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28924-21-2

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28924-21-2 Usage

Chemical Properties

beige crystalline powde

Uses

3,5-Dibenzyloxyacetophenone is used in the synthesis of enantiomerically pure B-ring modified analogs of (-)-epicatechin gallate.

Check Digit Verification of cas no

The CAS Registry Mumber 28924-21-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,9,2 and 4 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 28924-21:
(7*2)+(6*8)+(5*9)+(4*2)+(3*4)+(2*2)+(1*1)=132
132 % 10 = 2
So 28924-21-2 is a valid CAS Registry Number.
InChI:InChI=1/C22H20O3/c1-17(23)20-12-21(24-15-18-8-4-2-5-9-18)14-22(13-20)25-16-19-10-6-3-7-11-19/h2-14H,15-16H2,1H3

28924-21-2 Well-known Company Product Price

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  • TCI America

  • (D2085)  3',5'-Dibenzyloxyacetophenone  

  • 28924-21-2

  • 10g

  • 370.00CNY

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  • Alfa Aesar

  • (A19614)  3',5'-Dibenzyloxyacetophenone, 98%   

  • 28924-21-2

  • 10g

  • 408.0CNY

  • Detail
  • Alfa Aesar

  • (A19614)  3',5'-Dibenzyloxyacetophenone, 98%   

  • 28924-21-2

  • 50g

  • 1342.0CNY

  • Detail
  • Alfa Aesar

  • (A19614)  3',5'-Dibenzyloxyacetophenone, 98%   

  • 28924-21-2

  • 250g

  • 6082.0CNY

  • Detail

28924-21-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-[3,5-bis(phenylmethoxy)phenyl]ethanone

1.2 Other means of identification

Product number -
Other names 3',5'-Dibenzyloxyacetophenone

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:28924-21-2 SDS

28924-21-2Synthetic route

3,5-dihydroxyacetophenone
51863-60-6

3,5-dihydroxyacetophenone

benzyl bromide
100-39-0

benzyl bromide

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In acetone at 100℃; for 3h;100%
Stage #1: 3,5-dihydroxyacetophenone With potassium carbonate In acetone for 0.166667h;
Stage #2: benzyl bromide In acetone at 20℃; for 10h;
97%
With potassium carbonate In acetone for 18h; Reflux;86%
2-bromo-1-[3,5-bis(phenylmethoxy)phenyl]ethanone
28924-18-7

2-bromo-1-[3,5-bis(phenylmethoxy)phenyl]ethanone

A

2-bromo-1-(3,5-bis(benzyloxy)phenyl)ethanol
103145-39-7

2-bromo-1-(3,5-bis(benzyloxy)phenyl)ethanol

B

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

C

(R)-1-(3,5-dibenzyloxyphenyl)ethanol

(R)-1-(3,5-dibenzyloxyphenyl)ethanol

Conditions
ConditionsYield
With sodium formate; cetyltrimethylammonim bromide; sodium dodecyl-sulfate; (R,R)-TsDPEN; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 28℃; for 2.5h;A 90%
B n/a
C n/a
1-(3,5-Bis-benzyloxy-phenyl)-ethanone oxime
87975-69-7

1-(3,5-Bis-benzyloxy-phenyl)-ethanone oxime

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

Conditions
ConditionsYield
With triethylammonium chlorochromate(VI) In 1,2-dichloro-ethane for 2h;88%
3,5-dihydroxyacetophenone
51863-60-6

3,5-dihydroxyacetophenone

benzyl chloride
100-44-7

benzyl chloride

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; Reagent/catalyst; Temperature;85%
With potassium carbonate In acetone at 60℃; for 4h; Temperature;82%
With potassium carbonate Alkylation;
1-(3,5-Dibenzyloxyphenyl)-2-methylsulfonyl-1-ethanon
90664-17-8

1-(3,5-Dibenzyloxyphenyl)-2-methylsulfonyl-1-ethanon

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

Conditions
ConditionsYield
With zinc In methanol; acetic acid for 0.0833333h;72%
1-(3,5-Bis-benzyloxy-phenyl)-hexane-1,3,5-trione

1-(3,5-Bis-benzyloxy-phenyl)-hexane-1,3,5-trione

A

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

B

3,5-dibenzyloxybenzoic acid
28917-43-3

3,5-dibenzyloxybenzoic acid

Conditions
ConditionsYield
With manganese triacetate; acetic acid for 22h; Ambient temperature;A 3%
B 4%
(3,5-di-benzyloxy)benzoic acid benzyl ester
50513-72-9

