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| | 2-Methyl-4,6-dinitrophenol Basic information |
| Product Name: | 2-Methyl-4,6-dinitrophenol | | Synonyms: | DNOC Styrene polymerisation retarder;4,6-Dinitro-o-cresol,98%;4,6-Dinitro-2-methylphenol (2-Methyl-4,6-dinitrophenol);2-METHYL-4,6-DINITRO PHENOL,1X1ML,MEOH,5 00UG/ML;DNOC PESTANAL, 250 MG;2-METHYL-4,6-DINITROPHENOL, 1000MG, NEAT;4,6-DINITRO-O-CRESOL, 1GM,NEAT;2-METHYL-4,6-DINITROPHENOL, 1X1ML MEOH 5 000UG/ML | | CAS: | 534-52-1 | | MF: | C7H6N2O5 | | MW: | 198.13 | | EINECS: | 208-601-1 | | Product Categories: | Nitro;Pesticide Intermediate;Organics;Phenoles and thiophenoles | | Mol File: | 534-52-1.mol |  |
| | 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) | | Fp | 11 °C | | storage temp. | 0-6°C | | solubility | Solubility Sparingly soluble in water; readily soluble in ethanol, acetone, ether | | form | neat | | 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) |
| | 2-Methyl-4,6-dinitrophenol Usage And Synthesis |
| Chemical Properties | yellow to yellow-green crystals or cryst. powder | | 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 | 4,6-Dinitro-o-cresol is used as a selective herbicide as well as an insecticide. | | 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.
| | 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. | | 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). |
| | 2-Methyl-4,6-dinitrophenol Preparation Products And Raw materials |
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