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Tris(2,6-xylenyl)phosphate

HCID 8460
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
121-06-2
Standard SMILES
Cc1cccc(C)c1OP(=O)(Oc1c(C)cccc1C)Oc1c(C)cccc1C
InChIKey
QLORRTLBSJTMSN-UHFFFAOYSA-N
Molecular formula
C24H27O4P
Average molar mass
410.4 g/mol
Monoisotopic mass
410.16469634

Names & identifiers

Preferred name
Tris(2,6-xylenyl)phosphate
IUPAC
tris(2,6-dimethylphenyl) phosphate
English name
2-bis(2,6-dimethylphenoxy)phosphoryloxy-1,3-dimethyl-benzene
Molecular formula
C24H27O4P
Molecular weight
410.44

Names & synonyms

121-06-2Tri(2,6-xylenyl)phosphateTri-2,6-xylyl phosphate2,6-Xylyl phosphateTri(2,6-dimethylphenyl) phosphateTris(2,6-dimethylphenyl)phosphate2,6-Xylenol, phosphate (3:1)TRIS(2,6-XYLENYL)PHOSPHATEPhenol, 2,6-dimethyl-, phosphate (3:1)2,6-Dimethylphenol phosphate (3:1)HSDB 3910Phosphoric acid, tris(dimethylphenyl) ester
Show more names
TRIS-(2,6-DIMETHYLPHENYL)PHOSPHATEPhosphoric acid tri(2,3-dimethylphenyl) esterTris(2,6-dimethylphenyl) phosphate in isooctane2-bis(2,6-dimethylphenoxy)phosphoryloxy-1,3-dimethyl-benzene
NSC 152822,6-Xylyl phosphate, (C8H9O)3POBRN 3491836R4QU4542WQAI3-26997NSC-152824-06-00-03121 (Beilstein Handbook Reference)2,6-XYLYL PHOSPHATE ((C8H9O)3PO)

Database identifiers

CAS
121-06-2
PubChem CID
8460
DTXSID
DTXSID70891326

Properties

Computed structural properties

XLogP
7.2
Topological polar surface area
44.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
6
Heavy atoms
29
Formal charge
0
Complexity
461

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organophosphates, Other
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
DensityInflammable; pour point= -60 °C; density: 1.14 kg/l /Trixylyl phosphate/
Color/FormWax
Solubility · 2 items

log Kow= 5.63; water solubility= 0.89 ppm at 25 °C /Kronitex TXP/

Sol in benzene; slightly soluble in ethanol and hexane.

Boiling Point262-264 °C @ 6 mm Hg
Melting Point137.8 °C
Vapor Pressure0.00000001 [mmHg]
Physical DescriptionSolid; [HSDB]

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.

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 153 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryThere are 5 isomers of Tris(x,y-xylenyl)phosphate; [HSDB] See Tris(3,5-xylenyl)phosphate.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

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 1.1X10+5(SRC), determined from a structure estimation method(2), indicates that tris(2,6-xylenyl)phosphate is expected to be immobile in soil(SRC). Volatilization of tris(2,6-xylenyl)phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.2X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Tris(2,6-xylenyl)phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.4X10-9 mm Hg(SRC), determined from a fragment constant method(4). Tris(2,6-xylenyl)phosphate may be susceptible to hydrolysis in alkaline soils based on aquatic data for other triaryl phosphates(6). Biodegradation of aryl phosphates may occur slowly in the environment based on activated sludge tests showing 13 to 65% biodegradation of trixylenyl phosphate over 14 and 25 weeks, respectively(5).

