N-(2-Bromoethyl)phthalimide supplier

Name
N-(2-Bromoethyl)phthalimide
EINECS 209-379-9
CAS No. 574-98-1
Article Data75
CAS DataBase
Density 1.657 g/cm³
Solubility 224 mg/L at 25 °C in water
Melting Point 80-83 °C
Formula C₁₀H₈BrNO₂
Boiling Point 342.9 °C at 760 mmHg
Molecular Weight 254.083
Flash Point 161.2 °C
Transport Information
Appearance white powder
Safety 24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms Phthalimide,N-(2-bromoethyl)- (6CI,7CI,8CI);1-Bromo-2-phthalimidoethane;2-(2-Bromoethyl)-1H-isoindole-1,3(2H)-dione;2-(2-Bromoethyl)isoindole-1,3-dione;2-(2-Bromoethyl)phthalimide;2-Phthalimidoethyl bromide;N-(b-Bromoethyl)phthalimide;NSC 2688;beta-Phthalimidoethyl bromide;
PSA 37.38000
LogP 1.61540

Synthetic route

: 1074-82-4
potassium phtalimide

: 106-93-4
ethylene dibromide

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

Conditions

Conditions	Yield
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%

: 2439-85-2
N-bromophthalimide

: 74-85-1
ethene

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

Conditions

Conditions	Yield
With silver tetrafluoroborate; indium(III) bromide In dichloromethane at 20℃; for 12h; Darkness;	95%

: 136918-14-4
phthalimide

: 106-93-4
ethylene dibromide

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

Conditions

Conditions	Yield
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%

: 3891-07-4
N-(2-Hydroxyethyl)phthalimide

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

Conditions

Conditions	Yield
With phosphorus tribromide for 0.5h; Reflux;	88.1%
With phosphorus tribromide
With phosphorus tribromide In chloroform for 3h; Heating;
With phosphorus tribromide

: 1074-82-4
potassium phtalimide

: 106-93-4
ethylene dibromide

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

B: 607-26-1
N,N'-ethylenediphthalimide

Conditions

Conditions	Yield
for 20h; Heating;	A 75% B n/a
With 18-crown-6 ether In toluene at 100℃; for 6h;	A 45% B 39%

...Expand

: 3339-73-9
3-phthalimidopropanoic acid

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

Conditions

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

: 33081-78-6
sodium phthalimide

: 106-93-4
ethylene dibromide

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

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux;	68.1%

: 19263-21-9
2-bromoethyl p-toluenesulfonate

: 1074-82-4
potassium phtalimide

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

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

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 50℃;	A 60% B 13%

...Expand

: 3481-09-2
N-chlorophthalimide

: 106-93-4
ethylene dibromide

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

Conditions

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

: 136918-14-4
phthalimide

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

Conditions

Conditions	Yield
With potassium carbonate In water; ethylene dibromide	52%
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

: 85-44-9
phthalic anhydride

: 2576-47-8
2-bromoethylamine hydrobromide

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

Conditions

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

anhydro-: anhydro-

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

Conditions

Conditions	Yield
With hydrogen bromide

: 1074-82-4
potassium phtalimide

: 106-93-4
ethylene dibromide

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

B N.N'-ethylene-di-phthalimide: N.N'-ethylene-di-phthalimide

...Expand

: 13162-05-5
n-vinylformamide

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

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 65℃; for 5h;

: C8H5NO2*CH4

: 106-93-4
ethylene dibromide

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

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 24h;

: 85-44-9
phthalic anhydride

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 h / Reflux 2: phosphorus tribromide / 0.5 h / Reflux View Scheme

: 110-89-4
piperidine

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

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

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile	100%
With benzene
With potassium carbonate; toluene
In acetone for 12h; Heating;
With potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃;

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

: phenylmagnesium bromide

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

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 48h;	100%
In tetrahydrofuran for 4h; Heating;	82%

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

: 17356-08-0
thiourea

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

Conditions

Conditions	Yield
In ethanol for 18h; Heating;	100%
In ethanol for 18h; Heating / reflux;	100%
In ethanol for 24h; Reflux;	79%

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

: 6921-34-2
benzylmagnesium chloride

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

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 48h;	100%

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

: 106-53-6
para-bromobenzenethiol

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

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 24h;	100%

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

: 58258-01-8
4-diphenylmethoxypiperidine

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

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In chloroform; butanone	100%

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

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

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

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃;	100%
With potassium carbonate In N,N-dimethyl-formamide at 120℃;

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

: 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

Conditions

Conditions	Yield
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%

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

: 143-33-9
sodium cyanide

: 3589-45-5
3-phthalimidopropionitrile

Conditions

Conditions	Yield
In dimethyl sulfoxide at 65℃; for 6h;	99%
In dimethyl sulfoxide at 65℃; for 6h;	84%

: 387827-25-0
N-[3-(piperidin-4-yl)phenyl]-acetamide

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

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

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 70℃; for 18h;	99%

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

: 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

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In butanone for 5h; Heating;	98%

