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Tris(isopropylphenyl)phosphate

HCID 33661
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Basic information

CAS
26967-76-0
Standard SMILES
CC(C)c1ccccc1OP(=O)(Oc1ccccc1C(C)C)Oc1ccccc1C(C)C
InChIKey
LIPMRGQQBZJCTM-UHFFFAOYSA-N
Molecular formula
C27H33O4P
Average molar mass
452.5 g/mol
Monoisotopic mass
452.21164653

Names & identifiers

Preferred name
Tris(isopropylphenyl)phosphate
IUPAC
tris(2-propan-2-ylphenyl) phosphate
English name
Tris(isopropylphenyl)phosphate
Molecular formula
C27H33O4P
Molecular weight
452.52

Names & synonyms

TRIS(ISOPROPYLPHENYL)PHOSPHATERefChem:900334(1Methylethyl)phenol phosphate (3:1)Phenol, (1methylethyl), phosphate (3:1)Phenol, (1methylethyl), phosphate (3:1) (9CI)Tris(2-isopropylphenyl) phosphate64532-95-2tris(2-propan-2-ylphenyl) phosphateTris[2-(propan-2-yl)phenyl] phosphateo-Cumenyl phosphateTris[2-(2-methylethyl)phenyl] phosphateTris(o-isopropylphenyl)phosphate
Show more names
o-Cumenyl phosphate (6ci)2-(1-Methylethyl)phenol Phosphate2-(1-Methylethyl)phenol 1,1',1''-Phosphate
BRN 35013152-(1-Methylethyl)phenol phosphate (3:1)Phenol, 2-(1-methylethyl)-, phosphate (3:1)T2iPPPSCHEMBL182520-06-00-00504 (Beilstein Handbook Reference)SCHEMBL29352226DTXSID00214802

Database identifiers

CAS
26967-76-0、64532-95-2
PubChem CID
33661
DTXSID
DTXSID00214802
Nikkaji
J180.507J

Properties

Computed structural properties

XLogP
8.3
Topological polar surface area
44.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
9
Heavy atoms
32
Formal charge
0
Complexity
524

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Organophosphates, Other

Organophosphate

Density · 2 items

1.159 at 20 °C

Clear transparent liquid. Density: 1179 kg/cu m at 20 °C; viscosity; 60 mPa.s at 25 °C /Phosflex 31L/

Color/FormYellow waxy solid
Boiling Point220-270 °C/0.53 kPa
DecompositionWhen heated to decomposition it emits toxic vapors of /phosphorous oxides/.
Melting Point-25 °C
Physical DescriptionYellow solid; [CAMEO]
Collision Cross Section204.49 Ų [M+H]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]

Physicochemical properties

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 SummaryThis testing regimen showed that isopropyl triphenyl phosphate produced an effect on neurotoxic esterase at the biochemical level without producing clinical or neurohistologic abnormalities in treated hens. [HSDB]

Safety & protection

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 1 item

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+6(SRC), determined from a structure estimation method(2), indicates that tris(isopropylphenyl)phosphate is expected to be immobile in soil(SRC). Volatilization of tris(isopropylphenyl)phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-7 atm-cu m/mole for the 4-isomer(SRC), using a fragment constant estimation method(3). Tris(isopropylphenyl)phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.1X10-8 mm Hg at 25 °C for the 4-isomer(SRC), determined from a fragment constant method(2). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(4) suggests that biodegradation is not an important environmental fate process in soil(SRC).

