| Identification | More | [Name]
9-Fluorenylmethyl chloroformate | [CAS]
28920-43-6 | [Synonyms]
9-FLUORENEMETHYL CHLOROFORMATE
9-FLUORENMETHYL CHLOROFORMATE
9-FLUORENYLMETHOXYCARBONYL CHLORIDE
9-FLUORENYLMETHYL CHLOROFORMATE
9-FLUORENYLMETHYLOXYCARBONYL CHLORIDE
9-FLUOROENYLMETHYL CHLOROFORMATE
9h-fluoren-9-ylmethyl chloroformate
CARBONOCHLORIDIC ACID, 9H-FLUOREN-9-YLMETHYL ESTER
CHLOROFORMIC ACID 9-FLUORENYLMETHYL ESTER
EMOCCI
FMOC-CHLORIDE
fmoc-ci
FMOC-CL
N-9-FLUORENYLMETHYL CHLOROFORMATE
RARECHEM FM OC 0001
1-(9-fluorenyl)methylchloroformate
chloro-formicacifluoren-9-ylmethylester
Formicacid,chloro-,fluoren-9-ylmethylester
9-FLUORENYLMETHYL CHLOROFORMATE (FMOC CL)
Fmoc-Cl(9-FluorenylmethoxycarbonylChloride) | [EINECS(EC#)]
249-313-6 | [Molecular Formula]
C15H11ClO2 | [MDL Number]
MFCD00001138 | [Molecular Weight]
258.7 | [MOL File]
28920-43-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off white crystalline powder | [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 | [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 | [CAS DataBase Reference]
28920-43-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
C,T | [Risk Statements ]
R34:Causes burns.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S27:Take off immediately all contaminated clothing . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [RTECS ]
LQ6250000
| [F ]
10-21 | [TSCA ]
No | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29159020 | [Safety Profile]
A poison. Mutation
data reported. A corrosive. When heated to
decomposition it emits toxic vapors of Cl-. |
| Hazard Information | Back Directory | [Description]
9-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]. | [Chemical Properties]
White to off white crystalline powder | [Uses]
9-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.
| [Uses]
9-Fluorenylmethyl chloroformate can be used as N-protecting reagent for oligonucleotide and peptide syntheses.
| [Uses]
9-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 Description]
Fmoc chloride is a derivatizing agent. | [Flammability and Explosibility]
Notclassified | [Purification Methods]
If 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.] | [References]
[1] S. TANTRY; V. V B; G Vasanthakumar. Synthesis of peptides employing 9-fluorenylmethyl chloroformate as a coupling agent[J]. Letters in peptide science?: LIPS, 2006, 10 1: 51-55. DOI:10.1007/BF02443642.
[2] H. A. MOYE A. B. A Versatile Fluorogenic Labelling Reagent for Primary and Secondary Amines: 9-Fluorenylmethyl Chloroformate[J]. Analytical Letters, 1979, 12 1: 25-35. DOI:10.1080/00032717908082516. |
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