Bis(2-ethylhexyl) phosphate
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Bis(2-ethylhexyl) phosphate
structure -
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CAS No:
298-07-7
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Formula:
C16H35O4P
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Chemical Name:
Bis(2-ethylhexyl) phosphate
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Synonyms:
Phosphoric acid,bis(2-ethylhexyl) ester;1-Hexanol,2-ethyl-,hydrogen phosphate;Bis(2-ethylhexyl) phosphate;Di(2-ethylhexyl)orthophosphoric acid;2-Ethyl-1-hexanol hydrogen phosphate;HDEHP;Di-2-ethylhexyl hydrogen phosphate;Bis(2-ethylhexyl) hydrogen phosphate;Bis(2-ethylhexyl) orthophosphate;O,O-Bis(2-ethylhexyl)phosphoric acid;O,O-Di(2-ethylhexyl)phosphoric acid;Hydrogen bis(2-ethylhexyl) phosphate;Di(2-ethylhexyl) phosphate;D 2EHPA;DP 8R;P 204 (acid);P 204;LB 58;Hostarex PA 216;Phosphoric acid di(2-ethylhexyl) ester;Orthophosphoric acid 2-ethylhexyl alcohol diester;Di(2-ethylhexyl)phosphoric acid;Dioctyl orthophosphate;Dioctyl phosphate;Dioctyl hydrogen phosphate;DEHAP;JB 58;HDEHPA;TOPS 99;DP 8;A 208 (phosphate);A 208;Baysolvex D 2EHPA;Phoslex A 208;1179814-34-6
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CAS No:
Description
clear colorless to light yellow liquid
Di-(2-ethylhexyl)phosphoric acid is an odorless light yellow liquid. Floats on water. (USCG, 1999)|Liquid|COLOURLESS OR AMBER LIQUID.
Di-(2-ethylhexyl)phosphoric acid is an odorless light yellow liquid. Floats on water. (USCG, 1999)
Bis(2-ethylhexyl) phosphate Basic Attributes
322.42000
322.42
225-615-3
2Z4W0L3H06
1412
1902
DTXSID1027134
Viscous liquid|Amber liquid
29190090
Characteristics
65.57000
5.55280
Odorless light yellow liquid.
0.973 g/cm3 @ Temp: 25 °C
-50 °C
48ºC (12 mmHg)
137ºC
1.44-1.444
H2O: slightly soluble
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Corrosives ar
0mmHg at 25°C
LD50 orally in Rabbit: 4940 mg/kg LD50 dermal Rabbit 1250 mg/kg
ODORLESS
Henry's Law constant = 4.1X10-8 atm-cu m/mol at 25 °C (est)
pKa = 1.47 (est)
Decomposes at 1 atm; estimated liquid-water interfacial tension 30 dynes/cm= 0.030 n/m a 20 °C|Hydroxyl radical reaction rate constant = 6.2X10-11 cu cm/molec-sec at 25 °C (est)
No rapid reaction with air. No rapid reaction with water.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Organophosphates, such as DI-(2-ETHYLHEXYL)PHOSPHORIC ACID, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Mildly corrosive to most metals; may form flammable hydrogen gas (USCG, 1999).
-13,970 BTU/LB= -7,760 CAL/G= -325X10+5 J/KG
Mildly corrosive to most metals
Safety Information
III
8
UN 1902
1
R21; R34
S25-S36/37/39-S45
TB7875000
C
Separated from metals.
Stable under normal temperatures and pressures.
P280-P305 + P351 + P338-P310
H312-H314
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.
The U.S. high production volume (HPV) chemicals are those which are manufactured in or imported into the United States in amounts equal to or greater than one million pounds per year. Robust Summaries include health effects, ecotoxicity data, and environment fate information for selected chemicals. EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Available from: http://www.epa.gov/chemrtk/viewsrch.htm on phosphates as of January 19, 2006. /Phosphates/|WHO; Diseases Caused by Phosphorus and Its Toxic Compounds; Early Detection of Occupational Diseases pg 53-62 (1986). Review of diseases and health related effects resulting from exposure to phosphorus or phosphorus cmpd.
Special Hazards of Combustion Products: Irritating phosphorus oxides may be released. (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
|Danger|H302+H312 (43.79%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]|P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P362, P363, P405, and P501|Aggregated GHS information provided by 1049 companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P405, and P501
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Neutralizing Agents for Acids and Caustics: Sodium bicarbonate or lime solution (USCG, 1999)
Goggles or face shield; rubber gloves; protective clothing. (USCG, 1999)|Goggles or face shield; rubber gloves; protective clothing.|Respiratory protection (supplied-air respirator with full facepiece or self-contained breathing apparatus) should be available where these compounds are manufactured or used and should be worn in case of emergency and overexposure. /Phosphorus compounds/
Slight, when exposed to heat or flame.|May form flammable hydrogen gas.