Chemistry & industry

Uses & manufacturing

Uses · 4 items

Used as plasticizer; [HSDB]

Plasticizer

Reofos 95 is a flame retardant plasticizer used primarily in PVC and phenolic resins ... recommended as a flame retardant for PVC, flexible polyurethanes, cellulosic resins, and synthetic rubber. ... also recommended as a flame retardant processing aid for engineering resins, such as modified PPO, polycarbonate and polycarbonate blends ... particularly suitable as a flame retardant for PVC cables /Triaryl phosphates Isopropylated; 68937-41-7/

Lubricants and additives; hydraulic fluids and additives; paints, lacquers and varnishes; cutting fluids; construction materials; surface treatment; flame retardants and extinguishing agents; adhesives, binding agents. /Isopropylated triphenyl phosphates/

Methods of Manufacturing · 1 item

Isopropylphenol is made by reaction of phenol with propylene. The resulting product is a mixture of mainly ortho- and para-isomers with varying degrees of alkylation. The product of this reaction is then mixed with phenol and reacted with phosphorus oxychloride to produce the phosphate ester. The relative amounts of phenol and isopropylated phenol can be varied to give a range of products with a corresponding range of properties. /Triisopropylphenyl phosphate/

Formulations/PreparationsTrade names: Durad 100; Durad MP280(sup R) hydraulic fluid; Duran MP280(sup R); Durad 300; Kronitex 50; Kronitex 100, 200 and 300; Reofos 35, 50, 65, 95, 120; Proprietary G
General Manufacturing Information · 2 items

Isopropylated triphenyl phosphates are substituted with isopropyl groups at ortho, meta and/or para positions on one, two or three of the phenyl rings. Thus, the number of potential isomers is large.

Often occurs together with triphenyl phosphate in commercial products

Applications

UsesTris(2-isopropylphenyl)phosphate is a neurotoxic agent.

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Boiling point
494.1 · 494.1±44.0 °C(Predicted)
Density
1.108 · 1.108±0.06 g/cm3(Predicted)
solubility
Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
form
Oil to Solid
color
Colourless to Pale Yellow
Stability
Hygroscopic, Moisture Sensitive
EWG's Food Scores
1 · 1
RIDADR
3082 · 3082
HazardClass
9 · 9
PackingGroup
III

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+6(SRC), determined from a structure estimation method(2), indicates that tris(isopropylphenyl)phosphate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-7 atm-cu m/mole for the 4-isomer(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), a BCF range of 6.9 to 43(5) suggests bioconcentration in aquatic organisms is low(SRC). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tris(isopropylphenyl)phosphate, which has an estimated vapor pressure for the 4-isomer of 2.1X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase tris(isopropylphenyl)phosphate may be removed from the air by wet and dry deposition(SRC). Tris(isopropylphenyl)phosphate does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of tris(isopropylphenyl)phosphate can be estimated to be 1.2X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that tris(isopropylphenyl)phosphate is expected to be immobile in soil.

Human Toxicity Excerpts/OTHER TOXICITY INFORMATION/ Skin irritation was not reported among workers exposed to hydraulic fluids containing isopropylated triphenyl phosphate. /Isopropylated Triphenyl Phosphates/
Artificial Pollution SourcesTris(isopropylphenyl)phosphate's production and use as a flame retardant primarily in PVC plastics(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAEROBIC: Tris(isopropylphenyl)phosphate, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1).
Environmental Bioconcentration · 1 item

BCF ranges of 6.9 to 17 and 20 to 43 were reported in fish for tris(isopropylphenyl)phosphate at concentrations of 2 and 0.2 mg/L respectively, using carp (Cyprinus carpio) which were exposed over an 8-week period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for tris(4-iisopropylphenyl)phosphate is estimated as 2.9X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). By analogy, this Henry's Law constant indicates that tris(isopropylphenyl)phosphate is expected to be essentially nonvolatile from water or moist soil surfaces(2). Tris(isopropylphenyl)phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.1X10-8 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5 items

/LABORATORY ANIMALS: Acute Exposure/ Five male and 5 female Wistar rats received a single oral dose of 20,000 mg/kg bw of isopropylated triphenyl phosphates. The animals were observed for 14 days, after which they were sacrificed, necropsied and their organs examined for gross lesions. No male rats died but 4 of the 5 females. No clinical signs were reported. /Isopropylated triphenyl phosphates/

