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574-98-1

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574-98-1 Usage

Chemical Properties

white powder

Uses

N-(2-Bromoethyl)phthalimide is an intermediate used in organic synthesis. It can react with phenyl magnesium bromide to get 2-(2-bromo-ethyl)-3-hydroxy-3-phenyl-isoindolin-1-one.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 2425, 1949 DOI: 10.1021/ja01175a052Organic Syntheses, Coll. Vol. 1, p. 119, 1941

Purification Methods

The following is to be carried out in an efficient FUME HOOD. Dissolve the compound (180g) in CS2 (500 mL) by refluxing for 15minutes (to cause the separation of the most likely impurity, 1,2-diphthalimidoethane), filter and evaporate under reduced pressure. The product forms light tan crystals (m 78-80o). Recrystallise it from EtOH (charcoal) [the compound (50g) is dissolved in hot 75% EtOH (200mL), boiled for ca 10 minutes, carbon is added (5g, Norite), filter and cool to 0o], to give white crystals (40g) which can be recrystallised (m 80-81o); and further recrystallisation gives m 82-83o. [Salzberg & Supniewski Org Synth Coll Vol I 119 1932, Landini & Rolla Synthesis 389 1976, Beilstein 21/10 V 275.]

Check Digit Verification of cas no

The CAS Registry Mumber 574-98-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,7 and 4 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 574-98:
(5*5)+(4*7)+(3*4)+(2*9)+(1*8)=91
91 % 10 = 1
So 574-98-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H8BrNO2/c11-5-6-12-9(13)7-3-1-2-4-8(7)10(12)14/h1-4H,5-6H2

574-98-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A12164)  N-(2-Bromoethyl)phthalimide, 98+%   

  • 574-98-1

  • 25g

  • 287.0CNY

  • Detail
  • Alfa Aesar

  • (A12164)  N-(2-Bromoethyl)phthalimide, 98+%   

  • 574-98-1

  • 100g

  • 924.0CNY

  • Detail
  • Alfa Aesar

  • (A12164)  N-(2-Bromoethyl)phthalimide, 98+%   

  • 574-98-1

  • 500g

  • 3066.0CNY

  • Detail
  • Aldrich

  • (B66302)  N-(2-Bromoethyl)phthalimide  95%

  • 574-98-1

  • B66302-25G

  • 518.31CNY

  • Detail
  • Aldrich

  • (B66302)  N-(2-Bromoethyl)phthalimide  95%

  • 574-98-1

  • B66302-100G

  • 1,278.81CNY

  • Detail

574-98-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(2-Bromoethyl)phthalimide

1.2 Other means of identification

Product number -
Other names 2-(2-bromoethyl)-1H-isoindole-1,3-dione

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:574-98-1 SDS

574-98-1Synthetic route

potassium phtalimide
1074-82-4

potassium phtalimide

ethylene dibromide
106-93-4

ethylene dibromide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With tetrabutylammomium bromide In acetonitrile for 5h; Heating;95%
In N,N-dimethyl-formamide for 15h; Inert atmosphere;89.6%
In N,N-dimethyl-formamide at 20℃; for 24h;88.9%
N-bromophthalimide
2439-85-2

N-bromophthalimide

ethene
74-85-1

ethene

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With silver tetrafluoroborate; indium(III) bromide In dichloromethane at 20℃; for 12h; Darkness;95%
phthalimide
136918-14-4

phthalimide

ethylene dibromide
106-93-4

ethylene dibromide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate at 20℃; for 1h; Neat (no solvent);90%
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 40℃; for 18h;88%
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 50 - 80℃; for 5h;81%
N-(2-Hydroxyethyl)phthalimide
3891-07-4

