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N-(Hydroxymethyl)phthalimide

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Name

N-(Hydroxymethyl)phthalimide

EINECS 204-241-4
CAS No. 118-29-6 Density 1.462 g/cm3
Solubility Melting Point 147-149 °C
Formula C9H7NO3 Boiling Point 332 °C at 760 mmHg
Molecular Weight 177.16 Flash Point 154.6 °C
Transport Information Appearance white crystalline powder
Safety 22-24/25 Risk Codes
Molecular Structure Molecular Structure of 118-29-6 (1H-Isoindole-1,3(2H)-dione,2-(hydroxymethyl)-) Hazard Symbols
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;

 

N-(Hydroxymethyl)phthalimide Consensus Reports

Reported in EPA TSCA Inventory.

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.



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.



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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