Conditions | Yield |
---|---|
With N-methylpyrrolidine zinc borohydride In tetrahydrofuran at 20℃; for 4h; | 100% |
With sodium tetrahydroborate In methanol at 0℃; | 100% |
With triethylamine; 2-hydroxyethanethiol In acetonitrile for 23h; Irradiation; | 100% |
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With water | 100% |
Conditions | Yield |
---|---|
With aniline; (ϖ-allyl)palladium triflate based catalyst at 30℃; for 0.333333h; | 99% |
With ammonium formate; palladium on activated charcoal In methanol for 0.5h; Heating; | 96% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 4.5h; Product distribution; Further Variations:; Reagents; reagent ratios; | 96% |
With [Zn(BH4)2(py)] In tetrahydrofuran for 3.6h; Heating; | 92% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With zirconium(IV) borohydride In tetrahydrofuran at 25℃; for 2h; Reduction; | 96% |
With zinc(II) tetrahydroborate; cyclohexene In tetrahydrofuran for 4h; Heating; | 72% |
With lithium aluminium tetrahydride In diethyl ether | |
With sodium tetrahydroborate In methanol; 1,2-dimethoxyethane for 1h; Reduction; Heating; |
1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With methanol; trimethylsilyl bromide at 20℃; for 5h; chemoselective reaction; | 96% |
With methanesulfonic acid In methanol at 20℃; for 1.33333h; | 94% |
sulfated SnO2 In methanol at 20℃; for 16h; | |
With trifluoroacetic acid In methanol at 25℃; for 0.333333h; Reagent/catalyst; |
p-hydroxymethylphenylboronic acid
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With urea hydrogen peroxide adduct In acetonitrile at 27 - 29℃; for 0.5h; Green chemistry; chemoselective reaction; | 95% |
With 1-carboxymethyl-3-methylimidazolium tetrachloroferrate; dihydrogen peroxide In neat (no solvent) at 20℃; for 0.133333h; | 91% |
With 1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine; oxygen; hydrazine hydrate In methanol; 2,2,2-trifluoroethanol at 20℃; under 760.051 Torr; for 2h; | 74% |
4-trityloxymethyl-phenol
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With sodium hydrogen sulfate; silica gel In methanol; dichloromethane at 20℃; for 2h; | 93% |
4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)phenol
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
ruthenium trichloride In water; acetonitrile at 20℃; for 0.416667h; | 92% |
With lithium borohydride In methanol at 20℃; for 0.5h; | 90% |
With sulfuric acid; silica gel In methanol at 20℃; for 2.16667h; | 83% |
4-(trimethylsilyloxymethyl)phenoxytrimethylsilane
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium chloride at 20℃; for 12h; | 92% |
Conditions | Yield |
---|---|
With aluminum oxide In neat (no solvent) at 35℃; for 0.0166667h; microwave irradiation; | 89% |
1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide at 100℃; for 3h; | 88% |
[4-(2-trimethylsilanylethoxy)phenyl]methanol
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
Stage #1: [4-(2-trimethylsilanylethoxy)phenyl]methanol With cesium fluoride In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere; Stage #2: With water In N,N-dimethyl-formamide Inert atmosphere; | 88% |
(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With sodium L-ascorbate; fluorescein free acid In aq. phosphate buffer for 0.5h; pH=7.4; Reagent/catalyst; Irradiation; | 88% |
(E)-6-(4-hydroxybenzyloxy)hex-3-en-2-one
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
Stage #1: (E)-6-(4-hydroxybenzyloxy)hex-3-en-2-one With sodium hydride In N,N-dimethyl-formamide at 22℃; for 1h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide | 87% |
4-iodo-benzyl alcohol
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With copper(l) iodide; triethanolamine; tetrabutylammomium bromide; water; potassium hydroxide at 120℃; for 24h; Inert atmosphere; | 86% |
With copper(l) iodide; triethanolamine; tetrabutylammomium bromide; potassium hydroxide In water at 120℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry; | 86% |
With oxygen; triethylamine In acetonitrile at 32℃; for 24h; Schlenk technique; UV-irradiation; | 53% |
4-trimethylsilyloxymethylphenol