Extinguish with dry chemical, alcohol foam or carbon dioxide; water or foam may cause frothing.
Collect leaking liquid in covered dry, plastic containers. Absorb remaining liquid in sand or inert absorbent and remove to safe place.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Diisooctyl acid phosphate/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. 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. /Diisooctyl acid phosphate/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Diisooctyl acid phosphate/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Diisooctyl acid phosphate/|For more DOT Emergency Guidelines (Complete) data for BIS(2-ETHYLHEXYL) PHOSPHATE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Contact with liquid irritates eyes. ... Also causes skin irritation on contact. Vapors are non-irritating to the eyes and throat.
Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking liquid in covered dry plastic containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Separated from metals.
Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.
The substance is corrosive to the eyes and skin.
NO open flames.
PREVENT GENERATION OF MISTS! STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!
Use local exhaust.
Protective gloves. Protective clothing.
Wear face shield.
| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.
Toxicity
LD50 Rabbit ip 1250 mg/kg bw|LD50 Rat oral 4,940 mg/kg bw|LD50 Rabbit dermal 1200 mg/kg bw/24 hr|LD50 Rat ip 50 mg/kg
/AQUATIC SPECIES/ The toxicity was studied in Chlorella emersonii (green alga), Salmo gairdneri and bacteria Cellulomonas and Sporocytophaga myxococcoides. Bis(2-ethylhexyl) phosphate inhibited growth at concn in range 0.3-100 mg/L.
Bis(2-ethylhexyl) phosphate's production and use as a metal extraction agent, a textile lubricant and antistatic agent, an extreme pressure additive, an intermediate for wetting agents and detergent, and a feedstock for chemical synthesis(1-3) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.7X10+4(SRC), determined from a structure estimation method(2), indicates that bis(2-ethylhexyl) phosphate is expected to be immobile in soil(SRC). The estimated pKa of bis(2-ethylhexyl) phosphate is 1.47(3), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of bis(2-ethylhexyl) phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.1X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Bis(2-ethylhexyl) phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-8 mm Hg(SRC), determined from a fragment constant method(6). Bis(2-ethylhexyl) phosphate, present at 100 mg/L, reached 0-17% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(7) and therefore this compound may not biodegrade rapidly in terrestrial environments(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.7X10+4(SRC), determined from a structure estimation method(2), indicates that bis(2-ethylhexyl) 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 4.1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The estimated pKa of bis(2-ethylhexyl) phosphate is 1.47(5), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon than their neutral counterparts(6). The sorption of organophosphorus compounds in soil depends on both organic matter and clay content of soil and the sorption increases as the pH of soil decreases(7). In a study on the sorption of bis(2-ethylhexyl) phosphate on kaolinite and amectite, the acidic phosphoric group reacted rapidly and almost irreversibly with the surface cations of the clay mineral structure(7), therefore, adsorption to suspended solids and sediments is expected to be pH dependent. According to a classification scheme(8), measured BCF values of 1-2.4 and 2.7-6.0(9) suggest the potential for bioconcentration in aquatic organisms is low(SRC). Bis(2-ethylhexyl) phosphate, present at 100 mg/L, reached 0-17% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(9) and therefore this compound is not expected to biodegrade rapidly in aquatic environments(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(2-ethylhexyl) phosphate, which has an estimated vapor pressure of 4.7X10-8 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 bis(2-ethylhexyl) phosphate may be removed from the air by wet or dry deposition(SRC). Bis(2-ethylhexyl) phosphate does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of bis(2-ethylhexyl) phosphate with photochemically-produced hydroxyl radicals has been estimated as 6.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Bis(2-ethylhexyl) phosphate is expected to undergo hydrolysis in the environment due to the presence of functional groups (esters) that hydrolyze under environmental conditions(2). The hydrolysis half-life of the analog dimethyl phosphoric acid in neutral solution at 100 °C was found to be 2.4 days(3). Increasing the carbon chain substituent on phosphoric acid (as in the case of bis(2-ethylhexyl) phosphate) may not increase the rate of hydrolysis(3). Bis(2-ethylhexyl) phosphate does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
4.37|BCF values of 1-2.4 and 2.7-6.0 were measured for bis(2-ethylhexyl) phosphate at concentrations of 1 and 0.1 mg/L, respectively, using carp which were exposed over an 6-week period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of bis(2-ethylhexyl) phosphate can be estimated to be 1.7X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that bis(2-ethylhexyl) phosphate is expected to be immobile in soil. The estimated pKa of bis(2-ethylhexyl) phosphate is 1.47(3), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon than their neutral counterparts(4). The sorption of organophosphorus compounds in soil depends on both organic matter and clay content of soil and the sorption increases as the pH of soil decreases(5). In a study on the sorption of bis(2-ethylhexyl) phosphate on kaolinite and amectite, the acidic phosphoric group reacted rapidly and almost irreversibly with the surface cations of the clay mineral structure(5).
