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Ethane, 1,2-bis(2-bromoethoxy)-, also known as Bromo-PEG2-bromide, is a PEG (polyethylene glycol) linker containing two bromide groups. The bromide (Br) is a very good leaving group for nucleophilic substitution reactions, and the hydrophilic PEG spacer increases solubility in aqueous media. Ethane, 1,2-bis(2-bromoethoxy)is commonly used in chemical synthesis and pharmaceutical applications due to its unique properties.

31255-10-4

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31255-10-4 Usage

Uses

Used in Chemical Synthesis:
Ethane, 1,2-bis(2-bromoethoxy)is used as a synthetic intermediate for the creation of various chemical compounds. The expression is: Ethane, 1,2-bis(2-bromoethoxy)is used as a synthetic intermediate for [application reason], which is its ability to facilitate nucleophilic substitution reactions due to the presence of the bromide groups.
Used in Pharmaceutical Applications:
Ethane, 1,2-bis(2-bromoethoxy)is used as a building block in the development of pharmaceutical compounds. The expression is: Ethane, 1,2-bis(2-bromoethoxy)is used as a building block for [application reason], which is its ability to enhance the solubility and bioavailability of drug molecules in aqueous media, thanks to the hydrophilic PEG spacer.
Used in Drug Delivery Systems:
In the pharmaceutical industry, Ethane, 1,2-bis(2-bromoethoxy)is used as a component in drug delivery systems. The expression is: Ethane, 1,2-bis(2-bromoethoxy)is used as a component in drug delivery systems for [application reason], which is its potential to improve the delivery, bioavailability, and therapeutic outcomes of various drugs by enhancing their solubility and stability in aqueous environments.
Used in Bioconjugation:
Ethane, 1,2-bis(2-bromoethoxy)is also used in bioconjugation, a process that involves the attachment of biologically active molecules to other molecules, such as drugs or imaging agents. The expression is: Ethane, 1,2-bis(2-bromoethoxy)is used as a bioconjugation agent for [application reason], which is its ability to facilitate the covalent attachment of target molecules through nucleophilic substitution reactions.

Check Digit Verification of cas no

The CAS Registry Mumber 31255-10-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,1,2,5 and 5 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 31255-10:
(7*3)+(6*1)+(5*2)+(4*5)+(3*5)+(2*1)+(1*0)=74
74 % 10 = 4
So 31255-10-4 is a valid CAS Registry Number.

31255-10-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2-bis(2-bromoethoxy)ethane

1.2 Other means of identification

Product number -
Other names AmbotzPEG1075

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:31255-10-4 SDS

31255-10-4Synthetic route

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

Conditions
ConditionsYield
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With carbon tetrabromide In dichloromethane for 0.25h; Appel reaction;
Stage #2: With triphenylphosphine In dichloromethane at 20℃; Appel reaction;
90%
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 1h;90%
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 12h;87%
triethylene glycol di-(p-toluenesulfonate)
19249-03-7

triethylene glycol di-(p-toluenesulfonate)

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

Conditions
ConditionsYield
With ammonium bromide In N,N-dimethyl-formamide at 85℃; for 5h; Product distribution; Further Variations:; Solvents;76%
With ammonium bromide In N,N-dimethyl-formamide at 85℃; for 5h; Product distribution / selectivity;76%
With lithium bromide In acetone Reflux;
sulfurous dibromide
507-16-4

sulfurous dibromide

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

Conditions
ConditionsYield
With pyridine In benzine at 65℃; for 17h; Reflux;60%
oxirane
75-21-8

oxirane

ethene
74-85-1

ethene

A

1,1'-oxybis(2-bromo-ethane)
5414-19-7

1,1'-oxybis(2-bromo-ethane)

B

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

Conditions
ConditionsYield
With bromine
1,4-dioxane
123-91-1

1,4-dioxane

ethene
74-85-1

ethene

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

Conditions
ConditionsYield
With bromine
1-bromo-2-(chloromethoxy)ethane
1462-35-7

1-bromo-2-(chloromethoxy)ethane

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

Conditions
ConditionsYield
With sodium; N,N-dimethyl-aniline In benzene
1,4-dioxane
123-91-1

1,4-dioxane

A

1,1'-oxybis(2-bromo-ethane)
5414-19-7

1,1'-oxybis(2-bromo-ethane)

