Product Name

  • Name

    N-Hydroxyphthalimide

  • EINECS 208-358-1
  • CAS No. 524-38-9
  • Article Data78
  • CAS DataBase
  • Density 1.638 g/cm3
  • Solubility slightly soluble in the water
  • Melting Point 233 °C (dec.)(lit.)
  • Formula C8H5NO3
  • Boiling Point 370.3 °C at 760 mmHg
  • Molecular Weight 163.133
  • Flash Point 177.8 °C
  • Transport Information
  • Appearance yellow moist powder
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 524-38-9 (N-Hydroxyphthalimide)
  • Hazard Symbols IrritantXi
  • Synonyms Phthalimide,N-hydroxy- (6CI,7CI,8CI);2-Hydroxy-1H-isoindole-1,3(2H)-dione;2-Hydroxyisoindole-1,3-dione;2-Hydroxyphthalimide;F 802;NSC 770;
  • PSA 57.61000
  • LogP 0.60970

Synthetic route

3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione
1582289-49-3

3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
at 130℃; for 3h; Inert atmosphere;99%
N-acetoxyphthalimide
17720-64-8

N-acetoxyphthalimide

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With methanol; potassium permanganate at 25℃; chemoselective reaction;96%
phthalic anhydride
85-44-9

phthalic anhydride

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride; acetic anhydride for 4h; Heating;95%
With hydroxylamine hydrochloride; triethylamine In isopropyl alcohol at 95℃; for 0.7h; Reagent/catalyst; Temperature;94.6%
With hydroxyammonium sulfate; sodium hydroxide In water at 90℃; Product distribution / selectivity;89.7%
tert-butyl 1,3-dioxoisoindoline-2-carboxylate
150220-29-4

tert-butyl 1,3-dioxoisoindoline-2-carboxylate

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With hydroxylamine In acetonitrile at 20℃;95%
3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione
1582289-49-3

3-(1-methylethenyl)-1H-2,3-benzoxazine-1,4(3H)-dione

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

3H-benzo[d][1,2]oxazine-1,4-dione
31583-39-8

3H-benzo[d][1,2]oxazine-1,4-dione

Conditions
ConditionsYield
In water; acetonitrile for 1h; Time; Reflux;A 7%
B 93%
Isopropylbenzene
98-82-8

Isopropylbenzene

ethyl 2-(((1,3-dioxoisoindolin-2-yl)oxy)methyl)acrylate
1313016-88-4

ethyl 2-(((1,3-dioxoisoindolin-2-yl)oxy)methyl)acrylate

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

ethyl 4-methyl-2-methylene-4-phenylpentanoate

ethyl 4-methyl-2-methylene-4-phenylpentanoate

Conditions
ConditionsYield
With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 24h;A n/a
B 91%
...Expand
ethylbenzene
100-41-4

ethylbenzene

2-((2-phenylallyl)oxy)isoindoline-1,3-dione
1608461-37-5

2-((2-phenylallyl)oxy)isoindoline-1,3-dione

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

pent-1-ene-2,4-diyldibenzene
38212-18-9

pent-1-ene-2,4-diyldibenzene

Conditions
ConditionsYield
With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 29h;A n/a
B 89%
...Expand
2-phenethoxyisoindoline-1,3-dione
92856-14-9

2-phenethoxyisoindoline-1,3-dione

benzene
71-43-2

benzene

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

Conditions
ConditionsYield
With aluminium trichloride for 0.5h; Ambient temperature;A 76%
B 86%
...Expand
ethylbenzene
100-41-4

ethylbenzene

ethyl 2-(((1,3-dioxoisoindolin-2-yl)oxy)methyl)acrylate
1313016-88-4

ethyl 2-(((1,3-dioxoisoindolin-2-yl)oxy)methyl)acrylate

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

ethyl 2-methylene-4-phenylpentanoate

ethyl 2-methylene-4-phenylpentanoate

Conditions
ConditionsYield
With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 17h;A n/a
B 85%
...Expand
1,3-dioxoisoindolin-2-yl benzoate
58585-84-5

