9-Methylene-9H-fluorene (HCID 78147)

Names & identifiers

Preferred name: 9-Methylene-9H-fluorene
IUPAC: 9-methylidenefluorene
English name: 9-Methylene-9H-fluorene
Molecular formula: C14H10
Molecular weight: 178.23

Names & synonyms

4425-82-59-Methylene-9H-fluorene9H-Fluorene, 9-methylene-dibenzofulvene9299E1P3CCDTXSID90196082RefChem:549473DTXCID00118573817-307-89-methylidenefluorene9-methylenefluorene9-Methylene-fluorene

Show more names

Dibenzofulvene (DBF) Oligomer-9-Methylene-9H-fluorene

9-METHYLIDENE-9H-FLUORENEfluorenylidenemethaneMFCD11850122UNII-9299E1P3CC1,2:3,4-Dibenzofulvene; 9-Methylene-9H-fluorene; 9-Methylenefluorene; Dibenzfulvene; Dibenzofulvene; Fluorenylidenemethane9-Methylene-9H-fluorene #SCHEMBL45149orb3027164

Database identifiers

CAS: 4425-82-5
PubChem CID: 78147
DTXSID: DTXSID90196082
UNII: 9299E1P3CC
EC Number: 817-307-8
Nikkaji: J131.545E

Properties

Computed structural properties

XLogP: 3.7
Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 0
Heavy atoms: 14
Formal charge: 0
Complexity: 216

Experimental & physicochemical properties

Kovats Retention Index292.4；292.28；292.28；279.3；291.8

Physicochemical properties

Melting point: 46 · 46-48 °C
Boiling point: 305.9 · 305.9±12.0 °C(Predicted)
Density: 1.12 · 1.12±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Solid
color: Off-White to Pale Beige
Stability: Light Sensitive
InChI: InChI=1S/C14H10/c1-10-11-6-2-4-8-13(11)14-9-5-3-7-12(10)14/h2-9H,1H2
InChIKey: ZYASLTYCYTYKFC-UHFFFAOYSA-N
SMILES: C1(=C)C2=C(C=CC=C2)C2=C1C=CC=C2
FDA UNII: 9299 E1P3CC · 9299E1P3CC
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (100%)

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 2 items

Description9-Methylene-9H-fluorene is a fluorescent probe that can be used to detect the presence of hydroxyl groups in vitro. It reacts with the hydroxyl group on the substrate film and emits light, which is then detected using a fluorometer. The reaction mechanism is shown below. Fluorophores are often used for sample preparation because they are relatively stable and can be easily removed from the final product. 9-Methylene-9H-fluorene has been shown to enhance cationic polymerization, which can lead to improved efficacy in some applications.

Uses9-Methylidenefluorene is an analog of 9-Methylfluorene (M305335); a compound that has been shown to be mutagenic in Salmonella typhimurium TA98 and TA100 in the presence of 9000 X g supernantant from Aroclor-induced rats.

Preparation methods · 1 item

PreparationA suspension of methyl triphenylphosphonium bromide (31.22 g; 87.3 mmol) in 500 mL of ether was added at -30°C. 10M n-butyllithium in hexane (8.73 mL; 87.3 mmol) was added to the mixture, and the mixture was stirred at room temperature for 1-2 hours. To the above mixture, 15 g (83.2 mmol) of 9-fluorenone in 50 mL of tetrahydrofuran was added, and the mixture was refluxed for 1 hour. After cooling the above mixture to 0°C, 9-Methylene-9H-fluorene was obtained after purification.