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2050-16-0

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2050-16-0 Usage

General Description

4,4'-azobis(phenol) is a chemical compound that is commonly used as an initiator for free radical polymerization reactions. It is an azo compound, meaning it contains two nitrogen atoms connected by a double bond, and it is derived from phenol. When heated or exposed to high temperatures, 4,4'-azobis(phenol) decomposes into two phenoxyl radicals, which then initiate the radical polymerization process. This process is widely used in the production of various types of polymers, such as plastics, adhesives, and coatings. However, 4,4'-azobis(phenol) is also known to be a hazardous substance, and proper handling and storage are required to minimize the risk of exposure.

Check Digit Verification of cas no

The CAS Registry Mumber 2050-16-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,5 and 0 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2050-16:
(6*2)+(5*0)+(4*5)+(3*0)+(2*1)+(1*6)=40
40 % 10 = 0
So 2050-16-0 is a valid CAS Registry Number.

2050-16-0SDS

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 4-[(4-hydroxyphenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one

1.2 Other means of identification

Product number -
Other names Phenol, 4,4‘-azobis-

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:2050-16-0 SDS

2050-16-0Synthetic route

4-nitro-phenol
100-02-7

4-nitro-phenol

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
Stage #1: 4-nitro-phenol In ethanol for 0.0333333h;
Stage #2: With sodium tetrahydroborate In ethanol for 0.666667h; Reflux;
91%
With potassium hydroxide at 210 - 215℃;90%
With 4,4'-di-tert-butylbiphenyl; lithium; iron(II) chloride In tetrahydrofuran for 3.5h; Heating;81%
4-amino-phenol
123-30-8

4-amino-phenol

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With cetyl-trimethylammonium dichromate In chloroform for 3h; Heating;85%
Stage #1: 4-amino-phenol With hydrogenchloride In water at 23 - 25℃; for 0.5h;
Stage #2: With sodium nitrite In water at 0℃; for 2h;
Stage #3: With ammonium hydroxide; copper(ll) sulfate pentahydrate; hydroxylamine hydrochloride In water at 0℃;
54%
Stage #1: 4-amino-phenol With hydrogenchloride In water at 20℃; for 0.5h;
Stage #2: With sodium nitrite In water for 3h;
Stage #3: With copper(ll) sulfate pentahydrate; hydroxylamine hydrochloride; ammonia In water
51%
4-amino-phenol
123-30-8

4-amino-phenol

phenol
108-95-2

phenol

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With hydrogenchloride; sodium nitrite In water at 0 - 20℃;
Stage #2: phenol With sodium hydroxide In water at 20℃; for 12h;
70.1%
Stage #1: 4-amino-phenol With hydrogenchloride; sodium nitrite In methanol; water at 0℃;
Stage #2: phenol With potassium hydroxide In methanol; water at 20℃; for 2h;
56.1%
Stage #1: 4-amino-phenol With hydrogenchloride; sodium nitrite In methanol; water at 0℃;
Stage #2: phenol With sodium hydroxide In methanol; water at 20℃; for 2h;
56.1%
methanol
67-56-1

methanol

N,N'-Bis-(4-fluoro-phenyl)-diazene N-oxide
326-04-5, 32213-80-2, 51789-07-2

N,N'-Bis-(4-fluoro-phenyl)-diazene N-oxide

A

5-methoxy-2-phenyl-2H-indazole
120455-03-0

5-methoxy-2-phenyl-2H-indazole

B

5-methoxy-2-(4-methoxyphenyl)-2H-indazole
120455-06-3

5-methoxy-2-(4-methoxyphenyl)-2H-indazole

C

4,4'-dimethoxyazoxybenzene
1562-94-3, 21650-70-4, 51437-65-1

4,4'-dimethoxyazoxybenzene

D

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With N-doped TiO2 In water at 20℃; for 3h; UV-irradiation; Inert atmosphere;A 13%
B 55%
C 11%
D 10%
methanol
67-56-1

