N,N'-Disuccinimidyl carbonate supplier

Name
N,N'-Disuccinimidyl carbonate
EINECS 277-730-3
CAS No. 74124-79-1
Article Data8
CAS DataBase
Density 1.69 g/cm³
Solubility Soluble in dimethyl sulfoxide, hot pyridine, acetonitrile and most organic solvents. Insoluble in water.
Melting Point 190 °C
Formula C₉H₈N₂O₇
Boiling Point 383.7 °C at 760 mmHg
Molecular Weight 256.172
Flash Point 185.9 °C
Transport Information
Appearance white to slightly yellow crystalline powder
Safety 26-37/39
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Disuccinimidyl carbonate;Disuccininidyl carbonate;N,N'-Disuccinimido carbonate;Carbonic acid,bis(2,5-dioxo-1-pyrrolidinyl) ester;2,5-Pyrrolidinedione,1,1'-[carbonylbis(oxy)]bis- (9CI);1-[[[(2,5-Dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]-2,5-pyrrolidinedione;Bis(N-succinimidyl) carbonate;Bis(succinimidyl) carbonate;Carbonic acidbis(2,5-dioxopyrrolidin-1-yl) ester;Di-(2,5-dioxopyrrolidin-1-yl)carbonate;Disuccimidyl carbonate;
PSA 110.29000
LogP -0.85660

Synthetic route

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

: 32315-10-9
bis(trichloromethyl) carbonate

: 74124-79-1
di(succinimido) carbonate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane 1.) 0 deg C, 3 h, 2.) 0-20 deg C, 6 h, 3.) reflux, 2 h;	94%
With tributyl-amine In tetrahydrofuran for 14h; Ambient temperature;	89%
With Pinene In tetrahydrofuran for 12h; Heating;	76%

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

: 503-38-8
trichloromethyl chloroformate

: 74124-79-1
di(succinimido) carbonate

Conditions

Conditions	Yield
	80%

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

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

A: 74124-79-1
di(succinimido) carbonate

B: 102774-86-7
9-fluorenylmethyl N-succinimidyl carbonate

Conditions

Conditions	Yield
With tributyl-amine In tetrahydrofuran at -2 - 5℃; Temperature; Large scale;	A 95 kg B 119 kg

...Expand

: 74124-79-1
di(succinimido) carbonate

: 5105-78-2
4-(benzyloxycarbonylamino)butyric acid

: 60722-88-5
N-hydroxysuccinimide ester of 4-<(carbobenzyloxy)amino>butyric acid

Conditions

Conditions	Yield
With pyridine	100%

: 74124-79-1
di(succinimido) carbonate

: 2483-46-7
Boc-Lys(Boc)-OH

: 30189-36-7
N,N'-di-t-butyloxycarbonyl-(S)-lysine N-hydroxysuccinimide ester

Conditions

Conditions	Yield
With pyridine	100%

: 74124-79-1
di(succinimido) carbonate

: 86087-23-2
(S)-3-hydroxytetyrahydrofurane

: 138499-08-8
1-({[(3S)-tetrahydro-3-furanyloxy]carbonyl}oxy)-2,5-pyrrolidinedione

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 18h;	100%
With triethylamine In acetonitrile at 20℃; for 18h;	100%
With triethylamine In acetonitrile at 20℃; for 21.5h;	94%

: 74124-79-1
di(succinimido) carbonate

: 139115-91-6
2-(2-tert-butyloxycarbonylaminoethoxy)ethanol

: 261364-63-0
tert-butyl (2-(2-((((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)oxy)ethoxy)ethyl)carbamate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 2h;	100%
With pyridine In chloroform at 25 - 30℃; Acylation;	96%
With triethylamine In acetonitrile at 40℃; for 1h;	70%

: 74124-79-1
di(succinimido) carbonate

: 693-23-2
1,12-dodecanedioic acid

: 75472-90-1
dodecanedioic acid bis(2,5-dioxopyrrolidin-1-yl) ester

Conditions

Conditions	Yield
With pyridine In acetonitrile at 20℃; for 7h;	100%
With pyridine In acetonitrile at 20℃; for 7h; Inert atmosphere;	100%
With pyridine In acetonitrile at 20℃; for 3h;	90%

: 74124-79-1
di(succinimido) carbonate

: 100-49-2
cyclohexylmethyl alcohol

: 922723-33-9
N-succinimidyl carbonic acid cyclohexylmethyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%

: 74124-79-1
di(succinimido) carbonate

: 1017575-24-4
benzyl (4S)-4-(2,5-dioxopyrrolidin-1-yloxycarbonylamino)azepane-1-carboxylate

Conditions

Conditions	Yield
Stage #1: C5H7NO3*C14H20N2O2 With triethylamine In acetonitrile at 5℃; Stage #2: di(succinimido) carbonate In acetonitrile at 2 - 2.5℃; for 0.833333h;	100%