(3,5-di-benzyloxy)benzoic acid benzyl ester

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) r.t., 1 h
2: 3 percent / manganese(III) acetate, acetic acid / 22 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 1) 50percent NaH / 1) DMSO, 60 deg C, 90 min, 2) THF, 60 deg C, 1 h
2: 72 percent / Zn / methanol; acetic acid / 0.08 h
View Scheme
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

2-bromo-1-[3,5-bis(phenylmethoxy)phenyl]ethanone
28924-18-7

2-bromo-1-[3,5-bis(phenylmethoxy)phenyl]ethanone

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In tetrahydrofuran; methanol at 20℃; for 24h;100%
With bromine In dichloromethane at 20℃;80%
With phenyltrimethylammonium tribromide In dichloromethane at 20℃; for 3h;38%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

1-[3,5-bis(benzyloxy)phenyl]-2-bromoethanol

1-[3,5-bis(benzyloxy)phenyl]-2-bromoethanol

Conditions
ConditionsYield
Stage #1: 3,5-dibenzyloxyacetophenone With copper(ll) bromide In dichloromethane for 3h; Reflux;
Stage #2: With potassium borohydride In methanol at 10 - 15℃; for 1h; Solvent; Reagent/catalyst;
98%
2-Aminobenzyl alcohol
5344-90-1

2-Aminobenzyl alcohol

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

C29H23NO2

C29H23NO2

Conditions
ConditionsYield
With iron(III) oxide; potassium tert-butylate In toluene for 15h; Inert atmosphere; Sealed tube;95%
4,6-dibenzyloxy-2-methoxymethyloxybenzaldehyde
863237-41-6

4,6-dibenzyloxy-2-methoxymethyloxybenzaldehyde

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

3',4,5',6-tetrabenzyloxy-2-methoxymethyloxy-E-retro-chalcone
863237-49-4

3',4,5',6-tetrabenzyloxy-2-methoxymethyloxy-E-retro-chalcone

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; ethanol at 20℃; for 16h;94%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

(Z)-4-((2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl)benzaldehyde

(Z)-4-((2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl)benzaldehyde

C33H25NO5S
1407180-34-0

C33H25NO5S

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide Heating;94%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

2-Bromo-3,5-Bisphenylmethoxyacetophenone

2-Bromo-3,5-Bisphenylmethoxyacetophenone

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 10h; Darkness;91%
triethyl phosphonoacetate
36032-75-4

triethyl phosphonoacetate

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

ethyl-3-(3,5-dibenzyloxyphenyl)-2-butenoate

ethyl-3-(3,5-dibenzyloxyphenyl)-2-butenoate

Conditions
ConditionsYield
Stage #1: triethyl phosphonoacetate With sodium ethanolate at 25℃; for 2.5h;
Stage #2: 3,5-dibenzyloxyacetophenone In ethanol at 20℃; for 72h; Horner-Emmons reaction;
90%
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

benzothiazol-2-yl(3,5-bis(benzyloxy)phenyl)methanone

benzothiazol-2-yl(3,5-bis(benzyloxy)phenyl)methanone

Conditions
ConditionsYield
With copper(l) iodide; tetrafluoroboric acid In water; dimethyl sulfoxide at 130℃; for 9h; Inert atmosphere; Sealed tube; chemoselective reaction;90%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

((buta-1,3-diene-2,3-diylbis(benzene-5,3,1-triyl)tetrakis(oxy))tetrakis(methylene))tetrabenzene

((buta-1,3-diene-2,3-diylbis(benzene-5,3,1-triyl)tetrakis(oxy))tetrakis(methylene))tetrabenzene

Conditions
ConditionsYield
Stage #1: 3,5-dibenzyloxyacetophenone With toluene-4-sulfonic acid hydrazide In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere;
Stage #2: With bis-triphenylphosphine-palladium(II) chloride; p-benzoquinone; lithium tert-butoxide In 1,4-dioxane; N,N-dimethyl-formamide at 100℃; Inert atmosphere; Molecular sieve; regioselective reaction;
82%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

2-(3',5'-dibenzyloxyphenyl)propene
929030-83-1

2-(3',5'-dibenzyloxyphenyl)propene

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h;
Stage #2: 3,5-dibenzyloxyacetophenone In tetrahydrofuran; hexane at -78 - 20℃; for 19h; Wittig olefination;
73%
2-aminopyridine
504-29-0

2-aminopyridine

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

3,5-bis(benzyloxy)-N-(pyridin-2-yl)benzamide

3,5-bis(benzyloxy)-N-(pyridin-2-yl)benzamide

Conditions
ConditionsYield
With oxygen; sodium docusate; copper(l) chloride In water at 80℃; under 760.051 Torr; for 3h; Green chemistry; chemoselective reaction;73%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