methanol

4,4'-bis(chloro)azoxybenzene
614-26-6

4,4'-bis(chloro)azoxybenzene

A

5-methoxy-2-phenyl-2H-indazole
120455-03-0

5-methoxy-2-phenyl-2H-indazole

B

5-methoxy-2-(4-methoxyphenyl)-2H-indazole
120455-06-3

5-methoxy-2-(4-methoxyphenyl)-2H-indazole

C

4,4'-dimethoxyazoxybenzene
1562-94-3, 21650-70-4, 51437-65-1

4,4'-dimethoxyazoxybenzene

D

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With N-doped TiO2 In water at 20℃; for 3h; UV-irradiation; Inert atmosphere;A 15%
B 45%
C 12%
D 10%
methanol
67-56-1

methanol

N,N'-Bis-(4-fluoro-phenyl)-diazene N-oxide
326-04-5, 32213-80-2, 51789-07-2

N,N'-Bis-(4-fluoro-phenyl)-diazene N-oxide

A

5-methoxy-2-phenyl-2H-indazole
120455-03-0

5-methoxy-2-phenyl-2H-indazole

B

5-methoxy-2-(4-methoxyphenyl)-2H-indazole
120455-06-3

5-methoxy-2-(4-methoxyphenyl)-2H-indazole

C

4,4'-dimethoxyazoxybenzene
1562-94-3, 21650-70-4, 51437-65-1

4,4'-dimethoxyazoxybenzene

D

4-hydroxyazobenzene
1689-82-3

4-hydroxyazobenzene

E

4-methoxyazobenzene
2396-60-3

4-methoxyazobenzene

F

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With N-doped TiO2 In water at 20℃; for 3h; sunlight; Inert atmosphere;A 10%
B 44%
C 15%
D 7%
E 6%
F 15%
4-nitro-phenol
100-02-7

4-nitro-phenol

A

4-amino-phenol
123-30-8

4-amino-phenol

B

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C

4,4'-dihydroxyazoxybenzene
15596-57-3, 117823-25-3

4,4'-dihydroxyazoxybenzene

Conditions
ConditionsYield
With hydrazine hydrate; nickel(II) nitrate; zinc In tert-butyl alcohol for 0.833333h; Heating;A 26 % Chromat.
B 8 % Chromat.
C 40%
With hydrazine hydrate; nickel(II) nitrate; zinc In ethanol for 4h; Heating;A 18%
B 17 % Chromat.
C 20%
methanol
67-56-1

methanol

4,4'-bis(chloro)azoxybenzene
614-26-6

4,4'-bis(chloro)azoxybenzene

A

5-methoxy-2-phenyl-2H-indazole
120455-03-0

5-methoxy-2-phenyl-2H-indazole

B

5-methoxy-2-(4-methoxyphenyl)-2H-indazole
120455-06-3

5-methoxy-2-(4-methoxyphenyl)-2H-indazole

C

4-hydroxyazobenzene
1689-82-3

4-hydroxyazobenzene

D

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With N-doped TiO2 In water at 20℃; for 3h; sunlight; Inert atmosphere;A 8%
B 40%
C 7%
D 15%
bis-(4-oxo-cyclohexa-2,5-dienylidene)-hydrazine
20638-42-0

bis-(4-oxo-cyclohexa-2,5-dienylidene)-hydrazine

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With diethyl ether; sulphurous acid
With phenylhydrazine; benzene
p-nitrosophenol
104-91-6

p-nitrosophenol

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With potassium hydroxide at 180℃;
bis-(4-methoxymethoxy-phenyl)-diazene

bis-(4-methoxymethoxy-phenyl)-diazene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With hydrogenchloride; ethanol
Azobenzene
1227476-15-4

Azobenzene

A

(bis-4-hydroxyphenyl)-4,4'-diazobiphenyl
4998-22-5

(bis-4-hydroxyphenyl)-4,4'-diazobiphenyl

B

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With sulfuric acid at 10 - 12℃; Electrolysis.Oxydation an einer Platin-Anode;
4-[(4-hydroxy)phenylazo]benzenesulfonic acid
2918-83-4

4-[(4-hydroxy)phenylazo]benzenesulfonic acid

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With potassium hydroxide at 250℃;
4,4'-azo-bis-benzenesulfonic acid
2779-21-7

4,4'-azo-bis-benzenesulfonic acid

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With potassium hydroxide at 250℃;
4,4'-diethoxyazoxybenzene
588-52-3

4,4'-diethoxyazoxybenzene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With hydrogenchloride at 180℃;
4-[(4-hydroxy)phenylazo]benzenesulfonic acid
2918-83-4

