| | 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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