B

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

C

1-bromo-2-{2-[2-(2-bromoethoxy)ethoxy]-ethoxy}ethane
31255-26-2

1-bromo-2-{2-[2-(2-bromoethoxy)ethoxy]-ethoxy}ethane

Conditions
ConditionsYield
With titanium(IV) bromide 1.) CH2Cl2, room temperature, 2.) CH2Cl2, reflux, 21 d; Yield given. Multistep reaction. Yields of byproduct given;
triethyleneglycol dimesylate
80322-82-3

triethyleneglycol dimesylate

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

Conditions
ConditionsYield
With lithium bromide In acetone for 20h; Heating;
With tetrabutylammomium bromide In acetonitrile at 50℃; for 16h; Inert atmosphere;2.84 g
dihexylamine
143-16-8

dihexylamine

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

{2-[2-(2-Dihexylamino-ethoxy)-ethoxy]-ethyl}-dihexyl-amine

{2-[2-(2-Dihexylamino-ethoxy)-ethoxy]-ethyl}-dihexyl-amine

Conditions
ConditionsYield
With sodium carbonate In acetonitrile at 81℃; for 18h;98%
1,5,9-Tritosyl-1,5,9-triazanonane
35980-64-4

1,5,9-Tritosyl-1,5,9-triazanonane

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

7,11,15-tris(p-tolylsulphonyl)-1,4-dioxa-7,11,15-triazacycloheptadecane
60147-31-1

7,11,15-tris(p-tolylsulphonyl)-1,4-dioxa-7,11,15-triazacycloheptadecane

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 10h; Heating;96%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In water; toluene for 9h; Heating;96%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N,N'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide)
59945-35-6

N,N'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide)

Conditions
ConditionsYield
With sodium carbonate In water for 4h; Heating;96%
With sodium carbonate 1.) 2 h, heated, 2.) 4 h, reflux; Yield given. Multistep reaction;
3-ethyl-3,4-dihydroquinoxalin-2(1H)-one
13297-35-3

3-ethyl-3,4-dihydroquinoxalin-2(1H)-one

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

1,8-bis(3-ethyl-1,2-dihydro-2-oxoquinoxalin-1-yl)-3,6-dioxaethane
827324-66-3

1,8-bis(3-ethyl-1,2-dihydro-2-oxoquinoxalin-1-yl)-3,6-dioxaethane

Conditions
ConditionsYield
With potassium hydroxide In 1,4-dioxane for 5h; Heating;96%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

diethylamine
109-89-7

diethylamine

1,8-bis(diethylamino)-3,6-dioxaoctane
42070-24-6

1,8-bis(diethylamino)-3,6-dioxaoctane

Conditions
ConditionsYield
at 21℃; for 48h;94%
With benzene
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

1,8-diazido-3,6-dioxaoctane
59559-06-7

1,8-diazido-3,6-dioxaoctane

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 60℃; for 12h;93%
With sodium azide In N,N-dimethyl-formamide at 60℃; for 6h;82%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

methyl salicylate
119-36-8

methyl salicylate

1,10-bis(2'-methyl benzoate)-1,4,7,10-tetraoxadecane
201596-36-3

1,10-bis(2'-methyl benzoate)-1,4,7,10-tetraoxadecane

Conditions
ConditionsYield
With potassium carbonate In acetone for 168h; Heating;92%
With potassium carbonate In acetone Heating;
1,4,7-tritosyl-1,4,7-triazaheptane
56187-04-3

1,4,7-tritosyl-1,4,7-triazaheptane

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

7,10,13-tris(p-tolylsulphonyl)-1,4-dioxa-7,10,13-triazacyclopentadecane
60147-29-7

7,10,13-tris(p-tolylsulphonyl)-1,4-dioxa-7,10,13-triazacyclopentadecane

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 10h; Heating;90%
With lithium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 10h; Heating;80%
1,5,9-Tritosyl-1,5,9-triazanonane
35980-64-4

1,5,9-Tritosyl-1,5,9-triazanonane

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

7,10,13-tris(p-tolylsulphonyl)-1,4-dioxa-7,10,13-triazacyclopentadecane
60147-29-7

