N-(9-Fluorenylmethoxycarbonyloxy)succinimide

Iupac Name：(2,5-dioxopyrrolidin-1-yl) 9H-fluoren-9-ylmethyl carbonate

Molecular Weight：337.3261

Modify Date.: 2022-11-29 05:36

Introduction: N-(9-Fluorenylmethoxycarbonyloxy)succinimide is used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides. View more+

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1. Names and Identifiers

1.1 Name: N-(9-Fluorenylmethoxycarbonyloxy)succinimide
1.2 Synonyms: (2,5-dioxopyrrolidin-1-yl) 9H-fluoren-9-ylmethyl carbonate 1-{[(9H-Fluoren-9-ylmethoxy)carbonyl]oxy}-2,5-pyrrolidinedione 1-{[(9H-Fluoren-9-ylmethoxy)carbonyl]oxy}pyrrolidin-2,5-dion 1-{[(9H-fluoren-9-ylmethoxy)carbonyl]oxy}pyrrolidine-2,5-dione 2,5-dioxotetrahydro-1H-pyrrol-1-yl (9H-fluoren-9-ylmethyl) carbonate 2,5-Pyrrolidinedione, 1-(((9H-fluoren-9-ylmethoxy)carbonyl)oxy)- 2,5-Pyrrolidinedione, 1-[[(9H-fluoren-9-ylmethoxy)carbonyl]oxy]- 9-Fluorenylmethyl succinimidyl carbonate EINECS 433-520-5 Fmoc-OSu MFCD00010733 N-(9-Fluorenylmethoxycarbonyloxy) succinimide

1.3 CAS No.: 82911-69-1

1.4 CID: 134122

1.5 EINECS(EC#): 433-520-5

1.6 Molecular Formula: C19H15NO5 (isomer)

1.7 Inchi: InChI=1S/C19H15NO5/c21-17-9-10-18(22)20(17)25-19(23)24-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16H,9-11H2

1.8 InChkey: WMSUFWLPZLCIHP-UHFFFAOYSA-N

1.9 Canonical Smiles: C1CC(=O)N(C1=O)OC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

1.10 Isomers Smiles: C1CC(=O)N(C1=O)OC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

2. Properties

2.1 Density: 1.42

2.1 Melting point: 150-153℃

2.1 Boiling point: 150-153°C

2.1 Refractive index: 1.661

2.1 Flash Point: 252.7°C

2.1 Precise Quality: 337.09500

2.1 PSA: 72.91000

2.1 logP: 2.95400

2.1 Solubility: Soluble in dimethyl sulfoxide and dimethyl formamide.

2.2 Appearance: White or almost white Microfine Powder

2.3 Storage: Keep Cold. Moisture Sensitive.

2.4 Chemical Properties: White powder

2.5 Color/Form: White to Yellow Solid

2.6 Water Solubility: soluble in dimethyl sulfoxide and dimethyl formamide.

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Purification Methods: Recrystallise the carbonate from CHCl3/Et2O, or from pet ether (b 40-60o). [Pauet Can J Chem 60 976 1982, Lapatsaris et al. Synthesis 671 1983.] N-(9-Fluorenylmethoxycarbonyloxy)succinimide Preparation Products And Raw materials Preparation Products

3.2 Usage: N-(9-Fluorenylmethoxycarbonyloxy)succinimide is used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.

4. Safety and Handling

4.1 Symbol: GHS07, GHS09

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S24/25

4.1 Hazard Class: 9

4.1 Hazard Declaration: H302-H317-H411

4.1 RIDADR: OTH

4.1 Caution Statement: P273-P280

4.1 WGK Germany: 3

4.1 Safety: Hazard Codes:Xi
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:22-24/25-26/37/39-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:3
Hazard Note:Moisture Sensitive
HS Code:29251995

4.2 Sensitive: Moisture Sensitive

4.3 Specification: White powder
usageEng:Used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.
Safety Statements:22-24/25-26/37/39-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : KBr disc

IR : nujol mull

Raman : 4880 A,200 M,powder

Mass

7. Synthesis Route

82911-69-1Total: 4 Synthesis Route

101-83-7 115 Suppliers

82911-69-1 282 Suppliers

Literatures:
Canadian Journal of Chemistry, , vol. 60, p. 976 - 980
Yield: null

6066-82-6 453 Suppliers

28920-43-6 225 Suppliers

82911-69-1 282 Suppliers

Literatures:
Synthesis, , # 8 p. 671 - 673
Yield: ~96%

28920-43-6 225 Suppliers

82911-72-6

82911-69-1 282 Suppliers

Literatures:
Canadian Journal of Chemistry, , vol. 60, p. 976 - 980
Yield: ~89%

View all

8. Precursor and Product

precursor:

28920-43-6

15149-73-2

6066-82-6

82911-72-6

101-83-7

24324-17-2

product :

172695-33-9

187223-15-0

35661-58-6

285996-74-9

35661-51-9

103321-57-9

73731-37-0

73724-48-8

203866-20-0

117106-21-5

117087-82-8

77128-72-4

475160-85-1

176039-39-7

35737-10-1

71989-31-6

84771-20-0

29022-11-5

88050-17-3

193885-60-8

71989-38-3

156017-42-4

95753-56-3

204376-55-6

84418-43-9

View all

9. Other Information

9.0 Usage: N-(9-Fluorenylmethoxycarbonyloxy)succinimide is the most efficient reagent for the selective preparation of N-(9-fluorenylmethoxycarbonyl) derivatives of hydroxy-amino acids. Dipeptide formation is lower than with the chloroformate, Fmoc-Cl. It is also employed in the synthesis of glycopeptides.

9.1 Mesh Entry Terms: 9-fluorenylmethylsuccinimidyl carbonate

10. Computational chemical data

Molecular Weight: 337.3261g/mol
Molecular Formula: C₁₉H₁₅NO₅
Compound Is Canonicalized: True
XLogP3-AA: 2.7
Exact Mass: 337.09502258
Monoisotopic Mass: 337.09502258
Complexity: 524
Rotatable Bond Count: 5
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 72.9
Heavy Atom Count: 25
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccB6OAAAAAAAAAAAAAAAAAAAAeIAAAAwYAAAAAAAAGABQAAAHgAEAAAADQChmAIwCIIQBACIAiFSGAACAAAgAAAoiAEAAIgYIDKAkRCEIAAkxCGMiAeFwPAOgAAAAAAQAAAAAAAAACAAAQAACAAAAA==

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