Deoxyarbutin supplier | CasNO.53936-56-4

Name
Deoxyarbutin
EINECS 1308068-626-2
CAS No. 53936-56-4
Article Data22
CAS DataBase
Density 1.174 g/cm³
Solubility
Melting Point 83-88℃
Formula C₁₁H₁₄O₃
Boiling Point 349.779 °C at 760 mmHg
Molecular Weight 194.23
Flash Point 165.341 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-(Tetrahydro-2H-pyran-2-yloxy)phenol;
PSA 38.69000
LogP 2.29760

Synthetic route

: 53936-79-1
4-benzyloxyphenyl 2-tetrahydropyranyl ether

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; under 3000.3 Torr; for 3h; Autoclave;	100%
With aluminum oxide; hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; Product distribution / selectivity;	82%
With hydrogen; calcium carbonate; palladium on activated charcoal In ethyl acetate at 20℃; Product distribution / selectivity;	80%

: 134142-87-3
2-(4-Acetoxyphenoxy)tetrahydropyran

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions

Conditions	Yield
With sodium perborate In methanol at 25℃; for 0.25h;	84%

: 110-87-2
3,4-dihydro-2H-pyran

: 123-31-9
hydroquinone

A: 2139-44-8
2-(4-(tetrahydro-2H-pyran-2-yloxy)phenoxy)tetrahydro-2H-pyran

B: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions

Conditions	Yield
With iron(III) sulfate In acetone for 1h;	A 12% B 72%
With aluminium trichloride

...Expand

: 110-87-2
3,4-dihydro-2H-pyran

: 123-31-9
hydroquinone

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions

Conditions	Yield
With ruthenium(III) acetate at 20℃; for 12h;	72%
With pyridinium p-toluenesulfonate In dichloromethane at 10 - 25℃; for 16h; Inert atmosphere;	52.7%
With pyridinium p-toluenesulfonate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	49.6%

: 36637-44-2
(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)magnesium bromide

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions

Conditions	Yield
With air In tetrahydrofuran at -25℃; under 12929 Torr; for 0.0566667h; Green chemistry;	64%

: 2-(4-allyloxy-phenoxy)-tetrahydro-pyran

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions

Conditions	Yield
With sodium acetate; nickel In N,N-dimethyl-formamide for 18h; Ambient temperature;	25%

: 103-16-2
4-Benzyloxyphenol

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / 20 °C / Inert atmosphere; Cooling with ice 2: 5%-palladium/activated carbon; hydrogen / ethanol / 3 h / 20 °C / 3000.3 Torr / Autoclave View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 6 h / 20 °C / Inert atmosphere; Cooling with ice 2: pyridine; 5%-palladium/activated carbon; hydrogen / tetrahydrofuran; ethanol / 8 h / 50 °C / 3750.38 Torr View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 7 h / 20 °C / Cooling with ice 2: 5%-palladium/activated carbon; hydrogen / ethanol; tetrahydrofuran / 8 h / 50 °C / 3750.38 Torr View Scheme

: 110-87-2
3,4-dihydro-2H-pyran

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / 20 °C / Inert atmosphere; Cooling with ice 2: 5%-palladium/activated carbon; hydrogen / ethanol / 3 h / 20 °C / 3000.3 Torr / Autoclave View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 6 h / 20 °C / Inert atmosphere; Cooling with ice 2: pyridine; 5%-palladium/activated carbon; hydrogen / tetrahydrofuran; ethanol / 8 h / 50 °C / 3750.38 Torr View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / dichloromethane / 7 h / 20 °C / Cooling with ice 2: 5%-palladium/activated carbon; hydrogen / ethanol; tetrahydrofuran / 8 h / 50 °C / 3750.38 Torr View Scheme

: 777078-65-6
6-(2-acryloyloxyethoxy)capronic acid

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 1187579-83-4
C22H30O7

Conditions

Conditions	Yield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide In chloroform at 20℃; Inert atmosphere; Cooling with ice;	94%

: 2009-83-8
6-chloro-1-hexanol

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 161841-10-7
C17H26O4

Conditions

Conditions	Yield
With potassium carbonate In ISOPROPYLAMIDE at 90 - 100℃; Inert atmosphere;	91%
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; Inert atmosphere;	91%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;	84.9%

: N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenoxy)propanamide

Conditions

Conditions	Yield
With potassium carbonate In isopropyl alcohol for 3h; Reflux;	91%

: 762-04-9
phosphonic acid diethyl ester

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 866927-59-5
O,O-diethyl O-4-tetrahydro-2H-2-pyranyloxyphenyl phosphate

Conditions

Conditions	Yield
With triethylamine In tetrachloromethane	88%

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 202982-89-6
3-(4-bromobutoxy)oxetane

: 202983-46-8
2-{4-[4-(oxetan-3-yloxy)-butoxy]-phenoxy}-tetrahydro-pyran

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Etherification;	87%

: 79-41-4
poly(methacrylic acid)

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: C15H18O4

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 16h; Inert atmosphere; Cooling with ice;	83.6%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 7h; Inert atmosphere; Cooling with ice;	9 g

: 626-89-1
4-Methyl-1-pentanol

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 2-[4-{(4-methylpentyl)oxy}phenoxy]tetrahydropyran

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	78%

: 847386-22-5
3-bromo-2-(4-fluorophenyl)-6-methoxybenzo[b]thiophene 1-oxide

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 2-(4-fluorophenyl)-6-methoxy-3-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenoxy)benzo[b]thiophene-1-oxide

Conditions

Conditions	Yield
Stage #1: 4-(tetrahydro-2H-2-pyranyloxy)phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Stage #2: 3-bromo-2-(4-fluorophenyl)-6-methoxybenzo[b]thiophene 1-oxide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;	75%

