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6066-82-6

Basic Information
CAS No.: 6066-82-6
Name: N-Hydroxysuccinimide
Molecular Structure:
Molecular Structure of 6066-82-6 (N-Hydroxysuccinimide)
Formula: C4H5NO3
Molecular Weight: 115.09 .
Synonyms: Succinimide, N-hydroxy-;2,5-Pyrrolidinedione, 1-hydroxy-;Hydroxysuccinimide;Succinimide, N-hydroxy- (8CI);1-Hydroxy-2,5-pyrrolidinedione;1-Hydroxysuccinimide;1-Hydroxy-pyrrolidine-2,5-dione;N-Hydroxy Succinimide;
EINECS: 228-001-3
Density: 1.649 g/cm3
Melting Point: 95-98 °C(lit.)
Boiling Point: 262.4 °C at 760 mmHg
Flash Point: 112.5 °C
Solubility: Soluble in water
Appearance: white to pale yellow
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-26-36
Transport Information:
PSA: 57.61000
LogP: -0.53750
Synthetic route

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

78-81-9

isobutylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-35-0

diisopropyl (2-(isobutylamino)-2-oxoethyl)phosphonate

C

C13H29N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; isobutylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 99%
C n/a

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

22013-33-8

6-amino-3,4-benzodioxane

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-37-2

diisopropyl (2-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)amino)-2-oxoethyl)phosphonate

C

C13H29N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; 6-amino-3,4-benzodioxane In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 99%
C n/a

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

2393-23-9

4-methoxy-benzylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-38-3

diisopropyl (2-((4-methoxybenzyl)amino)-2-oxoethyl)phosphonate

C

C13H29N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; 4-methoxy-benzylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 99%
C n/a
1426294-34-9

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate

123-46-6

girard's reagent T

120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-48-5

diisopropyl (1-((3,4-dimethoxyphenethyl)amino)-1-oxopropan-2-yl)phosphonate

C

C14H31N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate; 2-(3,4-dimethoxyphenyl)-ethylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 99%
C n/a

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

64-04-0

phenethylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-39-4

diisopropyl (2-oxo-2-(phenethylamino)ethyl)phosphonate

C

C13H29N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; phenethylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 99%
C n/a

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

55-81-2

4-Methoxyphenethylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-40-7

diisopropyl (2-((4-methoxyphenethyl)amino)-2-oxoethyl)phosphonate

C

C13H29N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; 4-Methoxyphenethylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 99%
C n/a
53053-08-0

4-azidobenzoic acid N-hydroxysuccinimide ester

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Conditions
ConditionsYield
With chitosan In aq. phosphate buffer; dichloromethane at 50℃; for 5h; Solvent; Temperature; Microwave irradiation;98.2%

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-41-8

diisopropyl (2-((3,4-dimethoxyphenethyl)amino)-2-oxoethyl)phosphonate

C

C13H29N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; 2-(3,4-dimethoxyphenyl)-ethylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 96%
C n/a
1426294-34-9

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate

123-46-6

girard's reagent T

100-46-9

benzylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-46-3

diisopropyl (1-(benzylamino)-1-oxopropan-2-yl)phosphonate

C

C14H31N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate; benzylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 95%
C n/a
110-15-6

succinic acid

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Conditions
ConditionsYield
With hydroxylamine hydrochloride; potassium carbonate; acetic acid In cyclohexane at 65℃; for 9h; Product distribution / selectivity;94.7%
With hydroxyammonium sulfate; boric acid; hypophosphorous acid; sodium hydroxide In toluene at 95℃; Temperature; Reflux;85.5%
With hydroxylamine; acetic acid In cyclohexane; water for 6 - 9h; Product distribution / selectivity; Heating / reflux;64.9%
1426294-34-9

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate

123-46-6

girard's reagent T

64-04-0

phenethylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-47-4

diisopropyl (1-oxo-1-(phenethylamino)propan-2-yl)phosphonate

C

C14H31N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate; phenethylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 94%
C n/a
41839-96-7