Chemistry & industry

Uses & manufacturing

UsesNon-flammable hydraulic fluid (steel works, furnaces, mines); polyvinyl chloride plasticizer /Trixylyl phosphate/
ImpuritiesTri-o-cresyl phosphate and other o-cresyl-components /TXP formulations/
U.S. Imports · 2 items

(1981) 90,401 million pounds /Trixylyl phosphate/

(1983) 9,921 million pounds /Trixylyl phosphate/

U.S. ProductionIn million pounds: (1980) 5.0; (1981) 4.1; (1982) 3.4; (1983) 3.4; (1984) 3.7 /Trixylyl phosphate/
Methods of ManufacturingXylenol, mixed + phosphorus oxychloride (dehydrochlorination) /Trixylyl phosphate/
General Manufacturing Information · 2 items

Phenol, 2,6-dimethyl-, phosphate (3:1): ACTIVE

TRI-2,6-XYLYL PHOSPHATE IS EFFECTIVE AS SYNERGIST OF MALATHION AGAINST RESISTANT HOUSEFLIES AND MOSQUITOES.

Suppliers3 total

山东鑫牧源化工科技有限公司19105383610 · [email protected]
Alfa Chemistry+1-5166625404 · [email protected]
安阳鸿蒙新材料有限公司19588588067 · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
UNII
R4QU4542WQ
EC Number
654-405-8
Nikkaji
J173.957C
Melting point
137.8 °C · 137.8°C
Boiling point
243.75 °C · 243.75°C (estimate)
Density
1.17 · 1.170 (estimate)
form
solid
Henry's Law Constant
1.4 · 1.4×102 mol/(m3Pa) at 25℃, HSDB (2015)
FDA UNII
4 QU4542WQ · R4QU4542WQ
EPA Substance Registry System
2 · Phenol, 2,6-dimethyl-, phosphate (3:1) (121-06-2)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
335 · H335-H319-H315-H413
Precautionary statements
264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
TSCA
TSCA listed
Hazardous Substances Data
121 · 121-06-2(Hazardous Substances Data)

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.1X10+5(SRC), determined from a structure estimation method(2), indicates that tris(2,6-xylenyl)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 7.2X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Tris(2,6-xylenyl)phosphate may be stable to degradation in waters having slightly acidic and neutral pH values; however, decomposition of tris(2,6-xylenyl)phosphate may occur in alkaline waters(8). According to a classification scheme(5), an estimated BCF of 720(SRC), from a log Kow of 5.63(6), measured for Kronitex TXP, a commercial product containing a mixture of trixylenyl and triethylphenyl phosphate isomers, and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation of aryl phosphates may occur slowly in the environment based on activated sludge tests showing 13 to 65% biodegradation of trixylenyl phosphate over 14 and 25 weeks, respectively(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tris(2,6-xylenyl)phosphate, which has an estimated vapor pressure of 6.4X10-9 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(2,6-xylenyl)phosphate may be removed from the air by wet and dry deposition(SRC).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for tris(2,6-xylenyl)phosphate can be estimated to be 1.1X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that tris(2,6-xylenyl)phosphate is expected to be immobile in soil.

Fish/Seafood ConcentrationsTrixylenyl phosphate, isomer not specified, was detected in sturgeon from the Columbia River near Longview, OR at a concentration of 0.08 ng/g(1).
Artificial Pollution Sources · 1 item

Specific use information for tris(2,6-xylenyl)phosphate was not located. However, trixylenyl phosphates are produced and used as flame retardants and plasticizers(1) and hydraulic fluids(2) and tris(2,6-xylenyl)phosphate may be released to the environment through various waste streams during such production and/or use(SRC).

Environmental Biodegradation · 1 item

No specific biodegradation data were located for tris(2,6-xylenyl)phosphate in either soil or aquatic systems. TXP (trixylenyl phosphate) added at 3 mg/L/day was biodegraded by 65% over 14 weeks in the SCAS test using activated sludge as an inoculum; at an initial concentration of 13 mg/L/day, using the same test method, only 13% biodegradation was reported over a 25-week period(1). Kronitex TXP is a commercial product primarily consisting of the 2,5-, 3,4-, 3,5- and/or the 2,4-isomers of trixylylphosphates along with mixes of xylenyl phosphates or xylenyl/ethylphenyl phosphates(2). The degradation of specific isomers within the mixture was not quantified(1). In general the biodegradability of triaryl phosphates decreases with increasing number and size of substituent groups on the phenolic ring(1,3). Therefore based on the evidence pertaining to TXP(1), tris(2,6-xylenyl)phosphate may be susceptible to biodegradation(1).