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With water In dichloromethane at 20℃; for 0.916667h; | 85% |
With Kaolinitic clay; water for 0.025h; Irradiation; microwave; | 82% |
4-(trimethylsilyloxymethyl)phenoxytrimethylsilane
A
(4-hydroxyphenyl)methanol
B
(4-Trimethylsilanyloxy-phenyl)-methanol
Conditions | Yield |
---|---|
With Dowex CCR-2 In ethanol for 10h; Ambient temperature; | A 19% B 82% |
With Dowex CCR-2 resin In ethanol for 10h; Product distribution; Ambient temperature; competitive desilylation with other TMS ethers, investigation; | A 19% B 82% |
(S)-1-((S)-2-tert-Butoxycarbonylamino-propionyl)-pyrrolidine-2-carboxylic acid 4-phenylacetoxy-benzyl ester
A
(4-hydroxyphenyl)methanol
B
N-tert-butoxycarbonyl-L-alanyl-L-proline
Conditions | Yield |
---|---|
With penicillin G acylase In methanol; phosphate buffer pH=7; Enzymatic reaction; | A n/a B 82% |
(S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-phenyl-propionic acid 4-phenylacetoxy-benzyl ester
A
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With penicillin G acylase In methanol; phosphate buffer pH=7; Enzymatic reaction; | A n/a B 82% |
formaldehyd
phenol
A
(4-hydroxyphenyl)methanol
B
salicylic alcohol
Conditions | Yield |
---|---|
With sodium metaborate tetrahydrate In water at 60℃; Green chemistry; regioselective reaction; | A 10% B 80% |
With sodium hydroxide In water at 30℃; for 1h; Product distribution; other reagents, reagent concentrations, time and solvents; | |
With sodium hydroxide; HP-β-cyclodextrin In water at 4℃; for 240h; Product distribution; further additives; |
(S)-2-((S)-2-Allyloxycarbonylamino-3-methyl-butyrylamino)-propionic acid 4-phenylacetoxy-benzyl ester
A
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With penicillin G acylase In methanol; phosphate buffer pH=7; Enzymatic reaction; | A n/a B 80% |
(2S,3S)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-3-methyl-pentanoic acid 4-phenylacetoxy-benzyl ester
A
(4-hydroxyphenyl)methanol
B
N-Boc-L-Ser-Ile-OH
Conditions | Yield |
---|---|
With penicillin G acylase In methanol; phosphate buffer pH=7; Enzymatic reaction; | A n/a B 80% |
Conditions | Yield |
---|---|
With 1-N-ferrocenylmethyl benzimidazole tagged polymer In N,N-dimethyl-formamide Reflux; | 79% |
With 1-butylpyridinium bromide for 0.05h; microwave irradiation; | 78% |
With [2Fe-2S] ferredoxin HaPux; CYP199A4 from the rhodopseudomonas palustrisstrain HaA2 (S244D); flavin-dependent ferredoxin reductase HaPuR; oxygen; NADH In aq. buffer pH=7.4; Catalytic behavior; Reagent/catalyst; regioselective reaction; |
L-Cysteine
A
aminoferrocene
B
(4-hydroxyphenyl)methanol
C
3-carboxy-5-oxoperhydro-1,4-thiazepine
Conditions | Yield |
---|---|
With 2-amino-4-mercaptobutyric acid; GLUTATHIONE Electrochemical reaction; | A n/a B n/a C 79% |
Conditions | Yield |
---|---|
With triethanolamine In water at 20℃; for 18h; Sonication; Irradiation; Green chemistry; | 78% |
Conditions | Yield |
---|---|
With air; cetyltrimethylammonim bromide at 30℃; | A n/a B 77% |
4-tert-butyl-butyldimethylsilyloxybenzyl alcohol THP ether
(4-hydroxyphenyl)methanol
Conditions | Yield |
---|---|
With iodine In methanol for 2h; desilylation; Heating; | 75% |
Conditions | Yield |
---|---|
With zinc(II) tetrahydroborate In tetrahydrofuran for 4h; Inert atmosphere; Reflux; | 70% |
With ethanol; potassium tert-butylate; C39H41FeMnN2O5P(1+)*Br(1-) In tert-butyl alcohol at 100℃; for 22h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 10% |
With lithium aluminium tetrahydride; diethyl ether |
formaldehyd
phenol
A
4H-1,3,2-benzodioxin
B
(4-hydroxyphenyl)methanol
C
salicylic alcohol
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid at 65℃; for 20h; | A 3% B 68% C 7% |
Conditions | Yield |
---|---|
With Candida cylindracea lipase In hexane for 4h; | 100% |
novozyme 435 In acetonitrile at 20℃; for 6h; Enzymatic reaction; | 99% |
iodine at 20℃; for 2h; | 95% |
With porcine pancreatic lipase (PPL, Type II) In tetrahydrofuran at 42 - 45℃; for 48h; Acetylation; | 80% |
With Pseudomonas cepacia PS lipase In di-isopropyl ether at 25℃; for 0.5h; |
Conditions | Yield |
