Benzene, (1-methylethyl)-

Benzene, (1-methylethyl)-
Compound Structure:
Synonyms: CUMENE;Isopropylbenzene;2-Phenylpropane;(1-Methylethyl)benzene;Cumol;Benzene, (1-methylethyl)-;Isopropylbenzol;Cumeen;Isopropilbenzene;Isopropylbenzeen;2-Fenilpropano;2-Fenyl-propaan;Isopropyl-benzol;Benzene, isopropyl;Propane, 2-phenyl;(propan-2-yl)benze
Compound ID: NMPC-626
PubChem ID:

7406

Molecular Formula: C9H12
Canonical SMILES: CC(C)C1=CC=CC=C1
InChIKey: RWGFKTVRMDUZSP-UHFFFAOYSA-N
About the compound:

Cumene, also known as isopropylbenzene, is a chemical compound that exhibits a clear, colorless appearance and emits a distinctive aromatic scent. It is characterized by a flash point of 115 °F and is notable for being less dense than water while remaining insoluble in it. Its vapors, denser than air, can pose moderate toxic risks through inhalation, ingestion, or skin contact. Chemically, cumene is classified as an alkylbenzene, distinguished by the presence of an isopropyl group attached to a benzene ring. This compound finds extensive use across various petroleum-based products. Short-term exposure to cumene through inhalation can lead to symptoms like headaches, dizziness, drowsiness, mild coordination impairment, and in extreme cases, unconsciousness in humans. Additionally, cumene is known for its significant depressant effects on the central nervous system (CNS) in animals, characterized by a gradual onset and prolonged duration of narcotic impact. Furthermore, cumene has been identified as an irritant to both skin and eyes. While there is limited data on the long-term, reproductive, developmental, or carcinogenic effects of cumene in humans, animal studies have highlighted potential health impacts, including increased liver, kidney, and adrenal weights following inhalation exposure. The Environmental Protection Agency (EPA) has categorized cumene in Group D, indicating that its potential as a human carcinogen remains unclassified. In its industrial application, nearly all produced cumene is utilized as a precursor in the cumene process, where it is converted into cumene hydroperoxide. This intermediate is critical for synthesizing other important industrial chemicals, particularly phenol and acetone. As a component of both crude oil and refined fuels, cumene is a flammable liquid, boiling at 152 °C, and plays a vital role in the chemical industry.

GHS Hazard Statements

H226: Flammable liquid and vapor [Warning Flammable liquids]

H304: May be fatal if swallowed and enters airways [Danger Aspiration hazard]

H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H350: May cause cancer [Danger Carcinogenicity]

H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Properties:

Chemical and Physical Properties

Computed Properties

Property Name

Property Value

Molecular Weight

120.19 g/mol

XLogP3

3.7

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

0

Rotatable Bond Count

1

Exact Mass

120.093900383 g/mol

Monoisotopic Mass

120.093900383 g/mol

Topological Polar Surface Area

0²

Heavy Atom Count

9

Formal Charge

0

Complexity

68.1

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

Cumene appears as a clear colorless liquid with an aromatic odor. Flash point 115 °F. Less dense than water and insoluble in water. Vapors heavier than air. May be moderately toxic by inhalation, ingestion and skin absorption.

Boiling Point

306.3 °F at 760 mmHg (USCG, 1999)

Melting Point

-140.9 °F (USCG, 1999)

Density

0.866 at 59 °F (USCG, 1999)

Solubility 

Miscible with ethanol, ethyl ether, acetone, benzene, petroleum ether, carbon tetrachloride

Vapor Pressure

25.85 mmHg (USCG, 1999)

Source: PubChem

Source Species: Annona senegalensis
Terminalia catappa
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