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

Description

9-FLUORENYLMETHYL N-HYDROXYCARBAMATE, also known as Fmoc-NHOH, is a white solid compound with significant applications in the field of organic chemistry and pharmaceuticals. It is primarily used as a reactant in the synthesis of various chemical compounds, including N-Fmoc-aminooxy-2-chlorotrityl polystyrene, a solid-phase resin utilized in the production of hydroxamic acids and peptidyl hydroxamic acids. Additionally, it can be used to prepare 9-Fluorenylmethyl nosyloxycarbamate (Fmoc-NHONs) by reacting with nosyl chloride.

Uses

Used in Organic Chemistry:
9-FLUORENYLMETHYL N-HYDROXYCARBAMATE is used as a reactant for the synthesis of [N-Fmoc-aminooxy-2-chlorotrityl polystyrene] because it serves as a solid-phase resin in the production of hydroxamic acids and peptidyl hydroxamic acids, which are essential in various chemical and pharmaceutical applications.
Used in Pharmaceutical Industry:
9-FLUORENYLMETHYL N-HYDROXYCARBAMATE is used as a reactant for the synthesis of [9-Fluorenylmethyl nosyloxycarbamate (Fmoc-NHONs)] for [reacting with nosyl chloride], which is an important step in the development of new pharmaceutical compounds and drug candidates.

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

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

Downstream Products

• 729579-11-7 9-fluorenylmethyl nosyloxycarbamate 
• 1262306-23-9 (9H-fluoren-9-yl)methyl 4-chlorobenzoyloxycarbamate 
• 1305311-09-4 H-Asp(OtBu)-D-Phe-Val-Arg(Pbf)-Gly-aldoxime 
• 1312412-32-0 (9H-fluoren-9-yl)methyl hydroxy(2-phenylallyl)carbamate 
• 1352786-35-6 (9H-fluoren-9-yl)methyl benzoyloxycarbamate 
• 1391993-19-3 N-Fmoc-hydroxyamine O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 1391993-20-6 N-Fmoc-hydroxyamine O-2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 1391993-21-7 N-Fmoc-hydroxyamine O-2,3,4-tri-O-benzoyl-6-deoxy-α-L-rhamnopyranoside 
• 1391993-22-8 N-Fmoc-hydroxyamine O-2,3,4-tri-O-benzoyl-6-deoxy-α-L-talopyranoside 
• 1440756-26-2 (9H-fluoren-9-yl)methyl (2,4,6-trichlorobenzoyl)oxycarbamate 
• 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.