Phenanthrene

Phenanthrene
Compound Structure:
Synonyms: PHENANTHRENE ;85-01-8; Phenanthren; Phenanthracene; Phenanthrin
Compound ID: NMPC-1395
PubChem ID:

995

Molecular Formula: C14H10
Canonical SMILES: C1=CC=C2C(=C1)C=CC3=CC=CC=C32
InChIKey: YNPNZTXNASCQKK-UHFFFAOYSA-N
About the compound:

Phenanthrene, a polycyclic aromatic hydrocarbon (PAH) with the formula C14H10, is composed of three fused benzene rings. This compound appears as a colorless, crystal-like solid, but it can also present a yellow hue. It has a variety of industrial applications, including the manufacture of dyes, plastics, pesticides, explosives, and drugs. Phenanthrene is also involved in the synthesis of bile acids, cholesterol, and steroids. Naturally occurring as well as man-made, phenanthrene is commonly encountered by humans, with inhalation of cigarette smoke being a typical route of exposure. Animal studies have suggested that phenanthrene may be a potential carcinogen, but the International Agency for Research on Cancer (IARC) has not classified it as a probable, possible, or confirmed human carcinogen. Structurally, the three fused rings of phenanthrene are angled similarly to those in the phenacenes, rather than being aligned straight as in the acenes. A compound with a phenanthrene skeleton that features nitrogens at the 4 and 5 positions is known as phenanthroline. Phenanthrene presents as colorless monoclinic crystals and emits a faint aromatic odor. In solution, it exhibits a characteristic blue fluorescence. This property and its physical form were documented by the National Toxicology Program (NTP) in 1992. In addition to its industrial uses, phenanthrene plays roles as an environmental contaminant and a mouse metabolite. It is classified as an ortho-fused polycyclic arene, an ortho-fused tricyclic hydrocarbon, and a member of the phenanthrenes group. Its presence in the environment and potential biological impact underscore the importance of monitoring and regulating its usage and emissions.

GHS Hazard Statements

H302 (99.69%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (13.73%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H400 (16.69%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (15.6%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

First Aid

Eyes: If the victim has contact lenses, remove them. Flush the eyes with water or saline for 20-30 minutes while contacting a hospital or poison control center. Do not use any ointments, oils, or medications without a physician's instructions. Transport the victim to a hospital immediately after flushing, even if no symptoms appear.

Skin: Immediately rinse the affected skin with water, removing any contaminated clothing. Wash the skin thoroughly with soap and water. If symptoms like redness or irritation occur, call a physician and prepare to transport the victim to a hospital.

Inhalation: Leave the contaminated area immediately and breathe fresh air. If symptoms such as wheezing or coughing occur, call a physician and prepare to transport the victim to a hospital. Rescuers should use respiratory protection, preferably a Self-Contained Breathing Apparatus (SCBA).

Ingestion: Do not induce vomiting. If the victim is conscious and not convulsing, give them 1-2 glasses of water to dilute the chemical and call for medical help immediately. If the victim is convulsing or unconscious, keep their airway open and position them with their head lower than their body. Transport them to a hospital immediately (NTP, 1992).

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

178.23 g/mol

XLogP3

4.5

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

0

Rotatable Bond Count

0

Exact Mass

178.078250319 g/mol

Monoisotopic Mass

178.078250319 g/mol

Topological Polar Surface Area

0Ų

Heavy Atom Count

14

Formal Charge

0

Complexity

174

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Phenanthrene appears as colorless monoclinic crystals with a faint aromatic odor. Solutions exhibit a blue fluorescence. (NTP, 1992)

Boiling Point

338.4 °C

Melting Point

99 °C

Density

1.025

Solubility 

Soluble in ethanol, diethyl ether, acetone, benzene, and carbon disulfide.

Vapor Pressure

0.000121 [mmHg]

Source: PubChem

Source Species: Crateva adansonii
Luffa cylindrica
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