N-(tert-butoxycarbonyl)-succinimide

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Conditions
ConditionsYield
With hydroxylamine In acetonitrile at 20℃;93%
23405-15-4

benzoic acid N-hydroxysuccinimide ester

109-76-2

Trimethylenediamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

68388-03-4

N,N'-(propane-1,3-diyl)dibenzamide

Conditions
ConditionsYield
In methanol at 25℃; for 0.166667h;A n/a
B 92%

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

106-49-0

p-toluidine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

C13H29N3O5P(1+)*Cl(1-)

C

16634-86-9

diisopropyl (2-oxo-2-(p-tolylamino)ethyl)phosphonate

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; p-toluidine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B n/a
C 92%
108-30-5

succinic acid anhydride

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In water at 0 - 25℃; for 0.5h; Large scale;90%
With hydroxylamine hydrochloride; sodium methylate a) methanol, 60 deg C, 1.5 h, b) xylene, reflux, 4 h;41%
With pyridine; hydroxylamine hydrochloride for 4h; Heating; Inert atmosphere;
With hydroxylamine at 160℃;
With sulfuric acid; hydroxylamine hydrochloride In water at 100 - 160℃; Reagent/catalyst;
51-67-2

tyrosamine

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-42-9

diisopropyl (2-((4-hydroxyphenethyl)amino)-2-oxoethyl)phosphonate

C

C13H29N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: tyrosamine; 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 89%
C n/a
96-15-1

2-Methylbutylamine

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-36-1

diisopropyl (2-((2-methylbutyl)amino)-2-oxoethyl)phosphonate

C

C13H29N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2-Methylbutylamine; 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 87%
C n/a
123-75-1

pyrrolidine

1426294-34-9

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate

123-46-6

girard's reagent T

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-44-1

diisopropyl (1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)phosphonate

C

C14H31N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: pyrrolidine; 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 86%
C n/a
1426294-34-9

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate

123-46-6

girard's reagent T

78-81-9

isobutylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-43-0

diisopropyl (1-(isobutylamino)-1-oxopropan-2-yl)phosphonate

C

C14H31N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate; isobutylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 83%
C n/a
128-08-5

N-Bromosuccinimide

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Conditions
ConditionsYield
With water In ethanol at 20℃; for 2h;82%

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

100-46-9

benzylamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

C13H29N3O5P(1+)*Cl(1-)

C

113368-98-2

diisopropyl (2-(benzylamino)-2-oxoethyl)phosphonate

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate; benzylamine In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B n/a
C 81%
74124-79-1

di(succinimido) carbonate

α-methyl-ω-(1-(4-hydroxymethyl-2,6-dimethylphenoxy)-acet-2-oxy)poly(ethylene glycol)

α-methyl-ω-(1-(4-hydroxymethyl-2,6-dimethylphenoxy)-acet-2-oxy)poly(ethylene glycol)

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

α-methyl-ω-(1-(4-(N-succinimidyloxycarbonyloxymethyl)-2,6-dimethylphenoxy)-acet-2-oxy)poly(ethylene glycol)

α-methyl-ω-(1-(4-(N-succinimidyloxycarbonyloxymethyl)-2,6-dimethylphenoxy)-acet-2-oxy)poly(ethylene glycol)

Conditions
ConditionsYield
With pyridine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 20h;A n/a
B 79%
23405-15-4

benzoic acid N-hydroxysuccinimide ester

109-76-2

Trimethylenediamine

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

6108-74-3

N-(3-aminopropyl)benzamide

C

68388-03-4

N,N'-(propane-1,3-diyl)dibenzamide

Conditions
ConditionsYield
In methanol at 25℃; for 2h;A n/a
B 20%
C 77%
In methanol at 25℃; for 0.116667h;A n/a
B 63%
C 31%
1426294-34-9

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate

123-46-6

girard's reagent T

22013-33-8

6-amino-3,4-benzodioxane

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

1426294-45-2

diisopropyl (1-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)amino)-1-oxopropan-2-yl)phosphonate

C

C14H31N3O5P(1+)*Cl(1-)