N-(2-Hydroxyethyl)phthalimide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With phosphorus tribromide for 0.5h; Reflux;88.1%
With phosphorus tribromide
With phosphorus tribromide In chloroform for 3h; Heating;
With phosphorus tribromide
potassium phtalimide
1074-82-4

potassium phtalimide

ethylene dibromide
106-93-4

ethylene dibromide

A

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

B

N,N'-ethylenediphthalimide
607-26-1

N,N'-ethylenediphthalimide

Conditions
ConditionsYield
for 20h; Heating;A 75%
B n/a
With 18-crown-6 ether In toluene at 100℃; for 6h;A 45%
B 39%
3-phthalimidopropanoic acid
3339-73-9

3-phthalimidopropanoic acid

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With Ag(Phen)2OTf; dibromoisocyanuric acid In 1,2-dichloro-ethane at 40℃; for 120h; Inert atmosphere; Schlenk technique;70%
sodium phthalimide
33081-78-6

sodium phthalimide

ethylene dibromide
106-93-4

ethylene dibromide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;68.1%
2-bromoethyl p-toluenesulfonate
19263-21-9

2-bromoethyl p-toluenesulfonate

potassium phtalimide
1074-82-4

potassium phtalimide

A

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

B

2-(1,3-dioxoisoindolin-2-yl)ethyl 4-methylbenzenesulfonate
5460-83-3

2-(1,3-dioxoisoindolin-2-yl)ethyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 50℃;A 60%
B 13%
N-chlorophthalimide
3481-09-2

N-chlorophthalimide

ethylene dibromide
106-93-4

ethylene dibromide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; for 2h;56%
phthalimide
136918-14-4

phthalimide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With potassium carbonate In water; ethylene dibromide52%
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol; water / Reflux
2: 12 h / 180 - 190 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol; methanol / 3 h / 20 °C
2: potassium carbonate / acetone / 8 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 2 h / Reflux
2: tetrabutylammomium bromide / N,N-dimethyl-formamide / 2 h / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 2 h / Reflux
2: tetrabutylammomium bromide / N,N-dimethyl-formamide / 2 h / 70 °C
View Scheme
phthalic anhydride
85-44-9

phthalic anhydride

2-bromoethylamine hydrobromide
2576-47-8

2-bromoethylamine hydrobromide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
In neat (no solvent) at 140℃; for 3h; Inert atmosphere; Schlenk technique;49%
anhydro-

anhydro-

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With hydrogen bromide
potassium phtalimide
1074-82-4

potassium phtalimide

ethylene dibromide
106-93-4

ethylene dibromide

A

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

B

N.N'-ethylene-di-phthalimide

N.N'-ethylene-di-phthalimide

n-vinylformamide
13162-05-5

n-vinylformamide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) at 65℃; for 5h;
C8H5NO2*CH4

C8H5NO2*CH4

ethylene dibromide
106-93-4

ethylene dibromide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 24h;
phthalic anhydride
85-44-9

phthalic anhydride

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.5 h / Reflux
2: phosphorus tribromide / 0.5 h / Reflux
View Scheme
piperidine
110-89-4

piperidine

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

2-(2-piperidinylethyl)-1H-isoindole-1,3(2H)-dione
4667-75-8

2-(2-piperidinylethyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With potassium carbonate In acetonitrile100%
With benzene
With potassium carbonate; toluene
In acetone for 12h; Heating;
With potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃;
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

phenylmagnesium bromide

phenylmagnesium bromide

2,3-dihydro-9b-phenyloxazolo<2,3-a>isoindol-5(9bH)-one
17494-19-8

2,3-dihydro-9b-phenyloxazolo<2,3-a>isoindol-5(9bH)-one

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 48h;100%
In tetrahydrofuran for 4h; Heating;82%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

thiourea
17356-08-0

thiourea

(2-phthalimidoethyl)isothiuronium hydrobromide
52208-11-4

(2-phthalimidoethyl)isothiuronium hydrobromide

Conditions
ConditionsYield
In ethanol for 18h; Heating;100%
In ethanol for 18h; Heating / reflux;100%
In ethanol for 24h; Reflux;79%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

benzylmagnesium chloride
6921-34-2

benzylmagnesium chloride

9b-benzyl-2,3-dihydrooxazolo[2,3-a]isoindol-5-(9bH)-one
876065-74-6

9b-benzyl-2,3-dihydrooxazolo[2,3-a]isoindol-5-(9bH)-one

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 48h;100%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

para-bromobenzenethiol
106-53-6

para-bromobenzenethiol

N-[2-(4-bromo-phenylsulfanyl)-ethyl]-phthalimide
269743-56-8

N-[2-(4-bromo-phenylsulfanyl)-ethyl]-phthalimide

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 24h;100%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

