N-(Hydroxymethyl)phthalimide supplier

Name
N-(Hydroxymethyl)phthalimide
EINECS 204-241-4
CAS No. 118-29-6
Article Data53
CAS DataBase
Density 1.462 g/cm³
Solubility
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
Appearance white crystalline powder
Safety 22-24/25
Risk Codes
Molecular Structure
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;
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

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

: 7732-18-5
water

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

: 136918-14-4
phthalimide

formaldehyde <10%>: formaldehyde <10%>

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

Conditions

Conditions	Yield
at 100℃;

: 732-11-6
Phosmet

: 67-63-0
isopropyl alcohol

A: 136918-14-4
phthalimide

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

C: 1954-06-9
N-(methoxymethyl)phthalimide

D: 1954-04-7
2-<(isopropyloxy)methyl>-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
for 15h; UV-irradiation;	A n/a B n/a C n/a D 5 mg

...Expand

: 732-11-6
Phosmet

A: 136918-14-4
phthalimide

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

C: 1954-06-9
N-(methoxymethyl)phthalimide

Conditions

Conditions	Yield
In methanol for 7h; Product distribution; Further Variations:; Solvents; UV-irradiation;

...Expand

: 85-44-9
phthalic anhydride

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: water / Destillation des entstandenen sauren phthalsauren Methylamins 2: bromine / 160 - 170 °C 3: water View Scheme
Multi-step reaction with 2 steps 1: urea / 0.33 h / 140 °C 2: water / 1 h / Reflux View Scheme

: 550-44-7
N-methylphthalimide

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine / 160 - 170 °C 2: water View Scheme

: 17564-64-6
N-(chloromethyl)phthalimide

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
Multi-step reaction with 2 steps 1: sodium iodide / acetone / 4 h / 20 °C / Darkness 2: diethylzinc / hexane; dichloromethane / 2 h / 20 °C / Inert atmosphere View Scheme

...Expand

: 17564-64-6
N-(chloromethyl)phthalimide

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium iodide / acetone / 4 h / 20 °C / Darkness 2: dimethyl zinc(II) / n-heptane; dichloromethane / 18 h / 20 °C / Inert atmosphere View Scheme

: 136918-14-4
phthalimide

: 1634-04-4
tert-butyl methyl ether

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

B: 1373155-17-9
2-(tert-butoxymethyl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide at 75℃; for 5h; Sealed tube; Overall yield = 65 %;

...Expand

: 82524-62-7
1,3-Dioxo-1,3-dihydro-isoindole-2-carbaldehyde

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

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 20℃; Inert atmosphere; Sealed tube;

: 942-01-8
1,2,3,4-tetrahydrocarbazole

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

: 68375-17-7
N-(5,6,7,8-tetrahydro-carbazol-3-ylmethyl)-phthalimide

Conditions

Conditions	Yield
In sulfuric acid for 30h; Ambient temperature;	100%

: 91-55-4
2,3-dimethylindole

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

: 36798-28-4
N-(2,3-dimethyl-indol-5-ylmethyl)-phthalimide

Conditions

Conditions	Yield
In sulfuric acid for 30h; Ambient temperature;	98%

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

: 119071-84-0
2,8-Dimethyl-4-phenoxathiinessigsaeure-10,10-dioxid

: 100815-36-9
2,8-dimethyl-4-(carboxymethyl)-6-(phthalimidomethyl)-phenoxathiin S-dioxide

Conditions

Conditions	Yield
With sulfuric acid for 168h; Ambient temperature;	98%

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

: 79-42-5
2-mercaptopropanoic acid

: 2-(phthalimidomethylsulfanyl)propionic acid

Conditions

Conditions	Yield
With trifluoromethylsulfonic anhydride In trifluoroacetic acid	98%

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

: 10118-90-8
MINOCYCLINE

: C41H37N5O11

Conditions

Conditions	Yield
Stage #1: 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione; MINOCYCLINE With hydrogenchloride; sulfuric acid; trifluoroacetic acid at 40 - 50℃; Inert atmosphere; Stage #2: With monomethanolamine	97%

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

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

Conditions

Conditions	Yield
With sulfuric acid; hydrogen bromide In water at 0 - 70℃; for 17.25h;	96.4%
With sulfuric acid; hydrogen bromide In water at 70℃; Cooling with ice;	95%
With phosphorus tribromide In dichloromethane	80%

: 95-20-5
2-methyl-1H-indole

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

: 58867-56-4
2-methyl-5-(phtalimidomethyl)indole

Conditions

Conditions	Yield
In sulfuric acid for 30h; Ambient temperature;	96%

: 67-56-1
methanol

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

: 3-methoxy-2-(methoxymethyl)isoindolin-1-one

Conditions

Conditions	Yield
With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 130℃; under 11251.1 Torr; for 18h; Autoclave;	96%

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

: 2,3,3-trimethyl-3H-indolium

: 5-phthalimidomethyl-2,3,3-trimethylindolenine

Conditions

Conditions	Yield
Stage #1: 2,3,3-trimethyl-3H-indolium With sulfuric acid for 0.333333h; Inert atmosphere; Reflux; Stage #2: 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione for 70h;	95.8%

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

: 608-33-3
2,6-dibromophenol

: C15H9Br2NO3

Conditions

Conditions	Yield
With sulfuric acid In tetrahydrofuran at 20℃; Cooling with ice;	95%

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

: 7149-70-4
2-bromo-5-nitrotoluene

: 1312290-85-9
2-[(2-bromo-3-methyl-5-nitrophenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione

