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Cas Database |
| Name |
N-(2-Bromoethyl)phthalimide |
EINECS | 209-379-9 |
| CAS No. | 574-98-1 | Density | 1.657 g/cm3 |
| PSA | 37.38000 | LogP | 1.61540 |
| 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 | N/A | Appearance | white powder |
| Safety | 24/25 | Risk Codes | 36/37/38 |
| Molecular Structure |
|
Hazard Symbols | N/A |
| 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; |
Article Data | 75 |
N-(2-Bromoethyl)phthalimide Synthetic route
- 1074-82-4
potassium phtalimide
- 106-93-4
ethylene dibromide
- 574-98-1
2-(2-bromoethyl)isoindoline-1,3-dione
| 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% |
| Conditions | Yield |
|---|---|
| With silver tetrafluoroborate; indium(III) bromide In dichloromethane at 20℃; for 12h; Darkness; | 95% |
| 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% |
| 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 | Yield |
|---|---|
| for 20h; Heating; | A 75% B n/a |
| With 18-crown-6 ether In toluene at 100℃; for 6h; | A 45% B 39% |
| Conditions | Yield |
|---|---|
| With Ag(Phen)2OTf; dibromoisocyanuric acid In 1,2-dichloro-ethane at 40℃; for 120h; Inert atmosphere; Schlenk technique; | 70% |
| 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 | Yield |
|---|---|
| In N,N-dimethyl-formamide at 50℃; | A 60% B 13% |
| 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 | 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 |
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.
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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.
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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
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