4-[(4-hydroxy)phenylazo]benzenesulfonic acid

potassium hydroxide

potassium hydroxide

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
at 250℃;
hydrogenchloride
7647-01-0

hydrogenchloride

4,4'-diethoxyazoxybenzene
588-52-3

4,4'-diethoxyazoxybenzene

A

chloroethane
75-00-3

chloroethane

B

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
at 130℃;
potassium phenolate
100-67-4

potassium phenolate

1-oxy-benzenediazonium nitrate-(4)

1-oxy-benzenediazonium nitrate-(4)

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With water
4-hydroxyphenyldiazonium chloride
1073-71-8, 50909-74-5

4-hydroxyphenyldiazonium chloride

ammoniacal copper oxide

ammoniacal copper oxide

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

4-(2-Amino-[1]naphthylazo)-phenol
148692-51-7

4-(2-Amino-[1]naphthylazo)-phenol

A

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

B

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C

phenol
108-95-2

phenol

4,4'-azo-di-phenol; compound with [1,4]benzoquinon-azine

4,4'-azo-di-phenol; compound with [1,4]benzoquinon-azine

sulfur dioxide

sulfur dioxide

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4-amino-phenol
123-30-8

4-amino-phenol

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

p-nitrosophenol
104-91-6

p-nitrosophenol

C

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

D

4,4'-dihydroxyazoxybenzene
15596-57-3, 117823-25-3

4,4'-dihydroxyazoxybenzene

Conditions
ConditionsYield
With [(-Ti(H2O)(OH)-O-Ti(H2O)(OH)-O-)*(O*-O-)]n; dihydrogen peroxide In methanol at 25℃; for 0.75h;
4-(4-nitrophenoxy)butanoic acid
28341-54-0

4-(4-nitrophenoxy)butanoic acid

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzene
2: aq.-ethanolic sodium acetate / an einer Nickel-Kathode; Behandlung des Reaktionsgemisches mit Luft
3: hydrogen chloride; ethanol
View Scheme
1-(methoxymethoxy)-4-nitrobenzene
880-03-5

1-(methoxymethoxy)-4-nitrobenzene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq.-ethanolic sodium acetate / an einer Nickel-Kathode; Behandlung des Reaktionsgemisches mit Luft
2: hydrogen chloride; ethanol
View Scheme
1-ethoxy-4-nitrobenzene
100-29-8

1-ethoxy-4-nitrobenzene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: alcohol; potassium hydroxide; zinc / Darstellung
2: hydrochloric acid / 180 °C
View Scheme
4-Hydroxy-4'-methoxyazobenzene
2496-25-5, 103939-79-3

4-Hydroxy-4'-methoxyazobenzene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With boron tribromide In dichloromethane
4-nitro-phenol
100-02-7

4-nitro-phenol

A

4-amino-phenol
123-30-8

4-amino-phenol

B

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With cage-bridged Au-Pd dimer at 20℃; Irradiation;
p-bromobenzyl chloride
589-17-3

p-bromobenzyl chloride

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

bis-[4-(4-bromo-benzyloxy)-phenyl]-diazene

bis-[4-(4-bromo-benzyloxy)-phenyl]-diazene

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 for 3h; Heating;99%
1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

bis-[4-(4-chloro-benzyloxy)-phenyl]-diazene

bis-[4-(4-chloro-benzyloxy)-phenyl]-diazene

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 for 3h; Heating;98%
1-chloromethyl-4-fluorobenzene
352-11-4

1-chloromethyl-4-fluorobenzene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

bis-[4-(4-fluoro-benzyloxy)-phenyl]-diazene

bis-[4-(4-fluoro-benzyloxy)-phenyl]-diazene

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 for 3h; Heating;97%
4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With zinc In methanol at 25℃; for 0.166667h; Inert atmosphere;96%
With magnesium In methanol at 25℃; for 0.2h; Inert atmosphere;95%
With sodium dithionite; water In dimethyl sulfoxide at 20℃; pH=7.4; Kinetics; phosphate buffer;
With hydrogenchloride; tin(ll) chloride
With sodium hydroxide; zinc
4-Methylbenzyl chloride
104-82-5

4-Methylbenzyl chloride

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C28H26N2O2
41005-19-0

C28H26N2O2

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 for 3h; Heating;96%
1,3-dimethyl 5-(bromomethyl)benzene-1,3-dicarboxylate
42268-88-2