1,3-dioxoisoindolin-2-yl benzoate

benzene
71-43-2

benzene

A

benzophenone
119-61-9

benzophenone

B

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With aluminium trichloride for 0.5h; Ambient temperature;A 81%
B 74%
...Expand
2-((2-phenylallyl)oxy)isoindoline-1,3-dione
1608461-37-5

2-((2-phenylallyl)oxy)isoindoline-1,3-dione

toluene
108-88-3

toluene

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

2,4-diphenylbut-1-ene
16606-47-6

2,4-diphenylbut-1-ene

Conditions
ConditionsYield
With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 24h;A n/a
B 77%
...Expand
Isopropylbenzene
98-82-8

Isopropylbenzene

2-((2-phenylallyl)oxy)isoindoline-1,3-dione
1608461-37-5

2-((2-phenylallyl)oxy)isoindoline-1,3-dione

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

2,4-diphenyl-4-methyl-pent-1-ene
6362-80-7

2,4-diphenyl-4-methyl-pent-1-ene

Conditions
ConditionsYield
With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 29h;A n/a
B 76%
...Expand
2-[(hydroxyamino)carbonyl]benzoic acid
17698-09-8

2-[(hydroxyamino)carbonyl]benzoic acid

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
In water at 90℃; for 0.25h; pH=3.7; pH-value;69.7%
at 45 - 50℃;
at 45 - 50℃;
ethyl 2-(((1,3-dioxoisoindolin-2-yl)oxy)methyl)acrylate
1313016-88-4

ethyl 2-(((1,3-dioxoisoindolin-2-yl)oxy)methyl)acrylate

toluene
108-88-3

toluene

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

ethyl 2-phenethylpropenoate
27356-87-2

ethyl 2-phenethylpropenoate

Conditions
ConditionsYield
With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 42h;A n/a
B 48%
...Expand
N-(benzyloxy)phthalimide
16653-19-3

N-(benzyloxy)phthalimide

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In butanone43.8%
With Pd/SrCO3; butanone Hydrogenation;
phthalimide
136918-14-4

phthalimide

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; ammonia
hydroxyimino-phthalide
57685-30-0

hydroxyimino-phthalide

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With hydrogenchloride; water
With N,N-dimethyl-formamide
2-hydroxy-isoquinoline-1,3,4-trione
21573-32-0

2-hydroxy-isoquinoline-1,3,4-trione

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With water; bromine
Diethyl phthalate
84-66-2

Diethyl phthalate

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With ethanol; hydroxylamine; sodium ethanolate
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With water; hydroxylamine
Phthaloyl dichloride
88-95-9

Phthaloyl dichloride

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; water; sodium carbonate
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / 24 h / 0 - 20 °C / Inert atmosphere
2: 3 h / 130 °C / Inert atmosphere
View Scheme
With hydroxylamine hydrochloride; triethylamine In toluene at 0℃; for 3h; Reflux;23.5 g
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

N-carbamate
116849-45-7

N-carbamate

Conditions
ConditionsYield
With hydroxylamine In water at 30℃; Rate constant; effect of pH; various amines; acetate buffer;
N-carbamate
116849-45-7

N-carbamate

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
With hydroxylamine In water at 30℃; Rate constant; pH= 5.18-7.84;;
hydrogenchloride
7647-01-0

hydrogenchloride

hydroxyimino-phthalide
57685-30-0

hydroxyimino-phthalide

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

...Expand
2-hydroxy-isoquinoline-1,3,4-trione
21573-32-0

2-hydroxy-isoquinoline-1,3,4-trione

bromine water

bromine water

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

hydroxylamine salt of/the/ phthalmonohydroxamic acid

hydroxylamine salt of/the/ phthalmonohydroxamic acid

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Conditions
ConditionsYield
at 130 - 135℃;
With hydrogenchloride
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

phthalimide N-oxyl
3229-40-1

phthalimide N-oxyl

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

2-carboxybenzyl radical
141814-31-5

2-carboxybenzyl radical

Conditions
ConditionsYield
In acetic acid at 25℃; Kinetics;
...Expand
Benzaldehyde-d
3592-47-0