---|---|
With Oxone In ethanol at 20℃; for 2h; Catalytic behavior; | 100% |
With tert.-butylhydroperoxide; V/SiO2 In decane; tert-butyl alcohol at 25℃; for 3h; | 99.1% |
With titanium(IV) oxide; oxygen at 29.84℃; under 760.051 Torr; for 6h; Sealed tube; Irradiation; | 99% |
(4-hydroxyphenyl)methanol
tert-butyldimethylsilyl chloride
4-((tert-butyldimethylsilyloxy)methyl)phenol
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.75h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1.5h; Cooling with ice; | 95% |
With sodium hydride In N,N-dimethyl-formamide | 95.6% |
2-nitropropane
(4-hydroxyphenyl)methanol
1-nitro-1,1-dimethyl-2-(4-hydroxyphenyl]ethane
Conditions | Yield |
---|---|
With potassium tert-butylate In diethylene glycol dimethyl ether at 20 - 137℃; for 6h; | 99.6% |
With potassium tert-butylate In diethylene glycol dimethyl ether Cooling with ice; Reflux; | 83% |
With tetrabutyl ammonium fluoride at 130℃; for 15h; | 73% |
(4-hydroxyphenyl)methanol
tert-butyldimethylsilyl chloride
1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; for 4h; | 99% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere; | 99% |
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; | 97% |
(4-hydroxyphenyl)methanol
[4-(2-phenyl-quinolin-4-ylmethoxy)-phenyl]-methanol
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; | 99% |
(4-hydroxyphenyl)methanol
[4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)phenyl]methanol
Conditions | Yield |
---|---|
Stage #1: 2-chloro[1,3]thiazolo[4,5-b]pyridine hydrochloride With potassium carbonate In acetonitrile at 50℃; for 3h; Inert atmosphere; Stage #2: (4-hydroxyphenyl)methanol In acetonitrile for 3h; Reflux; | 99% |
(4-hydroxyphenyl)methanol
benzyl alcohol
A
benzaldehyde
B
4-hydroxy-benzaldehyde
Conditions | Yield |
---|---|
With air; potassium carbonate at 20℃; for 12h; | A 99% B 11% |
Conditions | Yield |
---|---|
With palladium dichloride In methanol at 40℃; for 24h; Inert atmosphere; Green chemistry; chemoselective reaction; | A 99% B 99% |
Conditions | Yield |
---|---|
With 50wtpercent Cs2.5H0.5PW12O40 supported on MCM-41 In acetonitrile at 50℃; for 0.5h; | 98% |
With potassium fluoride at 80℃; for 7h; | 94% |
With potassium fluoride at 20℃; | 82% |
With sulfuric acid | |
In ethyl acetate at 30℃; for 8h; |
NH-pyrazole
(4-hydroxyphenyl)methanol
4-((1H-pyrazol-1-yl)methyl)phenol
Conditions | Yield |
---|---|
In water at 120℃; for 12h; Microwave irradiation; Sealed tube; | 98% |
at 160℃; for 0.5h; | 47% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 98% |
With potassium carbonate In acetone for 12h; Reflux; Inert atmosphere; | 91% |
With potassium carbonate; potassium iodide In acetone for 24h; Etherification; Heating; | 84% |
(4-hydroxyphenyl)methanol
propargyl bromide
(4-(prop-2-yn-1-yloxy)phenyl)methanol
Conditions | Yield |
---|---|
With potassium carbonate In toluene; acetonitrile at 70℃; for 20h; Inert atmosphere; | 98% |
With potassium carbonate In toluene; acetonitrile at 50℃; for 48h; | 95.5% |
Stage #1: (4-hydroxyphenyl)methanol With potassium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: propargyl bromide In toluene; acetonitrile at 50℃; for 40h; | 89% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 20h; Heating / reflux; | 98% |
With potassium carbonate In acetone Reflux; | 98% |
With potassium carbonate In acetone Heating; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 98% |
(4-hydroxyphenyl)methanol
di-tert-butyl dicarbonate
tert-butyl (4-(hydroxymethyl)phenyl)carbonate
Conditions | Yield |
---|---|
With carbon tetrabromide at 65℃; for 0.75h; Neat (no solvent); chemoselective reaction; | 98% |
With 6,7-dimethoxyisoquinoline In dichloromethane at 20℃; for 10h; Inert atmosphere; chemoselective reaction; | 95% |
triphenylphosphine at 65℃; for 1h; | 85% |
(4-hydroxyphenyl)methanol
(R)-dimethyl 2-(3-(chloromethyl)benzamido)pentanedioate
(R)-dimethyl 2-(3-((4-(hydroxymethyl)phenoxy)methyl)benzamido)pentanedioate
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile at 70℃; for 5h; | 98% |
Conditions | Yield |
---|---|
