24324-17-2

Basic information

• Product Name: 9-Fluorenemethanol
• Synonyms: Fluorenemethanol;TIMTEC-BB SBB008508;AKOS MSC-0133;9-FLUOROENYLMETHANOL;9-FLUORENYLMETHANOL;9-FLUORENEMETHANOL;9-(HYDROXYMETHYL)-FLUOREN;9-(HYDROXYMETHYL)FLUORENE
• CAS NO: 24324-17-2
• Molecular Formula: C₁₄H₁₂O
• Molecular Weight: 196.24
• EINECS: 246-167-5
• Product Categories: Peptide coupling agents;Amino Acid Derivatives;Fluorene Derivatives;Benzocycles;Fluorenes, Flurenones;Alkohols;N-Protecting Reagents;Fluorenes;Fluorenes & Fluorenones;Amino alcohols
• Mol File: 24324-17-2.mol

Chemical Properties

• Melting Point: 105-107 °C(lit.)
• Boiling Point: 293.14°C (rough estimate)
• Flash Point: 167.4 °C
• Appearance: White to pale yellow/Crystalline Powder
• Density: 1.0304 (rough estimate)
• Vapor Pressure: 6.2E-06mmHg at 25°C
• Refractive Index: 1.5385 (estimate)
• Storage Temp.: Store at 0-5°C
• Solubility: Soluble in methanol.
• PKA: 13.68±0.10(Predicted)
• BRN: 2330017
• CAS DataBase Reference: 9-Fluorenemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Fluorenemethanol(24324-17-2)
• EPA Substance Registry System: 9-Fluorenemethanol(24324-17-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-27-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 24324-17-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9-Fluorenemethanol is used as a N-protecting reagent for the synthesis of peptides. It plays a crucial role in the development of new drugs and therapeutic agents by protecting the peptide's nitrogen atom during synthesis, ensuring the desired product is obtained.
Used in Chemical Synthesis:
9-Fluorenemethanol is used in the preparation of deoxynucleoside 9-fluorenemethyl phosphorodithioates, which are important intermediates in the synthesis of nucleoside analogs. These analogs have potential applications in the development of antiviral and anticancer drugs.
Used in Material Science:
9-Fluorenemethanol is used to prepare 9-(fluoromethyl)fluorene, a compound with potential applications in the development of advanced materials and polymers.
Used in Electrochemistry:
9-Fluorenemethanol is involved in the electropolymerization with boron trifluoride diethyl etherate, yielding low-potential electrodeposition of semiconducting poly(9-fluorenemethanol) (PFMO) film. This film has potential applications in the development of electronic devices and sensors.

InChI:InChI=1/C14H12O/c15-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14-15H,9H2

Upstream product

• 67-56-1 methanol 
• 832-80-4 9-diazofluorenone 
• 50-00-0 formaldehyd 
• 86-73-7 9H-fluorene 
• 881-04-9 9H-fluoren-9-yllithium 
• 85055-70-5 (9H-fluoren-9-yl)methyl benzoate 
• 85055-72-7 fluoren-9-ylmethyl 4-methoxy-benzoate 
• 109-94-4 formic acid ethyl ester 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 56954-81-5 9-(bromomethyl)fluorene 
• 190431-89-1 9-({[(4'-bromophenyl)sulfonyl]oxy}methyl)fluorene 
• 75-89-8 2,2,2-trifluoroethanol 
• 540-72-7 sodium thiocyanide 
• 127-09-3 sodium acetate 