1,3-dimethyl 5-(bromomethyl)benzene-1,3-dicarboxylate

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

tetramethyl 5,5’-(((diazene-1,2-diylbis(4,1-phenylene))bis(oxy))bis(methylene))diisophthalate

tetramethyl 5,5’-(((diazene-1,2-diylbis(4,1-phenylene))bis(oxy))bis(methylene))diisophthalate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 10h;96%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 8h;
1-chloro-2-(chloromethyl)benzene
611-19-8

1-chloro-2-(chloromethyl)benzene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

bis-[4-(2-chloro-benzyloxy)-phenyl]-diazene

bis-[4-(2-chloro-benzyloxy)-phenyl]-diazene

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 for 3h; Heating;95%
1-Chloromethylnaphthalene
86-52-2

1-Chloromethylnaphthalene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4,4'-bis(1-naphthyl)methoxyazobenzene

4,4'-bis(1-naphthyl)methoxyazobenzene

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 for 3h; Heating;93%
4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

<3,3',5,5'-(2)H4>-4,4'-dihydroxyazobenzene
86412-28-4

<3,3',5,5'-(2)H4>-4,4'-dihydroxyazobenzene

Conditions
ConditionsYield
With water-d2; triethylamine at 160℃; for 48h;90%
benzyl alcohol
100-51-6

benzyl alcohol

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4-(benzylamino)phenol
103-14-0

4-(benzylamino)phenol

Conditions
ConditionsYield
With 2 wtpercent of Pd on TiO2 In water at 29.84℃; for 8h; UV-irradiation; Inert atmosphere;90%
p-Xylylene dichloride
623-25-6

p-Xylylene dichloride

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C28H20Cl2N2O4

C28H20Cl2N2O4

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 25h;88%
9,1-bis(chloromethyl)anthracene
10387-13-0

9,1-bis(chloromethyl)anthracene

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C112H81ClN8O8

C112H81ClN8O8

Conditions
ConditionsYield
With potassium carbonate In ethanol for 5h; Heating;87%
1-Bromooctadecane
112-89-0

1-Bromooctadecane

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4-hydroxy-4'(4-octadecyloxy)diazobenzene
55385-04-1

4-hydroxy-4'(4-octadecyloxy)diazobenzene

Conditions
ConditionsYield
With potassium hydroxide In cyclohexanol for 3h; Heating;84.5%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;57%
6-chloro-1-hexanol
2009-83-8

6-chloro-1-hexanol

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4,4’-bis(6-hydroxyhexyloxy)azobenzene

4,4’-bis(6-hydroxyhexyloxy)azobenzene

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 12h; Reflux; Inert atmosphere;82.4%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 24h; Inert atmosphere; Reflux;80.5%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 120℃; for 20h;46%
With potassium hydroxide; potassium iodide In ethanol; water for 50h; Heating;41%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 90℃; for 12h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4-N-tert-butoxycarbonylaminophenol
54840-15-2

4-N-tert-butoxycarbonylaminophenol

Conditions
ConditionsYield
With polymethylhydrosiloxane; palladium on activated charcoal In ethanol at 20℃; for 5h;80%
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

ethyl 4-{4-[4-(3-carboethoxypropoxy)phenylazo]phenoxy}butyrate
1280725-24-7

ethyl 4-{4-[4-(3-carboethoxypropoxy)phenylazo]phenoxy}butyrate

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux; Inert atmosphere;80%
4-bromomethyl pyridine hydrobromide
73870-24-3

4-bromomethyl pyridine hydrobromide

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C24H20N4O2

C24H20N4O2

Conditions
ConditionsYield
With potassium carbonate In acetone for 80h; Reflux; Inert atmosphere;78%
1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

Bis-[4-(5-bromo-pentyloxy)-phenyl]-diazene
948040-78-6

Bis-[4-(5-bromo-pentyloxy)-phenyl]-diazene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 24h;76.9%
With sodium hydroxide In ethanol Heating;17%
With potassium carbonate In acetonitrile Microwave irradiation;
potassium tetrachloropalladate(II)
10025-98-6

potassium tetrachloropalladate(II)

water
7732-18-5

water

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

[((4,4'-bis(hydroxy)-azobenzene)(-H))Pd(μ-Cl)]2*3H2O

[((4,4'-bis(hydroxy)-azobenzene)(-H))Pd(μ-Cl)]2*3H2O

Conditions
ConditionsYield
In 1,4-dioxane; water dissolving of nitrogen compd. and palladiun compd. in dioxane/water (1:1), stirring at room temp. for one week; concn. under vacuum, isolation of ppt., washing with ethanol and diethylether, drying under vacuum, elem. anal.;76%
toluene-4-sulfonic acid 3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxymethyl}-propyl ester

toluene-4-sulfonic acid 3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxymethyl}-propyl ester

