1730-37-6

Basic information

• Product Name: 1-METHYLFLUORENE
• Synonyms: 1-METHYLFLUORENE;1-Methyl-9H-fluorene;Fluorene, 1-methyl-;METHYLFLUORENE;9H-FLUORENE,1-METHYL-;1-Methylfluorene 98%
• CAS NO: 1730-37-6
• Molecular Formula: C₁₄H₁₂
• Molecular Weight: 180.25
• EINECS: 217-048-5
• Product Categories: Arenes;Building Blocks;Organic Building Blocks;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 1730-37-6.mol
• Article Data: 24

Chemical Properties

• Melting Point: 84-86 °C(lit.)
• Boiling Point: 313.08°C (rough estimate)
• Flash Point: 148.5°C
• Appearance: /
• Density: 1.0414 (estimate)
• Vapor Pressure: 0.00091mmHg at 25°C
• Refractive Index: 1.6470 (estimate)
• Water Solubility: 1.09mg/L(25 oC)
• CAS DataBase Reference: 1-METHYLFLUORENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYLFLUORENE(1730-37-6)
• EPA Substance Registry System: 1-METHYLFLUORENE(1730-37-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1730-37-6(Hazardous Substances Data)

Usage

Description

1-METHYLFLUORENE is an organic compound that belongs to the family of polycyclic aromatic hydrocarbons. It is characterized by its unique molecular structure, which consists of a fluorene ring with a methyl group attached to it. 1-METHYLFLUORENE is known for its distinct chemical properties and has been identified as a volatile constituent in Greek tobacco. Interestingly, it has been found to not possess mutagenic activity, which sets it apart from other compounds in its class.

Uses

Used in Tobacco Industry:
1-METHYLFLUORENE is used as a volatile constituent in the Greek tobacco industry for its distinct chemical properties and aroma. The compound contributes to the overall flavor and sensory experience of the tobacco product without causing any mutagenic effects, making it a preferred choice for this application.
Used in Chemical Research:
1-METHYLFLUORENE serves as a valuable compound in the field of chemical research due to its unique molecular structure and properties. It can be used as a starting material or intermediate in the synthesis of various complex organic molecules, including pharmaceuticals, dyes, and other specialty chemicals. Its non-mutagenic nature also makes it a safer option for research purposes.
Used in Environmental Monitoring:
Given its presence in Greek tobacco and its non-mutagenic properties, 1-METHYLFLUORENE can be utilized in environmental monitoring and assessment programs. It can help in understanding the impact of tobacco-related emissions on air quality and human health, as well as in the development of strategies to mitigate potential risks associated with exposure to such compounds.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 751, 1946 DOI: 10.1021/ja01209a011

InChI:InChI=1/C14H12/c1-10-5-4-8-13-12-7-3-2-6-11(12)9-14(10)13/h2-8H,9H2,1H3

Upstream product

• 5501-37-1 1-methylfluoren-9-one 
• 73728-55-9 fluoren-1-yl-methanol 
• 107413-01-4 1-bromomethyl-fluorene 
• 854305-91-2 2',3-dimethyl-[1,1'-biphenyl]-2-amine 
• 75-16-1 methylmagnesium bromide 
• 7235-16-7 2,3,4,9-tetrahydro-1H-fluoren-1-one 
• 4119-38-4 (1RS,4aRS,9aRS)-1,2,3,4a,9a-hexahydro-1,4a-dimethylfluorene-1-carboxylic acid 
• 4061-15-8 neutrale Frakt_. v. Kp(0,3) 125-130grad aus rac.-2-cis-Benzyl-1-trans-methoxycarbonyl-3-cis-hydroxy-1ref.3-trans-dimethyl-cyclohexan 
• 6276-03-5 9H-fluorene-1-carboxylic acid 
• 86659-18-9 4a-methyl-4aH-fluorene 
• 4061-12-5 2-Benzyl-3-methyl-cyclohexanon 
• 1575-80-0 3-Methoxycarbonyl-1-methyl-2-oxo-1.2.3.4-tetrahydrofluoren 
• 110-82-7 cyclohexane 
• 166985-48-4 1-methyl-9-diazofluorene 