4-diphenylmethoxypiperidine
58258-01-8

4-diphenylmethoxypiperidine

2-[2-(4-benzhydryloxy-piperidin-1-yl)-ethyl]-isoindole-1,3-dione

2-[2-(4-benzhydryloxy-piperidin-1-yl)-ethyl]-isoindole-1,3-dione

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In chloroform; butanone100%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

ethyl 3,5-dichloro-4-hydroxybenzoate
17302-82-8

ethyl 3,5-dichloro-4-hydroxybenzoate

ethyl 3,5-dichloro-4-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethoxy]benzoate
942998-89-2

ethyl 3,5-dichloro-4-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethoxy]benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃;100%
With potassium carbonate In N,N-dimethyl-formamide at 120℃;
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

tert-butyl N-methyl-N-[[(2S)-morpholin-2-yl]methyl]carbamate

tert-butyl N-methyl-N-[[(2S)-morpholin-2-yl]methyl]carbamate

tert-butyl N-[[(2S)-4-[2-(1,3-dioxoisoindolin-2-yl)ethyl]morpholin-2-yl]methyl]-N-methyl-carbamate

tert-butyl N-[[(2S)-4-[2-(1,3-dioxoisoindolin-2-yl)ethyl]morpholin-2-yl]methyl]-N-methyl-carbamate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 12h;100%
With potassium carbonate; potassium iodide In acetonitrile at 80℃; for 12h; Inert atmosphere;100%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

sodium cyanide
143-33-9

sodium cyanide

3-phthalimidopropionitrile
3589-45-5

3-phthalimidopropionitrile

Conditions
ConditionsYield
In dimethyl sulfoxide at 65℃; for 6h;99%
In dimethyl sulfoxide at 65℃; for 6h;84%
N-[3-(piperidin-4-yl)phenyl]-acetamide
387827-25-0

N-[3-(piperidin-4-yl)phenyl]-acetamide

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

N-(3-{1-[2-(1,3-dioxoisoindolin-2-yl)ethyl]piperidin-4-yl}phenyl)acetamide
875004-84-5

N-(3-{1-[2-(1,3-dioxoisoindolin-2-yl)ethyl]piperidin-4-yl}phenyl)acetamide

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 70℃; for 18h;99%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

1,2,3,4,6,7,8,9-octahydro-1,3-dimethylpyrimido[2,1-f]purine-2,4,8-trione
114431-63-9

1,2,3,4,6,7,8,9-octahydro-1,3-dimethylpyrimido[2,1-f]purine-2,4,8-trione

8-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-1,3-dimethyl-5,6-dihydro-1H,8H-1,3,4b,8,9-pentaaza-fluorene-2,4,7-trione

8-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-1,3-dimethyl-5,6-dihydro-1H,8H-1,3,4b,8,9-pentaaza-fluorene-2,4,7-trione

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In butanone for 5h; Heating;98%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

diethylamine
109-89-7

diethylamine

2-(2-diethylaminoethyl)-1H-isoindole-1,3(2H)-dione
6821-06-3

2-(2-diethylaminoethyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
In toluene98%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

N-(2-Nitrophenylsulfonyl)-O-(tetrahydro-2H-pyran-2-yl)hydroxylamine

N-(2-Nitrophenylsulfonyl)-O-(tetrahydro-2H-pyran-2-yl)hydroxylamine

C21H21N3O8S
1048037-16-6

C21H21N3O8S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;98%
1-Butylimidazole
4316-42-1