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C30H46N2O10

C30H46N2O10

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 14h; Inert atmosphere;76%
chloroacetic acid
79-11-8

chloroacetic acid

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4,4'-bis(carboxymethoxy)azobenzene
97788-42-6

4,4'-bis(carboxymethoxy)azobenzene

Conditions
ConditionsYield
With sodium hydroxide73%
N-(chloromethyl)phthalimide
17564-64-6

N-(chloromethyl)phthalimide

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C30H20N4O6

C30H20N4O6

Conditions
ConditionsYield
With potassium carbonate In ethanol for 0.166667h; Heating;70%
4-oxo-4-((2-(prop-2-yn-1-yl)pent-4-yn-1-yl)oxy)butanoic acid

4-oxo-4-((2-(prop-2-yn-1-yl)pent-4-yn-1-yl)oxy)butanoic acid

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C36H34N2O8

C36H34N2O8

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 96h; Inert atmosphere; Cooling with ice; Schlenk technique;70%
1-dodecylbromide
143-15-7

1-dodecylbromide

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

4-<(4-(dodecyloxy)phenyl)azo>phenol
87102-54-3

4-<(4-(dodecyloxy)phenyl)azo>phenol

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 10h;69.5%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;53%
With potassium carbonate In acetone for 6h; Reflux;30%
With potassium hydroxide In ethanol at 50℃; for 24h;
1,12-dibromododecane
3344-70-5

1,12-dibromododecane

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C36H56O2N2Br2

C36H56O2N2Br2

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 24h;68.5%
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
942428-83-3

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C40H46N2O20

C40H46N2O20

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In acetonitrile at 20℃; Molecular sieve;68%
C31H56O5S

C31H56O5S

4,4'-dihydroxyazobenzene
2050-16-0

4,4'-dihydroxyazobenzene

C36H58N2O4

C36H58N2O4

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 14h; Inert atmosphere;67%

2050-16-0Relevant articles and documents

Shape memory polyurethanes containing azo exhibiting photoisomerization function

Zhang, Yaoming,Wang, Chao,Pei, Xianqiang,Wang, Qihua,Wang, Tingmei

, p. 9976 - 9981 (2010)

A series of azobenzene-containing polyurethanes (azoPU) was synthesized. The structure of the azoPU and the synthesis process were detected by FTIR and nuclear magnetic resonance (NMR), and the transition temperature was determined by differential scanning calorimetry (DSC). Tensile and cyclic thermomechanical experiment results revealed that excellent mechanical properties, shape fixity (Rf), and shape recovery (Rr) were obtained by the addition of azo to the chain of PU. Rr and Rf of azoPU increased with the increase of hard segment (HS) content. The higher HS content enhanced interaction among polymer chains as the chances of induced dipole-dipole interaction between aromatic rings increased in the presence of azo in the main chain. The materials presented trans-cis isomerization under UV irradiation in addition to the shape memory effect. The UV-vis spectrum indicated that photoisomerization occurred both in solution and solid state. It is expected that the work may be helpful in expanding the application of shape memory PU in areas of drug release and optical data storage.

Functionalized azobenzene platinum(II) complexes as putative anticancer compounds

Samper, Katia G.,Lorenzo, Julia,Capdevila, Mercè,Palacios, òscar,Bayón, Pau

, p. 435 - 453 (2021)

The synthesis and characterization of four platinum(II) complexes using azobenzenes conveniently functionalized as ligands has been carried out. The characteristic photochemical behavior of the complexes due to the presence of azobenzene-type ligands and the role of the ligands in the activation of the complexes has been studied. Their promising cytotoxicity observed in HeLa cells prompted us to study the mechanism of action of these complexes as cytostatic agents. The interaction of the compounds with DNA, studied by circular dichroism, revealed a differential activity of the Pt(II) complexes upon irradiation. The intercalation abilities of the complexes as well as their reactivity with common proteins present in the blood stream allows to confirm some of the compounds obtained as good anticancer candidates.