Benzaldehyde-d

phthalimide N-oxyl
3229-40-1

phthalimide N-oxyl

A

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

B

benzoyl radical
2652-65-5

benzoyl radical

Conditions
ConditionsYield
In acetic acid at 25℃; Kinetics;
...Expand
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

diethyl 1-hydroxyethylphosphonate
15336-73-9

diethyl 1-hydroxyethylphosphonate

O,O-diethyl-(1-phthalimido)-N-oxyethylphosphonate
124810-58-8

O,O-diethyl-(1-phthalimido)-N-oxyethylphosphonate

Conditions
ConditionsYield
With diethyl azodicarbonate; triphenylphosphine In tetrahydrofuran for 14h; Ambient temperature;100%
With triphenylphosphine; diethylazodicarboxylate
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

diethyl (1-hydroxy-3-phenylpropyl)phosphonate
81364-33-2

diethyl (1-hydroxy-3-phenylpropyl)phosphonate

[1-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-3-phenyl-propyl]-phosphonic acid diethyl ester
145459-53-6

[1-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-3-phenyl-propyl]-phosphonic acid diethyl ester

Conditions
ConditionsYield
With diethyl azodicarbonate; triphenylphosphine In tetrahydrofuran Ambient temperature;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Diethoxymethyl-(1-hydroxy-propyl)-phosphinic acid ethyl ester
145433-26-7

Diethoxymethyl-(1-hydroxy-propyl)-phosphinic acid ethyl ester

Diethoxymethyl-[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propyl]-phosphinic acid ethyl ester
145433-32-5

Diethoxymethyl-[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propyl]-phosphinic acid ethyl ester

Conditions
ConditionsYield
With diethyl azodicarbonate; triphenylphosphine In tetrahydrofuran at 20℃;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

i-propyl hydroxymethane(phenyl)phosphinate
145433-29-0

i-propyl hydroxymethane(phenyl)phosphinate

(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxymethyl)-phenyl-phosphinic acid isopropyl ester
145433-36-9

(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxymethyl)-phenyl-phosphinic acid isopropyl ester

Conditions
ConditionsYield
With diethyl azodicarbonate; triphenylphosphine In tetrahydrofuran at 20℃;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Diethoxymethyl-(1-hydroxy-butyl)-phosphinic acid ethyl ester
145433-27-8

Diethoxymethyl-(1-hydroxy-butyl)-phosphinic acid ethyl ester

Diethoxymethyl-[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-butyl]-phosphinic acid ethyl ester
145433-33-6

Diethoxymethyl-[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-butyl]-phosphinic acid ethyl ester

Conditions
ConditionsYield
With diethyl azodicarbonate; triphenylphosphine In tetrahydrofuran at 20℃;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Diethoxymethyl-(1-hydroxy-3-methylsulfanyl-propyl)-phosphinic acid ethyl ester
145433-28-9

Diethoxymethyl-(1-hydroxy-3-methylsulfanyl-propyl)-phosphinic acid ethyl ester

Diethoxymethyl-[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-3-methylsulfanyl-propyl]-phosphinic acid ethyl ester
145433-34-7

Diethoxymethyl-[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-3-methylsulfanyl-propyl]-phosphinic acid ethyl ester

Conditions
ConditionsYield
With diethyl azodicarbonate; triphenylphosphine In tetrahydrofuran at 20℃;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Diethoxymethyl-(1-hydroxy-2-phenyl-ethyl)-phosphinic acid ethyl ester
124810-84-0

Diethoxymethyl-(1-hydroxy-2-phenyl-ethyl)-phosphinic acid ethyl ester

Diethoxymethyl-[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-2-phenyl-ethyl]-phosphinic acid ethyl ester
145433-35-8

Diethoxymethyl-[1-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-2-phenyl-ethyl]-phosphinic acid ethyl ester