7,10,13-tris(p-tolylsulphonyl)-1,4-dioxa-7,10,13-triazacyclopentadecane

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In water; toluene for 9h; Heating;90%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

(15)N-2-nitro-4-methylphenol
87668-43-7

(15)N-2-nitro-4-methylphenol

(15)N-1,8-di-2-nitro-4-methylphenoxy-3,6-dioxaoctane

(15)N-1,8-di-2-nitro-4-methylphenoxy-3,6-dioxaoctane

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃;90%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

N,0-dimethylhydroxylamine
1117-97-1

N,0-dimethylhydroxylamine

N-(2-{2-[2-(Methoxy-methyl-amino)-ethoxy]-ethoxy}-ethyl)-O,N-dimethyl-hydroxylamine

N-(2-{2-[2-(Methoxy-methyl-amino)-ethoxy]-ethoxy}-ethyl)-O,N-dimethyl-hydroxylamine

Conditions
ConditionsYield
at 50℃; for 42h;90%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

tribenzylphosphine
7650-89-7

tribenzylphosphine

[ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis[tribenzylphosphonium] dibromide
143251-93-8

[ethane-1,2-diylbis(oxyethane-2,1-diyl)]bis[tribenzylphosphonium] dibromide

Conditions
ConditionsYield
In acetonitrile for 48h; Heating;89%
In acetonitrile Heating;
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

3,7-dithianonane-1,9-dithiol
25676-62-4

3,7-dithianonane-1,9-dithiol

1,4,8,11-Tetrathia-14,17-dioxacyclononadecane
79028-44-7

1,4,8,11-Tetrathia-14,17-dioxacyclononadecane

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 45 - 50℃;88%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

N,N',N'',N'''-tetratosyl-1,10-diamino-4,7-diazadecane
74676-47-4

N,N',N'',N'''-tetratosyl-1,10-diamino-4,7-diazadecane

7,11,14,18-tetrakis(p-tolylsulphonyl)-1,4-dioxa-7,11,14,18-tetra-azacycloicosane
120808-62-0

7,11,14,18-tetrakis(p-tolylsulphonyl)-1,4-dioxa-7,11,14,18-tetra-azacycloicosane

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 10h; Heating;88%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In water; toluene for 9h; Heating;88%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

C13H17BrO4

C13H17BrO4

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 0.5h;86%
3,6-dithiaoctan-1,8-dithiol
25423-55-6

3,6-dithiaoctan-1,8-dithiol

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

1,3,6,9-Tetrathia-18-crown-6
79028-42-5

1,3,6,9-Tetrathia-18-crown-6

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 45 - 50℃;85%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

1,2-Bis-(2-selenocyanato-ethoxy)-ethane

1,2-Bis-(2-selenocyanato-ethoxy)-ethane

1, 10-diselana-4,7,13,16-tetraoxacyclooctadecane

1, 10-diselana-4,7,13,16-tetraoxacyclooctadecane

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; ethanol at 40 - 50℃; for 13h;85%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

dimethyl amine
124-40-3

dimethyl amine

1,2-bis-(2-dimethylamino-ethoxy)-ethane
3065-46-1

1,2-bis-(2-dimethylamino-ethoxy)-ethane

Conditions
ConditionsYield
at 25℃; for 40h;85%
4-(hydroxymethyl)-2-methoxy-5-nitrophenol
260417-00-3

4-(hydroxymethyl)-2-methoxy-5-nitrophenol

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

C14H20BrNO7

C14H20BrNO7

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 9h;85%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

7,16-bis<2-(p-tolylsulphonylamino)ethyl>-1,4,10-tetraoxa-7,16-diazacyclo-octadecane
76343-82-3

7,16-bis<2-(p-tolylsulphonylamino)ethyl>-1,4,10-tetraoxa-7,16-diazacyclo-octadecane

4,13-bis(p-tolylsulphonyl)-7,10,19,22,27,30-hexaoxa-1,4,13,16-tetra-aza<14.8.8>dotriacontane
113917-92-3

4,13-bis(p-tolylsulphonyl)-7,10,19,22,27,30-hexaoxa-1,4,13,16-tetra-aza<14.8.8>dotriacontane

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide Heating;84%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;84%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;84%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

7,13-bis<2-(tolylsulphonylamino)ethyl>-1,4,10-trioxa-7,13-diazacyclopentadecane
113917-86-5