Conditions
ConditionsYield
Stage #1: 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)propanoate; 6-amino-3,4-benzodioxane In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B 73%
C n/a
50-28-2

estradiol

N-Hydroxysulfosuccinimide sodium salt

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

481-96-9

estradiol-3-sulfate

Conditions
ConditionsYield
With AST In acetone Enzymatic reaction;A n/a
B 68%
123-75-1

pyrrolidine

2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate

123-46-6

girard's reagent T

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

C13H29N3O5P(1+)*Cl(1-)

C

66932-77-2

diisopropyl (2-oxo-2-(pyrrolidin-1-yl)ethyl)phosphonate

Conditions
ConditionsYield
Stage #1: pyrrolidine; 2,5-dioxopyrrolidin-1-yl 2-(diisopropoxyphosphoryl)acetate In dichloromethane at 20℃; for 4h;
Stage #2: girard's reagent T In methanol; dichloromethane
A n/a
B n/a
C 59%
869669-06-7

hydroxylamine succinic acid salt

64-19-7

acetic acid

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

B

546-88-3

acetylhydroxamic acid

Conditions
ConditionsYield
for 10 - 15h; Product distribution / selectivity; Heating / reflux;A 54.4%
B 3.7%
14464-29-0

N-acetoxysuccinimide

menthyl alcohol

A

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

acetic acid mentyl ester

Conditions
ConditionsYield
With tetrabutylammonium tricarbonylnitrosylferrate In hexane at 20 - 80℃; Molecular sieve; Inert atmosphere;A n/a
B 5%
4743-99-1

N-hydroxysuccinimide

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Conditions
ConditionsYield
beim Aufbewahren ueber Schwefelsaeure;
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

108-24-7

acetic anhydride

14464-29-0

N-acetoxysuccinimide

Conditions
ConditionsYield
for 15h;100%
With triethylamine for 0.5h;90%
With hydrogenchloride for 0.25h; Heating;79.9%
59-67-6

nicotinic acid

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

78348-28-4

nicotinic acid succinimidyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 48h;85%
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;80%
143-07-7

lauric acid

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

14565-47-0

N-succinimidyl laurate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane for 24h;100%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 3h;98%
With dicyclohexyl-carbodiimide In ethyl acetate for 6h;98%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

111-16-0

heptanedioic acid

74648-14-9

1-({7-[(2,5-dioxo-1-pyrrolidinyl)oxy]-7-oxoheptanoyl}-oxy)-2,5-pyrrolidine-dione

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 18h;100%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 18h;71%
With dicyclohexyl-carbodiimide
With dicyclohexyl-carbodiimide In tetrahydrofuran for 6h;
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

13734-41-3

t-Boc-L-valine

3392-12-9

Boc-Val-ONSu

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 72h; Inert atmosphere; Sealed tube;100%
In tetrahydrofuran at 0 - 20℃; for 16h;72%
With dicyclohexyl-carbodiimide In 1,2-dimethoxyethane at 5℃; for 6h;69.5%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

13139-15-6

N-tert-butoxycarbonyl-L-leucine

3392-09-4

Boc-Leu-ONSu

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 4℃;100%
With dicyclohexyl-carbodiimide In 1,4-dioxane Ambient temperature;93%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 18h;93%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

2488-15-5

N-tert-butoxycarbonyl-L-methionine

3845-64-5

tertbutoxycarbonyl-L-methionine N-hydroxysuccinimide ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 18h;100%
With N-ethylmorpholine;; benzotriazol-1-ol In dichloromethane 1) 0 deg C, 2 h, 2) overnight, r.t.;66%
With dicyclohexyl-carbodiimide In ethyl acetate a.) 0 deg C, 2 h, b.) r.t., 18 h;
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

619-58-9

4-iodobenzoic acid

39028-25-6

2,5-dioxopyrrolidin-1-yl 4-iodobenzoate

Conditions
ConditionsYield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 2h; Heating;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;100%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 24.85℃; for 24h;99%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

2566-19-0

CbzGlyGly

32943-08-1

Cbz-Gly-Gly-OSucc

Conditions
ConditionsYield
With benzotriazol-1-ol In dichloromethane Condensation;100%
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 4℃;
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