: 123-00-2
4-(3-Aminopropyl)morpholine

: 938455-56-2
C17H17F3O3

: 74124-79-1
di(succinimido) carbonate

: C25H31F3N2O5

Conditions

Conditions	Yield
Stage #1: C17H17F3O3; di(succinimido) carbonate With triethylamine In acetonitrile at 20℃; for 1h; Stage #2: 4-(3-Aminopropyl)morpholine In acetonitrile at 20℃; for 0.25h; Further stages.;	100%

...Expand

: 3731-51-9
(2-aminomethylpyridine)

: 938455-56-2
C17H17F3O3

: 74124-79-1
di(succinimido) carbonate

: C24H23F3N2O4

Conditions

Conditions	Yield
Stage #1: C17H17F3O3; di(succinimido) carbonate With triethylamine In acetonitrile at 20℃; for 1h; Stage #2: 2-(Aminomethyl)pyridine In acetonitrile at 20℃; for 0.25h; Further stages.;	100%

...Expand

: 214770-65-7
methyl (2R,3S)-2-amino-3-(1H-indol-3-yl)butanoate

: 74124-79-1
di(succinimido) carbonate

: 10272-49-8
4-phenylpiperidine hydrochloride

: methyl (2R,3S)-3-(1H-indol-3-yl)-2-[((4-phenyl-piperidine)carbonyl)-amino]butanoate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 17h;	100%

...Expand

: C29H33N2O8S2(1-)*H(1+)

: 74124-79-1
di(succinimido) carbonate

: C33H36N3O10S2(1-)*H(1+)

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 55 - 60℃; for 1.5h;	100%

: PCD680H COONa

: 74124-79-1
di(succinimido) carbonate

: PCD680H NHS

Conditions

Conditions	Yield
In dimethyl sulfoxide at 55℃;	100%

: 4-chloro-N-(2,5-difluorophenyl)-N-(rac-2-hydroxy-1-methylethyl)benzenesulfonamide

: 74124-79-1
di(succinimido) carbonate

: carbonic acid rac-2-{[(4-chlorophenyl)sulfonyl]-(2,5-difluorophenyl)amino}-propyl ester 2,5-dioxopyrrolidin-1-yl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3h;	100%

: 74124-79-1
di(succinimido) carbonate

: 407-91-0
6-(trifluoroacetamido)hexanoic acid

: 117032-51-6
N-ε-trifluoroacetylaminohexanoic acid N-hydroxysuccinimide ester

Conditions

Conditions	Yield
With pyridine In acetonitrile at 20℃; for 13h;	100%

: 877864-03-4
acetic acid 2-(2-hydroxyethyldithio)ethyl ester

: 74124-79-1
di(succinimido) carbonate

: C11H15NO7S2

Conditions

Conditions	Yield
	100%

: 74124-79-1
di(succinimido) carbonate

: 1019207-66-9
(3R,4R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2-aminophenylamino)piperidine-1-carboxylic acid tert-butyl ester

: 1019207-63-6
(3R,4R)-3-(tert-butyldimethylsilanyloxymethyl)-4-(2-oxo-2,3-dihydrobenzimidazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 48h;	100%

: 74124-79-1
di(succinimido) carbonate

: 1069066-95-0
C2HF3O2*C33H51N7O12S2

: 1069066-85-8
C38H54N8O16S2

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;	100%

: 74124-79-1
di(succinimido) carbonate

: 1105506-46-4
6-(9-hydroxy-3-methoxy-9-(4-methoxyphenyl)-9H-xanthen-6-yl)hex-5-ynoic acid

: 1105506-47-5
6-(9-hydroxy-3-methoxy-9-(4-methoxyphenyl)-9H-xanthen-6-yl)hex-5-ynoate-N-hydroxysuccinimide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%

: 74124-79-1
di(succinimido) carbonate

: 138499-16-8
2-[(tert-butyldiphenylsilyl)oxy]ethanol

: 1364788-77-1
C23H27NO6Si

Conditions

Conditions	Yield
With pyridine In acetonitrile at 22℃;	100%

: 74124-79-1
di(succinimido) carbonate

: 2516-33-8
Cyclopropylmethanol

: 959425-11-7
cyclopropylmethyl 2,5-dioxopyrrolidin-1-yl carbonate

Conditions

Conditions	Yield
With triethylamine In acetonitrile	100%
With triethylamine In acetonitrile	100%
With pyridine In acetonitrile at 40℃; for 4h;	99%
With triethylamine In acetonitrile

: 74124-79-1
di(succinimido) carbonate

: 395645-69-9
C16H27N3O5

: 1364788-93-1
C21H30N4O9

Conditions

Conditions	Yield
With pyridine In acetonitrile at 22℃; Inert atmosphere;	100%

: 74124-79-1
di(succinimido) carbonate

: 705-76-0
3,5-dimethoxybenzyl alcohol

: 1383617-02-4
3,5-dimethoxybenzyl-N-succinimidyl carbonate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 0.333333h; Inert atmosphere;	100%