(+/-)-1-(3,5-dibenzyloxyphenyl)ethanol

(+/-)-1-(3,5-dibenzyloxyphenyl)ethanol

Conditions
ConditionsYield
With sodium tetrahydroborate; sodium hydrogencarbonate In ethanol at 20℃;70%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

acetonitrile
75-05-8

acetonitrile

4-(3,5-bis(benzyloxy)phenyl)-2,6-dimethylpyrimidine

4-(3,5-bis(benzyloxy)phenyl)-2,6-dimethylpyrimidine

Conditions
ConditionsYield
With sodium hydroxide; copper dichloride at 120℃; for 24h; Schlenk technique; Inert atmosphere;67%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

ethyl vinyl ether
109-92-2

ethyl vinyl ether

C24H24O4

C24H24O4

Conditions
ConditionsYield
Stage #1: ethyl vinyl ether With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; Inert atmosphere;
Stage #2: 3,5-dibenzyloxyacetophenone In tetrahydrofuran; pentane at -78 - 20℃; for 3h; Inert atmosphere;
65%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

[(p-methylphenyl)sulfonylmethyl]isonitrile
38622-91-2, 36635-61-7

[(p-methylphenyl)sulfonylmethyl]isonitrile

2-(3',5'-dibenzyloxyphenyl)propionitrile
101479-10-1

2-(3',5'-dibenzyloxyphenyl)propionitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,2-dimethoxyethane; tert-butyl alcohol for 2.5h; Ambient temperature;63%
ethyl 1-(4-methoxybenzyl)-1H-tetrazole-5-carboxylate
70978-35-7

ethyl 1-(4-methoxybenzyl)-1H-tetrazole-5-carboxylate

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

1-(3,5-bis-benzyloxy-phenyl)-3-hydroxy-3-[1-(4-methoxy-benzyl)-1H-tetrazol-5-yl]-propenone

1-(3,5-bis-benzyloxy-phenyl)-3-hydroxy-3-[1-(4-methoxy-benzyl)-1H-tetrazol-5-yl]-propenone

Conditions
ConditionsYield
Stage #1: 3,5-dibenzyloxyacetophenone With lithium hexamethyldisilazane In tetrahydrofuran at -20℃; for 2h;
Stage #2: ethyl 1-(4-methoxybenzyl)-1H-tetrazole-5-carboxylate In tetrahydrofuran at -78 - 20℃; for 3h; Further stages.;
60%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

(E)-1-(3,5-bis(benzyloxy)phenyl)-3-(2-nitrophenyl)prop-2-en-1-one

(E)-1-(3,5-bis(benzyloxy)phenyl)-3-(2-nitrophenyl)prop-2-en-1-one

Conditions
ConditionsYield
With potassium carbonate; sodium hydroxide In neat (no solvent) at 20℃; for 0.166667h; Schlenk technique;56%
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

A

3,5-dihydroxyacetophenone
51863-60-6

3,5-dihydroxyacetophenone

B

3-Benzyloxy-5-hydroxyacetophenon
81732-54-9

3-Benzyloxy-5-hydroxyacetophenon

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In acetoneA n/a
B 48%
N-Methylhydroxylamine
593-77-1

N-Methylhydroxylamine

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

Triethylphosphonoacetate

Triethylphosphonoacetate

C32H31NO5

C32H31NO5

Conditions
ConditionsYield
Multistep reaction;
1-Chloro-3-methoxypropane
36215-07-3

1-Chloro-3-methoxypropane

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

2-(3,5-dibenzyloxyphenyl)-5-methoxypentan-2-ol
99237-53-3

2-(3,5-dibenzyloxyphenyl)-5-methoxypentan-2-ol

Conditions
ConditionsYield
With sulfuric acid; iodine; magnesium 1.) ether, 3-4 h, reflux; 2.) ether; Yield given. Multistep reaction;
1-chloro-3-ethoxypropane
36865-38-0

1-chloro-3-ethoxypropane

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

2-(3,5-dibenzyloxyphenyl)-5-ethoxypentan-2-ol

2-(3,5-dibenzyloxyphenyl)-5-ethoxypentan-2-ol

Conditions
ConditionsYield
With sulfuric acid; iodine; magnesium 1.) ether, 3-4 h, reflux; 2.) ether; Multistep reaction;
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

