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6066-82-6

Basic Information
CAS No.: 6066-82-6
Name: N-Hydroxysuccinimide
Article Data: 72
Cas Database
Molecular Structure:
Molecular Structure of 6066-82-6 (N-Hydroxysuccinimide)
Formula: C4H5NO3
Molecular Weight: 115.089
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: N/A
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%
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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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  • 6066-82-6  	N-Hydroxysuccinimide

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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