: 74124-79-1
di(succinimido) carbonate

: 5-(diisopropyloxyphosphoryl)-5-methyl-4-hydroxymethyl-1-pyrroline N-oxide

: (4R*,5R*)-5-diisopropyloxyphosphoryl-5-methyl-4-(succinimidyloxycarbonyloxymethyl)-1-pyrroline N-oxide

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	100%

: 143-07-7
lauric acid

: 74124-79-1
di(succinimido) carbonate

: 14565-47-0
N-succinimidyl laurate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 1h;	100%

: 74124-79-1
di(succinimido) carbonate

: 506-30-9
Arachidic acid

: 69888-87-5
N-(eicosanoyloxy)succinimide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃; for 1h;	100%

: 74124-79-1
di(succinimido) carbonate

: 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethan-1-ol

: 2,5-dioxopyrrolidin-1-yl (4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl) carbonate

Conditions

Conditions	Yield
With pyridine In acetonitrile at 20℃; for 4h;	100%

: 74124-79-1
di(succinimido) carbonate

: methyl (phenyl 5-amino-8-O-tert-butyldimethylsilyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

: methyl (phenyl 5-amino-8-O-tert-butyldimethylsilyl-5-N,4-O-carbonyl-7-O,9-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; for 4h;	100%

: 4-(5,5-difluoro-1,3,7,9-tetramethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2’,1’-f][1,3,2]diazaborinin-10-yl)butanoic acid

: 74124-79-1
di(succinimido) carbonate

: 10-(4-((2,5-dioxopyrrolidin-1-yl)oxy)-4-oxobutyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2 ′,1 ′-f ][1,3,2]diazaborinin-4-ium-5-uide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;	99.9%

: 594859-92-4
5-(3-tert-butyldimethylsilyloxyphenyl)-4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran

: 74124-79-1
di(succinimido) carbonate

: 594859-93-5
5-(3-tert-butyldimethylsilyloxyphenyl)-4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran N-hydroxysuccinimide ester

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 1h; Inert atmosphere;	99.8%

: 74124-79-1
di(succinimido) carbonate

: 58885-58-8
N-tert-butoxycarbonyl-3-aminopropanol

: 613666-84-5
3-(tert-butoxycarbonylamino)propyl N-hydroxysuccinimidyl carbonate

Conditions

Conditions	Yield
With triethylamine at 20℃; for 2h;	99%
With triethylamine In acetonitrile at 0℃; for 3h; Inert atmosphere;	80%

N,N'-Disuccinimidyl carbonate Specification

The systematic name of N,N'-Disuccinimidyl carbonate is 1,1'-[carbonylbis(oxy)]dipyrrolidine-2,5-dione. With the CAS registry number 74124-79-1, it is also named as Di(succinimido) carbonate. The product's categories are Medical Intermediates; Coupling Reagent; N-Protecting Reagents; Biochemistry; Condensation & Active Esterification; Coupling Reactions (Peptide Synthesis); N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Succinimides; Peptide Synthesis; Synthetic Organic Chemistry; Amino Ester. It is white to slightly yellow crystalline powder which 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: -3.06; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 9; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 110.29 Å²; (7)Index of Refraction: 1.596; (8)Molar Refractivity: 51.45 cm³; (9)Molar Volume: 151 cm³; (10)Polarizability: 20.39×10^-24cm³; (11)Surface Tension: 79.2 dyne/cm; (12)Flash Point: 185.9 °C; (13)Enthalpy of Vaporization: 63.23 kJ/mol; (14)Boiling Point: 383.7 °C at 760 mmHg; (15)Vapour Pressure: 4.31E-06 mmHg at 25°C.

Preparation of N,N'-Disuccinimidyl carbonate: It can be obtained by N-hydroxy-succinimide and carbonic acid bis-trichloromethyl ester. This reaction needs reagent i-Pr₂EtN and solvent acetonitrile CH₂Cl₂. The yield is 94%.

Uses of N,N'-Disuccinimidyl carbonate: It is used as dehydrating agent and pharmaceutical intermediate. It also can react with 2-amino-pyridin-3-ol to get 3H-oxazolo[4,5-b]pyridin-2-one. This reaction needs solvent acetonitrile at ambient temperature. The reaction time is 8 hours. The yield is 78%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also 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=C2N(OC(=O)ON1C(=O)CCC1=O)C(=O)CC2
2. InChI:InChI=1/C9H8N2O7/c12-5-1-2-6(13)10(5)17-9(16)18-11-7(14)3-4-8(11)15/h1-4H2
3. InChIKey:PFYXSUNOLOJMDX-UHFFFAOYAN

Product Name

N,N'-Disuccinimidyl carbonate

Synthetic route

N,N'-Disuccinimidyl carbonate Specification

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