3-(2-methoxyethoxy)-1-chloropropane
24255-59-2

3-(2-methoxyethoxy)-1-chloropropane

2-(3,5-Bis-benzyloxy-phenyl)-5-(2-methoxy-ethoxy)-pentan-2-ol

2-(3,5-Bis-benzyloxy-phenyl)-5-(2-methoxy-ethoxy)-pentan-2-ol

Conditions
ConditionsYield
With sulfuric acid; iodine; magnesium 1.) ether, 3-4 h, reflux; 2.) ether; Multistep reaction;
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

ethyl 3-<3,5-bis(benzyloxy)phenyl>-3-methylpropenoate
63790-21-6

ethyl 3-<3,5-bis(benzyloxy)phenyl>-3-methylpropenoate

Conditions
ConditionsYield
With sodium hydride 1.) THF, RT, 1.5 h, 2.) THF, RT, 72 h; Multistep reaction;
3,5-dibenzyloxyacetophenone
28924-21-2

3,5-dibenzyloxyacetophenone

Diethyl carbonate
105-58-8

Diethyl carbonate

3,4-dibenzyloxyabenzoylacetic ethyl ester
909007-90-5

3,4-dibenzyloxyabenzoylacetic ethyl ester

Conditions
ConditionsYield
With sodium hydride Condensation; Claisen condensation; Heating;

28924-21-2Relevant articles and documents

Design, synthesis, and properties of nonlinear optical chromophores based on a verbenone bridge with a novel dendritic acceptor

Sun, Hejing,Li, Zhong'An,Wu, Jieyun,Jiang, Zhenhua,Luo, Jingdong,Jen, Alex K.-Y.

, p. 2840 - 2847 (2018)

Two novel second order nonlinear optical (NLO) chromophores based on N,N-diethylaniline as a donor, verbenone based tetraene as a bridge, and tricyanofuran (TCF) or tricyanofuran derivatives with a dendritic moiety as an acceptor have been synthesized in good overall yields and systematically characterized. Besides, a facile applicable synthetic approach for a NLO dendritic acceptor was developed. Compared with C7, after introducing dendritic derivative steric hindrance groups into the acceptor, chromophore C8 had good thermal stabilities with high thermal decomposition temperatures which were 33 °C higher than that of chromophore C7. At the same time, cyclic voltammetry (CV) experiments were performed to determine the different redox properties. The conjugated verbenone tetraene segments in two chromophores could significantly improve the glass-forming ability and molecular polarization of chromophores as revealed by UV-vis-NIR absorption measurements. The bulky dendritic moiety linked by a short C-C bond is closer to the TCF acceptor, which is the most polar part in the chromophore, compared to conventional isolation groups. The results obtained from electro-optic (EO) coefficients indicate that this TCF acceptor with a unique dendritic structure can prevent antiparallel packing between chromophores, improving the poling efficiency and enhancing the EO performance. These properties, together with the good solubility, suggest the potential use of these new chromophores as materials for advanced photonic devices.

Preparation method of terbutaline sulfate (by machine translation)

-

Paragraph 0032-0036; 0047-0051, (2020/04/17)

The method adopts,hydroxyacetophenone as the starting material 3,5 - to obtain, di 3,5 -benzyloxyacetophenone, 3,5 - dibenzyloxyacetophenone and then generates, DMSO-benzyloxy 3,5 -phenyl,tert-butylamino 1 - [3,5 - ethanol (by hydrogenation debenzil) and sulfuric acid into a salt to obtain dibenzyloxybenzenethanone aldehyde] - 2 - (and then reductive amination with tertiary butylamine.) reaction conditions under, reaction conditions, are avoided, The method disclosed by the invention is cheap and easy to obtain and avoids the use of high-risk highly-toxic agents, by reductive amination . The method disclosed by the invention is low, reaction conditions . The method disclosed by the invention is cheap and easily available. (by machine translation)

A synthesis method of terbutaline sulfate (by machine translation)

-

Paragraph 0040-0043, (2018/10/04)

The invention provides a method for synthesis of terbutaline sulfate, the specific synthetic route is: to 3, 5 - dihydroxy acetophenone as raw materials, after phenmethyl protection, oxidation, esterification, reduction ammoniation, debenzylation, finally with sulfuric acid to form the salt to obtain the terbutaline sulfate. The invention provides a preparation method of the terbutaline sulfate, the beneficial effect that: 1, using dimethyl sulfoxide (DMSO) to replace the two connecting selenium dioxide, avoid the use of high-risk reagent, safety and high efficiency; 2, [...] process, small pollution to the environment; 3, the operation is simple, mild reaction conditions, the step is short, low cost, is more suitable for industrial production. (by machine translation)

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