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15485-65-1

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15485-65-1 Usage

Chemical Properties

Tan Solid

Uses

Different sources of media describe the Uses of 15485-65-1 differently. You can refer to the following data:
1. Genistein intermediate.
2. α-(4’-Hydroxyphenyl)phloroacetophenone is a Genistein intermediate.

Preparation

Preparation by reaction of p-hydroxyphenyl-acetonitrile with phloroglucinol (Hoesch reaction) (58%).

Check Digit Verification of cas no

The CAS Registry Mumber 15485-65-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,4,8 and 5 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 15485-65:
(7*1)+(6*5)+(5*4)+(4*8)+(3*5)+(2*6)+(1*5)=121
121 % 10 = 1
So 15485-65-1 is a valid CAS Registry Number.
InChI:InChI=1/C14H12O5/c15-9-3-1-8(2-4-9)5-11(17)14-12(18)6-10(16)7-13(14)19/h1-4,6-7,15-16,18-19H,5H2

15485-65-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone

1.2 Other means of identification

Product number -
Other names 4-hydroxybenzyl 2,4,6-trihydroxyphenyl ketone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:15485-65-1 SDS

15485-65-1Synthetic route

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 0℃; for 5h;83%
With boron trifluoride diethyl etherate In various solvent(s) at 90℃; for 0.0666667h; Friedel-Crafts reaction; microwave irradiation;67%
With boron trifluoride diethyl etherate at 85℃; for 1.5h; Condensation;
Stage #1: 3,5-dihydroxyphenol; 4-hydroxyphenylacetate With boron trifluoride diethyl etherate at 70 - 80℃; Heating / reflux;
Stage #2: In DMF (N,N-dimethyl-formamide)
With boron trifluoride diethyl etherate at 85℃; for 1.5h;
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

4-cyanomethylphenol
14191-95-8

4-cyanomethylphenol

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Conditions
ConditionsYield
Stage #1: 3,5-dihydroxyphenol; 4-cyanomethylphenol With hydrogenchloride In acetic acid methyl ester at 5 - 20℃; for 19h; Hoesch reaction;
Stage #2: With sodium hydroxide; ethanol; water In ethyl acetate at 75 - 101℃; for 7h; pH=4.0; Product distribution / selectivity; Heating / reflux;
78.6%
With hydrogenchloride In diethyl ether at 0℃; for 24h;72%
With bis(trifluoromethanesulfonyl)amide In various solvent(s) at 90℃; for 0.0666667h; Hoesch reaction; microwave irradiation;65%
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Conditions
ConditionsYield
With sodium hydroxide at 60℃;65%
4,6-Dihydroxy-2-(4-hydroxy-phenyl)-benzofuran-3-one
19858-38-9

4,6-Dihydroxy-2-(4-hydroxy-phenyl)-benzofuran-3-one

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol
C14H13NO4*ClH
1260505-68-7

C14H13NO4*ClH

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Conditions
ConditionsYield
With hydrogenchloride; water Reflux;
With hydrogenchloride; water In methanol for 12h; Reflux; Industrial scale;59.1 kg
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen
2: tetrabutylammomium bromide
3: zinc(II) chloride; hydrogenchloride / 1,2-dimethoxyethane / 10 - 20 °C / Industrial scale
4: water; hydrogenchloride / methanol / 12 h / Reflux; Industrial scale
View Scheme
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc(II) chloride; hydrogenchloride / 1,2-dimethoxyethane / 10 - 20 °C / Industrial scale
2: water; hydrogenchloride / methanol / 12 h / Reflux; Industrial scale
View Scheme
4-cyanomethylphenol
14191-95-8

4-cyanomethylphenol

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc(II) chloride; hydrogenchloride / 1,2-dimethoxyethane / 10 - 20 °C / Industrial scale
2: water; hydrogenchloride / methanol / 12 h / Reflux; Industrial scale
View Scheme
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrabutylammomium bromide
2: zinc(II) chloride; hydrogenchloride / 1,2-dimethoxyethane / 10 - 20 °C / Industrial scale
3: water; hydrogenchloride / methanol / 12 h / Reflux; Industrial scale
View Scheme
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