7,13-bis<2-(tolylsulphonylamino)ethyl>-1,4,10-trioxa-7,13-diazacyclopentadecane

4,13-bis(p-tolylsulphonyl)-7,10,19,22,27-pentaoxa-1,4,13,16-tetra-azabicyclo<14.8.5>-nonacosane
113917-91-2

4,13-bis(p-tolylsulphonyl)-7,10,19,22,27-pentaoxa-1,4,13,16-tetra-azabicyclo<14.8.5>-nonacosane

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide Heating;83%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;83%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;83%
NH-pyrazole
288-13-1

NH-pyrazole

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

1,8-di(pyrazol-1-yl)-3,6-dioxaoctane
1170671-38-1

1,8-di(pyrazol-1-yl)-3,6-dioxaoctane

Conditions
ConditionsYield
Stage #1: NH-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h;
Stage #2: 1,2-bis-(2-bromo-ethoxy)-ethane In dimethyl sulfoxide at 80℃; for 1h;
83%
phthalimide
136918-14-4

phthalimide

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

2-(2-(2-(2-bromoethoxy)ethoxy)ethyl)-isoindole-1,3(2H)-dione
86927-04-0

2-(2-(2-(2-bromoethoxy)ethoxy)ethyl)-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide for 240h; Ambient temperature;82.5%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

1,11-bis(p-tolylsulphonylamino)-3,6,9-trioxaundecane
59945-36-7

1,11-bis(p-tolylsulphonylamino)-3,6,9-trioxaundecane

10,19-bis-(p-tolylsulphonyl)-1,4,7,13,16-pentaoxa-10,19-diazacyclohemicosane
120808-60-8

10,19-bis-(p-tolylsulphonyl)-1,4,7,13,16-pentaoxa-10,19-diazacyclohemicosane

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In water; toluene for 9h; Heating;82%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

1-hexadecyl-1H-imidazole
58175-55-6

1-hexadecyl-1H-imidazole

C44H84N4O2(2+)*2Br(1-)

C44H84N4O2(2+)*2Br(1-)

Conditions
ConditionsYield
In ethanol at 80℃; for 72h; Sealed tube;82%
piperidine
110-89-4

piperidine

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

1,2-bis-(2-piperidino-ethoxy)-ethane
76331-19-6

1,2-bis-(2-piperidino-ethoxy)-ethane

Conditions
ConditionsYield
at 70℃; for 13h;81%
With benzene
morpholine
110-91-8

morpholine

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

4,4'-(3,6-dioxa-octane-1,8-diyl)-bis-morpholine
110422-21-4

4,4'-(3,6-dioxa-octane-1,8-diyl)-bis-morpholine

Conditions
ConditionsYield
at 26℃; for 10h;81%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

N,N'-Bis(p-tolylsulfonyl)-1,5-diamino-3-oxapentane
59945-34-5

N,N'-Bis(p-tolylsulfonyl)-1,5-diamino-3-oxapentane

7,13-bis(p-tolylsulphonyl)-1,4,10-trioxa-7,13-diazacyclopentadecane
74461-33-9

7,13-bis(p-tolylsulphonyl)-1,4,10-trioxa-7,13-diazacyclopentadecane

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 10h; Heating;80%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In water; toluene for 9h; Heating;80%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 10h; Heating;77%
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

N,N'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide)
59945-35-6

N,N'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(4-methylbenzenesulfonamide)

7,16-bis(p-tolylsulphonyl)-1,4,10,13-tetraoxa-7,16-diazacyclo-octadecane
52601-78-2

7,16-bis(p-tolylsulphonyl)-1,4,10,13-tetraoxa-7,16-diazacyclo-octadecane

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 10h; Heating;80%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 10h; Heating;79%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In water; toluene for 9h; Heating;79%

31255-10-4Relevant academic research and scientific papers

Manganese porphyrin-incorporated conjugated polymer nanoparticles for T1-enhanced magnetic resonance and fluorescent imaging

Yang, Tianshe,Feng, Wenguo,Hu, Changyong,Lv, Zhuang,Wei, Huanjie,Jiang, Jiayang,Liu, Shujuan,Zhao, Qiang

, p. 604 - 611 (2017)