Designing ternary Co-crystals with stacking interactions and weak hydrogen bonds. 4,4′-bis-hydroxyazobenzene

Chakraborty, Shaunak,Rajput, Lalit,Desiraju, Gautam R.

, p. 2571 - 2577 (2014)

Three ternary co-crystals of the title compound are reported. The design strategy hinges on the identification of a robust synthon with O-H...N hydrogen bonds in a binary co-crystal. Construction of this module allows the tuning of π...π stacking interactions and weak hydrogen bonds to incorporate the third component into the crystal structure. Screening of various co-formers showed that a delicate balance of electrostatics is required for stacking to favor the formation of ternaries. A C-H...N hydrogen-bonded motif was also found to occur repetitively in the ternary co-crystals. The directional nature of weak hydrogen bonds allows them to be used effectively in this study.

Synthesis and characterization of azobenzene-functionalized hyperbranched polymers

Alam, Md. Zahangir,Ogata, Tomonari,Kuwahara, Yutaka,Kurihara, Seiji

, p. 25 - 31 (2010)

Azobenzene functionalized hyperbranched polymers (HBAzPs) have been synthesized by polycondensation of 4,4'-di((2-hydroxyethoxy)azobenzene and 1,3,5-benzenetricarboxylic acid chloride in presence of triethylamine at room temperature through A2+B3 polymerization approach. The structure and properties of HBAzPs were characterized by 1H NMR, IR, GPC, DSC and UV-Visible spectrometry. Molecular weights as well as properties of HBAzPs were found to be greatly influenced by molar ratio of monomers, amount of triethylamine and monomer concentration. HBAzP solutions in THF showed absorbances at 356nm and 450nm corresponding to -* and n-* electronic transitions of azobenzene chromophores, respectively. A reversible trans-cis photoisomerization of HBAzPs was observed upon irradiation of UV and visible light. Taylor & Francis Group, LLC.

Rational design of a photoswitchable DNA glue enabling high regulatory function and supramolecular chirality transfer

Crespi, Stefano,Dohno, Chikara,Feringa, Ben L.,Kobauri, Piermichele,Kobayashi, Shotaro,Nakatani, Kazuhiko,Simeth, Nadja A.,Szymanski, Wiktor

, p. 9207 - 9220 (2021)

Short, complementary DNA single strands with mismatched base pairs cannot undergo spontaneous formation of duplex DNA (dsDNA). Mismatch binding ligands (MBLs) can compensate this effect, inducing the formation of the double helix and thereby acting as a molecular glue. Here, we present the rational design of photoswitchable MBLs that allow for reversible dsDNA assembly by light. Careful choice of the azobenzene core structure results in excellent band separation of theEandZisomers of the involved chromophores. This effect allows for efficient use of light as an external control element for duplex DNA formation and for an in-depth study of the DNA-ligand interaction by UV-Vis, SPR, and CD spectroscopy, revealing a tight mutual interaction and complementarity between the photoswitchable ligand and the mismatched DNA. We also show that the configuration of the switch reversibly dictates the conformation of the DNA strands, while the dsDNA serves as a chiral clamp and translates its chiral information onto the ligand inducing a preference in helical chirality of theZisomer of the MBLs.

Azobenzene-siloxane hybrids with lamellar structures from bridge-type alkoxysilyl precursors

Guo, Sufang,Chaikittisilp, Watcharop,Okubo, Tatsuya,Shimojima, Atsushi

, p. 25319 - 25325 (2014)

Lamellar azobenzene-siloxane hybrids were prepared by controlled hydrolysis and polycondensation of three types of precursors, where azobenzene is sandwiched by mono-, di- and triethoxysilyl groups using propylene linkers. All precursors underwent reversible and fast trans-cis isomerization upon UV/Vis irradiation in dilute solution. Upon hydrolysis of the triethoxysilylated precursor in a homogeneous solution under acidic conditions, precipitation occurred by self-assembly of hydrolyzed monomers into a lamellar structure. Although di- and mono-ethoxysilylated precursors produced less ordered products under identical conditions, highly ordered lamellar films were obtainable either by evaporation induced self-assembly of the hydrolyzed monomers or by solid-state reactions of precursor films. The degree of trans-cis isomerization of azobenzene moieties in the hybrid films was enhanced by decreasing the cross-linking degree of siloxane networks using precursors with less condensable alkoxy groups.

