2-Methyl-4,6-dinitrophenol Chemical Properties

Melting point:

83-85 °C(lit.)

Boiling point:

196°C 1012mm

Density 

1.5928 (rough estimate)

vapor pressure 

5.2(x 10^-5 mmHg) at 25 °C (Melnikov, 1971)5(x 10^-5 mmHg) at 20 °C (ACGIH, 1986)

refractive index 

1.5460 (estimate)

Flash point:

11 °C

storage temp. 

0-6°C

solubility 

Solubility Sparingly soluble in water; readily soluble in ethanol, acetone, ether

pka

4.42(at 25℃)

color 

Yellow prisms

PH Range

Colorless (2.4) to yellow (3.8)

Water Solubility 

slightly soluble

Merck 

3279

BRN 

2054389

Henry's Law Constant

1.4(x 10^-6 atm?m³/mol) at 25 °C (gas stripping-UV spectrophotometry, Warner et al., 1987)

Exposure limits

NIOSH REL: TWA 0.2 mg/m3, IDLH 5 mg/m3; OSHA PEL: TWA 0.2 mg/m3.

Major Application

Explosives, fungicides, herbicides, insecticides, pesticides, antitumor agent

CAS DataBase Reference

534-52-1(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 2-methyl-4,6-dinitro-(534-52-1)

EPA Substance Registry System

4,6-Dinitro-o-cresol (534-52-1)

Safety Information

Hazard Codes 

T+,N,T,F

Risk Statements 

26/27/28-38-41-43-44-50/53-68-40-39/23/24/25-23/24/25-11-52/53-51/53

Safety Statements 

36/37-45-60-61-16-7

RIDADR 

UN 1598 6.1/PG 2

OEB

C

OEL

TWA: 0.2 mg/m3 [skin]

WGK Germany 

2

RTECS 

GO9625000

HazardClass 

6.1(a)

PackingGroup 

II

Hazardous Substances Data

534-52-1(Hazardous Substances Data)

Toxicity

LD50 in rats (mg/kg): 25-40 orally, 200-600 dermally (Ben-Dyke)

IDLA

5 mg/m3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Methyl-4,6-dinitrophenol Usage And Synthesis

Description

DNOC exists in 9 isomeric forms of which4,6-dinitro-o-cresol is the most important commercially andthe most heavily regulated. It is a noncombustible, yellowcrystalline solid. Molecular weight= 198.15; Boilingpoint= 312℃; Freezing/Melting point = 88℃; Vaporpressure = 5 3 1025 mmHg. Hazard Identification (based onNFPA-704 M Rating System): Health 3, Flammability 0,Reactivity 0. Practically insoluble in water;solubility 5 0.01%.

Chemical Properties

yellow to yellow-green crystals or cryst. powder

Uses

4,6-Dinitro-o-cresol is used as a selective herbicide as well as an insecticide.

Uses

DNOC is a dinitrophenolic compound which exhibits insecticidal, acaricidal and herbicidal activities. It is a non-selective insecticide and controls aphids, Lepidoptera larva and scale insects on pome fruits and stone fruit trees.

Uses

2-Methyl-4,6-dinitrophenol can be used as dormant ovicidal spray for fruit trees (highly phytotoxic and cannot be used successfully on actively growing plants); herbicide; insecticide.

Production Methods

o-Cresol is sulfonated in excess 75 % sulfuric acid to give the disulfonic acid. The sulfonation mass is diluted with water, and 2 equivalents of nitric acid are added at 70 ℃ to form the dinitro derivative. The product is separated while molten and washed with hot water.

Definition

ChEBI: A hydroxytoluene that is o-cresol carrying nitro substituents at positions 4 and 6.

General Description

A yellow solid. Emits toxic oxides of nitrogen fumes when heated to decomposition. Toxic by skin absorption, inhalation or ingestion. Soluble in alcohol, acetone, ether and solutions of sodium or potassium hydroxides.

Air & Water Reactions

Slightly soluble in water.

Health Hazard

Extremely toxic material; probable oral lethal dose is 5-50 mg/kg in humans or between 7 drops and 1 teaspoonful for a 70 kg (150 lb.) person.