sodium formate
141-53-7

sodium formate

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate With propionyl chloride In acetone at 21 - 32℃; for 1h;
Stage #2: With triethylamine In acetone at 20 - 32℃; for 2.5h;
Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h; Product distribution / selectivity;
94.8%
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate With acetyl chloride In acetone at 12 - 25℃; for 2h;
Stage #2: With triethylamine In acetone at 18 - 32℃; for 3h;
Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h; Product distribution / selectivity;
91.7%
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate With isobutyryl chloride In acetone at 21 - 32℃; for 2h;
Stage #2: With triethylamine In acetone at 18 - 32℃; for 2.5h;
Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h; Product distribution / selectivity;
90.2%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

sodium formate
141-53-7

sodium formate

propionyl chloride
79-03-8

propionyl chloride

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
Stage #1: sodium formate; propionyl chloride In acetone at 21 - 35℃; for 3h;
Stage #2: 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In acetone at 20 - 22℃; for 2h;
Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h;
93%
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate; propionyl chloride In acetone at 21 - 35℃; for 2h;
Stage #2: With triethylamine In acetone at 18 - 35℃; for 3h;
Stage #3: With sulfuric acid; water In acetone at 60 - 70℃; for 1.5h;
92.2%
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate; propionyl chloride In formic acid ethyl ester at 23 - 35℃; for 3h;
Stage #2: With triethylamine In formic acid ethyl ester at 18 - 22℃; for 16h;
Stage #3: With sulfuric acid; water In formic acid ethyl ester at 80℃;
92.7%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

sodium formate
141-53-7

sodium formate

isobutyryl chloride
79-30-1

isobutyryl chloride

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate; isobutyryl chloride In acetone at 21 - 32℃; for 3h;
Stage #2: With triethylamine In acetone at 18 - 32℃; for 2h;
Stage #3: With sulfuric acid; water In acetone at 60 - 70℃; for 3h;
90.3%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; methanesulfonyl chloride In N,N-dimethyl-formamide at 50℃; for 12h; Molecular sieve;90%
With methanesulfonyl chloride In N,N-dimethyl-formamide at 60 - 70℃; for 1h;53%
Multi-step reaction with 2 steps
1: pyridine / Behandeln des Reaktionsprodukts mit wss. Natronlauge
2: 325 °C
View Scheme
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With phosphorus pentachloride at 55℃; for 0.333333h; Chlorination;
Stage #2: 2,4,4',6-tetrahydroxydeoxybenzoin With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 20℃; for 1h; Cycloaddition;
90%
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 50 - 60℃; Cooling with ice;
Stage #2: N,N-dimethyl-formamide With methanesulfonyl chloride at 50 - 70℃;
84%
With boron trifluoride diethyl etherate; methanesulfonyl chloride 1.) irradiation, reflux, 15 s, 2.) irradiation, reflux, 1 min; Yield given. Multistep reaction;
With phosphorus pentachloride; boron trifluoride diethyl etherate at 20℃; for 1h; Cyclization;
With boron trifluoride diethyl etherate; methanesulfonyl chloride at 50 - 100℃;
glutaric anhydride,
108-55-4

glutaric anhydride,

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

4-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-2-yl]butanoic acid
272463-80-6

4-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-2-yl]butanoic acid

Conditions
ConditionsYield
Stage #1: glutaric anhydride,; 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In 1,4-dioxane at 100℃; for 0.5h;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 100℃;
Stage #3: With sulfuric acid In 1,4-dioxane; water at 80℃;
88%
formic acid
64-18-6

formic acid

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

propionic acid anhydride
123-62-6

propionic acid anhydride

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
Stage #1: formic acid; propionic acid anhydride at 25 - 45℃; for 2h;
Stage #2: 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In acetone at 20 - 40℃; for 19h;
Stage #3: With sulfuric acid; water In acetone at 60℃;
86.5%
Stage #1: formic acid; 2,4,4',6-tetrahydroxydeoxybenzoin; propionic acid anhydride at 25 - 45℃; for 2h;
Stage #2: With triethylamine at 20 - 40℃; for 19h;
Stage #3: With sulfuric acid; water at 75℃; for 2.5h;
82.5%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Propionic formic anhydride
10500-31-9

Propionic formic anhydride

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; Propionic formic anhydride With triethylamine In acetone at 25 - 40℃; for 3h;
Stage #2: With sulfuric acid; water In acetone at 20 - 60℃;
84%
formic acid
64-18-6

formic acid

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
Stage #1: formic acid; 2,4,4',6-tetrahydroxydeoxybenzoin With acetic anhydride; triethylamine at 20℃; for 24h; Industrial scale;
Stage #2: With hydrogenchloride; water In methanol at 20℃; for 22h; Industrial scale;
79.5%
1,3,5-Triazine
290-87-9

