9-Fluorenylmethyl chloroformate
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Basic information
- CAS
28920-43-6- Standard SMILES
O=C(Cl)OCC1c2ccccc2-c2ccccc21- InChIKey
IRXSLJNXXZKURP-UHFFFAOYSA-N- Molecular formula
- C15H11ClO2
- Average molar mass
- 258.7 g/mol
- Monoisotopic mass
- 258.04475727
Overview
used for tagging silica-based derivatization reagents in HPLC
Names & identifiers
- Preferred name
- 9-Fluorenylmethyl chloroformate
- IUPAC
- 9H-fluoren-9-ylmethyl carbonochloridate
- English name
- 9-Fluorenylmethyl chloroformate
- Molecular formula
- C15H11ClO2
- Molecular weight
- 258.7
Names & synonyms
28920-43-69-Fluorenylmethyl chloroformate9-Fluorenylmethoxycarbonyl chloride1-(9-Fluorenyl)methyl chloroformateFluoren-9-ylmethyl chloroformate9PLB0BTT90FORMIC ACID, CHLORO-, FLUOREN-9-YLMETHYL ESTERDTXSID10183116RefChem:746059-FLMCDTXCID20105607249-313-6
Show more names
FoMc-ClFMOC-Cfmoc-ci9-FluorenylmethylFMOC-C1Fluorenylmethyloxycarbonyl chloride
Fmoc-ClFmoc-chloride(9h-fluoren-9-yl)methyl carbonochloridateFmoc chlorideCarbonochloridic acid, 9H-fluoren-9-ylmethyl ester9H-Fluoren-9-ylmethyl chloroformate9H-fluoren-9-ylmethyl carbonochloridate(9H-Fluoren-9-ylmethoxy)carbonyl Chloride
Database identifiers
- CAS
28920-43-6- PubChem CID
- 34367
- DTXSID
DTXSID10183116- UNII
- 9PLB0BTT90
- EC Number
- 249-313-6
- Nikkaji
- J311E
Properties
Computed structural propertiesFilling in
- XLogP
- 4.3
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 296
Physicochemical properties
- Melting point
- 62 · 62-64 °C(lit.)
- Boiling point
- 365.79 °C · 365.79°C (rough estimate)
- Density
- 1.178 · 1.1780 (rough estimate)
- refractive index
- 1.533 · 1.5330 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 0.1 g/mL, · dioxane: 0.1 g/mL, clear, colorless
- form
- Crystalline Powder
- color
- White to very pale yellow
- Sensitive
- Moisture Sensitive
- BRN
- 2279177 · 2279177
- Stability
- Hygroscopic, Moisture Sensitive
- 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
- SMILES
- C(Cl)(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O
- LogP
- 3.45 · 3.45
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (17.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 80 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Carbonochloridic acid, 9H-fluoren-9-ylmethyl ester
Status: Active Update: 29-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/28092
(9-Fluorenylmethyl) chloroformate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Hazard Classes and CategoriesAcute Tox. 4 (17.5%)
Safety data
- F
- 10-21
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- No
- rtecs
- LQ6250000
- ridadr
- UN 3261 8/PG 2
- hs_code
- 29159020
- risk_code
- 34-20/21/22
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Applications
Description9-Fluorenylmethyl chloroformate (Fmoc-C1) is a significant biochemical reagent introduced by Carpino. It has been widely utilized as a reagent for the introduction of the 9-fluorenylmethoxycarbonyl (Fmoc moiety) in both peptide and nucleotide synthesis, as well as serving as a coupling agent in peptide synthesis[1]. Furthermore, Fmoc-C1 can function as a versatile fluorescent labeling reagent for primary and secondary amines[2].
Uses9-Fluorenylmethyl chloroformate can be used as N-protecting reagent for oligonucleotide and peptide syntheses. It 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 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).
General DescriptionFmoc chloride is a derivatizing agent.
Upstream & downstream products
Upstream raw materials
Related reactions
332 records
Compound notes
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