1-Butylimidazole

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

1-(2-(phthalamido)ethyl)-3-nbutylimidazolium bromide
942411-44-1

1-(2-(phthalamido)ethyl)-3-nbutylimidazolium bromide

Conditions
ConditionsYield
In toluene for 24h; Inert atmosphere; Schlenk technique; Reflux;98%
Stage #1: 1-Butylimidazole; 2-(2-bromoethyl)isoindoline-1,3-dione In toluene at 70℃; for 48h;
Stage #2: In mineral oil
53%
In toluene at 80℃; for 48h; Inert atmosphere;
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

1-(6-fluoropyridin-2-yl)piperazine
223514-16-7

1-(6-fluoropyridin-2-yl)piperazine

2-(2-(4-(6-fluoropyridin-2-yl)piperazin-1-yl)ethyl)isoindoline-1,3-dione
1351411-98-7

2-(2-(4-(6-fluoropyridin-2-yl)piperazin-1-yl)ethyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 120℃; for 0.666667h; Microwave irradiation;98%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

N-(2,4,6-trimethylphenyl)imidazole
25364-44-7

N-(2,4,6-trimethylphenyl)imidazole

C22H22N3O2(1+)*Br(1-)

C22H22N3O2(1+)*Br(1-)

Conditions
ConditionsYield
In tetrahydrofuran at 90℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;98%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

C3H14B9S(1-)*C16H36N(1+)

C3H14B9S(1-)*C16H36N(1+)

C13H22B9NO2S

C13H22B9NO2S

Conditions
ConditionsYield
In ethanol at 20℃; for 15.25h; Reflux;98%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

potassium phthalimide-15N
53510-88-6

potassium phthalimide-15N

15N-ethylenediamine bis(phthalic acid imide)

15N-ethylenediamine bis(phthalic acid imide)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 90℃; for 12h; Condensation;97%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

N-(2-Nitrophenylsulfonyl)-O-(phenylmethyl)hydroxylamine
77925-80-5

N-(2-Nitrophenylsulfonyl)-O-(phenylmethyl)hydroxylamine

C23H19N3O7S
1048037-17-7

C23H19N3O7S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;97%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

1-lithio-2-tert-butyldimethylsilyl-1,2-dicarba-closo-dodecaborane(12)
361544-93-6

1-lithio-2-tert-butyldimethylsilyl-1,2-dicarba-closo-dodecaborane(12)

2-(3'-tert-butyldimethylsiloxy-1'-oxo-1',3'-dihydroisoindol-3'-yl)-1,2'-ethano-1,2-dicarba-closo-dodecaborane

2-(3'-tert-butyldimethylsiloxy-1'-oxo-1',3'-dihydroisoindol-3'-yl)-1,2'-ethano-1,2-dicarba-closo-dodecaborane

Conditions
ConditionsYield
In diethyl ether; benzene cooled soln. (0°C) of B compd. in benzene-Et2O treated dropwise with benzene-Et2O soln. of C6H4(CO)2N(CH2)2Br (molar ratio 1:1.08); warmed to room temp.; gradually brought to reflux; refluxed for 2 d; solvent removed on rotary evaporator; treated with MeOH; cooled (-10°C) overnight; filtered; solid washed (chilled MeOH); dried in vac.; further crops obtained by redn. of solvent vol. and cooling (-10°C); evapd. (hexane-Et2O); elem. anal.;97%
3-mercapt-2-(pivaloylamino)pyridine

3-mercapt-2-(pivaloylamino)pyridine

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

3-[2-(phthalimido)ethyl]-2-(pivaloylamino)pyridine
155966-12-4

3-[2-(phthalimido)ethyl]-2-(pivaloylamino)pyridine

Conditions
ConditionsYield
With triethylamine In ethanol; ethyl acetate96.3%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