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

: 109-89-7
diethylamine

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

Conditions

Conditions	Yield
In toluene	98%

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

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

: 1048037-16-6
C21H21N3O8S

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	98%

: 4316-42-1
1-Butylimidazole

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

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

Conditions

Conditions	Yield
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;

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

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

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

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 120℃; for 0.666667h; Microwave irradiation;	98%

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

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

: C22H22N3O2(1+)*Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran at 90℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;	98%

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

: C3H14B9S(1-)*C16H36N(1+)

: C13H22B9NO2S

Conditions

Conditions	Yield
In ethanol at 20℃; for 15.25h; Reflux;	98%

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

: 53510-88-6
potassium phthalimide-15N

: 15N-ethylenediamine bis(phthalic acid imide)

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 12h; Condensation;	97%

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

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

: 1048037-17-7
C23H19N3O7S

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	97%

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

: 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

Conditions

Conditions	Yield
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%

Yield

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

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

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

Conditions

Conditions	Yield
With triethylamine In ethanol; ethyl acetate	96.3%

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

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

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

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile for 15h; Heating;	95.6%

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

: 57991-39-6
sodium [13C]cyanide

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

Conditions

Conditions	Yield
In dimethyl sulfoxide at 65℃; for 6h;	95%
In dimethyl sulfoxide at 65℃; for 6h;	80%

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

: 2-mercaptomethyl-1-methylbenzimidazole

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

Conditions

Conditions	Yield
With sodium ethanolate In ethanol for 24h; Heating;	95%

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

: 1117-97-1
N,0-dimethylhydroxylamine

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

Conditions

Conditions	Yield
With sodium iodide In dimethyl sulfoxide at 80℃; for 9h;	95%

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

: 603-35-0
triphenylphosphine

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

Conditions

Conditions	Yield
In acetonitrile for 24h; Heating;	95%
In acetonitrile at 200℃; for 0.25h; Microwave irradiation;

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

: 1048037-12-2
C8H10N2O5S

: 1048037-15-5
C18H17N3O7S

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	95%

: 110-91-8
morpholine

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

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

Conditions

Conditions	Yield
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-formamide	80%
With potassium carbonate In acetonitrile Reflux;
With triethylamine In N,N-dimethyl-formamide at 100℃; for 24h;

N-(2-Bromoethyl)phthalimide Specification

The IUPAC name of 1H-Isoindole-1,3(2H)-dione,2-(2-bromoethyl)- is 2-(2-bromoethyl)isoindole-1,3-dione. With the CAS registry number 574-98-1, it is also named as 1-Bromo-2-phthalimidoethane. The product's categories are N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Phthalimides; Bifunctional Crosslinkers Organic Building Blocks; Carbonyl Compounds; Cyclic Imides; Linkers; Peptide Synthesis. Besides, it is white powder, which is insoluble in water. In addition, its molecular formula is C₁₀H₈BrNO₂ and molecular weight is 254.08.

The other characteristics of this product can be summarized as: (1)EINECS: 209-379-9; (2)ACD/LogP: 2.53; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.53; (5)ACD/LogD (pH 7.4): 2.53; (6)ACD/BCF (pH 5.5): 49.61; (7)ACD/BCF (pH 7.4): 49.61; (8)ACD/KOC (pH 5.5): 569.27; (9)ACD/KOC (pH 7.4): 569.27; (10)#H bond acceptors: 3; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 2; (13)Index of Refraction: 1.632; (14)Molar Refractivity: 54.7 cm³; (15)Molar Volume: 153.3 cm³; (16)Surface Tension: 57.4 dyne/cm; (17)Density: 1.657 g/cm³; (18)Flash Point: 161.2 °C; (19)Melting Point: 80-83 °C; (20)Water Solubility: 224 mg/L at 25 °C; (21)Enthalpy of Vaporization: 58.67 kJ/mol; (22)Boiling Point: 342.9 °C at 760 mmHg; (23)Vapour Pressure: 7.3E-05 mmHg at 25 °C.

Preparation of 1H-Isoindole-1,3(2H)-dione,2-(2-bromoethyl)-: this chemical can be prepared by condensation and bromination of Phthalic anhydride.

This reaction needs Ethanolamine and PBr₃.

Uses of 1H-Isoindole-1,3(2H)-dione,2-(2-bromoethyl)-: this chemical is an intermediate used in organic synthesis. Additionally, it can react with phenylmagnesium bromide to get 2-(2-bromo-ethyl)-3-hydroxy-3-phenyl-isoindolin-1-one.

This reaction needs diethyl ether and benzene.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. You should avoid contact with skin and eyes.

People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CCBr
(2)InChI: InChI=1S/C10H8BrNO2/c11-5-6-12-9(13)7-3-1-2-4-8(7)10(12)14/h1-4H,5-6H2
(3)InChIKey: CHZXTOCAICMPQR-UHFFFAOYSA-N

Product Name

N-(2-Bromoethyl)phthalimide

Synthetic route

N-(2-Bromoethyl)phthalimide Specification

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