Conditions
ConditionsYield
With diethyl azodicarbonate; triphenylphosphine In tetrahydrofuran at 20℃;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

Diazo-(2,2-dimethyl-benzo[1,3]dioxol-5-yl)-acetic acid methyl ester
172795-74-3

Diazo-(2,2-dimethyl-benzo[1,3]dioxol-5-yl)-acetic acid methyl ester

(2,2-Dimethyl-benzo[1,3]dioxol-5-yl)-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-acetic acid methyl ester
172795-78-7

(2,2-Dimethyl-benzo[1,3]dioxol-5-yl)-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-acetic acid methyl ester

Conditions
ConditionsYield
In benzene Heating;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

4-(1,3-dioxo-1,3-dihydroisoindole-2-yloxy)butyric acid ethyl ester
27091-83-4

4-(1,3-dioxo-1,3-dihydroisoindole-2-yloxy)butyric acid ethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 80℃;100%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 80℃;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;91%
With sodium acetate 1.) DMSO, 60 deg C, 10 min, 2.) DMSO, reflux, 30 min; Multistep reaction;
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃;
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

1-phenyl-1-(2-tetrahydropyranyloxy)-5-pentanol
230285-14-0

1-phenyl-1-(2-tetrahydropyranyloxy)-5-pentanol

1-phenyl-5-(N-phthalimidoxy)-1-(2-tetrahydropyranyloxy)pentane
230285-15-1

1-phenyl-5-(N-phthalimidoxy)-1-(2-tetrahydropyranyloxy)pentane

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;100%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 24h;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

ethylamine
75-04-7

ethylamine

N,N'-diethylphthalic diamide
22011-24-1

N,N'-diethylphthalic diamide

Conditions
ConditionsYield
at 20℃; under 600.048 - 750.06 Torr; Addition; solid-gas reaction; ring cleavage;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

methylamine
74-89-5

methylamine

N1,N2-dimethylphthalamide
19532-98-0

N1,N2-dimethylphthalamide

Conditions
ConditionsYield
at 20℃; under 600.048 - 750.06 Torr; Addition; solid-gas reaction; ring cleavage;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

t-butyl (1,3-dioxo-1,3-dihydroisoindol-2-yloxy)acetate
54224-25-8

t-butyl (1,3-dioxo-1,3-dihydroisoindol-2-yloxy)acetate

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 20 - 50℃; Inert atmosphere;100%
In N,N-dimethyl-formamide97%
With triethylamine In tetrahydrofuran at 0 - 20℃;90%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

acetic anhydride
108-24-7

acetic anhydride

N-acetoxyphthalimide
17720-64-8

N-acetoxyphthalimide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 3h; Inert atmosphere;100%
With pyridine at 20℃; for 12h;79%
for 4h;
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

2-(tert-butoxy)isoindoline-1,3-dione
51951-30-5

2-(tert-butoxy)isoindoline-1,3-dione

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 24h; Inert atmosphere;100%
With perchloric acid In 1,4-dioxane at 20℃; for 40h;99%
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 24h;83%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

homoalylic alcohol
627-27-0

homoalylic alcohol

2-(but-3-en-1-yloxy)isoindoline-1,3-dione
80042-17-7

2-(but-3-en-1-yloxy)isoindoline-1,3-dione

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere;100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 4.5h; Mitsunobu Displacement; Inert atmosphere;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 16.5h;
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

3-[(N-benzyloxycarbonyl)amino]propanol
34637-22-4

3-[(N-benzyloxycarbonyl)amino]propanol

N-[3-(Benzyloxycarbonylamino)-1-propoxy]phthalimide
226569-23-9

N-[3-(Benzyloxycarbonylamino)-1-propoxy]phthalimide

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; dichloromethane; ethyl acetate100%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

(S,S)-[2-(2-carbamoylpyrrolidin-1-yl)-1-hydroxymethyl-2-oxoethyl]-carbamic acid tert-butyl ester
701249-55-0

