3-Nitrotoluene Chemical Properties

Melting point:

15 °C

Boiling point:

230-231 °C(lit.)

Density 

1.157 g/mL at 25 °C(lit.)

vapor density 

4.73 (vs air)

vapor pressure 

1 mm Hg ( 50.2 °C)

refractive index 

n20/D 1.541(lit.)

Flash point:

215 °F

storage temp. 

2-8°C

solubility 

0.419g/l

form 

Liquid

color 

Clear yellow to yellow-brownish

explosive limit

2.2%(V)

Water Solubility 

insoluble

Merck 

14,6650

BRN 

1906910

Henry's Law Constant

9.31 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)

Exposure limits

NIOSH REL: TWA 2 ppm (11 mg/m³), IDLH 200 ppm; OSHA PEL: TWA 5 ppm (30 mg/m³); ACGIH TLV: TWA 2 ppm (adopted).

Dielectric constant

23.800000000000001

Stability:

Stable. Combustible. Incompatible with reducing agents, strong oxidizing agents, strong bases.

LogP

2.4

CAS DataBase Reference

99-08-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-methyl-3-nitro-(99-08-1)

IARC

3 (Vol. 65) 1996

EPA Substance Registry System

m-Nitrotoluene (99-08-1)

Safety Information

Hazard Codes 

T,F,Xn

Risk Statements 

23/24/25-33-51/53-36/37/38-11-36-20/21/22

Safety Statements 

36/37-45-61-37-28A-27-16-26

RIDADR 

UN 1664 6.1/PG 2

OEB

A

OEL

TWA: 2 ppm (11 mg/m3) [skin]

WGK Germany 

2

RTECS 

XT2975000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29042000

Hazardous Substances Data

99-08-1(Hazardous Substances Data)

Toxicity

Acute oral LD50 for guinea pigs 3,600 mg/kg, mice 330 mg/kg, rats 1,072 mg/kg, rabbits 2,400 (quoted, RTECS, 1985).

MSDS

• Language:English Provider:m-Nitrophenylmethane
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Nitrotoluene Usage And Synthesis

Chemical Properties

Nitrotoluene is formed in 3 isomeric forms. The o-and m-forms are yellow liquids or solids. The p-form is a pale yellow crystalline solid. All have weak aromatic odors. The Odor Thresholds are: 0.05 mg/L (o-isomer); 1.74 ppm (m-isomer).

Physical properties

3-Nitrotoluene is a light yellow oily liquid with a nitrobenzene-like odor. The relative density is 1.1571, the melting point is 16°C, and the boiling point is 230-231°C. Almost insoluble in water, soluble in ethanol, ether, chloroform and benzene. Can volatilize with water vapor.

Uses

3-Nitrotoluene is mainly used in organic synthesis as an intermediate for pesticides, dyes, explosives, medicines, color developers, plastics, synthetic fibers and auxiliaries.

Preparation

3-Nitrotoluene is obtained by fractional distillation and purification after nitration of toluene with mixed acid below 50℃. Toluene nitration can get different products with different reaction conditions and catalysts, such as o-nitrotoluene, p-nitrotoluene, m-nitrotoluene, 2,4-dinitrotoluene and 2,4,6-trinitrotoluene Toluene etc.

Application

Catalytic hydrogenation or reduction with iron converts 3-nitrotoluene to m-toluidine, which provides important coupling components for azo dyes, usually after N-alkylation.

Definition

ChEBI: 3-nitrotoluene is a mononitrotoluene carrying a nitro group at position 3.

General Description

Yellow crystals that melt at 59°F to a yellow liquid. Often therefore encountered as a liquid. Flash point 223°F. Boiling point 450°F. Insoluble in water. Toxic by inhalation and ingestion.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3-Nitrotoluene reacts with sulfuric acid, strong oxidizing agents and reducing agents.

Hazard

Toxic by inhalation, ingestion, skin absorption. Methemoglobinemia. Probable carcinogen.

Health Hazard

INHALATION, INGESTION OR SKIN ABSORPTION: Headache, flushing of face, dizziness, difficult breathing, cyanosis, nausea, vomiting, muscular weakness, increased pulse and respiratory rate, irritability and convulsions. EYES: Slight irrita- tion. SKIN: Slight irritation.

Potential Exposure

The nitrotoluenes are used in the production of toluidines and other dye intermediates. All isomers are used in manufacture of agriculture and rubber chemicals and in various dyes.

Environmental Fate

Biological. Under anaerobic conditions using a sewage inoculum, 3-nitrotoluene and 4- nitrotoluene both degraded to toluidine (Hallas and Alexander, 1983). Robertson et al. (1992) reported that toluene dioxygenases from Pseudomonas putida F1 and Pseudomonas sp. Strain JS 150 oxidized the methyl group forming 3-nitrobenzyl alcohol.

Shipping

UN1664 Nitrotoluenes, (o-; m-; p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Dry 3-nitrotoluene over P2O5 for 24hours, then fractionally distil it under reduced pressure. [Clark & Taylor Org. Synth Coll Vol I 415 1941, Beilstein 5 IV 847.]

Incompatibilities

Decomposes on contact with strong oxidizers; strong acids; reducing agents; strong bases; ammonia, amines producing toxic fumes, causing fire and explosion hazard. Heat above 190C may cause explosive decomposition. Attacks some plastics, rubbers, and coatings.

Waste Disposal

Controlled incineration-care must be taken to maintain complete combustion at all times. Incineration of large quantities may require scrubbers to control the emission of nitrogen oxides.

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