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Cas Database |
| Name |
N-(Hydroxymethyl)phthalimide |
EINECS | 204-241-4 |
| CAS No. | 118-29-6 | Density | 1.462 g/cm3 |
| PSA | 57.61000 | LogP | 0.17030 |
| Solubility | N/A | Melting Point |
147-149 °C |
| Formula | C9H7NO3 | Boiling Point | 332 °C at 760 mmHg |
| Molecular Weight | 177.159 | Flash Point | 154.6 °C |
| Transport Information | N/A | Appearance | white crystalline powder |
| Safety | 22-24/25 | Risk Codes | N/A |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
N-Hydroxymethyl Phthalimide;Phthalimide,N-(hydroxymethyl)- (6CI,7CI,8CI);(Hydroxymethyl)phthalimide;2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dione;2-(Hydroxymethyl)isoindoline-1,3-dione;N-Methylolphthalimide;NSC 27350;NSC 27471;NSC39723;Phthalimidomethyl alcohol; |
Article Data | 53 |
N-(Hydroxymethyl)phthalimide Synthetic route
| Conditions | Yield |
|---|---|
| In water at 100℃; for 4h; | 99% |
| In water for 0.0666667h; hydroxymethylation; Heating; ultrasound irradiation; | 97% |
| In water for 1.5h; Reflux; | 96% |
| Conditions | Yield |
|---|---|
| With cesium formate In methanol for 18h; Reflux; Inert atmosphere; | 95% |
| With water |
- 136918-14-4
phthalimide
- 50-00-0
formaldehyd
- 762-04-9
phosphonic acid diethyl ester
- 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione
| Conditions | Yield |
|---|---|
| In 1,1,2,2-tetrachloroethylene at 110℃; for 8h; | 84% |
- 124536-28-3
2-(2-Hydroperoxy-2-methoxy-ethyl)-isoindole-1,3-dione
A
- 550-44-7
N-methylphthalimide
B
- 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione
C
- 107-31-3
Methyl formate
D
- 23244-58-8
N-phthaloylglycine methyl ester
| Conditions | Yield |
|---|---|
| In acetonitrile at 0℃; Irradiation; | A 3% B 72% C 79% D 5% |
| In acetonitrile at 0℃; Irradiation; other solvents; other phthalimide; | A 3% B 72% C 79% D 5% |
- 203255-55-4
2-(iodomethyl)isoindoline-1,3-dione
- 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione
| Conditions | Yield |
|---|---|
| With dimethyl zinc(II) In n-heptane; dichloromethane at 20℃; for 18h; Inert atmosphere; | 43% |
- 124536-28-3
2-(2-Hydroperoxy-2-methoxy-ethyl)-isoindole-1,3-dione
A
- 550-44-7
N-methylphthalimide
B
- 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione
C
- 23244-58-8
N-phthaloylglycine methyl ester
| Conditions | Yield |
|---|---|
| In dimethyl sulfoxide Irradiation; | A 15% B 35% C 40% |
- 203255-55-4
2-(iodomethyl)isoindoline-1,3-dione
A
- 550-44-7
N-methylphthalimide
B
- 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione
C
- 1380112-97-9
1,3,4,5-tetrahydro-2,4-benzoxazepine-1,5-dione
| Conditions | Yield |
|---|---|
| With diethylzinc In hexane; dichloromethane at 20℃; for 2h; Inert atmosphere; | A 39% B 14% C 22% |
- 5332-26-3
N-(bromomethyl)phtalimide
- 108-18-9
diisopropylamine
A
- 136918-14-4
phthalimide
B
- 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione
| Conditions | Yield |
|---|---|
| In benzene for 12h; Heating; Title compound not separated from byproducts; |
| Conditions | Yield |
|---|---|
| With sodium methylate 1.) electrolysis, current density 0.05 A/cm2, 1.5 h, 2.) electrolysis, current density 0.02 A/cm2, 5 h; Yield given. Multistep reaction. Yields of byproduct given; |
| Conditions | Yield |
|---|---|
| With sodium methylate 1.) electrolysis, current density 0.05 A/cm2, 2 h, 2.) electrolysis, current density 0.02 A/cm2, 5 h; Yield given. Multistep reaction. Yields of byproduct given; |
N-(Hydroxymethyl)phthalimide Consensus Reports
N-(Hydroxymethyl)phthalimide Specification
The IUPAC name of N-(Hydroxymethyl)phthalimide is 2-(hydroxymethyl)isoindole-1,3-dione. With the CAS registry number 118-29-6, it is also named as 1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-. The product's categories are Pharmacetical; N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Phthalimides . Besides, it is white crystalline powder, which should be stored in a cool, ventilated warehouse. When you are using this chemical, please do not breathe dust. And you should avoid contact with skin and eyes. In addition, its molecular formula is C9H7NO3 and molecular weight is 177.16.
The other characteristics of this product can be summarized as: (1)EINECS: 204-241-4; (2)ACD/LogP: 0.76; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 0.76; (5)ACD/LogD (pH 7.4): 0.76; (6)ACD/BCF (pH 5.5): 2.23; (7)ACD/BCF (pH 7.4): 2.23; (8)ACD/KOC (pH 5.5): 61.74; (9)ACD/KOC (pH 7.4): 61.74; (10)#H bond acceptors: 4; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 2; (13)Index of Refraction: 1.644; (14)Molar Refractivity: 43.87 cm3; (15)Molar Volume: 121.1 cm3; (16)Surface Tension: 66.6 dyne/cm; (17)Density: 1.462 g/cm3; (18)Flash Point: 154.6 °C; (19)Melting Point: 147-149 °C; (20)Enthalpy of Vaporization: 60.67 kJ/mol; (21)Boiling Point: 332 °C at 760 mmHg; (22)Vapour Pressure: 5.96E-05 mmHg at 25 °C.
Preparation of N-(Hydroxymethyl)phthalimide: this chemical can be prepared by O-Phthalimide and Formaldehyde.
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This reaction will occur at temperature of 103-108 °C. The reaction time is 4 hours.
Uses of N-(Hydroxymethyl)phthalimide: this chemical is used in organic synthesis of pesticides, dyes, pigments and medicine. It is also used to produce the derivatives of N-Phthalimide. Moreover, it can react with acrylonitrile to get N-(acryloylamino-methyl)-phthalimide.
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This reaction needs cc. H2SO4 at temperature of 0 °C for 20 hours. The yield is 89.7 %.
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C2c1ccccc1C(=O)N2CO
(2)InChI: InChI=1/C9H7NO3/c11-5-10-8(12)6-3-1-2-4-7(6)9(10)13/h1-4,11H,5H2
(3)InChIKey: MNSGOOCAMMSKGI-UHFFFAOYAS
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