Description

1-(9-Fluorenyl)methyl chloroformate (CAS No. 28920-43-6), also known as Fmoc-Cl, is a highly reactive and versatile reagent extensively used in peptide synthesis and organic chemistry. With the molecular formula C₁₅H₁₁ClO₂, this compound serves as a critical protecting group for amines, enabling selective deprotection under mild basic conditions. Its IUPAC name, 9H-fluoren-9-ylmethyl carbonochloridate, reflects its fluorenylmethyl ester structure, which provides excellent stability during synthetic procedures while allowing efficient cleavage when required. Fmoc-Cl is widely preferred in solid-phase peptide synthesis (SPPS) due to its orthogonal protection strategy compatibility with other protecting groups like Boc (tert-butoxycarbonyl). Supplied as a white to off-white crystalline powder, it is moisture-sensitive and should be stored under inert conditions to maintain reactivity. Ideal for researchers and pharmaceutical developers, this high-purity reagent ensures consistent performance in complex molecular constructions.

Properties

• CAS Number: 28920-43-6
• Complexity: 296
• IUPAC Name: 9H-fluoren-9-ylmethyl carbonochloridate
• 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
• InChI Key: IRXSLJNXXZKURP-UHFFFAOYSA-N
• Exact Mass: 258.0447573
• Molecular Formula: C15H11ClO2
• Molecular Weight: 258.70
• SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)Cl
• Topological: 26.3
• Monoisotopic Mass: 258.0447573
• Synonyms: 28920-43-6, 9-Fluorenylmethyl chloroformate, Fmoc-Cl, Fmoc chloride, Carbonochloridic acid, 9H-fluoren-9-ylmethyl ester, 9H-Fluoren-9-ylmethyl chloroformate, 1-(9-Fluorenyl)methyl chloroformate, 9-fluorenylmethylchloroformate, Fluoren-9-ylmethyl chloroformate, CCRIS 2608, UNII-9PLB0BTT90, EINECS 249-313-6, 9PLB0BTT90, BRN 2279177, 9-fluorenylmethyl chlorocarbonate, DTXSID10183116, Carbonochloridic acid 9H-fluoren-9-ylmethyl ester, 9-FLUORENYLMETHYL CHLOROFORMATE [MI], 9-FLMC, DTXCID20105607, irxsljnxxzkurp-uhfffaoysa-n, Fmoc-chloride, (9h-fluoren-9-yl)methyl carbonochloridate, 9-Fluorenylmethoxycarbonyl chloride, (9H-fluoren-9-yl)methyl chloroformate, 9H-fluoren-9-ylmethyl carbonochloridate, (9H-Fluoren-9-ylmethoxy)carbonyl Chloride, MFCD00001138, Chloroformic Acid 9-Fluorenylmethyl Ester, FORMIC ACID, CHLORO-, FLUOREN-9-YLMETHYL ESTER, (9H-fluoren-9-yl)methylcarbonochloridate, 9-fluorenylmethyloxycarbonyl chloride, FmocCl, Fmoc chloride, 97%, Fmoc-Cl (9-Fluorenylmethyl chloroformate), SCHEMBL27547, 9-fluorenemethyl chloroformate, 9-fluorenylmethyl chlorformate, 9-flourenylmethyl chloroformate, 9-fluorenylmethyl-chloroformate, 9-fluoreneylmethyl chloroformate, (9-fluorenylmethyl) chloroformate, 9-fluorenylmethoxycarbonyl-chloride, 9-Fluorenylmethyoxycarbonyl chloride, STR02408, 9-Fluorenyl-methyloxycarbonyl chloride, 9H-fluoren-9-ylmethylcarbonochloridate, AKOS009157869, FF07779, AC-24425, BP-21051, 9H-Fluoren-9-ylmethyl chloridocarbonate #, DB-004014, Fmoc chloride, purum, >=98.0% (HPLC), F0197, NS00028578, ST51037556, EN300-37269, C93459, Fmoc chloride, BioReagent, >=99.0% (HPLC), FMOC-CL ChloroforMic acid 9-fluorenylMethyl ester, Q827647, F0001-0905, Fmoc chloride, for HPLC derivatization, >=99.0% (HPLC), Fmoc-Cl;9-Fluorenylmethoxycarbonyl-chloride; Fmoc-chloride, 9-Fluorenylmethyl chloroformate; Chloroformic acid 9-fluorenylmethyl ester, 9H-Fluoren-9-ylmethyl chloroformate;Chloroformic acid 9-Fluorenylmethyl ester;9-Fluorenylmethyl chloroformate

Application

1-(9-Fluorenyl)methyl chloroformate (Fmoc-Cl) is primarily employed in peptide synthesis as a transient protecting group for amino acids, facilitating stepwise elongation while preventing unwanted side reactions. Its compatibility with solid-phase techniques makes it indispensable in automated peptide synthesizers and combinatorial chemistry workflows. Additionally, Fmoc-Cl is utilized in the preparation of modified nucleotides and glycopeptides, where selective amine protection is critical. The reagent’s cleavability under mild basic conditions (e.g., piperidine) allows for efficient deprotection without disrupting acid-labile functionalities. Researchers also leverage Fmoc-Cl in the synthesis of complex natural products and bioactive molecules requiring precise orthogonal protection strategies.

Safety and Hazards

GHS Hazard Statements

• H302 (17.5%): Harmful if swallowed [Warning Acute toxicity, oral]
• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H318 (11.2%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H332 (17.5%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statements

• 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

Hazard Classes and Categories

• Acute Tox. 4 (17.5%)
• Skin Corr. 1B (100%)
• Eye Dam. 1 (11.2%)
• Acute Tox. 4 (17.5%)

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