With oxygen In acetonitrile at 20℃; for 7.5h; Catalytic behavior; | 97% |
With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication; | 94% |
With tert.-butylhydroperoxide; ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 24h; chemoselective reaction; | 90% |
2-Methylcyclopentane-1,3-dione
(4-hydroxyphenyl)methanol
2-(4-hydroxybenzyl)-2-methyl-1,3-cyclopentanedione
Conditions | Yield |
---|---|
In water at 80℃; for 12h; | 97% |
With water at 80℃; for 12h; Inert atmosphere; | 80% |
(4-hydroxyphenyl)methanol
1,1,1,3,3,3-hexamethyl-disilazane
4-trimethylsilyloxymethylphenol
Conditions | Yield |
---|---|
With silica-coated iron nanoparticles-supported RuIII (OTf)Salophen In dichloromethane at 20℃; for 0.0166667h; Catalytic behavior; | 97% |
With titanium(IV) dioxide In acetonitrile at 20℃; for 0.0833333h; chemoselective reaction; | 95% |
With nano Fe3O4 supported CeO2/SO4 2-bifunctional solid acidcatalyst In neat (no solvent) at 25℃; for 0.416667h; | 91% |
With poly(N-bromobenzene-1,3-disulfonamide) for 0.07h; Irradiation; | 90% |
With lithium perchlorate for 0.0166667h; Irradiation; microwave; | 68% |
(4-hydroxyphenyl)methanol
propionic acid anhydride
4-propionyloxybenzyl propionate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 97% |
(4-hydroxyphenyl)methanol
glutamic acid di-tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: (4-hydroxyphenyl)methanol With phosgene; N-ethyl-N,N-diisopropylamine In dichloromethane; toluene; acetonitrile at 0℃; for 0.5h; Stage #2: glutamic acid di-tert-butyl ester With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene; acetonitrile at 0℃; | 97% |
(4-hydroxyphenyl)methanol
triphenylphosphine hydrogen iodide
Conditions | Yield |
---|---|
In acetonitrile at 90℃; for 12h; | 97% |
Conditions | Yield |
---|---|
With nickel dichloride at 20℃; for 0.5h; Neat (no solvent); | 96% |
With dmap; triethylamine In dichloromethane for 2.5h; | 95% |
With iron zirconium phosphate In neat (no solvent) at 40℃; for 0.166667h; Green chemistry; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Heating; | 96% |
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere; | 93% |
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; | 90% |
The 4-Hydroxybenzyl alcohol, with the CAS registry number 623-05-2, is also known as Benzenemethanol, 4-hydroxy-. It belongs to the product categories of Alcohols; C7 to C8; Linkers; Peptide Synthesis; Aromatics; Benzhydrols, Benzyl & Special Alcohols; Alphabetical Listings; Flavors and Fragrances; G-H; Bifunctional Crosslinkers Oxygen Compounds. Its EINECS registry number is 210-768-0. This chemical's molecular formula is C7H8O2 and molecular weight is 124.14. Its IUPAC name is called 4-(hydroxymethyl)phenol. The product should be sealed and stored in cool and dry place. What's more, it should be protected from strong oxides. It can be used as organic intermediates.
Physical properties of 4-Hydroxybenzyl alcohol: (1)ACD/LogP: 0.30; (2)ACD/LogD (pH 5.5): 0.3; (3)ACD/LogD (pH 7.4): 0.3; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 34.61; (7)ACD/KOC (pH 7.4): 34.45; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.595; (12)Molar Refractivity: 34.58 cm3; (13)Molar Volume: 101.6 cm3; (14)Surface Tension: 54.1 dyne/cm; (15)Density: 1.22 g/cm3; (16)Flash Point: 145.8 °C; (17)Enthalpy of Vaporization: 51.7 kJ/mol; (18)Boiling Point: 252 °C at 760 mmHg; (19)Vapour Pressure: 0.0104 mmHg at 25°C.
Preparation: this chemical can be prepared by 4-hydroxy-benzaldehyde. This reaction will need reagent Dowex1-x8, NaBH4 and solvent tetrahydrofuran. The reaction time is 30 min with reaction temperature of 20 °C. The yield is about 92%.
Uses of 4-Hydroxybenzyl alcohol: it can be used to produce 4-Methoxymethyl-phenol at temperature of 80 °C. This reaction will need reagent Yb(OTf)3 and solvent acetonitrile with reaction time of 5 hours. The yield is about 85%.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC(=CC=C1CO)O
(2)InChI: InChI=1S/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H2
(3)InChIKey: BVJSUAQZOZWCKN-UHFFFAOYSA-N
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