1,3,5-Triazine

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; acetic anhydride In diethyl ether; acetic acid Heating;78%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

methyl 10-chloro-10-oxodecanoate
14065-32-8

methyl 10-chloro-10-oxodecanoate

5,7,4'-Trihydroxy-2-[8-(methoxycarbonyl)octyl]isoflavone

5,7,4'-Trihydroxy-2-[8-(methoxycarbonyl)octyl]isoflavone

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In acetone for 46h; Cyclization; Heating;60%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

methyl 8-chloro-8-oxooctanoate
41624-92-4

methyl 8-chloro-8-oxooctanoate

5,7,4'-Trihydroxy-2-[6-(methoxycarbonyl)hexyl]isoflavone

5,7,4'-Trihydroxy-2-[6-(methoxycarbonyl)hexyl]isoflavone

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In acetone for 46h; Cyclization; Heating;56%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

sodium formate
141-53-7

sodium formate

benzoyl chloride
98-88-4

benzoyl chloride

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
Stage #1: sodium formate; benzoyl chloride In acetone at 21 - 40℃; for 3h;
Stage #2: 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In acetone at 21 - 35℃; for 3h;
Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h;
52.7%
ethyl glutaroyl chloride
5205-39-0

ethyl glutaroyl chloride

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

2-[3-(Ethoxycarbonyl)propyl]-5,7,4'-trihydroxyisoflavone

2-[3-(Ethoxycarbonyl)propyl]-5,7,4'-trihydroxyisoflavone

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In acetone for 34h; Cyclization; Heating;50%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

allyl bromide
106-95-6

allyl bromide

C26H28O5

C26H28O5

Conditions
ConditionsYield
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin With potassium carbonate In acetone at 60 - 75℃; for 1h;
Stage #2: allyl bromide In acetone for 24h; Inert atmosphere; Reflux;
50%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

methyl adipoyl chloride
35444-44-1

methyl adipoyl chloride

5,7,4'-Trihydroxy-2-[4-(methoxycarbonyl)butyl]isoflavone
218899-45-7

5,7,4'-Trihydroxy-2-[4-(methoxycarbonyl)butyl]isoflavone

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In acetone for 34h; Cyclization; Heating;49%
1,4-dioxane-2,6-dione
4480-83-5

1,4-dioxane-2,6-dione

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

{[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-2-yl]methoxy}acetic acid

{[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-2-yl]methoxy}acetic acid

Conditions
ConditionsYield
Stage #1: 1,4-dioxane-2,6-dione; 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In 1,4-dioxane at 100℃; for 0.5h;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 100℃;
Stage #3: With sulfuric acid In 1,4-dioxane; water at 80℃;
44%
succinic acid anhydride
108-30-5

succinic acid anhydride

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

3-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-2-yl]propanoic acid
263698-79-9

3-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-2-yl]propanoic acid

Conditions
ConditionsYield
Stage #1: succinic acid anhydride; 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In 1,4-dioxane at 100℃; for 0.5h;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 100℃;
Stage #3: With sulfuric acid In 1,4-dioxane; water at 80℃;
24%
cis-1,2-cyclopropanedicarboxylic acid anhydride
5617-74-3

cis-1,2-cyclopropanedicarboxylic acid anhydride

2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

2-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-2-yl]cyclopropanecarboxylic acid

2-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-2-yl]cyclopropanecarboxylic acid

Conditions
ConditionsYield
Stage #1: cis-1,2-cyclopropanedicarboxylic acid anhydride; 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In 1,4-dioxane at 100℃; for 0.5h;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 100℃;
Stage #3: With sulfuric acid In 1,4-dioxane; water at 80℃;
22%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

epichlorohydrin
106-89-8

epichlorohydrin

C26H28O9

C26H28O9

Conditions
ConditionsYield
With potassium carbonate; acetone In N,N-dimethyl-formamide at 70℃;20%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

epichlorohydrin
106-89-8

epichlorohydrin

C23H24O8

C23H24O8

Conditions
ConditionsYield
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; epichlorohydrin With tetrabutylammomium bromide for 1h; Reflux;
Stage #2: With sodium hydroxide In water at 20℃; for 1.25h;
19.6%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

5,7-dihydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid
22151-32-2

5,7-dihydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid

Conditions
ConditionsYield
With pyridine Behandeln des Reaktionsprodukts mit wss. Natronlauge;
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

5,7-dihydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid ethyl ester
111790-01-3