2-[(4,4'-bipiperidin)-1-yl]pyridine
648895-89-0

2-[(4,4'-bipiperidin)-1-yl]pyridine

1-phthalimidoethyl-1'-(2-pyridyl)-4,4'-bipiperidine
648896-00-8

1-phthalimidoethyl-1'-(2-pyridyl)-4,4'-bipiperidine

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetonitrile for 15h; Heating;95.6%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

sodium [13C]cyanide
57991-39-6

sodium [13C]cyanide

N-(2-cyano-<1-(13)C>-ethyl)phthalimide
88597-02-8

N-(2-cyano-<1-(13)C>-ethyl)phthalimide

Conditions
ConditionsYield
In dimethyl sulfoxide at 65℃; for 6h;95%
In dimethyl sulfoxide at 65℃; for 6h;80%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

2-mercaptomethyl-1-methylbenzimidazole

2-mercaptomethyl-1-methylbenzimidazole

1-methyl-2-(4'-phthalimido-2'-thiabutyl)benzimidazole
131072-02-1

1-methyl-2-(4'-phthalimido-2'-thiabutyl)benzimidazole

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 24h; Heating;95%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

N,0-dimethylhydroxylamine
1117-97-1

N,0-dimethylhydroxylamine

N-<2-(N-methoxy-N-methylamino)ethyl>phthalimide
132445-23-9

N-<2-(N-methoxy-N-methylamino)ethyl>phthalimide

Conditions
ConditionsYield
With sodium iodide In dimethyl sulfoxide at 80℃; for 9h;95%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

triphenylphosphine
603-35-0

triphenylphosphine

2-(1,3-dioxoisoindolin-2-yl)ethyltriphenylphosphonium bromide
65273-64-5

2-(1,3-dioxoisoindolin-2-yl)ethyltriphenylphosphonium bromide

Conditions
ConditionsYield
In acetonitrile for 24h; Heating;95%
In acetonitrile at 200℃; for 0.25h; Microwave irradiation;
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

C8H10N2O5S
1048037-12-2

C8H10N2O5S

C18H17N3O7S
1048037-15-5

C18H17N3O7S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;95%
morpholine
110-91-8

morpholine

2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

2-(2-morpholin-4-ylethyl)-1H-isoindole-1,3(2H)-dione
6820-90-2

2-(2-morpholin-4-ylethyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 18h;95%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide80%
With potassium carbonate In acetonitrile Reflux;
With triethylamine In N,N-dimethyl-formamide at 100℃; for 24h;

574-98-1Relevant articles and documents

Synthesis of lariat diazacrown ethers with terminal amino groups in the side chains

Lukyanenko,Kirichenko,Shcherbakov

, p. 343 - 350 (2004)

Treatment of diazacrown ethers with N-(haloalkyl)- and N-(haloethoxy) phthalimides gives the corresponding N,N′- substituted diazacrown ether. Hydrazinolysis of the latter then gives diazacrown ethers with terminal primary amino groups in the side chain. Their reductive methylation using formaldehyde in formic acid gives the dimethylamino derivatives. The presence of a lariat effect was demonstrated by treating the compounds obtained with picrates of alkali and alkaline-earth metals.

Lanthanide(iii) complexes of aminoethyl-DO3A as PARACEST contrast agents based on decoordination of the weakly bound amino group

Krchova, Tereza,Kotek, Jan,Jirak, Daniel,Havlickova, Jana,Cisarova, Ivana,Hermann, Petr

, p. 15735 - 15747 (2013)

