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2,6-Dinitro-4-octylphenol

HCID 20040
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationRelated reactionsCompound notes
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Basic information

CAS
4097-33-0
Standard SMILES
CCCCCCCCc1cc([N+](=O)[O-])c(O)c([N+](=O)[O-])c1
InChIKey
NYGISSDEOKKXOE-UHFFFAOYSA-N
Molecular formula
C14H20N2O5
Average molar mass
296.32 g/mol
Monoisotopic mass
296.13722174

Names & identifiers

Preferred name
2,6-Dinitro-4-octylphenol
IUPAC
2,6-dinitro-4-octylphenol

Names & synonyms

2,6-DINITRO-4-OCTYLPHENOLI7UAX8GLEDUNII-I7UAX8GLEDHSDB 3903Phenol, 2,6-dinitro-4-octyl-4097-33-0DTXSID801939692,6-DINITRO-4-OCTYLPHENOL [HSDB]RefChem:83349Phenol, 2,6dinitro4octylDTXCID70116460SCHEMBL1861075
Show more names
Q27280552

Database identifiers

CAS
4097-33-0
PubChem CID
20040
DTXSID
DTXSID80193969
UNII
I7UAX8GLED
Nikkaji
J1.553.710H

Properties

Computed structural properties

XLogP
5.8
Topological polar surface area
112 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
7
Heavy atoms
21
Formal charge
0
Complexity
315

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
Vapor Pressure0.00000001 [mmHg]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Hazards SummaryEmergency treatment: Dinitro phenol group; [HSDB] See Dinitrophenol.

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 30,500(SRC), determined from an estimated log Kow of 5.71(2) and a regression-derived equation(3), indicates that 2,6-dinitro-4-octylphenol is expected to be immobile in soil(SRC). Although no dissociation constant was located for this chemical, structurally similar compounds have pKa values in the range of 3-5(4), indicating that this compound will exist primarily as an anion in moist soils and anions have higher mobility than the neutral species(SRC). Volatilization of 2,6-dinitro-4-octylphenol from moist soil surfaces is not expected to be an important fate process(SRC) since the anion will not volatilize and the neutral species has an estimated Henry's Law constant of 6X10-10 atm-cu m/mole at 25 °C(SRC) using a fragment constant estimation method(5). 2,6-Dinitro-4-octylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon its estimated vapor pressure of 1X10-8 mm Hg at 25 °C(SRC) determined from a fragment constant method(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 30,500(SRC), determined from an estimated log Kow of 5.71(2,SRC) and a regression-derived equation(3), indicates that 2,6-dinitro-4-octylphenol is expected to adsorb to suspended solids and sediment in water(SRC). Although no dissociation constant value was located for this chemical, structurally similar compounds have pKa values in the range of 3-5(4), indicating that this compound will exist primarily as an anion in water surfaces. Volatilization of 2,6-dinitro-4-octylphenol from water surfaces is not expected to be an important fate process(SRC) since the anion will not volatilize and the neutral species has an estimated Henry's Law constant of 6X10-10 atm-cu m/mole at 25 °C(SRC) using a fragment constant estimation method(5). According to a classification scheme(5), an estimated BCF of 12,900(SRC), from an estimated log Kow(2,) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is very high.

Related reactions

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationRelated reactionsCompound notes

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,6-dinitro-4-octylphenol, which has an estimated vapor pressure of 1X10-8 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2,6-dinitro-4-octylphenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 40 hours(SRC) from its estimated rate constant of 9.7X10-12 cu cm/molecule-sec(3). Particulate-phase 2,6-dinitro-4-octylphenol may be removed from the air by wet and dry deposition(SRC). Nitrophenols exhibit strong absorption of UV light at wavelengths greater than 290 nm(4), suggesting that 2,6-dinitro-4-octylphenol has the potential to undergo direct photolysis in the environment(SRC).

Adverse EffectsNephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.
Soil Adsorption/Mobility · 1 item

The Koc of 2,6-dinitro-4-octylphenol is estimated as approximately 30,500(SRC), using an estimated log Kow of 5.71(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,6-dinitro-4-octylphenol is expected to be immobile in soil. Although no dissociation constant value was located for this chemical, structurally similar compounds have pKa values in the range of 3-5(4), indicating that this compound will exist primarily as an anion in moist soils and anions have higher mobility than the neutral species(SRC).