Conditions

Conditions	Yield
Stage #1: 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione With trifluorormethanesulfonic acid at 0℃; for 0.333333h; Tcherniak-Einhorn reaction; Stage #2: 2-bromo-5-nitrotoluene at 0 - 20℃; for 18h; Tcherniak-Einhorn reaction;	94%
Stage #1: 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione With trifluorormethanesulfonic acid at 0℃; for 0.333333h; Stage #2: 2-bromo-5-nitrotoluene at 0 - 20℃; for 18h;	94%

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

: 17564-64-6
N-(chloromethyl)phthalimide

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2.5h;	93%
With trichlorophosphate
With hydrogenchloride at 50℃;

: 828-94-4
2,3-dimethyl-5-methoxyindole

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

: 101004-44-8
2,3-dimethyl-5-methoxy-6-(phtalimidomethyl)indole

Conditions

Conditions	Yield
In sulfuric acid for 30h; Ambient temperature;	93%

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

: 141-97-9
ethyl acetoacetate

: 16880-35-6
ethyl 2-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-3-oxobutanoate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 24h;	93%
With boron trifluoride diethyl etherate at 0 - 20℃; for 0.5h;

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

: 540-59-0
1,2-Dichloroethylene

: 50667-66-8
2-chloro-3-phthalimido-propionaldehyde

Conditions

Conditions	Yield
With sulfuric acid	93%

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

: 1025687-97-1
1-methyl-1'-forrnyl-spiro[piperidine-4,3'-(2H)-indole]

: 1025687-98-2
5'-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-1'-formyl-1-methyl-spiro[piperidine-4,3'-(2H)-indole]

Conditions

Conditions	Yield
With sulfuric acid Tscherniac-Einhorn reaction;	93%
Stage #1: 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione; 1-methyl-1'-forrnyl-spiro[piperidine-4,3'-(2H)-indole] With sulfuric acid at 5 - 20℃; Inert atmosphere; Stage #2: With sodium carbonate In water pH=10;	93%

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

: 540-36-3
para-difluorobenzene

: 2-(2,5-difluorobenzyl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid Ambient temperature;	92%

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

: 28734-85-2
3-benzyl-2,3-dihydropyrimidin-4(1H)-one

: 10465-78-8
diamide

A: N-(3-benzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimid-1-yl)methylphthalimide

B: C18H24N6O4

Conditions

Conditions	Yield
With triphenylphosphine In N,N-dimethyl-formamide	A 0.3 % Chromat. B 92%

...Expand

: 100-02-7
4-nitro-phenol

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

: 2,6-bis(phthaloylmethyl)-4-nitrophenol

Conditions

Conditions	Yield
With sulfuric acid for 2h; Ambient temperature;	90%

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

: 298-81-7
9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one

A: 96548-68-4
5,5'-Bis-N-Phthalimidomethyl-8-methoxypsoralen

B: 81759-49-1
5-N-Phthalimidomethyl-8-methoxypsoralen

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic acid In dichloromethane for 6h; Ambient temperature;	A 90% B n/a

...Expand

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

: 4949-44-4
ethyl propanoylacetate

: ethyl α-(phenylimidomethyl)propionylacetate

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate	90%

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

: 19685-09-7
(S)-10-hydroxycamptothecin

: 1352172-54-3
C29H21N3O7

Conditions

Conditions	Yield
With sulfuric acid at 0 - 20℃; for 12h;	90%

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

: 75264-92-5
tetramethylammonium trifluoromethylselenate(0)

: 2-(((trifluoromethyl)selanyl)methyl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With calcium chloride In acetonitrile at 80℃; for 2h; Time; Inert atmosphere; Sealed tube; Glovebox;	90%

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

: 28177-48-2
2,6-difluorophenol

: C15H9F2NO3

Conditions

Conditions	Yield
With sulfuric acid In water at -5 - 20℃; for 24h;	90%

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

: 107-13-1
acrylonitrile

: 80500-94-3
N-(acryloylamino-methyl)-phthalimide

Conditions

Conditions	Yield
With sulfuric acid 0 deg C, than 18 deg C., 20 h;	89.7%
With sulfuric acid; acetic acid

: 53918-89-1
7-methoxy-2,3-dimethyl-1H-indole

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

: 101004-45-9
2-(7-Methoxy-2,3-dimethyl-1H-indol-6-ylmethyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
In sulfuric acid for 30h; Ambient temperature;	89%

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

: 21797-74-0
2,8-dimethylphenoxathiin 10,10-dioxide

: 154459-09-3
2,8-dimethyl-4,6-bis(phthalimidomethyl)-phenoxathiin-10,10-dioxide

Conditions

Conditions	Yield
With sulfuric acid for 168h; Ambient temperature;	89%

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

: 2873-29-2
D-glucal triacetate

: 354152-80-0
phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In toluene at -20℃; Ferrier rearrangement;	89%
With niobium pentachloride In tetrahydrofuran for 0.833333h; Ferrier rearrangement; Heating;	80%
With montmorillonite K-10 for 0.166667h; Ferrier rearrangement; microwave irradiation;	77%
With boron trifluoride diethyl etherate In benzene at 20℃; for 1.25h;	76.3%

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

Product Name

N-(Hydroxymethyl)phthalimide

Synthetic route

N-(Hydroxymethyl)phthalimide Consensus Reports

N-(Hydroxymethyl)phthalimide Specification

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