Downstream Products

• 85-01-8 phenanthrene 
• 85055-70-5 (9H-fluoren-9-yl)methyl benzoate 
• 71532-40-6 (9H-fluoren-9-yl)methyl 4-methylbenzenesulfonaye 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 85933-03-5 (S)-2-Benzyloxycarbonylamino-propionic acid 9H-fluoren-9-ylmethyl ester 
• 120542-17-8 C₂₃H₁₉NO₄ 
• 85812-92-6 Boc-L-Phe-OFm 
• 122235-68-1 (S)-4-(9H-Fluoren-9-ylmethoxycarbonylmethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 84418-43-9 9-fluorenylmethyl carbamate 
• 99272-71-6 4-[(2R,3R,4R,5R)-2-(4-Benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-[(2-chloro-phenoxy)-(9H-fluoren-9-ylmethoxy)-phosphoryloxy]-5-(9-phenyl-9H-xanthen-9-yloxymethyl)-tetrahydro-furan-3-yloxy]-4-methoxy-heptanedioic acid dimethyl ester 
• 99519-16-1 4-[(2R,3R,4R,5R)-2-(3-Benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-[(2-chloro-phenoxy)-(9H-fluoren-9-ylmethoxy)-phosphoryloxy]-5-(9-phenyl-9H-xanthen-9-yloxymethyl)-tetrahydro-furan-3-yloxy]-4-methoxy-heptanedioic acid dimethyl ester 
• 99272-72-7 4-[(2R,3R,4R,5R)-2-(6-Benzoylamino-purin-9-yl)-4-[(2-chloro-phenoxy)-(9H-fluoren-9-ylmethoxy)-phosphoryloxy]-5-(9-phenyl-9H-xanthen-9-yloxymethyl)-tetrahydro-furan-3-yloxy]-4-methoxy-heptanedioic acid dimethyl ester 
• 99272-73-8 4-[(2R,3R,4R,5R)-2-[2-(4-tert-Butyl-benzoylamino)-6-oxo-1,6-dihydro-purin-9-yl]-4-[(2-chloro-phenoxy)-(9H-fluoren-9-ylmethoxy)-phosphoryloxy]-5-(9-phenyl-9H-xanthen-9-yloxymethyl)-tetrahydro-furan-3-yloxy]-4-methoxy-heptanedioic acid dimethyl ester 
• 86-73-7 9H-fluorene 

Relevant articles and documents

Formation and verification of the structure of the 1-fluorenylmethyl chloroformative derivative of sulfamethazine

Sulfamethazine (SMZ) is derivatized with 1-fluorenylmethyl chloroformate (FMOC) to form the fluorescent adduct SMZ-FMOC. Conditions for formation are optimized with respect to pH, reagent concentration, and reagent ratio. Reagent and product profiles (including the hydrolysis byproduct FMOC-OH) versus time are followed by reversed phase HPLC with UV absorbance detection. FMOC-SMZ has been crystallized, its composition confirmed by microanalysis, and its structure corroborated by IR and NMR spectroscopy. From 10 down to 1 ppm, there is clear gentle curvature in the fluorescence intensity of SMZ-FMOC. The linear response range extends from above 100 ppb down to about 100 ppt, and an increase in sensitivity for the fluorescent detection of FMOC-SMZ (over the usual UV absorbance detection of SMZ) is calculated to be better than 3 orders of magnitude.

Application of the Curtius rearrangement to the synthesis of 1′-aminoferrocene-1-carboxylic acid derivatives

The shortest synthesis of N-protected 1′-aminoferrocene-1-carboxylic acid from readily available ferrocene-1,1′-dicarboxylic acid is reported. 1′-Azidocarbonylferrocene-1-carboxylic acid was first obtained by reaction of the latter with diphenylphosphoryl azide. It was then converted into four amino acids by a Curtius rearrangement conducted in the presence of tert-butanol, benzyl alcohol, 9-fluorenemethanol or allyl alcohol. The benzyl and allyl carbamate derivatives are reported and characterized for the first time. The four corresponding new succinimidyl activated esters were also prepared and their usefulness was demonstrated in peptide coupling. Various structures were elucidated by X-ray crystallography, including 1′-azidocarbonylferrocene-1-carboxylic acid and 1,1′-diazidocarbonylferrocene.

SAR of novel biarylmethylamine dopamine D4 receptor ligands

SAR for a novel series of dopamine D4 receptor ligands is shown. Very selective, highly potent compounds like 1-(2-pyrimidinyl)-4-(3-(3-thienyl)- benzyl)-piperazine (5f) and 2-(4-(1-fluorenylmethyl)-1-piperazinyl)- pyrimidine (8c) were obtained.