5,7-dihydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With pyridine
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

methyl chloroformate
79-22-1

methyl chloroformate

4,5,7-trihydroxy-3-(4-hydroxy-phenyl)-coumarin
100954-25-4

4,5,7-trihydroxy-3-(4-hydroxy-phenyl)-coumarin

Conditions
ConditionsYield
With potassium carbonate; acetone Behandeln des Reaktionsprodukts mit wss. Natronlauge;
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

dimethyl sulfate
77-78-1

dimethyl sulfate

2'-hydroxy-4',6-dimethoxy-2-(p-methoxyphenyl)acetophenone
39604-68-7

2'-hydroxy-4',6-dimethoxy-2-(p-methoxyphenyl)acetophenone

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;

15485-65-1Relevant articles and documents

Microwave-promoted synthesis of polyhydroxydeoxybenzoins in ionic liquids

Hakala, Ullastiina,W?h?l?, Kristiina

, p. 8375 - 8378 (2006)

A microwave-promoted synthesis of polyhydroxydeoxybenzoins and -phenylpropanones has been developed, using bis{(trifluoromethyl)sulfonyl}amine (HNTf2) or BF3·OEt2 in an ionic liquid solvent.

Identification of enterodiol as a masker for caffeine bitterness by using a pharmacophore model based on structural analogues of homoeriodictyol

Ley, Jakob P.,Dessoy, Marco,Paetz, Susanne,Blings, Maria,Hoffmann-Lücke, Petra,Reichelt, Katharina V.,Krammer, Gerhard E.,Pienkny, Silke,Brandt, Wolfgang,Wessjohann, Ludger

, p. 6303 - 6311 (2012)

Starting from previous structure-activity relationship studies of taste modifiers based on homoeriodictyol, dihydrochalcones, deoxybenzoins, and trans-3-hydroxyflavones as obvious analogues were investigated for their masking effect against caffeine. The most active compounds of the newly investigated taste modifiers were phloretin, the related dihydrochalcones 3-methoxy-2′,4,4′-trihydroxydihydrochalcone and 2′,4- dihydroxy-3-methoxydihydrochalcone, and the deoxybenzoin 2-(4-hydroxy-3- methoxyphenyl)-1-(4-hydroxyphenyl)ethanone. Starting with the whole set of compounds showing activity >22%, a (Q)SAR pharmacophore model for maskers of caffeine bitterness was calculated to explain the structural requirements. After docking of the pharmacophore into a structural model of the broadly tuned bitter receptor hTAS2R10 and docking of enterolactone and enterodiol as only very weakly related structures, it was possible to predict qualitatively their modulating activity. Enterodiol (25 mg L-1) reduced the bitterness of the 500 mg L-1 caffeine solution by about 30%, whereas enterolactone showed no masking but a slight bitter-enhancing effect.

Multifunctional deoxybenzoin-based monomers and resins having reduced flammability

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Page/Page column 10, (2016/08/10)

The invention provides a novel platform for minimal- or non-flammable polymers, which is based purely on hydrocarbon systems and does not need additives of any kind A key feature is that the hydrocarbons disclosed herein are characterized by degradation mechanisms that produce few flammable volatiles. For example, 2,4,4′,6-tetrahydroxydeoxybenzoin is employed as a multifunctional cross-linker in conjunction with bis-epoxydeoxybenzoin, affording new resins that combine excellent physical and mechanical properties with low flammability.

Multifunctional deoxybenzoin-based epoxies: Synthesis, mechanical properties, and thermal evaluation

Szyndler, Megan W.,Timmons, Justin C.,Yang, Zhan H.,Lesser, Alan J.,Emrick, Todd

, p. 4441 - 4446 (2014/10/15)

We describe 2,4,4′,6-tetrahydroxydeoxybenzoin (THDB) as a multifunctional cross-linker in conjunction with bis-epoxydeoxybenzoin (BEDB), affording new resins that combine excellent physical and mechanical properties with low flammability. The char residue and heat release capacity values of the cross-linked epoxies were measured by thermogravimetric analysis (TGA) and pyrolysis combustion flow calorimetry (PCFC), respectively. Resins fabricated from THDB exhibited low total heat release (13 kJ/g) and high char yields (34%), as well as good mechanical properties, making them suitable candidates for consideration in high performance adhesive applications. The desirable heat release and char yield properties of these structures are realized without the presence of any conventional flame retardant, such as halogenated structures or inorganic fillers that are commonly utilized in commercial materials.

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