Health Hazard

4,6-Dinitro-o-cresol exhibits cumulative toxicity in humans; the symptoms of poisoning are manifested when the blood levels of this compound exceeds 15–20 μg/g (ACGIH 1986). Thus chronic exposure to this compound can cause serious health hazard. The signs of toxicity in humans are headache, fever, profuse sweating, rapid pulse and respiration, cough, shortness of breath, and coma. Other symptoms noted are a decrease in hemoglobin, an increase in blood sugar, a loss of muscle tone, dyspnea, kidney and liver injury, and edema of the lung and brain.
LD50 value, oral (mice): 47 mg/kg
LD50 value, skin (rats): 200 mg/kg.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Agricultural Uses

Herbicide, Fungicide, Pesticide: DNOC is widely used in agriculture as a herbicide and pesticide; it is also used in the dyestuff industry. Although 4,6-dinitro-o-cresol (DNOC) is no longer registered for use in the United States, it was used as a blossom-thinning agent on fruit trees and as a fungicide, insecticide, and miticides on fruit trees during the dormant season. It is used in mushroom houses to control foreign fungi; to kill locusts and other insects; and as a pre-harvest desiccant of potatoes and leguminous seed crops. DNOC is used as free radical polymerization inhibitor and agricultural chemical intermediate; widely used in agriculture as a herbicide and pesticide; Hence, individuals formulating or spraying the compound incur the highest risk of exposure to the compound. Not approved for use in EU countries. DNOC’s registration in the U.S. as a pesticide was canceled in 1991. Currently, there are 39 global suppliers.

Trade name

ANTINONIN®; ANTINONNIN®; ARBOROL®; DEGRASSAN®; DEKRYSIL®; DETAL®; DILLEX®; DINOC®; DINURANIA®; DITROSOL®; DNOC®[C]; EFFUSAN®; EFFUSAN 3436®; ELGETOL®; ELGETOL 30®; ELIPOL®; EXTRAR®; FLAVIN-SANDOZ®; HEDOLIT®; HEDOLITE®; K III®; K IV®; KREOZAN®; KREZOTOL 50®; LIPAN®; NEUDORFF DN 50®; NITROFAN®; PROKARBOL®; RAFEX®; RAFEX 35®; RAPHATOX®; SANDOLIN®; SANDOLIN A®; SELINON®; SINOX®; WINTERWASH®

Safety Profile

Human poison by unspecified route. Experimental poison by ingestion, inhalation, skin contact, intraperitoneal, and intravenous routes. Human systemic effects by ingestion and inhalation: somnolence, headache, abnormal brain recordings from specific areas of the central nervous system, cardlac and gastrointestinal changes. Mutation data reported. An e~7e and skin irritant. Less toxic than the para form, but is still highly toxic. A pesticide. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS and other dinitrocresol entries.

Potential Exposure

AgriculturalChemical; Mutagen; Reproductive Effector; Human Data;Primary Irritant. DNOC is used as free radical polymerization inhibitor and agricultural chemical intermediate; widelyused in agriculture as an herbicide and pesticide; it is alsoused in the dyestuff industry. Although 4,6-dinitro-o-cresol(DNOC) is no longer manufactured in the United States, alimited quantity is imported and used as a blossom-thinningagent on fruit trees and as a fungicide, insecticide, and miticide, on fruit trees during the dormant season. Hence, individuals formulating or spraying the compound incur thehighest risk of exposure to the compound.

Carcinogenicity

In one chronic feeding study in rats DNOC did not cause an increased incidence of any type of tumor. DNOC was clastogenic, increasing the frequency of chromosomal aberrations both in vivo and in vitro. Conflicting results for mutagenicity have been obtained in bacterial assays.
The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) for dinitro-o-cresol is 0.2mg/m3 with a notation for skin absorption.

Environmental Fate

Soil/Plant. In plants and soils, the nitro groups reduced to amino groups (Hartley and Kidd, 1987). When 4,6-dinitro-o-cresol was statically incubated in the dark at 25°C with yeast extract and settled domestic wastewater inoculum, no signi?cant biodegradation and necessary acclimation for optimum biooxidation within the 4-week incubation period was observed (Tabak et al., 1981).
Chemical/Physical. 4,6-Dichloro-o-cresol will react with amines and alkali metals forming water-soluble salts which are indicative of phenols (Morrison and Boyd, 1971).

Metabolic pathway

DNOC is metabolised in soils, plants and animals via common metabolic pathways. The primary reaction is the reduction of the nitro groups to the corresponding amino-analogues. Acetylation and deamination via hydroxylation/elimination follow. N- and O-Conjugation as glucosides and glucuronides occurred in plants and animals. The metabolic pathways of DNOC are presented in Scheme 1.

Purification Methods

The cresol crystallises from aqueous EtOH. [Beilstein 6 H 369, 6 III 1276.]

Degradation

DNOC (1) is stable to hydrolytic and photolytic degradation at acidic pH and is readily degraded under alkaline conditions (Molnar, 1935).

Incompatibilities

Dust can form an explosive mixture withair. Keep away from strong oxidizers, strong bases. Protectfrom heat and shock

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