fbpx
Wikipedia

Phenanthrene

January 01, 1970

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fused benzene rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics, pesticides, explosives, and drugs. It has also been used to make bile acids, cholesterol and steroids.[3]

Phenanthrene
Names
Preferred IUPAC name
Phenanthrene
Identifiers
  • 85-01-8 Y
3D model (JSmol)
  • Interactive image
1905428
ChEBI
  • CHEBI:28851 N
ChemSpider
  • 970 N
ECHA InfoCard 100.001.437
EC Number
  • 266-028-2
28699
KEGG
  • C11422 Y
MeSH C031181
  • 995
UNII
  • 448J8E5BST Y
  • DTXSID6024254
  • InChI=1S/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H N
    Key: YNPNZTXNASCQKK-UHFFFAOYSA-N N
  • InChI=1/C14H10/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-10H
    Key: YNPNZTXNASCQKK-UHFFFAOYAC
  • C1=CC=C2C(=C1)C=CC3=CC=CC=C32
Properties
C14H10
Molar mass 178.234 g·mol−1
Appearance Colorless solid
Density 1.18 g/cm3[1]
Melting point 101 °C (214 °F; 374 K)[1]
Boiling point 332 °C (630 °F; 605 K)[1]
1.6 mg/L[1]
−127.9·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 171 °C (340 °F; 444 K)[1]
Structure
C2v[2]
0 D
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Phenanthrene occurs naturally and also is a man-made chemical. Commonly, humans are exposed to phenanthrene through inhalation of cigarette smoke, but there are many routes of exposure. Animal studies have shown that phenanthrene is a potential carcinogen.[3] However, according to IARC, it is not identified as a probable, possible or confirmed human carcinogen.[4]

Phenanthrene's three fused rings are angled as in the phenacenes, rather than straight as in the acenes. The compound with a phenanthrene skeleton and nitrogens at the 4 and 5 positions is known as phenanthroline.

Chemistry edit

Phenanthrene is nearly insoluble in water but is soluble in most low-polarity organic solvents such as toluene, carbon tetrachloride, ether, chloroform, acetic acid and benzene.

The Bardhan–Sengupta phenanthrene synthesis is a classic way to make phenanthrenes.[5]

 

This process involves electrophilic aromatic substitution using a tethered cyclohexanol group using diphosphorus pentoxide, which closes the central ring onto an existing aromatic ring. Dehydrogenation using selenium converts the other rings into aromatic ones as well. The aromatization of six-membered rings by selenium is not clearly understood, but it does produce H2Se.

Phenanthrene can also be obtained photochemically from certain diarylethenes.

Reactions of phenanthrene typically occur at the 9 and 10 positions, including:

Canonical forms edit

Phenanthrene is more stable than its linear isomer anthracene. A classic and well established explanation is based on Clar's rule. A novel theory invokes so-called stabilizing hydrogen–hydrogen bonds between the C4 and C5 hydrogen atoms.[citation needed]

Natural occurrences edit

Ravatite is a natural mineral consisting of phenanthrene.[11] It is found in small amounts among a few coal burning sites. Ravatite represents a small group of organic minerals.

In plants edit

Main article: Phenanthrenes

See also edit

References edit

  1. ^ a b c d e Record of CAS RN 85-01-8 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ Peter Atkins, J. D. P., Atkins' Physical Chemistry. Oxford: 2010. P. 443.
  3. ^ a b "Phenanthrene Fact Sheet" (PDF). archive.epa.gov. U.S. Environmental Protection Agency. Retrieved 19 July 2019.
  4. ^ "Phenanthrene". Sigma-Alrdich.
  5. ^ "Bardhan Sengupta Synthesis". Comprehensive Organic Name Reactions and Reagents. Vol. 49. 2010. pp. 215–219. doi:10.1002/9780470638859.conrr049. ISBN 9780470638859.
  6. ^ Organic Syntheses, Coll. Vol. 4, p. 757 (1963); Vol. 34, p. 76 (1954).
  7. ^ Organic Syntheses, Coll. Vol. 4, p. 313 (1963); Vol. 34, p. 31 (1954).
  8. ^ Organic Syntheses, Coll. Vol. 3, p. 134 (1955); Vol. 28, p. 19 (1948).
  9. ^ Organic Syntheses, Coll. Vol. 2, p. 482 (1943); Vol. 16, p. 63 (1936).
  10. ^ Organic Syntheses, Coll. Vol. 5, p. 489 (1973); Vol. 41, p. 41 (1961).
  11. ^ Ravatite Mineral Data