Method for high-selectivity synthesis of 9-fluorenylcarbinol

The invention discloses a method for high-selectivity synthesis of 9-fluorenylcarbinol. The method comprises the following steps: heating and dissolving fluorene in a DMSO solvent system at 50-55 DEG C in the presence of a sodium ethoxide ethanol solution alkali catalyst, adding an acylation reagent ethyl formate, carrying out acylation reaction at the same temperature to prepare 9-fluorenylformaldehyde, adding a soluble metal inorganic salt auxiliary agent, then using NaBH4 for a reduction reaction, adjusting the pH value of reaction liquid to be neutral, and separating out 9-fluorene methanol solid sediment. According to the method disclosed by the invention, fluorene is completely converted by utilizing a section of temperature, the 9-fluorene methanol can be obtained through high-selectivity reduction without solvent conversion by adding the soluble metal inorganic salt auxiliary agent, and the yield of the 9-fluorene methanol is improved on the premise of shortening the reaction time.

Me3SI-promoted chemoselective deacetylation: a general and mild protocol

A Me3SI-mediated simple and efficient protocol for the chemoselective deprotection of acetyl groups has been developedviaemploying KMnO4as an additive. This chemoselective deacetylation is amenable to a wide range of substrates, tolerating diverse and sensitive functional groups in carbohydrates, amino acids, natural products, heterocycles, and general scaffolds. The protocol is attractive because it uses an environmentally benign reagent system to perform quantitative and clean transformations under ambient conditions.

Preparation method of 9-hydroxymethyl-fluorene diacid

The invention provides a method for preparing 9-hydroxymethyl-fluorene diacid. The method comprises the following steps: (1) subjecting fluorene to reacting with paraformaldehyde to generate 9-hydroxymethylfluorene; (2) enabling the 9-hydroxymethylfluorene to react with acetyl chloride to generate (2,7-diacetyl-9H-fluoren-9-yl)methyl acetate; (3) enabling the (2,7-diacetyl-9H-fluoren-9-yl)methyl acetate to react with bromine to generate (2,7-bis(2,2-dibromoacetyl)-9H-fluoren-9-yl)methyl acetate; (4) enabling the(2,7-bis(2,2-dibromoacetyl)-9H-fluoren-9-yl)methyl acetate to react with bromine and sodium carbonate to generate 9-(acetoxymethyl)-9H-fluorene-2,7-dicarboxylic acid; and (5) subjecting 9-(acetoxymethyl)-9H-fluorene-2,7-dicarboxylic acid to reacting with an acidic solution to generate 9-hydroxymethyl-fluorene diacid. The method has the advantages of simple preparation process, accessible raw materials and high yield, and lowers the production cost of 9-hydroxymethyl-fluorene diacid.

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot

A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is

Additive-free cobalt-catalysed hydrogenation of carbonates to methanol and alcohols

Reduction of various organic carbonates to methanol and alcohols can be achieved in the presence of a molecularly-defined homogeneous cobalt catalyst. Specifically, the use of Co(BF4)2 in combination with either commercial or tailor-made tridentate phosphine ligands allows for additive-free hydrogenations of carbonates. Optimal results are obtained at relatively mild conditions (120 °C, 50 bar hydrogen pressure) in the presence of xylyl-Triphos L4.

Fmoc-OPhth, the reagent of Fmoc protection

Fmoc-OSu has been widely used for Fmoc protection of amino groups, especially amino acids, in solid phase peptide synthesis. However, it has been recognized that Fmoc-βAla-OH is formed as a by-product via the Lossen rearrangement during the reaction. Since we reconfirmed the formation of Fmoc-βAla-OH during the preparation of Fmoc-AA-OH by Fmoc-OSu, Fmoc-OPhth was designed and synthesized as a new Fmoc reagent to avoid the formation of Fmoc-βAla-OH. Furthermore, Fmoc protection by Fmoc-OPhth and Fmoc-SPPS were evaluated. The various Fmoc-amino acids prepared by Fmoc-OPhth were carried out in good yields and these are applicable in Fmoc-SPPS.

Preparation and characterization of a RHA/TiO2 nanocomposite: Introduction of an efficient and reusable catalyst for chemoselective trimethylsilyl protection and deprotection of alcohols and phenols

In this work, rice husk ash (RHA), as a natural source of amorphous silica, was used as a support for the synthesis of anatase-phase titania nanoparticles leading to the RHA/TiO2 nanocomposite. This nanocomposite was used as an efficient catalyst for the chemoselective trimethylsilylation of various alcohols and phenols and deprotection of the obtained trimethylsilyl ethers. The procedure gave the products in excellent yields in very short reaction times. Also this catalyst can be reused at least six times without loss of its catalytic activity.