2389-45-9

Boc-Lys(Z)-OH

34404-36-9

Boc-Lys(Z)-OSu

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide 1.) EtOAc, 25 deg C, 3 h, 2.) Et2O, overnight;100%
With dicyclohexyl-carbodiimide In tetrahydrofuran; N,N-dimethyl-formamide for 20h; Ambient temperature;
With diisopropyl-carbodiimide at 0 - 20℃; for 25h;
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 8h;
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

6427-66-3

4-azidobenzoic acid

53053-08-0

4-azidobenzoic acid N-hydroxysuccinimide ester

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 23℃; for 21h; Inert atmosphere; Darkness;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; Darkness;97%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; Darkness;97%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

13734-36-6

N-(tert-butoxycarbonyl)sarcosine

80621-90-5

tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-hydroxyethyl}-N-methylcarbamate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 20h;100%
With dicyclohexyl-carbodiimide In 1,2-dimethoxyethane at 0℃; for 0.5h;88%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide63%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

7536-58-5

BOC-L-aspartic acid 4-benzyl ester

13798-75-9

Nα-t-butoxycarbonylaspartic acid α-N-hydroxysuccinimide ester β-benzyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 18h;100%
With dicyclohexyl-carbodiimide In ethyl acetate at -5 - 4℃; for 5h;90%
With dicyclohexyl-carbodiimide In 1,4-dioxane73%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

27144-18-9

3-(tritylthio) propanoic acid

129431-12-5

3-(triphenylmethylthio)propionic acid N-hydroxysuccinimide ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane; ethyl acetate at 20℃;100%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;71%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;71%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

68858-20-8

Fmoc-Val-OH

130878-68-1

2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 9h;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 0 - 25℃;96%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;96%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

33125-05-2

Boc-D-Phg-OH

39249-27-9

N-(tert-butoxycarbonyl)-D-phenylglycine N-succinimido ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane100%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 43h;98%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide for 18h;
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

125050-13-7

α-N-carbobenzoxy-δ-acetoxy-D-norvaline

125076-27-9

5-Acetoxy-2-benzyloxycarbonylamino-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide100%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

124620-56-0

(N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl)-(N5-acetyl-N5-(benzyloxy)-L-ornithyl)-N5-acetyl-N5-(benzyloxy)-L-ornithine

131080-79-0

N5-acetyl-N5-(benzyloxy)-N2-(benzyloxycarbonyl)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithyl-N5-acetyl-N5-(benzyloxy)-L-ornithine succinimido ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran Ambient temperature;100%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

24277-39-2

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

81659-82-7

N-α-tert-butoxycarbonyl-L-glutamic acid γ-N-succinimidyl ester α-tert-butyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In diethyl ether at 20℃; for 24h; Temperature; Time;100%
With dicyclohexyl-carbodiimide; dimethylethylbenzylamine In diethyl ether at 22℃; for 48h;90%
With dicyclohexyl-carbodiimide In diethyl ether at 22℃; for 48h;90%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

130680-59-0

Cbz-ΔGlu-OMe

130680-61-4

(Z)-Cbz-ΔGlu(OSu)-OMe

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran100%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

114527-28-5

4-(4′-methyl-[2,2′-bipyridin]-4-yl)butanoic acid

130699-88-6

4-<3-carbonyl-3-(succinimidyl)propyl>-4'-methyl-2,2'-bipyridine

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;100%
With dicyclohexyl-carbodiimide In ethyl acetate for 12h; Ambient temperature;59%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

111042-78-5, 111042-79-6

(1R,3R,4S)-8-phenyl-p-menthan-3-yl hydrogen isopropylmalonate

2-Isopropyl-malonic acid 2,5-dioxo-pyrrolidin-1-yl ester (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 15h; Ambient temperature;100%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

136413-25-7

N-{3-[(tert-butoxycarbonyl)amino]propanoyl}-N-hydroxy-β-alanine

136413-26-8

3-[Benzyloxy-(3-tert-butoxycarbonylamino-propionyl)-amino]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride Ambient temperature;100%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