Downstream Products

• 174511-13-8 1-((R)-1-Methyl-9H-fluoren-9-yl)-naphthalene-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 1573-92-8 9-oxo-9H-fluorene-1-carboxylic acid 

Relevant articles and documents

Palladium-catalyzed synthesis of fluorenes by intramolecular c(sp 2)-h activation at room temperature

The synthesis of fluorenes by intramolecular Pd-catalyzed C(sp 2)-H activation of 2-arylbenzyl chlorides was conducted at room temperature by using commercially available triphenylphosphine and pivalic acid as ligands. The desired reactions proceeded efficiently at room temperature, and various substrates were converted into the corresponding fluorene derivatives in excellent yields.

Conformational Preference for the Binding of Biaryl Substrates and Inhibitors to the Active Site of Phenylethanolamine N-Methyltransferase

We have previously described regions of steric bulk tolerance in the aromatic-ring binding site of phenylethanolamine N-methyltransferase (PNMT, EC 2.1.1.28) for phenylethanolamine substrates and α-methylbenzylamine inhibitors.For bound substrates, this region is located in the vicinity of the para position of the aromatic ring, while for bound α-methylbenzylamine inhibitors, it is located in the region complementary to the meta position.In the present study, we sought to determine the preferred conformation of the biaryl portion of (m-phenylphenyl)- and (p-phenylphenyl)ethanolamine (4 and 5, respectively) as well as for m-phenyl and p-phenyl-α-methylbenzylamine (7 and 8, respectively) for PNMT active site interactions.Planar derivatives of 4,5,7, and 8 were obtained through the synthesis of 2-(1-fluorenyl)-2-hydroxyethylamine (9), 2-(2-fluorenyl)-2-hydroxyethylamine (10), 1-(1-fluorenyl)ethylamine (11), and 1-(2-fluorenyl)ethylamine (12).The four fluorene derivatives were examined for in vitro activity as substrates and inhibitors of the PNMT-catalyzed reaction.As in case of 4, 5, 7, and 8, we have observed a positional preference for the alkylamine side chain with respect to the biphenyl skeleton present in 9-12.Thus, fluorenylethanolamine 10 ("p-biphenyl") displays a Michaelis constant (Km = 26 μM) that is approximately 10 times lower than that for 9 ("m-bipenyl", Km = 297 μM); in the α-methylbenzylamine inhibitors, fluorenyl derivative 11 ("m-biphenyl", Ki = 4.14 μM) is approximately 40 times better than 12 ("p-biphenyl", Ki =185 μM) for in vitro inhibition of PNMT.In each case, conformational restriction of the biaryl system present in 4, 5, 7, and 8, such that the aromatic rings are coplanar, resulted in enhanced affinity for thr PNMT active site.Thus, conformational restriction of ethanolamine 5 (Km = 82 μM) and α-methylbenzylamine 7 (Ki = 89 μM) as in 11 (Ki = 4.14 μM) leads, in each case, to a stronger enzyme-ligand dissociable complex.These results, in conjunction with others from these laboratories, indicate that the PNMT active site beyond the zone that interacts with the central aromatic ring portion of phenylethanolamine substrates and α-methylbenzylamine inhibitors is essentially a flat, hydrophobic pocket.

Solid-state construction of zigzag periphery: Via intramolecular C-H insertion induced by alumina-mediated C-F activation

Caryl-F bond activation has become an important and quickly developing method for construction of carbon-based materials. We report that alumina-mediated C-F bond activation (AmCFA) enables construction of PAHs with zigzag periphery. This method includes

Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(sp2)-H Bond Functionalization

A highly efficient and operationally simple palladium-catalyzed formal [4 + 1] annulation reaction has been developed. The reaction is featured by the formation of two different C-C bonds on a carbenic center. It represents a concise method for the synthesis of a wide range of polycyclic aromatic hydrocarbons (PAHs) and 1H-indenes with easily available (trimethylsilyl)diazomethane as the carbene source. Metal carbene migratory insertion and C(sp2)-H bond activation are proposed as the key steps in this transformation. The reaction further demonstrates the versatility of the carbene-based coupling in combination with various transition-metal-catalyzed transformations.