N-Hydroxysuccinimide supplier

Name
N-Hydroxysuccinimide
EINECS 228-001-3
CAS No. 6066-82-6
Article Data72
CAS DataBase
Density 1.649 g/cm³
Solubility Soluble in water
Melting Point 95-98 °C(lit.)
Formula C₄H₅NO₃
Boiling Point 262.4 °C at 760 mmHg
Molecular Weight 115.089
Flash Point 112.5 °C
Transport Information
Appearance white to pale yellow
Safety 22-24/25-26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 53053-08-0
4-azidobenzoic acid N-hydroxysuccinimide ester

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

Conditions

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 110-15-6
succinic acid

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

Conditions

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 41839-96-7
N-(tert-butoxycarbonyl)-succinimide

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

Conditions

Conditions	Yield
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

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

...Expand

: 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

Conditions	Yield
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%

...Expand

: 108-30-5
succinic acid anhydride

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

Conditions

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 128-08-5
N-Bromosuccinimide

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

Conditions

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

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

...Expand

: 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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
With AST In acetone Enzymatic reaction;	A n/a B 68%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 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

Conditions	Yield
for 10 - 15h; Product distribution / selectivity; Heating / reflux;	A 54.4% B 3.7%

...Expand

: 14464-29-0
N-acetoxysuccinimide

: menthyl alcohol

A: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: acetic acid mentyl ester

Conditions

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

...Expand

: 4743-99-1
N-hydroxysuccinimide

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

Conditions

Conditions	Yield
beim Aufbewahren ueber Schwefelsaeure;

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 108-24-7
acetic anhydride

: 14464-29-0
N-acetoxysuccinimide

Conditions

Conditions	Yield
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

Conditions	Yield
With dicyclohexyl-carbodiimide In 1,4-dioxane	100%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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-formamide	63%

: 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

Conditions	Yield
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-dioxane	73%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With dicyclohexyl-carbodiimide In 1,4-dioxane	100%
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

Conditions	Yield
With dicyclohexyl-carbodiimide	100%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran	100%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With dicyclohexyl-carbodiimide In 1,4-dioxane	100%
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;	95%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 12h;	91%

N-Hydroxysuccinimide 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

Product Name

N-Hydroxysuccinimide

Synthetic route

N-Hydroxysuccinimide Specification

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