Conjugated polymer nanoparticles (CPNs) possess many useful and fascinating properties, including high brightness, excellent photostability, good water-dispersibility, low cytotoxicity, and easy functionalization, showing promising application in bioimaging. In this work, one kind of optical/magnetic conjugated polyelectrolyte has been designed and synthesized by introducing Mn(III) porphyrin (T1-weighted relaxivity) into a fluorescent fluorene based polymer backbone. Fluorescent/magnetic conjugated polymer nanoparticles (FM-CPNs) were prepared by self-assembly in the phosphate buffer solution caused by their amphiphilic structures with hydrophobic backbones and hydrophilic side chains. Their photophysical properties have been investigated in details via UV–vis absorption and fluorescent emission spectra. Investigation of its magnetic properties has shown that the FM-CPNs exhibit high T1-weighted relaxivity value, making them promising candidates for T1-enhanced magnetic resonance imaging agent. Further cell imaging has been realized successfully using FM-CPNs as staining label, and cytotoxicity was evaluated by the methyl thiazolyl tetrazolium (MTT) assay.

A delocalizable cationic headgroup together with an oligo-oxyethylene spacer in gemini cationic lipids improves their biological activity as vectors of plasmid DNA

Kumar, Krishan,Barrn-Berdn, Ana L.,Datta, Sougata,Muoz-beda, Mnica,Aicart-Ramos, Clara,Kondaiah, Paturu,Junquera, Elena,Bhattacharya, Santanu,Aicart, Emilio

, p. 1495 - 1506 (2015)

Lipoplex nano-aggregates constituted of plasmid DNA (pDNA) pEGFP-C3 and mixed cationic liposomes, consisting of several percentages of a gemini cationic lipid (GCL) of the 1,2-bis(hexadecyl imidazolium) oxyethylene series, referred to as (C16Im)2(C2O)n, with oxyethylene spacers (n = 1, 2 or 3) between the imidazolium cationic groups and the DOPE zwitterionic helper lipid, have been characterized by various biophysical and biological approaches carried out at several GCL compositions (α), and either the mass or the effective charge ratio of the lipoplex. The electrochemical study by ζ-potential confirms that the three GCLs yield a 10% lower effective charge than the nominal one, while compacted pDNA yields only a 25% effective negative charge. The SAXS study reveals, irrespective of the spacer length (n) and effective charge ratio (ρeff), the presence of two lamellar structures, i.e., one (Lα,main) in the whole GCL composition and another (Lα,DOPE,rich) with higher periodicity values that coexists with the previous one at low GCL composition (α = 0.2). The cryo-TEM analysis shows two types of multilamellar structures consisting of cationic lipidic bilayers with pDNA sandwiched between them: a cluster-type (C-type) at low α = 0.2 and a fingerprint-type (FP-type) at α ≥ 0.5, both with similar interlamellar spacing (d) in agreement with the Lα,main structure determined by SAXS. Transfection efficacies (TEs) of each lipid mixture were determined in four different cell lines (HEK293T, HeLa, Caco-2 and A549) at several α and ρeff values in the absence and presence of serum (FBS). The optimized formulations (α = 0.2 and ρeff = 2.0) substantially transfect cells much better than a commercial transfection reagent, Lipofectamine 2000 and previously studied efficient lipoplexes containing other cationic head groups or spacers both in the absence and presence of serum. The activity of optimized formulations may be attributed to the combination of several factors, such as: (a) the fusogenic character of DOPE which results in higher fluidity of the lipoplexes at α = 0.2, (b) the coexistence of two lamellar structures at α = 0.2 that synergizes the TE of these lipid vectors, and mainly (c) the higher biocompatibility of the GCLs reported in this work due to the presence of two imidazolium cationic groups together with an oligo-oxyethylene spacer. The length of the spacer in the GCL seems to have less impact, although (C16Im)2(C2O)n/DOPE-pDNA lipoplexes with n = 1 and 3 show higher gene transfection than n = 2. All the optimum formulations reported herein are all highly efficient with negligible levels of toxicity, and thus, may be considered as very promising gene vectors for in vivo applications. This journal is

Transmission of Unidirectional Molecular Motor Rotation to a Remote Biaryl Axis

Uhl, Edgar,Thumser, Stefan,Mayer, Peter,Dube, Henry

, p. 11064 - 11068 (2018)