(S,S)-[2-(2-carbamoylpyrrolidin-1-yl)-1-hydroxymethyl-2-oxoethyl]-carbamic acid tert-butyl ester

tert-butyl (1S)-2-[(2S)-2-carbamoyl-1-pyrrolidinyl]-1-[[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl]-2-oxoethylcarbamate
701249-56-1

tert-butyl (1S)-2-[(2S)-2-carbamoyl-1-pyrrolidinyl]-1-[[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl]-2-oxoethylcarbamate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 5℃; for 1h;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

rac-3-bromocyclohexene
1521-51-3

rac-3-bromocyclohexene

2-(cyclohex-2-en-1-yloxy)isoindoline-1,3-dione
76029-42-0

2-(cyclohex-2-en-1-yloxy)isoindoline-1,3-dione

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; for 2h; Inert atmosphere;100%
With triethylamine In N,N-dimethyl-formamide
With triethylamine In N,N-dimethyl-formamide
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

N-(tert-butoxycarbonyl)-L-prolinol
69610-40-8

N-(tert-butoxycarbonyl)-L-prolinol

tert-butyl (2S)-2-[[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]methyl]-pyrrolidine-1-carboxylate
952747-36-3

tert-butyl (2S)-2-[[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]methyl]-pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -10 - 20℃;100%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -10 - 20℃; for 16h;98%
Stage #1: N-(tert-butoxycarbonyl)-L-prolinol With 5,10,15,20-tetraphenyl-21H,23H-porphine; diethylazodicarboxylate In tetrahydrofuran at -10℃; for 0.833333h;
Stage #2: N-hydroxyphthalimide In tetrahydrofuran at 20℃; for 16h;		98%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

5-(chloromethyl)-2-(1H-pyrazol-1-yl)pyridine
748796-39-6

5-(chloromethyl)-2-(1H-pyrazol-1-yl)pyridine

2-(6-pyrazol-1-yl-pyridin-3-ylmethoxy)-isoindole-1,3-dione
748796-40-9

2-(6-pyrazol-1-yl-pyridin-3-ylmethoxy)-isoindole-1,3-dione

Conditions
ConditionsYield
Stage #1: N-hydroxyphthalimide With sodium hydride In DMF (N,N-dimethyl-formamide) for 0.5h;
Stage #2: 3-chloromethyl-6-(pyrazole-1-yl)pyridine In DMF (N,N-dimethyl-formamide) at 40 - 50℃; for 3h;		100%
4-chlorobutyl bromide
6940-78-9

4-chlorobutyl bromide

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

2-(2-chlorobutoxy)isoindoline-1,3-dione
59376-94-2

2-(2-chlorobutoxy)isoindoline-1,3-dione

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

(1R,4aS,8aS)-1-hydroxy-1-(2-hydroxyethyl)-5,5,8a-trimethyloctahydronaphthalen-1(2H)-one
1415010-34-2

(1R,4aS,8aS)-1-hydroxy-1-(2-hydroxyethyl)-5,5,8a-trimethyloctahydronaphthalen-1(2H)-one

2-(2-((1R,4aS,8aS)-1-hydroxy-5,5,8a-trimethyl-2-oxodecahydronaphthalen-1-yl)ethoxy)-1H-isoindole-1,3(2H)-dione
1415010-35-3

2-(2-((1R,4aS,8aS)-1-hydroxy-5,5,8a-trimethyl-2-oxodecahydronaphthalen-1-yl)ethoxy)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 1h; Inert atmosphere;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

tert-butyl 3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)propanoate
518044-32-1

tert-butyl 3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)propanoate

C23H33NO9
1415328-82-3

C23H33NO9

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Product distribution / selectivity;100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

(E)-2,4-pentadien-1-ol
4949-20-6

(E)-2,4-pentadien-1-ol

C13H11NO3
1443059-14-0

C13H11NO3

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

{[2-(2-hydroxyethoxy)thiazol-4-yl]-imino-methyl}carbamic acid tert-butyl ester
1448673-93-5

