2-Nitrobiphenyl

2-Nitrobiphenyl Property

Melting point:

36-38 °C(lit.)

Boiling point:

320 °C

Density 

1.44

vapor density 

5.9 (vs air)

vapor pressure 

2 mm Hg ( 140 °C)

refractive index 

1.613-1.615

Flash point:

>230 °F

form 

powder to lump

color 

White to Yellow to Green

Water Solubility 

Insoluble

Merck 

14,6591

InChI

InChI=1S/C12H9NO2/c14-13(15)12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9H

InChIKey

YOJKKXRJMXIKSR-UHFFFAOYSA-N

SMILES

C1(C2=CC=CC=C2)=CC=CC=C1[N+]([O-])=O

CAS DataBase Reference

86-00-0(CAS DataBase Reference)

NIST Chemistry Reference

1,1'-Biphenyl, 2-nitro-(86-00-0)

EPA Substance Registry System

o-Nitrobiphenyl (86-00-0)

Safety

Hazard Codes 

Xn

Risk Statements 

20/21/22-40-68-22

Safety Statements 

2-7-36-45-36/37

WGK Germany 

3

RTECS 

DV5530000

HS Code 

2904.20.5000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Nitrobiphenyl Chemical Properties,Usage,Production

Chemical Properties

Clear yellow liquid after melting. Insoluble in water, soluble in methanol, ethanol, acetone, dimethylformamide, and tetrahydrofurfuryl alcohol.

Uses

2-Nitrobiphenyl is used as a plasticizer for resins, cellulose acetate, cellulose nitrate, and polystyrenes; as a fungicide for textiles; as a wood preservative; and as a dye intermediate.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 6567, 1995 DOI: 10.1016/0040-4039(95)01327-E

General Description

Gold to tan crystals or brown solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Aromatic nitro compounds, such as 2-Nitrodiphenyl, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

Fire Hazard

2-Nitrodiphenyl is combustible.

Purification Methods

Crystallise it from EtOH (seeding required). Sublime it under vacuum. [Beilstein 5 H 582, 5 I 273, 5 II 487, 5 III 1750.]

References

[1] A. SEKINE. 2-nitrobiphenyl and 2,2’-dinitrobiphenyl[J]. Acta crystallographica. Section C, Crystal structure communications, 1994, 26 1: 1101-1104. DOI:10.1107/S0108270194001009.
[2] YOST Y. Carbazole from o-biphenylhydroxylamine and from 2-nitrobiphenyl and phenylmagnesium bromide[J]. Journal of Heterocyclic Chemistry, 1972, 9 1: 151-152. DOI:10.1002/jhet.5570090128.
[3] EVA HORAKOVA. Voltammetric Determination of 2-Nitrobiphenyl and 4-Nitrobiphenyl Using a Mercury Meniscus Modified Silver Solid Amalgam Electrode[J]. International Journal of Electrochemical Science, 2015, 10 3: Pages 2155-2169. DOI:10.1016/S1452-3981(23)04837-X.
[4] JIRO HIGUCHI. Electron paramagnetic resonance study on the triplet species produced from 2-nitrobiphenyl derivatives by UV irradiation[J]. Journal of Photochemistry and Photobiology A-chemistry, 1999, 124 1: Pages 53-65. DOI:10.1016/S1010-6030(99)00075-1.