/LABORATORY ANIMALS: Acute Exposure/ Three New Zealand White rabbits were treated with 0.1 mL (110 mg) isopropylated triphenyl phosphate in their conjunctival sac of the right eye. Each treated eye was held closed for about one second after administration. The eyes were evaluated for irritation using the Draize method at 1, 24, 48 and 72 hours after dosing. Slight conjunctival redness was observed in two treated eyes 24 hours after dosing. The irritation had disappeared by the 48-hour observation. The Primary Eye Irritation Index was 1.3 at 24 hours and 0 at 48 and 72 hours. Thus, isopropylated triphenyl phosphate caused very slight irritation. /Isopropylated triphenyl phosphates/

/LABORATORY ANIMALS: Acute Exposure/ Eye irritation from isopropylated triphenyl phosphate was investigated in 9 rabbits. The treated eyes of 6 rabbits were unwashed through the 7-day observation period whereas the eyes of 3 rabbits were washed about 4 seconds after treatment. The treated eyes were examined at 24, 48, 72 hours and 7 days after treatment. There was no irritation in any of the treated eyes at any of the observation times. /Isopropylated triphenyl phosphates/

/LABORATORY ANIMALS: Acute Exposure/ Isopropylated triphenyl phosphate (0.1 mL or 110 mg) was applied on the shaved backs of 3 New Zealand rabbits. The test site was wrapped with gauze, which was covered with cheesecloth. The test material was in contact with the skin for 4 hours. The sites were scored at 4.5, 24, 48 and 72 hours after they were unwrapped using the method of Draize. No irritation was observed and the test substance was classified as non-irritating. The Primary Irritation Score was 0. /Isopropylated triphenyl phosphates/

For more Non-Human Toxicity Excerpts (Complete) data for TRIS(ISOPROPYLPHENYL)PHOSPHATE (10 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 item

Tris(isopropylphenyl)phosphate is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(1). Aryl phosphates have been shown to hydrolyze, especially under basic conditions(2). Tris(isopropylphenyl)phosphate does not contain chromophores that absorb at wavelengths >290 nm(1) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human Exposure · 2 items

Occupational exposure to tris(isopropylphenyl)phosphate may occur through inhalation and dermal contact with this compound at workplaces where tris(isopropylphenyl)phosphate is produced or used. Use data indicate that the general population may be exposed to tris(isopropylphenyl)phosphate via inhalation of ambient air in the vicinity of fires involving PVC products. (SRC)

NIOSH (NOES Survey 1981-1983) has statistically estimated that 988 workers (797 of these were female) were potentially exposed to tri-(4-isopropylphenyl)phosphate in the US(1). /Tri-(4-isopropylphneyl)phosphate/

Environmental Fate/Exposure Summary · 1 item

Tris(isopropylphenyl)phosphate's production and use as a flame retardant primarily in PVC plastics may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure for the 4-isomer of 2.1X10-8 mm Hg at 25 °C indicates tris(isopropylphenyl)phosphate will exist solely in the particulate phase in the atmosphere. Particulate-phase tris(isopropylphenyl)phosphate will be removed from the atmosphere by wet and dry deposition. Tris(isopropylphenyl)phosphate does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight. If released to soil, tris(isopropylphenyl)phosphate is expected to be immobile based upon an estimated Koc of 1.2X10+6. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.9X10-7 atm-cu m/mole for the 4-isomer. Tris(isopropylphenyl)phosphate is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks indicating that biodegradation is not an important environmental fate process in soil or water. If released into water, tris(isopropylphenyl)phosphate is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. A BCF range of 6.9 to 42 suggests bioconcentration in aquatic organisms is low. Hydrolysis is expected to be an important environmental fate process since this compound contains functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to tris(isopropylphenyl)phosphate may occur through inhalation and dermal contact with this compound at workplaces where tris(isopropylphenyl)phosphate is produced or used. Use data indicate that the general population may be exposed to tris(isopropylphenyl)phosphate via inhalation of ambient air in the vicinity of fires involving PVC products. (SRC)

Antidote and Emergency Treatment · 3 items

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

Safety data

ridadr
3082
hazard_class
9
packing_group
III