Molecular motors undergo repetitive directional motions upon external energy input. A profound challenge is the defined transfer of directional motor motions to remote entities at the molecular scale. Herein, we present a molecular setup that allows for the transfer of the directional rotation of a light-powered motor unit onto a remote biaryl axis via an ethylene glycol chain link. Based on a combination of X-ray crystallographic analysis, ECD, and NMR experiments as well as a comprehensive theoretical assessment, we provide evidence for the coupled stepwise directional motions of both molecular units. With the presented setup, facile integration of molecular motor units into larger functional frameworks and complex molecular machines can be explored consciously in the future.

A platinum(II)-acetylide-based conjugated polyelectrolyte for hypoxia imaging via ratiometric and time-resolved luminescence microscopy

Li, Guo,Huang, Tianci,Xie, Mingjuan,Zhang, Xiangxiang,Yu, Qi,Liu, Shujuan,Yang, Tianshe,Zhao, Qiang

, p. 144 - 149 (2019)

A platinum(II)-acetylide-based conjugated polyelectrolyte has been designed and synthesized by using polyfluorenes as an O2-insensitive fluorophore and Pt(II) complex as an O2-sensitive phosphor, which can generate conjugated polyelectrolyte nanoparticle (CPE-nanoparticle) in the aqueous solution owing to their amphiphilic structures. The CPE-nanoparticle displays good sensitivity to O2 concentration and can detect oxygen levels reversibly. The intracellular ratiometric O2 sensing performance of the CPE-nanoparticle has been demonstrated by the remarkable variation in the Igreen/Iblue ratio values (0.18–0.85) in HeLa cells under different O2 levels. Furthermore, O2 level detection was carried out through time-resolved luminescence imaging (TRLI) to demonstrate the accuracy of the probe based on the CPE-nanoparticle. The CPE-nanoparticle shows a high phosphorescence quantum yield (19.98%) and oxygen quenching efficiency (0.975), which are superior to the existing O2 probe. The CPE-nanoparticle has been successfully applied in photoluminescence lifetime imaging and time-gated luminescence imaging for monitoring intracellular O2 levels.

Dynamic Assemblies of Molecular Motor Amphiphiles Control Macroscopic Foam Properties

Chen, Shaoyu,Feringa, Ben L.,Leung, Franco King-Chi,Stuart, Marc C. A.,Wang, Chaoxia

, p. 10163 - 10172 (2020)

Stimuli-responsive supramolecular assemblies controlling macroscopic transformations with high structural fluidity, i.e., foam properties, have attractive prospects for applications in soft materials ranging from biomedical systems to industrial processes, e.g., textile coloring. However, identifying the key processes for the amplification of molecular motion to a macroscopic level response is of fundamental importance for exerting the full potential of macroscopic structural transformations by external stimuli. Herein, we demonstrate the control of dynamic supramolecular assemblies in aqueous media and as a consequence their macroscopic foam properties, e.g., foamability and foam stability, by large geometrical transformations of dual light/heat stimuli-responsive molecular motor amphiphiles. Detailed insight into the reversible photoisomerization and thermal helix inversion at the molecular level, supramolecular assembly transformations at the microscopic level, and the stimuli-responsive foam properties at the macroscopic level, as determined by UV-vis absorption and NMR spectroscopies, electron microscopy, and foamability and in situ surface tension measurements, is presented. By selective use of external stimuli, e.g., light or heat, multiple states and properties of macroscopic foams can be controlled with very dilute aqueous solutions of the motor amphiphiles (0.2 weight%), demonstrating the potential of multiple stimuli-responsive supramolecular systems based on an identical molecular amphiphile and providing opportunities for future soft materials.

