9-Fluorenylmethyl chloroformate

9-Fluorenylmethyl chloroformate Basic information
Product Name:9-Fluorenylmethyl chloroformate
Synonyms:CHLOROFORMIC ACID 9-FLUORENYLMETHYL ESTER;EMOCCI;9-FLUORENYLMETHYL CHLOROFORMATE (FMOC CL);Fmoc-Cl(9-FluorenylmethoxycarbonylChloride);Fmoc-Clsee22072;FMOC-CL CHLOROFORMIC ACID 9-FLUORENYLMETHYL ESTER;9-Fluorenylmethoxycarbonyl chloride (Fmoc-Cl);FMOC-CL, 9-FLLUORENYLMETHYL CHLOROFOMATE
CAS:28920-43-6
MF:C15H11ClO2
MW:258.7
EINECS:249-313-6
Product Categories:Aromatic Esters;N-Protecting Reagents;Biochemistry;Fluorenes;Fluorenes & Fluorenones;Peptide Synthesis;Protection & Derivatization Reagents (for Synthesis);Protective Reagents (Peptide Synthesis);Synthetic Organic Chemistry;Fmoc-Amino acid series;peptides;bc0001
Mol File:28920-43-6.mol
9-Fluorenylmethyl chloroformate Structure
9-Fluorenylmethyl chloroformate Chemical Properties
Melting point 62-64 °C(lit.)
Boiling point 365.79°C (rough estimate)
density 1.1780 (rough estimate)
refractive index 1.5330 (estimate)
storage temp. 2-8°C
solubility dioxane: 0.1 g/mL, clear, colorless
form Crystalline Powder
color White to very pale yellow
Sensitive Moisture Sensitive
BRN 2279177
Stability:Hygroscopic, Moisture Sensitive
InChIInChI=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
InChIKeyIRXSLJNXXZKURP-UHFFFAOYSA-N
SMILESC(Cl)(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O
LogP3.45
CAS DataBase Reference28920-43-6(CAS DataBase Reference)
Safety Information
Hazard Codes C,T
Risk Statements 34-20/21/22
Safety Statements 26-36/37/39-45-27
RIDADR UN 3261 8/PG 2
WGK Germany 3
RTECS LQ6250000
10-21
TSCA No
HazardClass 6.1
PackingGroup II
HS Code 29159020
MSDS Information
ProviderLanguage
FMOC-Chloride English
SigmaAldrich English
ACROS English
ALFA English
9-Fluorenylmethyl chloroformate Usage And Synthesis
Chemical PropertiesWhite to off white crystalline powder
Uses9-Fluorenylmethyl chloroformate is an N-Protecting agent for peptides research and was used for the pre-column derivatization of the biogenic amines (BAs) cadaverine (Cad), histamine (Him), octopami ne (Ocp), phenylethylamine (Pea), putrescine (Put), spermidine (Spd), spermine (Spm), tyramine (Tym).
Uses9-Fluorenylmethyl chloroformate can act as reagent for the introduction of Fmoc-amino-protecting group, which is stable towards acids but is readily cleaved under mildly basic non-hydrolytic conditions.
Uses9-Fluorenylmethyl chloroformate can be used as N-protecting reagent for oligonucleotide and peptide syntheses.
General DescriptionFmoc chloride is a derivatizing agent.
Flammability and ExplosibilityNotclassified
Safety ProfileA poison. Mutation data reported. A corrosive. When heated to decomposition it emits toxic vapors of Cl-.
Purification MethodsIf the IR contains no OH bands (at ~3000 cm-1) due to the hydrolysis product 9-fluorenylmethanol, then purify it by recrystallisation from dry Et2O. IR (CHCl3) has a band at 1770 cm-1 (C=O), and the NMR (CDCl3) has  at 4-4.6 (m 2H, CHCH2) and 7.1-7.8 (m, 8 aromatic H) ppm. The azide (FMOC-N3) has m 89-90o (from -1hexane) and IR (CHCl3) at 2135 (N3) and 1730 (C=O) cm , and the carbazate (FMOC-NHNH2) has m 171o(dec) (from nitromethane), IR (KBr) 3310, 3202 (NH) and 1686 (CONH) cm-1. [Caprino & Han J Org Chem 37, 3404 1972 , J Am Chem Soc 92 5748 1970, Koole et al. J Org Chem 59 1657 1989, Fürst et al. J Chromatogr 499 537 1990.]
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