{[2-(2-hydroxyethoxy)thiazol-4-yl]-imino-methyl}carbamic acid tert-butyl ester

({2-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yloxy)ethoxy]thiazol-4-yl}-imino-methyl)carbamic acid tert-butyl ester
1448673-94-6

({2-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yloxy)ethoxy]thiazol-4-yl}-imino-methyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 20h;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

3-[4-(tert-butoxycarbonylamino-imino-methyl)phenoxy]-2-hydroxypropionic acid methyl ester
1448674-13-2

3-[4-(tert-butoxycarbonylamino-imino-methyl)phenoxy]-2-hydroxypropionic acid methyl ester

methyl 3-{4-[N-(tert-butoxycarbonyl)carbamimidoyl]phenoxy}-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]propanoate
1448674-95-0

methyl 3-{4-[N-(tert-butoxycarbonyl)carbamimidoyl]phenoxy}-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]propanoate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

2-Methoxybenzyl chloride
7035-02-1

2-Methoxybenzyl chloride

2-(2-methoxybenzyloxy)isoindoline-1,3-dione
321430-43-7

2-(2-methoxybenzyloxy)isoindoline-1,3-dione

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

cyclopentyl iodide
1556-18-9

cyclopentyl iodide

2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione
54224-24-7

2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; for 2h; Inert atmosphere;100%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

3-(1H-Indol-2-yl)propan-1-ol
90901-84-1

3-(1H-Indol-2-yl)propan-1-ol

C19H16N2O3

C19H16N2O3

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 60℃; for 2h; Mitsunobu Displacement;100%

N-Hydroxyphthalimide Consensus Reports

Reported in EPA TSCA Inventory.

N-Hydroxyphthalimide Specification

The IUPAC name of N-Hydroxyphthalimide is 2-hydroxyisoindole-1,3-dione. With the CAS registry number 524-38-9, it is also named as 1H-Isoindole-1,3(2H)-dione, 2-hydroxy-. The product's categories are biochemistry; carbon radical producing catalysts (environmentally-friendly oxidation); condensation & active esterification; coupling reactions (peptide synthesis); n-substituted maleimides, succinimides & phthalimides; peptide synthesis; synthetic organic chemistry; active esters/additives. It is yellow moist powder which is slightly soluble in the water. When heated to decomposition it emits toxic vapors of NOx. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.32; (4)ACD/LogD (pH 7.4): -0.9; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 32.24; (8)ACD/KOC (pH 7.4): 1.93; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Molar Volume: 99.5 cm3; (13)Polarizability: 15.55×10-24 cm3; (14)Surface Tension: 89.3 dyne/cm; (15)Flash Point: 177.8 °C; (16)Enthalpy of Vaporization: 65.12 kJ/mol; (17)Boiling Point: 370.3 °C at 760 mmHg; (18)Vapour Pressure: 3.87E-06 mmHg at 25°C; (19)Exact Mass: 163.026943; (20)MonoIsotopic Mass: 163.026943; (21)Topological Polar Surface Area: 57.6; (22)Heavy Atom Count: 12; (23)Complexity: 215.

Preparation of N-Hydroxyphthalimide: It can be obtained by phthalic acid anhydride with the reagents sodium carbonate, water and hydroxylamine hydrochloride.

Uses of N-Hydroxyphthalimide: It is used as intermediate of drugs such as amikacin. And it is also used as alkyl oxidant, catalyst and mineral collector. Additionally, it can react with 2-pyridin-2-yl-ethanol to get 2-(2-pyridin-2-yl-ethoxy)-isoindole-1,3-dione. This reaction needs reagent diethyl azodicarboxylate and PPh3 and solvent CHCl3 at ambient temperature. The reaction time is 1 hours. The yield is 75.5%.

When you are using this chemical, please be cautious about it as the following:  
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. 

People can use the following data to convert to the molecule structure.
1. SMILES:O=C2c1ccccc1C(=O)N2O
2. InChI:InChI=1/C8H5NO3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4,12H 
3. InChIKey:CFMZSMGAMPBRBE-UHFFFAOYAR

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 178mg/kg (178mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00747,

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