferred to a Pyrex pressure bottle which is internally threaded and fitted with a double o-ring screw cap. The mixture is then heated (150 C) for 1 h. Evaporation provides 10.8 g (98%) of a dark brown oil which is used directly in the next reaction; ^-NMR (500 MHz, CDC13); delta 3.42 (s, 3 H), 4.69 (s, 2 H), 6.8-7.22 (mm, 4 H), 7.78 (s, 1 H). |
58% | at 150℃; for 4.0h; | Preparation 77: 2-(Methoxymethyl)phenol A solution of 2-hydoxybenzyl alcohol (5 g, 40 mmol) in methanol (25 mL) was heated in a sealed vessel at 150 C. for 4 hours. The reaction mixture was then concentrated in vacuo and the residue was purified by fractional distillation (90 C./10 mm Hg) to afford the title compound as a colourless liquid in 58% yield, 3.22 g. LRMS APCI m/z 137 [M-H]- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With sodium chloride; In N-methyl-acetamide; | PREPARATION 1 2-Benzyloxybenzyltriphenylphosphonium chloride 151 g of potassium t-butoxide were added, whilst ice-cooling and stirring, to a solution of 152 g of salicyl alcohol in 600 ml of dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes; 160 ml of benzyl bromide were then added dropwise to the mixture. The reaction mixture was then stirred at a temperature of from 30 to 40 C. for 2 hours, after which it was partitioned between ethyl acetate and water. The organic layer was washed twice, each time with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The oily residue thus obtained was subjected to column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 228.5 g (yield 87%) of 2-benzyloxybenzyl alcohol as a colorless oil. |
87.8% | In isopropyl alcohol;Heating / reflux; | 13.78 g (80.5 mmol) of benzyl bromide, 10.00 g (80.5 mmol) of 2-hydroxybenzyl alcohol and 11.13 g (80.5 mmol) of potassium carbonate in 270 ml of 2-propanol are heated at reflux overnight. The suspension is cooled, taken up in ethyl acetate, washed with 1N aqueous sodium hydroxide solution and water, dried over magnesium sulfate and concentrated under reduced pressure.Yield: 15.15 g (87.8% of theory)Rf(SiO2, C4E1): 0.14 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With zinc(II) chloride; In 1,4-dioxane; at 100℃; for 24h; | (+/-)-Dichamanetm (2).; A solution of 4 (60 mg, 0.23 mmol, 1.0 equiv), <n="78"/>2-hydroxybenzyl alcohol 10 (61 mg, 0.48 mmol, 2.1 equiv), and anhydrous ZnCl2 (67 mg, 0.48 mmol, 2.1 equiv) in anhydrous dioxane (2 mL) was heated at 100 C for 24 h under an atmosphere of argon. After cooling, the solvent was removed in vacuo and the crude product was purified by flash column chromatography (0 to 30% EtOAc/Hexanes) to afford 2 (65 mg, 59%) as a light yellow solid, Rv 0.32 (30% EtOAc in Hexanes): 1H NMR (500 MHz5 CD3COCD3) delta 12.73 (s, IH), 9.15 (br s, 2H), 7.59 (d, J= 7.5 Hz, 2H),7.46-7.38 (m, 3H), 7.23-7.22 (m, IH), 7.09-7.07 (m, IH), 7.04-6.99 (m, 2H), 6.86 (t, J= 7.5 Hz, 2H), 6.77-6.69 (m, 2H), 5.64 (dd, J= 2.5, 10.0 Hz, 2H), 3.92-3.91 (two s, 4H), 3.23 (dd, J= 13.0, 4.0 Hz, IH), 2.90 (dd, J= 3.0, 14.0 Hz, IH); 13C NMR (125 MHz, CD3COCD3) delta 198.7, 163.6, 161.7, 160.6, 155.6, 141.2, 132.3, 132.1, 130.6, 130.5, 130.4, 129.03, 128.99, 128.7, 128.67, 128.3, 122.1, 122.0, 116.9, 116.8, 109.6, 108.7, 104.5, 81.0, 44.6, 24.4, 23.7; IR (CDCl3) 3427, 1631, 1489, 1457 cm"1; MS (ESI) m/z calcd for C29H24O6 (M + H)+ 469.17, found 469.98. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In N,N-dimethyl-formamide; for 3h;Reflux; | General procedure: A mixture of hydroxybenzyl alcohol 1a-i (8 mmol) and 5-aryltetrazole 2a-f (8 mmol) was refluxed for 3 h inDMF (8 ml). The reaction mixture was then cooled, pouredinto water, the precipitate that formed was filtered off,washed with water, and air-dried. In the case when twoisomers were formed, the obtained mixture was separatedby column chromatography (eluent 1,2-dichloroethane) andpurified by recrystallization from EtOH, unless statedotherwise. All the obtained compounds were colorlesscrystals. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | General procedure: In an oven-dried 10-mL round-bottom flask, 10 mg catalyst 4 (3.2 mol%) along with 1 mmol amine or hydroxyl amine was added to 7 mL absolute ethanol at ambient temperature.Then, 1 mmol of alcohol was added to the reaction mixture and stirred under O2 atmosphere (~1 atm.). After 14-60 min,yellow to red sediments were appeared which show successful oxidation of alcohols followed by imine formation. The product was filtered and added to 20 mL of hot methanol which just dissolved the imine compound. The filtration of the reaction mixture left a solid on the filter that was the catalyst 4. The remained solution set a side overnight for crystallization, and the recovered catalyst was reused for the next run (Scheme 2). | |
95% | General procedure: In a typical run, alcohol (10.0 mmol) and the catalyst (40 mg,0.5 mol % Mn) were added to 1.5mL H2O2 37% (10 mL round bottomflask). The reaction was stirred at room temperature in air atmospherefor 10 min. Then NH2OHHCl and/or amine (10.0 mmol) wasadded to the mixture. Progress of the reaction was monitored byTLC. After completion of the reaction, 10 mL of hot ethanol wasadded to the mixture, then the catalyst 9 was filter off by anexternal magnet. The product was isolated by removal of the solventunder reduced pressure followed by washing with deionizedwater (3 x 5 mL). Products were purified by recrystallization in hotethanol and then isolated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Mg/Fe mixed oxide catalyst with an Mg/Fe atomic ratio of 0.25; at 300℃; under 760.051 Torr;Flow reactor; Inert atmosphere; | General procedure: The reactivity test was carried out in a continuous-downflowreactor at different temperatures, from 250 to 450 C, at atmosphericpressure. The reactor was loaded with variable volumesof catalyst, shaped in particles with diameters ranging from 0.25to 0.6 mm. The reagent solution was fed by a Precidor Type 5003diffusion pump together with N2 as the carrier gas. The flow rateof the carrier and reagent solution depended on the desired contacttime. The reactor outlet was condensed in 25 ml of HPLC-gradeacetone. |
Tags: Salicyl alcohol | 2-Hydroxybenzyl alcohol | Aryls | Alcohols | Organic Building Blocks | 90-01-7
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P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
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P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
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P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
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