CAS 106-51-4 1,4-Benzoquinone - Materials / Alfa Chemistry

NAVIGATION

1,4-Benzoquinone

PRICE INQUIRY

Catalog Number

ACM106514-1

CAS Number

106-51-4

Product Name

1,4-Benzoquinone

Structure

Category

Charge Transfer Complexes; Molecular Conductors

Description

Benzoquinone appears as a yellowish-colored crystalline solid with a pungent, irritating odor. Poisonous by ingestion or inhalation of vapors. May severely damage skin, eyes and mucous membranes. Used to make dyes and as a photographic chemical.;Solid;YELLOW CRYSTALS WITH PUNGENT ODOUR. CAN SUBLIME EVEN AT ROOM TEMPERATURE.;Pale-yellow solid with an acrid, chlorine-like odor.

IUPAC Name

cyclohexa-2,5-diene-1,4-dione

Molecular Weight

108.09g/mol

Molecular Formula

C6H4O2;C6H4O2

Canonical SMILES

C1=CC(=O)C=CC1=O

InChI

InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H

InChI Key

AZQWKYJCGOJGHM-UHFFFAOYSA-N

Boiling Point

SUBLIMES (NTP, 1992);~180 °C;Sublimes

Melting Point

240.3 °F (NTP, 1992);115.7 °C;115.7 °C;115.7°C;116 °C;240°F

Flash Point

559 °F (NTP, 1992);100-200 °F (38-93 °C) (CLOSED CUP);38-93 °C;100-200°F

Density

1.318 at 68 °F (USCG, 1999);1.318 AT 20 °C/4 °C;Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0;1.32

Solubility

Slightly soluble (NTP, 1992);SOL IN ALKALIES, HOT PETROLEUM ETHER;> 10% in ether;> 10% in ethanol;Water solubility = 1.113X10+4 mg/l @ 18 °C;11.1 mg/mL at 18 °C;Solubility in water: poor;Slight

Application

1,4-Benzoquinone serves as a versatile chemical intermediate, playing a crucial role in various industrial and chemical processes. It is employed in the production of dyes, fungicides, and hydroquinone, and is particularly significant in the tanning of hides. Additionally, 1,4-Benzoquinone acts as an oxidizing agent and is involved in numerous reactions across industries, including its use as a polymerisation inhibitor and a reagent in synthetic organic chemistry. It is a key component in photographic applications, making gelatin insoluble and enhancing the strength of animal fibers. Furthermore, it participates in Diels-Alder reactions, integral to the synthesis of complex organic molecules like naphthoquinones. Its widespread utility is evident in its use as a dehydrogenation agent and its role in preventing double-bond migration during olefin metathesis reactions. As a precursor to hydroquinone, it is vital in photography and serves as a reducing agent and antioxidant in rubber production. Despite its pungent, irritating odor, reminiscent of chlorine, its functionalities have made it an indispensable component in the dye, textile, chemical, tanning, and cosmetic industries.

Color/Form

YELLOW MONOCLINIC PRISMS FROM WATER OR PETROLEUM ETHER;Greenish-yellowish solid;Pale-yellow solid.

Complexity

149

Covalently-Bonded Unit Count

EC Number

203-405-2

Exact Mass

108.021129g/mol

Formal Charge

Heavy Atom Count

ICSC Number

0779

Log P

0.2 (LogP);Log Kow = 0.20;0.20;0.2

MeSH Entry Terms

1,4-benzoquinone;2,5-cyclohexadiene-1,4-dione;benzoquinone;NSC-36324;NSC36324;p-benzoquinone;para-benzoquinone;quinone

Monoisotopic Mass

108.021129g/mol

NSC Number

36324

Odor

PENETRATING ODOR RESEMBLING THAT OF CHLORINE;Acrid, chlorine-like odor.

Other Experimental

SUBLIMES; DIPOLE MOMENT: 0.67;CONVERSION FACTORS: 1 MG/L IS EQUIVALENT TO 226.4 PPM & 1 PPM IS EQUIVALENT TO 0.00442 MG/L AT 25 °C, 760 MM HG;Ionization potential: 9.67 eV;Heat of fusion: 40.97 cal/g;Heat of sublimation: 15.00 kcal/mol @ 298 deg K;IR: 1300 (Documentation of Molecular Spectroscopy Collection) /1,2-Benzoquinone/;UV: 3-56 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /1,2-Benzoquinone/;MASS: 333 (Atlas of Mass Spectral Data, John Wiley & Sons, New York) /1,2-Benzoquinone/;Liquid molar volume = 0.099191 cu m/kmol (determined at triple point);IG Heat of Formation = -1.2290X10+8 J/kmol;Heat of fusion at melting point = 1.845X10+7 J/kmol

Rotatable Bond Count

RTECS Number

DK2625000

Stability

May darken on standing.

UNII

3T006GV98U

UN Number

2587;2587;2587;2587;2587

Vapor Density

3.7 (Air= 1);Relative vapor density (air = 1): 3.7

Vapor Pressure