64-19-7

acetic acid

14464-29-0

N-acetoxysuccinimide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;100%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 5 - 20℃; for 20h;93%
With dmap In dichloromethane for 1h; Ambient temperature;86%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

79-08-3

bromoacetic acid

42014-51-7

bromoacetic acid N-hydroxusuccinimidyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; for 2h;100%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 5℃; for 144h;97%
With dicyclohexyl-carbodiimide In 1,4-dioxane for 1h; Ambient temperature;96%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

544-63-8

n-tetradecanoic acid

69888-86-4

N-succinimidyl myristate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In acetonitrile for 1.5h;100%
With dicyclohexyl-carbodiimide In ethyl acetate for 6h;98%
With dicyclohexyl-carbodiimide In ethyl acetate Ambient temperature;88%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

55367-05-0

Benzyl 6α-(methylthio)-6β-(phenoxyacetamido)penicillanate

104702-12-7

Benzyl 6α-(succinimido-oxy)-6β-(phenoxyacetamido)penicillanate

Conditions
ConditionsYield
silver(I) acetate In N,N-dimethyl-formamide for 1h;100%
silver(I) acetate In N,N-dimethyl-formamide for 1.5h; -40 deg C to rt;100%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Boc-(Asn-Val-Orn(Z)-Leu-Pro)2-OH

Boc-(Asn-Val-Orn(Z)-Leu-Pro)2-ONSu

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0℃;100%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

65-85-0

benzoic acid

23405-15-4

benzoic acid N-hydroxysuccinimide ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h;97%
With 3-(5-nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1,-dioxide; triethylamine In dichloromethane -10 deg C -> r.t., overnight;93%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

69-72-7

salicylic acid

70120-40-0

salicylic acid succinimidyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane100%
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;95%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 12h;91%
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    Molecular Formula: C4H5NO3 Molecular Weight: 115.09 CAS Registry Number: 6066-82-6 EINECS: 228-001-3 Appearance:White powder Storage:Store in cool and dry place, away from sun light. Package:drum Application:Agrochemical Intermediates Transporta

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Specification

N-Hydroxysuccinimide, with the CAS NO.6066-82-6, is also called 1-hydroxy-5-pyrrolidinedione; 1-Hydroxysuccinimide; 5-Pyrrolidinedione,1-hydroxy-2. It belongs to the Product Categories of Peptide coupling agents; Medical Intermediates; Heterocycles; Other Reagents; Miscellaneous Reagents; Biochemistry. N-Hydroxysuccinimide is an organic compound with the formula C4H5NO3. Being slightly acidic, it is an irritant to skin, eyes and mucous membranes. N-Hydroxysuccinimide is widely used as an activating reagent for carboxylic acids in organic chemistry or biochemistry. Besides it is also used as leaving groups to activate covalent coupling of amine containing biomolecules onto surfaces in academic and commercial surface immobilizations, hence N-Hydroxysuccinimide is still used for protein modification.

Physical properties about N-Hydroxysuccinimide are: (1)ACD/LogP: -1.711; (2)ACD/LogD (pH 5.5): -1.71; (3)ACD/LogD (pH 7.4): -1.86; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 2.78; (7)ACD/KOC (pH 7.4): 2.01; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.6; (12)Molar Refractivity: 23.865 cm3; (13)Molar Volume: 69.761 cm3; (14)Polarizability: 9.461 10-24cm3; (15)Surface Tension: 88.9209976196289 dyne/cm; (16)Density: 1.65 g/cm3; (17)Flash Point: 112.519 °C; (18)Enthalpy of Vaporization: 58.095 kJ/mol; (19)Boiling Point: 262.438 °C at 760 mmHg; (20)Vapour Pressure: 0.0020000000949949 mmHg at 25°C

When you are using this chemical, please be cautious about it as the following:
1. Do not breathe dust;
2. Avoid contact with skin and eyes;
3. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
4. Wear suitable protective clothing;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2 ;
(2)InChIKey=NQTADLQHYWFPDB-UHFFFAOYSA-N ;
(3)SmilesO=C1N(O)C(=O)CC1