1580-20-7

Basic information

• Product Name: 1,2,3,4,5,6,7,8,9,10-decafluorophenanthrene
• Synonyms: 1,2,3,4,5,6,7,8,9,10-decafluorophenanthrene
• CAS NO: 1580-20-7
• Molecular Formula: C₁₄F₁₀
• Molecular Weight: 358.13
• Mol File: 1580-20-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 356.6°Cat760mmHg
• Flash Point: 123.8°C
• Appearance: /
• Density: 1.792g/cm³
• CAS DataBase Reference: 1,2,3,4,5,6,7,8,9,10-decafluorophenanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,5,6,7,8,9,10-decafluorophenanthrene(1580-20-7)
• EPA Substance Registry System: 1,2,3,4,5,6,7,8,9,10-decafluorophenanthrene(1580-20-7)

Safety Data

• Hazardous Substances Data: 1580-20-7(Hazardous Substances Data)

Usage

General Description

1,2,3,4,5,6,7,8,9,10-decafluorophenanthrene is a chemical compound composed of 10 fluorine atoms attached to a phenanthrene molecule. It is a member of the polycyclic aromatic hydrocarbon (PAH) family, which are organic compounds that are composed of multiple fused aromatic rings. 1,2,3,4,5,6,7,8,9,10-decafluorophenanthrene is commonly used as a starting material in the synthesis of various compounds, including pharmaceuticals and agrochemicals. It has several industrial applications, including as a precursor in the production of fluorinated polymers and as a chemical intermediate in the manufacturing of organic compounds. The compound is also known for its stable and non-reactive nature, making it a useful building block for the creation of more complex chemical structures. Additionally, 1,2,3,4,5,6,7,8,9,10-decafluorophenanthrene is being studied for its potential environmental impacts and health effects due to its widespread usage and presence in various products.

InChI:InChI=1S/C14F10/c15-5-1-2-4(10(20)14(24)12(22)6(2)16)8(18)7(17)3(1)9(19)13(23)11(5)21

Synthetic route

perfluoroperhydrophenanthrene (306-91-2) → decafluorophenanthrene (1580-20-7)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; iodine; aluminium; mercury dichloride In tetrahydrofuran Schlenk technique; Inert atmosphere;	28%
With benzophenone; sodium In tetrahydrofuran for 1.5h; -70 deg C to rt;	22%
With titanocene difluoride; aluminium; mercury dichloride In tetrahydrofuran for 24h; Ambient temperature;

phenanthrene (85-01-8) → decafluorophenanthrene (1580-20-7)

Conditions	Yield
(i) KCoF4, (heating), (ii) Fe2O3, (thermolysis); Multistep reaction;

1-perfluorooctyl bromide (423-55-2) → decafluorophenanthrene (1580-20-7)

decafluorophenanthrene (1580-20-7) → octafluorophenthra-9,10-quinone (1735-27-9)

Conditions	Yield
With fuming sulphuric acid at 100℃; for 3h; Schlenk technique; Inert atmosphere;	33%

decafluorophenanthrene (1580-20-7) + sodium methylate (124-41-4) → 2,7-Dimethoxy-octafluorphenanthren (32834-43-8)

Conditions	Yield
In methanol

decafluorophenanthrene (1580-20-7) → 2,2'-octafluorodiphenic Acid (16583-10-1)

Conditions	Yield
With potassium permanganate In acetone

decafluorophenanthrene (1580-20-7) + dimethyl amine (124-40-3) → 2,7-Bis-dimethylamino-octafluorphenanthren (32834-44-9)

Conditions	Yield
In ethanol

decafluorophenanthrene (1580-20-7) → 3,5,6,3',5',6'-Hexafluoro-4,4'-dimethoxy-biphenyl-2,2'-dicarboxylic acid (32834-45-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol 2: KMnO4 / acetone View Scheme

ferrocene (102-54-5) + decafluorophenanthrene (1580-20-7) → ferrocene * perfluorophenanthrene (210758-46-6)

Conditions	Yield
In not given crystn.;

bis(pentamethylcyclopentadienyl)iron(II) (12126-50-0) + decafluorophenanthrene (1580-20-7) → decamethylferrocene * perfluorophenanthrene (206071-26-3)

Conditions	Yield
In pentane equimolar amts.; crystn. on slow evapn. (2 d);

Upstream product

• 85-01-8 phenanthrene 
• 423-55-2 1-perfluorooctyl bromide 
• 306-91-2 perfluoroperhydrophenanthrene 

Relevant articles and documents

Group IV metallocene-mediated synthesis of fluoroaromatics via selective defluorination of saturated perfluorocarbons

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Distiboranes based onortho-phenylene backbones as bidentate Lewis acids for fluoride anion chelation

As part of our efforts in the chemistry of main group platforms that support anion sensing and transport, we are now reporting the synthesis of anitmony-based bidentate Lewis acids featuring theo-C6F4backbone. These compounds can be easily accessed by reaction of the newly synthesizedo-C6F4(SbPh2)2(5) witho-chloranil or octafluorophenanthra-9,10-quinone, affording the corresponding distiboranes6and7of general formulao-C6F4(SbPh2(diolate))2with diolate = tetrachlorocatecholate for6and octafluorophenanthrene-9,10-diolate for7, respectively. While6is very poorly soluble, its octafluorophenanthrene-9,10-diolate analog7readily dissolves in CH2Cl2and undergoes swift conversion into the corresponding fluoride chelate complex [7-μ2-F]?which has been isolated as a [nBu4N]+salt. Theo-C6H4analog of7, referred to as8, has also been prepared. Although less Lewis acidic than7,8also forms a very stable fluoride chelate complex ([8-μ2-F]?). Altogether, our experiental results, coupled with computational analyses and fluoride anion affinity calculations, show that7and8are some of the strongest antimony-based fluoride anion chelators prepared to date. Another notable aspect of this work concerns the use of the octafluorophenanthrene-9,10-diolate ligand and its ablity to impart advantageous solubility and Lewis acidity properties.