External links edit

  • Phenanthrene at scorecard.org

January 01, 1970
phenanthrene, polycyclic, aromatic, hydrocarbon, with, formula, c14h10, consisting, three, fused, benzene, rings, colorless, crystal, like, solid, also, appear, yellow, used, make, dyes, plastics, pesticides, explosives, drugs, also, been, used, make, bile, ac. Phenanthrene is a polycyclic aromatic hydrocarbon PAH with formula C14H10 consisting of three fused benzene rings It is a colorless crystal like solid but can also appear yellow Phenanthrene is used to make dyes plastics pesticides explosives and drugs It has also been used to make bile acids cholesterol and steroids 3 Phenanthrene Names Preferred IUPAC name Phenanthrene Identifiers CAS Number 85 01 8 Y 3D model JSmol Interactive image Beilstein Reference 1905428 ChEBI CHEBI 28851 N ChemSpider 970 N ECHA InfoCard 100 001 437 EC Number 266 028 2 Gmelin Reference 28699 KEGG C11422 Y MeSH C031181 PubChem CID 995 UNII 448J8E5BST Y CompTox Dashboard EPA DTXSID6024254 InChI InChI 1S C14H10 c1 3 7 13 11 5 1 9 10 12 6 2 4 8 14 12 13 h1 10H NKey YNPNZTXNASCQKK UHFFFAOYSA N NInChI 1 C14H10 c1 3 7 13 11 5 1 9 10 12 6 2 4 8 14 12 13 h1 10HKey YNPNZTXNASCQKK UHFFFAOYAC SMILES C1 CC C2C C1 C CC3 CC CC C32 Properties Chemical formula C 14H 10 Molar mass 178 234 g mol 1 Appearance Colorless solid Density 1 18 g cm3 1 Melting point 101 C 214 F 374 K 1 Boiling point 332 C 630 F 605 K 1 Solubility in water 1 6 mg L 1 Magnetic susceptibility x 127 9 10 6 cm3 mol Hazards NFPA 704 fire diamond 110 Flash point 171 C 340 F 444 K 1 Structure Point group C2v 2 Dipole moment 0 D Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Phenanthrene occurs naturally and also is a man made chemical Commonly humans are exposed to phenanthrene through inhalation of cigarette smoke but there are many routes of exposure Animal studies have shown that phenanthrene is a potential carcinogen 3 However according to IARC it is not identified as a probable possible or confirmed human carcinogen 4 Phenanthrene s three fused rings are angled as in the phenacenes rather than straight as in the acenes The compound with a phenanthrene skeleton and nitrogens at the 4 and 5 positions is known as phenanthroline Contents 1 Chemistry 1 1 Canonical forms 2 Natural occurrences 2 1 In plants 3 See also 4 References 5 External linksChemistry editPhenanthrene is nearly insoluble in water but is soluble in most low polarity organic solvents such as toluene carbon tetrachloride ether chloroform acetic acid and benzene The Bardhan Sengupta phenanthrene synthesis is a classic way to make phenanthrenes 5 nbsp This process involves electrophilic aromatic substitution using a tethered cyclohexanol group using diphosphorus pentoxide which closes the central ring onto an existing aromatic ring Dehydrogenation using selenium converts the other rings into aromatic ones as well The aromatization of six membered rings by selenium is not clearly understood but it does produce H2Se Phenanthrene can also be obtained photochemically from certain diarylethenes Reactions of phenanthrene typically occur at the 9 and 10 positions including Organic oxidation to phenanthrenequinone with chromic acid 6 Organic reduction to 9 10 dihydrophenanthrene with hydrogen gas and raney nickel 7 Electrophilic halogenation to 9 bromophenanthrene with bromine 8 Aromatic sulfonation to 2 and 3 phenanthrenesulfonic acids with sulfuric acid 9 Ozonolysis to diphenylaldehyde 10 Canonical forms edit Phenanthrene is more stable than its linear isomer anthracene A classic and well established explanation is based on Clar s rule A novel theory invokes so called stabilizing hydrogen hydrogen bonds between the C4 and C5 hydrogen atoms citation needed Natural occurrences editRavatite is a natural mineral consisting of phenanthrene 11 It is found in small amounts among a few coal burning sites Ravatite represents a small group of organic minerals In plants edit Main article PhenanthrenesSee also editChryseneReferences edit a b c d e Record of CAS RN 85 01 8 in the GESTIS Substance Database of the Institute for Occupational Safety and Health Peter Atkins J D P Atkins Physical Chemistry Oxford 2010 P 443 a b Phenanthrene Fact Sheet PDF archive epa gov U S Environmental Protection Agency Retrieved 19 July 2019 Phenanthrene Sigma Alrdich Bardhan Sengupta Synthesis Comprehensive Organic Name Reactions and Reagents Vol 49 2010 pp 215 219 doi 10 1002 9780470638859 conrr049 ISBN 9780470638859 Organic Syntheses Coll Vol 4 p 757 1963 Vol 34 p 76 1954 Organic Syntheses Coll Vol 4 p 313 1963 Vol 34 p 31 1954 Organic Syntheses Coll Vol 3 p 134 1955 Vol 28 p 19 1948 Organic Syntheses Coll Vol 2 p 482 1943 Vol 16 p 63 1936 Organic Syntheses Coll Vol 5 p 489 1973 Vol 41 p 41 1961 Ravatite Mineral DataExternal links editPhenanthrene at scorecard org Retrieved from https en wikipedia org w index php title Phenanthrene amp oldid 1216627749, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.