The Henry's Law constant for bis(2-ethylhexyl) phosphate is estimated as 4.1X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bis(2-ethylhexyl) phosphate is expected to be essentially nonvolatile from water surfaces(2). Bis(2-ethylhexyl) phosphate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Bis(2-ethylhexyl) phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.7X10-8 mm Hg(SRC), determined from a fragment constant method(3).
Occupational exposure to bis(2-ethylhexyl) phosphate may occur through dermal contact with this compound at workplaces where bis(2-ethylhexyl) phosphate is produced or used. (SRC)
Drug Information
Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/|Toxicants can be absorbed by inhalation, ingestion, and skin penetration. ...All undergo hydrolytic degradation in liver and other tissues, usually within hours of absorption. Degradation products are of low toxicity, and are excreted in urine and feces. /Organophosphate cholinesterase-inhibiting pesticides/
Plasma & tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric & phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Organophosphorus cmpd/
Contact with liquid irritates eyes and may cause serious injury; consult an eye specialist. Also causes skin irritation on contact. Ingestion produces irritation similar to that caused by strong vinegar. (USCG, 1999)|Corrosives
EYES: immediately flush with plenty of water for at least 15 min.; see a physician. SKIN: immediately flush with plenty of water for at least 15 min. INGESTION: induce vomiting and call a physician. (USCG, 1999)
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
/SRP:/ 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/|/SRP:/ 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/
/SIGNS AND SYMPTOMS/ Causes smarting of skin and first degree burns on short exposure and may cause second degree burns on long exposure. Irritating to skin and eyes.|/SIGNS AND SYMPTOMS/ Inhalation: Burning sensation. Cough. Sore throat.; Skin: Redness. Burning sensation. Pain. Blisters.; Eyes: Redness. Pain. Severe deep burns.
di(2-ethylhexyl)phosphate
The substance can be absorbed into the body by inhalation of its aerosol and through the skin.
Burning sensation. Cough. Sore throat.
Redness. Burning sensation. Pain. Blisters.
Redness. Pain. Severe burns.
Bis(2-ethylhexyl) phosphate Use and Manufacturing
... Produced by chlorinating bis(2-ethylhexyl) phosphonate to give the phosphate diester chloride, followed by hydrolysis, or by saponification of tris(2-ethylhexyl) phosphate|Formerly by reaction of phosphorus oxychloride and 2-ethylhexanol, followed by hydrolysis
Used as a solvent for chromatographic analysis and as an extractant for uranium and beryllium.Used as a rare earth extractant, and used to prepare surfactants.Solvent, used as raw material for rare earth metal extractant, wetting agent and surfactant, plasticizer for plastics.Used in textile, printing and dyeing, daily chemical and other industries.
Extraction Agent
Cleaning and furnishing care products
1,000,000 - 10,000,000 lb|This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|(1972) PROBABLY GREATER THAN 4.54X10+5 G|(1975) PROBABLY GREATER THAN 4.54X10+5 G|(1986) >1 million-10 million pounds|For more U.S. Production (Complete) data for BIS(2-ETHYLHEXYL) PHOSPHATE (8 total), please visit the HSDB record page.
Grades or purity: 92+%
Mining (except oil and gas) and support activities|Phosphoric acid, bis(2-ethylhexyl) ester: ACTIVE
BIS(2-ETHYLHEXYL) HYDROGEN PHOSPHATE IN WASTE WATER IS DETERMINED BY MEASURING THE VIOLET COLOR OF THE ADDUCT FORMED WITH METHYL VIOLET.
Health Hazards -> Corrosives
Computed Properties
Molecular Weight:322.42
XLogP3:5.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:14
Exact Mass:322.22729659
Monoisotopic Mass:322.22729659
Topological Polar Surface Area:55.8
Heavy Atom Count:21
Complexity:260
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
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