Human Toxicity Excerpts · 4 items

SYMPTOMATOLOGY: 1. MARKED FATIGUE, TREMENDOUS THIRST, PROFUSE SWEATING, FLUSHING OF FACE. 2. NAUSEA, VOMITING, ABDOMINAL PAIN, & OCCASIONALLY DIARRHEA. 3. RESTLESSNESS, ANXIETY, EXCITEMENT, OCCASIONALLY LEADING TO CONVULSIONS. /DINITROPHENOL/

SYMPTOMATOLOGY: 4. RISE IN BODY TEMP...ROUGHLY PROPORTIONAL TO TOXIC DOSE, MAY CULMINATE IN SEVERE HYPERPYREXIA... 5. TACHYCARDIA, HYPERPNEA, DYSPNEA, CYANOSIS, &...MUSCLE CRAMPS. 6. LOSS OF CONSCIOUSNESS, CESSATION OF BREATHING, & DEATH. /DINITROPHENOL/

SYMPTOMATOLOGY: 7. LATE COMPLICATIONS: A. DECR URINE OUTPUT WITH ALBUMINURIA, CASTS, PIGMENTS, SOMETIMES BLOOD CELLS, DUE TO TOXIC NEPHRITIS. B. JAUNDICE & TENDERNESS IN LIVER REGION DUE TO TOXIC HEPATITIS. /DINITROPHENOL/

SYMPTOMATOLOGY: 8. OCCASIONAL HYPERSENSITIVITY REACTIONS AFTER REPEATED EXPOSURES (OR IN CHRONIC POISONING) INCLUDE AGRANULOCYTIC ANGINA, SKIN RASHES, PERIPHERAL NEURITIS, & LATE CATARACT FORMATION. /DINITROPHENOL/

Environmental Bioconcentration · 1 item

An estimated BCF of 12,900 was calculated for 2,6-dinitro-4-octylphenol(SRC), using an estimated log Kow of 5.71(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high.

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 2,6-dinitro-4-octylphenol is estimated as 6X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,6-dinitro-4-octylphenol is not expected to volatilize from moist soil or water surfaces(2). 2,6-Dinitro-4-octylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1X10-8 mm Hg(SRC), determined from a fragment constant method(3). Although no dissociation constant value was located for this chemical, structurally similar compounds have pKa values in the range of 3-5(4), indicating that this compound will exist primarily as an anion in moist soils and water surfaces(SRC).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of 2,6-dinitro-4-octylphenol with photochemically-produced hydroxyl radicals has been estimated as 9.7X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 40 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,6-Dinitro-4-octylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Nitrophenols exhibit strong absorption of UV light at wavelengths greater than 290 nm(3), suggesting that 2,6-dinitro-4-octylphenol has the potential to undergo direct photolysis in the environment(SRC). Although no dissociation constant value was located for this chemical, structurally similar compounds have pKa values in the range of 3-5(4), indicating that this compound will exist primarily as an anion inthe environment(SRC).

Environmental Fate/Exposure Summary · 1 item

If released to air, an estimated vapor pressure of 1X10-8 mm Hg at 25 °C indicates 2,6-dinitro-4-octylphenol will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2,6-dinitro-4-octylphenol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 40 hours. Particulate-phase 2,6-dinitro-4-octylphenol will be removed from the atmosphere by wet and dry deposition. Nitrophenols absorb light at wavelengths greater than 290 nm, suggesting that photodegradation may be an important fate process although the kinetics of this reaction are unknown. If released to soil, 2,6-dinitro-4-octylphenol is expected to have no mobility based upon an estimated Koc of 30,500. However, the pKa of dinitrophenols is in the range of about 3-5, which indicates that this compound will exist primarily as an anion 0n moist soil surfaces and anions are expected to have higher mobility in moist soils than the neutral species. Volatilization from moist soil surfaces is not expected to be an important fate process since the anion will not volatilize and the neutral species has an estimated Henry's Law constant of 6X10-10 atm-cu m/mole at 25 °C. 2,6-Dinitro-4-octylphenol is not expected to volatilize from dry soil surfaces based upon its vapor. If released into water, 2,6-dinitro-4-octylphenol is expected to adsorb to suspended solids and sediment in the water column based upon the estimated Koc; however, the anion is not expected to adsorb. Volatilization from water surfaces is not expected to be an important fate process based upon the estimated Henry's Law constant and since this compound should exist primarily as an anion in water. An estimated BCF of 12,900 suggests the potential for bioconcentration in aquatic organisms is very high. (SRC)

Antidote and Emergency Treatment · 2 items

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes if immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . Rapid body cooling may be necessary in case of hyperthermia. Salicylates are contraindicated. /Dinitrophenol and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in severe respiratory distress. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with lactated Ringer's to treat dehydration. Watch for signs of fluid overload and pulmonary edema. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Dinitrophenol and related compounds/