190656-01-0

Basic information

• Product Name: 9-FLUORENYLMETHYL N-HYDROXYCARBAMATE
• Synonyms: N-(9-FLUORENYLMETYLOXYCARBONYL)-HYDROXYLAMINE;N-(9-FLUORENYLMETHOXYCARBONYL)HYDROXYLAMINE;9-FLUORENYLMETHYL N-HYDROXYCARBAMATE;FMOC-NH-OH;FMOC-HYDROXYLAMINE;N-(9-Fluorenylmethoxycarbonyl)hydroxylamine, N-Fmoc-hydroxylamine;9-Fluorenylmethyl N-hydroxycarbamate >=99.0%;N-Fmoc-hydroxylamine≥ 99%(HPLC)
• CAS NO: 190656-01-0
• Molecular Formula: C₁₅H₁₃NO₃
• Molecular Weight: 255.27
• Mol File: 190656-01-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 164.5 °C(lit.)
• Boiling Point: 503.2°C at 760 mmHg
• Flash Point: 258.2°C
• Appearance: /
• Density: 1.304g/cm³
• Vapor Pressure: 6E-11mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: 2-8°C
• BRN: 7712144
• CAS DataBase Reference: 9-FLUORENYLMETHYL N-HYDROXYCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-FLUORENYLMETHYL N-HYDROXYCARBAMATE(190656-01-0)
• EPA Substance Registry System: 9-FLUORENYLMETHYL N-HYDROXYCARBAMATE(190656-01-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 190656-01-0(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

9-Fluorenylmethyl N-hydroxycarbamate (Fmoc-NHOH) can be used as a reactant to prepare: N-Fmoc-aminooxy-2-chlorotrityl polystyrene, a solid-phase resin used to produce hydroxamic acids and peptidyl hydroxamic acids. 9-Fluorenylmethyl nosyloxycarbamate (Fmoc-NHONs) by reacting with nosyl chloride.

InChI:InChI=1/C15H13NO3/c17-15(16-18)19-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14,18H,9H2,(H,16,17)

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 144-55-8 sodium hydrogencarbonate 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Downstream Products

• 729579-11-7 9-fluorenylmethyl nosyloxycarbamate 
• 1352786-35-6 (9H-fluoren-9-yl)methyl benzoyloxycarbamate 
• 683217-51-8 (±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-cyclopropylpropanoic acid 
• 180181-93-5 (±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid 
• 282524-78-1 (±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-phenylbutanoic acid 
• 1440754-18-6 (9H-fluoren-9-yl)methyl (2-(pyridin-2-yl)phenyl)carbamate 

Relevant articles and documents

N-Fmoc-aminooxy-2-chlorotrityl polystyrene resin: A facile solid-phase methodology for the synthesis of hydroxamic acids

Using the new compound N-Fmoc-hydroxylamine 1 we have generated a facile route to a high loading, acid labile solid-phase resin bearing a hydroxylamine linker. The novel N-Fmoc-aminooxy-2-chlorotrityl polystyrene 2 showed generic utility for the construct

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

Mild and efficient Lewis acid-promoted detritylation in the synthesis of N-hydroxy amides: A concise synthesis of (-)-cobactin T

(Chemical Equation Presented) An efficient, high-yielding Lewis acid promoted deprotection of O-trityl hydroxylamine derivatives is described. A range of acid-labile protecting groups, such as N-Boc and O-TBS, were tolerated under these mild conditions. The present method is applicable to the synthesis of a broad range of hydroxylamine derivatives, including N-hydroxy amides (hydroxamic acids), N-hydroxy sulfonamides, and N-hydroxy ureas, which often exhibit significant biological activities. An application of this methodology for a concise synthesis of (-)-Cobactin T (18) is also demonstrated.