: C27H16ClNO4

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: C38H29NO7

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 120℃; for 3h;	75%

: 1871-57-4
2-chloromethyl-3-chloroprop-1-ene

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: C16H16O4

Conditions

Conditions	Yield
Stage #1: 2-chloromethyl-3-chloroprop-1-ene; 4-(tetrahydro-2H-2-pyranyloxy)phenol With sodium hydride In N,N-dimethyl-formamide Substitution; Stage #2: In ethanol alcoholysis; acidic solution;	74%

: 109-65-9
1-bromo-butane

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: C15H22O3

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 16h;	56%

: 106-93-4
ethylene dibromide

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 2-(4-(2-bromoethoxy)phenoxy)tetrahydro-2H-pyran

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 20℃; for 24h; Reflux;	46%
In tetrahydrofuran for 24h; Reflux; Alkaline conditions;

: 67-66-3
chloroform

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 70℃; for 3h; Reimer-Tiemann reaction;	41%

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 540-51-2
2-bromoethanol

: 777084-12-5
2-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenoxy)ethanol

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;	32%
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 100℃; for 4h;

: N-(6’-fluoro-2-methyl-5‘-morpholino-[3,3‘-bipyridin]-5-yl)-3-(trifluoromethyl)benzamide

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: N-(2-methyl-5'-morpholino-6'-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenoxy)-[3,3'-bipyridin]-5-yl)-3-(trifluoromethyl)benzamide

Conditions

Conditions	Yield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 15 - 140℃; for 2h; Microwave irradiation;	29%

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 3-(2-chloromethylphenoxy)-2-(2-chloromethylphenoxymethyl)propene

: C40H44O8

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 70℃; Alkylation;

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

chloromethyl polystyrene resin: chloromethyl polystyrene resin

chloromethyl polystyrene resin derivatized with quinol monotetrahydropyranyl ether: chloromethyl polystyrene resin derivatized with quinol monotetrahydropyranyl ether

Conditions

Conditions	Yield
With sodium methylate In N,N-dimethyl-formamide at 55℃; for 16h;	111.5 g

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 4,13-dimethylene-2,6,11,15-tetraoxa-tricyclo[14.2.2.27,10]docosa-1(19),7(22),8,10(21),16(20),17-hexaene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide 1.2: 74 percent / ethanol / acidic solution 2.1: 1 percent Spectr. / NaH / dimethylformamide / 24 h / 65 °C View Scheme

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: C40H40O8

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide 1.2: 74 percent / ethanol / acidic solution 2.1: 24 percent Spectr. / NaH / dimethylformamide / 24 h / 65 °C View Scheme

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: C60H60O12

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide 1.2: 74 percent / ethanol / acidic solution 2.1: 4 percent Spectr. / NaH / dimethylformamide / 24 h / 65 °C View Scheme

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: TIMEOUT: 5s

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide 1.2: 74 percent / ethanol / acidic solution 2.1: 4 percent Spectr. / NaH / dimethylformamide / 24 h / 65 °C View Scheme

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: C30H28O6

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH / dimethylformamide / 70 °C 2: H3O+ / ethanol View Scheme

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: C48H44O8

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaH / dimethylformamide / 70 °C 2: H3O+ / ethanol 3: 38 percent / NaH / dimethylformamide / 70 °C View Scheme

: 503474-64-4
4-[4-(3-ethyloxetane-3-ylmethoxy)butyloxy]benzoic acid

: 53936-56-4
4-(tetrahydro-2H-2-pyranyloxy)phenol

: 677033-32-8
C23H28O6

Conditions

Conditions	Yield
Stage #1: 4-[7-(3-ethyl-3-oxetanyl)-1,6-dioxaheptyl]benzoic acid; 4-(tetrahydro-2H-2-pyranyloxy)phenol With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.5h;

Deoxyarbutin Specification

The Deoxyarbutin with CAS registry number of 53936-56-4 is also known as Phenol,4-[(tetrahydro-2H-pyran-2-yl)oxy]-. The systematic name is 4-(Tetrahydro-2H-pyran-2-yloxy)phenol. In addition, the formula is C₁₁H₁₄O₃ and the molecular weight is 194.23.

Physical properties about Deoxyarbutin are: (1)ACD/LogP: 1.50; (2)# of Rule of 5 Violations: 0 ; (3)#H bond acceptors: 3; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 3; (6)Polar Surface Area: 38.69 Å²; (7)Index of Refraction: 1.552; (8)Molar Refractivity: 52.841 cm³; (9)Molar Volume: 165.414 cm³; (10)Polarizability: 20.948×10^-24cm³; (11)Surface Tension: 46.085 dyne/cm; (12)Density: 1.174 g/cm³; (13)Flash Point: 165.341 °C; (14)Enthalpy of Vaporization: 61.778 kJ/mol; (15)Boiling Point: 349.779 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
1. SMILES: O(c1ccc(O)cc1)C2OCCCC2
2. InChI: InChI=1/C11H14O3/c12-9-4-6-10(7-5-9)14-11-3-1-2-8-13-11/h4-7,11-12H,1-3,8H2
3. InChIKey: GFBCWCDNXDKFRH-UHFFFAOYAE
4. Std. InChI: InChI=1S/C11H14O3/c12-9-4-6-10(7-5-9)14-11-3-1-2-8-13-11/h4-7,11-12H,1-3,8H2
5. Std. InChIKey: GFBCWCDNXDKFRH-UHFFFAOYSA-N

Product Name

Deoxyarbutin

Synthetic route

Deoxyarbutin Specification

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