A versatile and robust vesicle based on a photocleavable surfactant for two-photon-tuned release

Li, Yi,Dong, Jianming,Xun, Zhiqing,Zeng, Yi,Yu, Tianjun,Han, Yongbin,Chen, Jinping,Li, Ying-Ying,Yang, Guoqiang

, p. 7931 - 7936 (2013)

A small amphiphile that contains a coumarin unit and alkynyl groups, as a two-cleavable segment and polymerizable groups, respectively, was designed and synthesized. The amphiphile showed a critical aggregation concentration of about 4.6×10-5M and formed a vesicle-type assembly. The formed vesicles were stabilized by insitu "click" polymerization without altering their morphology. Hydrophobic and hydrophilic guests can be encapsulated within the vesicle membrane and inside the aqueous core of the vesicle, respectively. The loaded guests can be released from the vesicle by using UV or near-IR stimuli, through splitting up the amphiphilic structure of the amphiphile. Distinguished dose-controlled photorelease of the polymeric vesicle is achieved with the maintenance of vesicular integrity, which makes the guest release dependent on the amount of cleavage of the amphiphilic structure during irradiation. This study provides a potential strategy for the development of versatile and stable drug-delivery systems that offer sustained and photo-triggered release. Copyright

Metal-organic frameworks constructed from crown ether-based 1,4-benzenedicarboxylic acid derivatives

Chen, Teng-Hao,Schneemann, Andreas,Fischer, Roland A.,Cohen, Seth M.

, p. 3063 - 3069 (2016)

A series of unprecedented crown ether- and thiacrown ether-derivatized benzene dicarboxylic acid (H2bdc) ligands has been synthesized and incorporated into the prototypical isoreticular metal-organic framework (IRMOF) and UiO-66 materials. In the case of UiO-66, only MOFs comprised from a mixed-ligand composition, requiring both unsubstituted bdc and crown ether containing ligands, could be prepared. These are among the few ligand derivatives, and resulting MOFs, that incorporate a macrocyclic group directly on the bdc ligand, providing a new, modular platform for exploring new supramolecular and coordination chemistry within MOFs.

Cationic amphitropic gemini surfactants with hydrophilic oligo(oxyethylene) spacer chains

Dreja, Michael,Gramberg, Susanne,Tieke, Bernd

, p. 1371 - 1372 (1998)

New gemini diammonium surfactants have been synthesized in which the spacer chain consists of oligo(oxyethylene) units and which exhibit thermotropic liquid crystalline lamellar α and β as well as lyotropic mesophases.

Novel gemini micelles from dimeric surfactants with oxyethylene spacer chain. Small angle neutron scattering and fluorescence studies

De, Soma,Aswal, Vinod K.,Goyal, Prem S.,Bhattacharya, Santanu

, p. 6152 - 6160 (1998)

Three new gemini surfactants containing mono-, di-, and trioxyethylene spacer chains have been synthesized. Small angle neutron scattering (SANS) cross sections from the micellar aggregates of these dimeric amphiphiles Br-, n-C16H33NMe2+-CH2(CH 2OCH2)pCH2-N+Me 2-n-C16H33, Br-, (where p = 1, 2, and 3) in aqueous media (D2O) have been measured. The data have been analyzed using the Hayter and Penfold model for macro-ion solution to compute the interparticle structure factor S(Q) taking into account the screened Coulomb interactions between the dimeric micelles. The SANS analysis showed that the micellar morphology depends on both the nature and the length of the spacer unit. Detailed analysis of the data further indicates that the introduction of oxyethylene spacer is not sufficient enough to prevent looping of the spacer chain. Thus the average separation between the dimethylammonium ion headgroups is considerably lower than is expected from a fully extended conformation of the spacer chain. The micelles from these surfactants have also been characterized in terms of their critical micelle concentrations (cmc), microviscosities, and micropolarities on the basis of the information provided by micelle-solubilized fluorescent probes. These results indicate little difference in their micellar properties such as cmc, microviscosity, and micropolarity.

Photochromic controlled permeable small molecule cross-linked vesicle as well as preparation method and application thereof

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Paragraph 0045-0047, (2021/09/01)

The invention discloses a photochromic controlled-permeation small-molecule crosslinked vesicle CSMVs as well as a preparation method and application thereof. Belong to micromolecule self-assembly technical field. The invention firstly synthesizes an azobenzene amphiphilic compound, and then further cross-linking to prepare the photochromic controllable permeable small-molecule cross-linked vesicle. The controlled release system is simple to prepare, high in stability, intelligent in control, and capable of exhibiting real-time controllable permeability in time and space, CSMVs at the molecular level due to the molecular structure of the vesicle wall, and instantaneous controlled release is exhibited. In cancer. The method has wide application prospects in the accurate treatment of diseases such as diabetes and bacterial infection.

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