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4-Chloro-3,5-dimethylphenol ( CASNO:88-04-0 )

Identification and Related Records
Name:
4-Chloro-3,5-dimethylphenol
CAS Registry number:
88-04-0
Iupac name:
4-chloro-3,5-dimethylphenol
Synonyms:
4-Chloro-3,5-xylenol
PCMX
4-Chloro-3,5-xylenol (OH=1)
5-M-Xylenol (Chloroxylenol)
4-Chloro-3,5-m-Xylenol
p-chloro-m-xylenol
4-chloro-m-xylenol
3,5-xylenol, 4-chloro-
4-chloro-1-hydroxy-3,5-dimethylbenzene
4-chloro-3,5-dimethyl-phenol
4-chloro-3-xylenol
EINECS(EC#):
201-793-8
Molecular Formula:
C8H9ClO
Molecular Weight:
156.61
Inchi:
InChI=1/C8H9ClO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,1-2H3
InChIKey:
OSDLLIBGSJNGJE-UHFFFAOYSA-N
Canonical SMILES:
CC1=CC(=CC(=C1Cl)C)O
Chemical and Physical Properties
Appearance:
white to off-white crystalline powder
Density:
1.183 g/cm3
Melting Point:
113-116℃
Boiling Point:
246℃
Refractive Index:
1.558
Flash Point:
132℃
Water:
0.3 g/L (20℃)
Solubilities:
Slightly soluble
Color/Form:
Crystals from benzene
Stability:
Stable. Incompatible with strong oxidizing agents.
HS Code:
29081000
Storage temp:
2-8°C
Spectral properties:
Raman: 1042 (Sadtler Research Laboratories Spectral Collection)
UV: 7-165 (Phillip et al., Organic Electronic Spectral Data, John Wiley & Sons, New York)
IR: 2i588G (Aldrich Library of Infrared Spectra, Aldrich Chemical Co., Milwaukee, WI)
MASS: 70768 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
Computed Properties:
Molecular Weight:156.60946 [g/mol]
Molecular Formula:C8H9ClO
XLogP3:2
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:0
Tautomer Count:5
Exact Mass:156.034193
MonoIsotopic Mass:156.034193
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Formal Charge:0
Complexity:104
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:1
Feature 3D Ring Count:1
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1
Safety and Handling
Hazard Codes:
Xn:Harmful
Risk Statements:
R22;R36/38;R43
Safety Statements:
S24;S37
Hazard Note:
Irritant
Skin, Eye, and Respiratory Irritations:
Chloroxylenol /is listed as one of/ common contact allergens /in/ antiseptics. /from Table/
Cleanup Methods:
If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.
After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.
Transport:
UN 3077
Formulations/Preparations:
Dettol (Reckitt and Colman, UK)
Exposure Standards and Regulations:
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloroxylenol is included in topical acne drug products.
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloroxylenol is included in dandruff/seborrheic dermatitis/psoriasis drug products..
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloroxylenol is included in topical antifungal drug products.
Other Preventative Measures:
Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.
Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.
Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.
Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.
Protective Equipment and Clothing:
Chloroxylenol /is listed as one of/ common contact allergens /in/ antiseptics. /from Table/
Octanol/Water Partition Coefficient:
log Kow = 3.27
Disposal Methods:
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.
Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

Prepared by treating 3,5-dimethylphenol with Cl2 or SO2Cl2... US patent 2350677 (1944).
U.S. Production

(1986) 10 thousand-500 thousand pounds
(1990) 10 thousand-500 thousand pounds
(1998) 10 thousand-500 thousand pounds
Usage:
Antiseptic and germicide.
Biomedical Effects and Toxicity
Pharmacological Action:
- Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
- Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed)
- Agents that act systemically to kill adult schistosomes.
Therapeutic Uses:
Antibacterial; antiseptic (topical and urinary).
(VET): Antiseptic (topical).
Biomedical Effects and Toxicity:
Mongrel dogs received iv and oral single doses of 200 and 2000 mg 4-chloro-3,5-xylenol, respectively. Low range of absorption was noted. Kidneys were not the major route for rapid elimination of unchanged 4-chloro-3,5-xylenol.
Tests of a 25 percent solution of chloroxylenol with Sprague-Dawley rats demonstrated the chemical was practically all eliminated in the first 24 hours, mostly in the urine, with small amounts in feces, after oral or dermal exposure. Following dermal exposure, about half of the material was not absorbed. High concentrations were found in the tissues of the kidney, which indicates excretion in urine. Concentrations in the lungs indicates some elimination in expired air.
In a study /with/ beagle dogs dosed orally excreted virtually all of the chloroxylenol in their urine within 24 hours. A small amount was present in feces, but essentially none remained in any tissue.
The pharmacokinetic and metabolic profile of p-chloro-m-xylenol (PCMX) was studied in healthy mongrel dogs after intravenous and oral administration of single doses of 200 and 2000 mg of PCMX, respectively. ... The mean half-life and mean residence time were 1.84 and 1.69 hr. respectively. The apparent volume of distribution at steady state was estimated to be 22.4 liters, and the plasma clearance was 14.6 liters/hr. The bioavailability of PCMX was 21%. ... PCMX's metabolite data show that a presystemic elimination process (first-pass effect) is also occurring. PCMX plasma concentrations after intravenous administration of 500-, 200-, and 100-mg doses were found to be proportional to the dose given.
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,400(SRC), determined from a log Kow of 3.27(2) and a regression-derived equation(3), indicates that chloroxylenol is expected to have low mobility in soil(SRC). Volatilization of chloroxylenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.1X10-7 atm-cu m/mol(SRC), derived using a fragment constant estimation method(4). Chloroxylenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Degradation of chloroxylenol appears to be slower than other phenol derivatives(5,6). Studies in sewage showed 95-80% of the original compound remaining after 2 days and 60-70% remaining after 7 days(5). This is consistent with other studies that showed less than 40% degradation in activated sludge over 7 days(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,400(SRC), determined from a log Kow of 3.27(2) and a regression-derived equation(3), indicates that chloroxylenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization of chloroxylenol from water surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.1X10-7 atm-cu m/mol(SRC) derived using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 66(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Degradation of chloroxylenol appears to be slower than other phenol derivatives(7,8). Studies in sewage showed 80-95% of the original compound remaining after 2 days and 60-70% remaining after 7 days(7). This is consistent with other studies that showed less than 40% degradation in activated sludge after 7 days(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloroxylenol, which has an estimated vapor pressure of 1.8X10-3 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloroxylenol 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 6 hours(SRC), calculated from its rate constant of 6.7X10-11 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Chloroxylenol does not contain chromophores that absorb at wavelengths >290 nm(4) and has been reported to be stable to sunlight for up 24 hours(5).
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