2-Aminoethyl DOTA analogues with unsubstituted (H3L 1), monomethylated (H3L2) and dimethylated (H3L3) amino groups were prepared by improved synthetic procedures. Their solid-state structures exhibit an extensive system of intramolecular hydrogen bonds, which is probably present in solution and leads to the rather high value of the last dissociation constant. The protonation sequence of H3L1 in solution corresponds to that found in the solid state. The stability constants of the H3L1 complexes with La3+ and Gd3+ (20.02 and 22.23, respectively) are similar to those of DO3A and the reduction of the pK A value of the pendant amino group from 10.51 in the free ligand to 6.06 and 5.83 in the La3+ and Gd3+ complexes, respectively, points to coordination of the amino group. It was confirmed in the solid state structure of the [Yb(L1)] complex, where disorder between the SA′ and TSA′ isomers was found. A similar situation is expected in solution, where a fast equilibration among the isomers hampers the unambiguous determination of the isomer ratio in solution. The PARACEST effect was observed in Eu(iii)-H3L1/H3L2 and Yb(iii)-H3L1/H3L2 complexes, being dependent on pH in the region of 4.5-7.5 and pH-independent in more alkaline solutions. The decrease of the PARACEST effect parallels with the increasing abundance of the complex protonated species, where the pendant amino group is not coordinating. Surprisingly, a small PARACEST effect was also observed in solutions of Eu(iii)/Yb(iii)-H3L3 complexes, where the pendant amino group is dimethylated. The effect is detectable in a narrow pH region, where both protonated and deprotonated complex species are present in equilibrium. The data points to the new mechanism of the PARACEST effect, where the slow coordination-decoordination of the pendant amine is coupled with the fast proton exchange between the free amino group and bulk water mediates the magnetization transfer. The pH-dependence of the effect was proved to be measurable by MRI and, thus, the complexes extend the family of pH-sensitive probes. This journal is The Royal Society of Chemistry 2013.

Tuning DNA Supramolecular Polymers by the Addition of Small, Functionalized Nucleobase Mimics

Lachance-Brais, Christophe,Hennecker, Christopher D.,Alenaizan, Asem,Luo, Xin,Toader, Violeta,Taing, Monica,Sherrill, C. David,Mittermaier, Anthony K.,Sleiman, Hanadi F.

supporting information, p. 19824 - 19833 (2021/11/30)

Nucleobase mimicking small molecules able to reconfigure DNA are a recently discovered strategy that promises to extend the structural and functional diversity of nucleic acids. However, only simple, unfunctionalized molecules such as cyanuric acid and melamine have so far been used in this approach. In this work, we show that the addition of substituted cyanuric acid molecules can successfully program polyadenine strands to assemble into supramolecular fibers. Unlike conventional DNA nanostructure functionalization, which typically end-labels DNA strands, our approach incorporates functional groups into DNA with high density using small molecules and results in new DNA triple helices coated with alkylamine or alcohol units that grow into micrometer-long fibers. We find that small changes in the small molecule functional group can result in large structural and energetic variation in the overall assembly. A combination of circular dichroism, atomic force microscopy, molecular dynamics simulations, and a new thermodynamic method, transient equilibrium mapping, elucidated the molecular factors behind these large changes. In particular, we identify substantial DNA sugar and phosphate group deformations to accommodate a hydrogen bond between the phosphate and the small-molecule functional groups, as well as a critical chain length of the functional group which switches this interaction from intra- to interfiber. These parameters allow the controlled formation of hierarchical, hybrid DNA assemblies simply through the addition and variation of small, functionalized molecules.

Synthesis of hydroxyethyl methyl morpholinium azide (HEM Morph)N3: A highly efficient new task specific azide-based ionic liquid and its dual application as an azide source and media for synthesis of some novel aromatic O-oxime ethers-1,2,3-triazole conjugates as a potential antihistaminic agents

Rad, Mohammad Navid Soltani,Behrouz, Somayeh,Saremi, Hossein,Mohammadtaghi-Nezhad, Javad

, (2019/12/27)

The synthesis, characterization and application of hydroxyethyl methyl morpholinium azide (HEM Morph)N3 as a new azide-based ionic liquid (ABIL) has been described. (HEM Morph)N3 is used as a source of azide and reaction media for three components ‘Click’ Huisgen cycloaddition reaction between O-propargyl oxime ether and alkyl bromide to acquire novel aromatic O-oxime ethers-1,2,3-triazole conjugates as potential antihistaminic agents in good yields. The influence of parameters like temperature, amount of IL, type of azide-based ionic liquids and its reusability is investigated. The (HEM Morph)N3 is proved to be an efficient, thermally stable, inexpensive and recyclable azide-based ionic liquid which can be easily synthesized and used as both azide's source and reaction media for ‘Click’ Huisgen cycloaddition reaction.

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