Environmental Bioconcentration · 1 item

An estimated BCF value of 720 was calculated for tris(2,6-xylenyl)phosphate(SRC) using a log Kow of 5.63(2) measured for Kronitex TXP, a commercial product primarily consisting of the trixylylphosphates along with mixes of xylenyl phosphates or xylenyl/ethylphenyl phosphates(1), and a regression-derived equation(3). The actual BCF of tris(2,6-xylenyl)phosphate would be expected to be slightly higher, for a greater Kow value would be anticipated for tris(2,6-xylenyl)phosphate due to the presence of lower molecular weight constituents among the TXP mixture. This is in keeping with this class of chemicals as analogous tri-p-cresyl phosphate has measured BCFs of 1,420 and 928 in rainbow trout and fathead minnows, respectively(4). According to a classification scheme(5), this BCF value suggests the potential for bioconcentration of tris(2,6-xylenyl)phosphate in aquatic organisms is high(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for tris(2,6-xylenyl)phosphate is estimated as 7.2X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tris(2,6-xylenyl)phosphate is expected to be essentially nonvolatile from water surfaces(2). Tris(2,6- xylenyl)phosphate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Tris(2,6-xylenyl)phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.4X10-9 mm Hg(SRC), determined from a fragment constant method(3).

Environmental Abiotic Degradation · 1 item

Triaryl phosphates are generally stable to hydrolysis at neutral pH values and undergo moderate hydrolysis in acidic solutions(1). Triaryl phosphates will degrade at appreciable rates in natural waters under alkaline conditions to apparently stable, water soluble, anionic diesters such as diaryl phosphates(1). No persistence data specific to tris(2,6-xylenyl)phosphate were available; however, based on data pertaining to triphenyl- and tricresyl- phosphates(1), tris(2,6-xylenyl)phosphate is expected to hydrolyze in natural alkaline waters. Tris(2,6-xylenyl)phosphate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

Probable Routes of Human Exposure · 1 item

Specific use information pertaining to tris(2,6-xylenyl)phosphate was not available, although triaryl phosphates are generally employed as flame-retardants and plasticizers(1) and in hydraulic fluids(2). Occupational exposure to tris(2,6-xylenyl)phosphate may occur through inhalation of dust particles and dermal contact with this compound at workplaces where tris(2,6-xylenyl)phosphate is produced or used(SRC).

Environmental Fate/Exposure Summary · 1 item

Tris(2,6-xylenyl)phosphate's production and use as a flame-retardant, plasticizer, or hydraulic fluid may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 6.4X10-9 mm Hg at 25 °C indicates tris(2,6-xylenyl)phosphate will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase tris(2,6-xylenyl)phosphate will be removed from the atmosphere by wet and dry deposition. If released to soil, tris(2,6-xylenyl)phosphate is expected to be immobile based upon an estimated Koc of 1.1X10+5. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 7.2X10-8 atm-cu m/mole. Tris(2,6-xylenyl)phosphate is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation of aryl phosphates may occur slowly in the environment based on activated sludge tests showing 13 to 65% biodegradation of trixylenyl phosphate over 14 and 25 weeks, respectively. Under alkaline conditions in soil and water environments, appreciable abiotic degradation may occur via hydrolysis. If released into water, tris(2,6-xylenyl)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. An estimated BCF of 720 suggests the potential for bioconcentration in aquatic organisms is high. Occupational exposure to tris(2,6-xylenyl)phosphate may occur through inhalation of dust particles and dermal contact with this compound at workplaces where tris(2,6-xylenyl)phosphate is produced or used. (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 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 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

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

Safety data

tsca
TSCA listed
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H335-H319-H315-H413
Precautionary statements
P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
Hazardous Substances Data
121-06-2(Hazardous Substances Data)