9H-fluoren-9-ylmethyl chloroformate

• ChemBase ID: 76540
• Molecular Formular: C15H11ClO2
• Molecular Mass: 258.69964
• Monoisotopic Mass: 258.04475727
• SMILES: O(CC1c2c(cccc2)c2c1cccc2)C(=O)Cl
• Canonical SMILES: ClC(=O)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C15H11ClO2/c16-15(17)18-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14H,9H2
• InChIKey: IRXSLJNXXZKURP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9H-fluoren-9-ylmethyl chloroformate
• IUPAC Traditional name: 9H-fluoren-9-ylmethyl chloroformate
• Synonyms: Chloroformic acid 9-fluorenylmethyl ester; 9-Fluorenylmethyl chloroformate; 9H-fluoren-9-ylmethyl chloridocarbonate; Fmoc chloride; (9H-Fluoren-9-yl)methyl carbonochloridoate; (9H-Fluoren-9-yl)methyl chloroformate; FMOC-Cl; 9-Fluorenylmethoxycarbonyl chloride; Fmoc chloride; 9-FLUORENYLMETHYL CHLOROFORMATE; 9-Fluorenylmethyl chloroformate; Fmoc-chloride; Fluorenylmethyloxycarbonyl chloride; 9-氯甲酸芴甲酯; 9-芴甲氧羰酰氯; 芴甲氧羰酰氯; 氯甲酸-9-芴基甲酯

Database IDs

• CAS Number: 28920-43-6
• EC Number: 249-313-6
• MDL Number: MFCD00001138
• Beilstein Number: 2279177
• PubChem SID: 24849875; 162041444; 24853862; 24853863
• PubChem CID: 34367
• Chemspider ID: 31647
• Wikipedia Title: Fluorenylmethyloxycarbonyl_chloride

CALCULATED PROPERTIES

• Acid pKa: 17.405373
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.1151657
• LogD (pH = 7.4): 4.1151657
• Log P: 4.1151657
• Molar Refractivity: 71.1382 cm^3
• Polarizability: 28.697273 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: dioxane: soluble0.1 g/mL, clear, colorless
• Melting Point: 33 - 35°C; 60-64°C; 61-63 °C; 61-64 °C; 62-64 °C; 62-64 °C(lit.); 62-64°C
• Hydrophobicity(logP): 4.081

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Moisture Sensitive; Toxic/Corrosive/Moisture Sensitive/Keep Cold/Store under Argon
• RTECS: LQ6250000
• European Hazard Symbols: Corrosive (C); X
• UN Number: 1759; 3261; UN2923
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 20/22-34; 34; R:34; R34
• Safety Statements: 26-36/37/39-45; S:26-27/28-36/37/39-46; S26 S36/37/39 S45
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H331-H314-H318; H314
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC); ≥99.0% (HPLC); 95%; 97%; 98%
• Grade: for HPLC derivatization; purum
• Empirical Formula (Hill Notation): C15H11ClO2

DETAILS

MP Biomedicals - 02150200

Base sensitive amino protecting group for solid-phase peptide synthesis.

Sigma Aldrich - F0378

Application
在氨基酸 HPLC 分析中，用于衍生化氨基酸；在固相肽合成中用于制备 N-Fmoc 氨基酸。

Sigma Aldrich - 160512

Application
Amino acid derivatizing agent for HLPC analysis.1 N-protecting reagent for peptide2 and oligonucleotide3 syntheses.
Reagent for amino group protection recently used in the synthesis of a bicyclic proline analog.
Reagent for derivatizing amino acids for HPLC amino acid analysis and for preparing N-Fmoc amino acids for solid-phase peptide synthesis.
Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 23186

Application
Reagent for derivatizing amino acids for HPLC amino acid analysis and for preparing N-Fmoc amino acids for solid-phase peptide synthesis.
Other Notes
Reagent for precolumn derivatization of amines for HPLC and fluorescent detection (abs.: 265 nm, em.: 315 nm)1,2,3; Used for capillary electrophoresis4

Sigma Aldrich - 23185

Application
Reagent for derivatizing amino acids for HPLC amino acid analysis and for preparing N-Fmoc amino acids for solid-phase peptide synthesis.
Other Notes
For the introduction of the 9-fluorenylmethoxycarbonyl (Fmoc) amino-protecting group, which is stable towards acids and catalytic hydrogenation, but readily cleaved under mildly basic non-hydrolytic conditions1,2; Use of the Fmoc-group for the protection of hydroxy groups3; protection of amino groups in nucleotides4

REFERENCES

• Carpino, L.A. and Han, G.Y., J. Org. Chem. , 37 : 3404 (1972).
• Chang, C.D., Waki, M., Ahmad, M., Meienhofer, J., Lundell, E.O. and Haug, J.D., Int. J. Peptide Protein Res. , 15 : 59 (1980).
• Reagent for the protection of amino groups in peptide synthesis (see Appendix 6) as their 9-fluorenylmethoxycarbonyl (Fmoc) derivatives: J. Org. Chem., 37, 3404 (1972); J. Am. Chem. Soc., 96, 4987 (1974); 99, 7363 (1977). Review: Acc. Chem. Res., 20, 401 (1987). They are particularly applicable in solid-phase peptide synthesis. The stability of Fmoc-protected amino acids to acidic conditions permits their conversion in many cases to the acid chlorides as active intermediates for peptide coupling, resistant to racemization, in contrast to other protected amino acid chlorides. For a review of peptide synthesis via amino acid halides, see: Acc. Chem. Res., 29, 268 (1996).
• In the presence of triethylamine, reacts with Pentafluorophenol, A15574, to give the PFP carbonate, a useful active ester for the preparation of Fmoc-amino acids. Moreover, the active PFP ester of the protected amino acid can be obtained by in situ DCC coupling with the liberated PFP: Synthesis, 303 (1986).
• Cleavage of the Fmoc group occurs under mildly basic conditions:
• Ethanolamine: J. Am. Chem. Soc., 92, 5748 (1970); J. Org. Chem., 37, 3404 (1972). Piperidine: J. Org. Chem., 52, 1197 (1987); applicable to solid-phase peptide synthesis.
• TBAF in DMF; rapid reaction at room temperature: Tetrahedron Lett., 28, 6617 (1987). For both the deblocking of Fmoc-protected amino acids and for the removal of excess reagent during the protection step, 4-(Aminomethyl)piperidine, L11577, has been recommended: J. Org. Chem., 51, 3732 (1986); 55, 721 (1990), particularly in conjunction with Fmoc-protected acid chlorides as the active species. Even better results have been obtained with Tris(2-aminoethyl)amine, B21789, in this type of chemistry: J. Org. Chem., 55, 1673 (1990).
• Limited use has also been made in the protection of alcohols as 9-fluorenylmethyl carbonates, rapidly cleaved by triethylamine: J. Chem. Soc., Chem. Commun., 672 (1982).