CAS No.118-29-6,N-(Hydroxymethyl)phthalimide Suppliers

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Basic Information

Molecular Structure:
CAS No.:	118-29-6
Name:	N-(Hydroxymethyl)phthalimide
Article Data:	53

Formula:	C₉H₇NO₃
Molecular Weight:	177.159
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;
EINECS:	204-241-4
Density:	1.462 g/cm³
Melting Point:	147-149 °C
Boiling Point:	332 °C at 760 mmHg
Flash Point:	154.6 °C
Appearance:	white crystalline powder
Safety:	22-24/25
PSA:	57.61000
LogP:	0.17030

Synthetic route

: 136918-14-4
phthalimide

: 50-00-0
formaldehyd

: 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

Conditions

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%

: 5332-26-3
N-(bromomethyl)phtalimide

: 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

Conditions

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

Conditions	Yield
In 1,1,2,2-tetrachloroethylene at 110℃; for 8h;	84%

...Expand

: 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

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%

...Expand

: 203255-55-4
2-(iodomethyl)isoindoline-1,3-dione

: 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

Conditions

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

Conditions	Yield
In dimethyl sulfoxide Irradiation;	A 15% B 35% C 40%

...Expand

: 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

Conditions	Yield
With diethylzinc In hexane; dichloromethane at 20℃; for 2h; Inert atmosphere;	A 39% B 14% C 22%

...Expand

: 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

C: N-(di-isopropylaminomethyl)phthalimide

Conditions

Conditions	Yield
In benzene for 12h; Heating; Title compound not separated from byproducts;

...Expand

: 67-56-1
methanol

: 119812-51-0
phthalimide DBU salt

A: 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

B: 3-hydroxy-2-(hydroxymethyl)isoindolin-1-one

Conditions

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;

...Expand

: 67-56-1
methanol

: 136918-14-4
phthalimide

A: 118-29-6
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

B: 3-hydroxy-2-(hydroxymethyl)isoindolin-1-one

Conditions

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;

...Expand

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Consensus Reports

Reported in EPA TSCA Inventory.

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