“Self-Lockable” Liquid Crystalline Diels–Alder Dynamic Network Actuators with Room Temperature Programmability and Solution Reprocessability

Han, Li,Jiang, Zhi-Chao,Xiao, Yao-Yu,Yin, Lu,Zhao, Yue

, p. 4925 - 4931 (2020)

Novel main-chain liquid crystalline Diels—Alder dynamic networks (LCDANs) were prepared that exhibit unprecedented ease for actuator programming and reprocessing compared to existing liquid crystalline network (LCN) systems. Following cooling from 125 °C, LCDANs are deformed with aligned mesogens self-locked at room temperature by slowly formed Diels–Alder (DA) bonds, which allows for the formation of solid 3D actuators capable of reversible shape change, and strip walker and wheel-capable light-driven locomotion upon either thermally or optically induced order–disorder phase transition. Any actuator can readily be erased at 125 °C and reprogrammed into a new one under ambient conditions. Moreover, LCDANs can be processed directly from melt (for example, fiber drawing) and from solution (for example, casting tubular actuators), which cannot be achieved with LCNs using exchangeable covalent bonds. The combined attributes of LCDANs offer significant progress toward developing easily programmable/processable LCN actuators.

Photoreversible Loading and Unloading of Q–Silsesquioxane Dynamic Network Sponges

Hu, Nai–hsuan,Furgal, Joseph Coy

, (2021)

The synthesis and mechanical properties of photoswitchable silsesquioxane/azobenzene hybrid 3D-polymers (“dynamic sponges”) are presented and discussed. The hybrid is capable of extensive macroscopic movement, and overcomes previously problematic crosslink locking issues. A hydride-functionalized Q-type silsesquioxane (Q8M8H) is reacted with di-allyloxyazobenzene using hydrosilylation methods. The properties of the resulting materials are controlled via careful choice of starting material ratios and solvent, leading to gels or films. Both morphologies show pronounced photoresponsive behavior in and on the surfaces of different solvents. Photoactuation is tracked by microscopy, dynamic mechanic analysis, and UV–vis spectroscopy. The gel system has a porous structure similar to a sponge. It undergoes shrinkage in volume by 18.3% in toluene under UV irradiation, and shows excellent recovery to the swollen state after irradiation with visible light. These novel photodynamic materials offer reversible modulus switching from 160?kPa in the swollen state to 500?kPa in the “wrung-out” sponge. The sponges can engage in uptake and release of a range of substances (i.e., reversible hydrophobic sponging), with overall performance determined by solvent specific quantities such as polarity and size. Such behavior gives these materials high potential for soft robotics applications and great promise as reusable environmental remediators.

New photochromic azoderivatives with potent acetylcholinesterase inhibition

Arroyo Ma?ez, Pau,Biscussi, Brunella,Murray, Ana Paula,Richmond, Victoria,Sequeira, Maria Alejandra

, (2021/06/12)

The design of photochromic cholinesterase inhibitors is a challenge of the photopharmacological approach towards the remote control of acetylcholinesterase (AChE) enzyme and its potential application in Alzheimer's disease therapy. In this work, a series of azoderivatives were designed, synthesized and evaluated as AChE inhibitors. The optimized microwave-assisted synthesis (two steps) showed excellent yields with a total reaction time no longer than 40 min. The results showed that all the synthesized compounds exhibited high AChE inhibitory activity at the micromolar range (IC50, 0.65–8.52 μM). Moreover, compound 19, with double four-hydrocarbon chain connected to piperidine, showed a powerful in vitro enzymatic response for its Z isomer (IC50: 0.43 μM) determined by Ellman's assay. Also, 19 showed a stable photostationary state monitored by UV/Vis absorption spectroscopy and 1H NMR spectra. These results indicate that 19 can act as an efficient photo-responsible probe to remote control AChE activity. Molecular modelling analysis of 19 Z revealed its affinity by the peripheral anionic site of AChE, providing understanding of its higher inhibition power. This study contributes to the development of new promising agents for photopharmacological treatment of Alzheimer's disease.

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