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trans-Stilbene

trans-Stilbene structure

trans-Stilbene 

structure
  • CAS No:

    103-30-0

  • Formula:

    C14H12

  • Chemical Name:

    trans-Stilbene

  • Synonyms:

    Benzene,1,1′-(1E)-1,2-ethenediylbis-;Stilbene,(E)-;Benzene,1,1′-(1,2-ethenediyl)bis-,(E)-;Stilbene,trans-;1,1′-(1E)-1,2-Ethenediylbis[benzene];trans-α,β-Diphenylethylene;trans-1,2-Diphenylethylene;trans-Stilbene;trans-1,2-Diphenylethene;(E)-1,2-Diphenylethylene;trans-Diphenylethene;(E)-1,2-Diphenylethene;(E)-Stilbene;NSC 2069

  • Categories:

    Specialty Chemicals

Description

PHYSICAL DESCRIPTION: Off-white crystals. Melting point of 122-124°C. Shows blue fluorescence. (NTP, 1992)


Trans-stilbene appears as off-white crystals. Melting point of 122-124°C. Shows blue fluorescence. (NTP, 1992)


Trans-stilbene appears as off-white crystals. Melting point of 122-124°C. Shows blue fluorescence. (NTP, 1992)|Stilbene is an olefinic compound and a member of benzenes.|Organic compounds that contain 1,2-diphenylethylene as a functional group.

trans-Stilbene Basic Attributes

180.25

180.25

203-098-5

3FA7NW80A0

2069

3077

DTXSID4026050

Crystals from 95% ethanol|Colorless or slightly yellow crystals

2902909090

Characteristics

0

4.8

Trans-stilbene appears as off-white crystals. Melting point of 122-124°C. Shows blue fluorescence. (NTP, 1992)

0.9707 g/cm3

124 °C

306-307 °C @ Press: 760 Torr

128.5±9.7 °C

1.659

2.90X10-1 mg/l in water at 25 deg C

2-8ºC

8.81X10-4 mm Hg @ 25 deg C

Sensitive to air and light. Insoluble in water.

Hydrocarbons, Aliphatic Unsaturated

TRANS-STILBENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release gaseous hydrogen.

Net heat of combustion of liquid = 17176 Btu/lb at 77 °F

Heat of vaporization = 133.91 Btu/lb at 583.70 °F.

Critical temperature = 982.13 °F; critical pressure = 397.40 psia

Safety Information

9

3077

2

9

S26-S36/37-S61

WJ4926500

Xn,N

VOLATILE WITH STEAM.

P273-P305 + P351 + P338

H302-H319-H411

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.

Flash point data for this chemical are not available, however it is probably combustible. (NTP, 1992)

|Warning|H302 (97.83%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P391, and P501|Aggregated GHS information provided by 48 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

LD50 Mouse oral 920 mg/kg|LD50 Mouse ip 6050 mg/kg

trans-1,2-Diphenylethylene's production and use in the manufacture of dyes and optical bleaches, and as phosphors and scintillators(1) 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 9,850(SRC), determined from a measured log Kow of 4.81(2) and a regression-derived equation(3), indicates that trans-1,2-diphenylethylene is expected to be immobile in soil(SRC). Volatilization of trans-1,2-diphenylethylene from moist soil surfaces is expected given an estimated Henry's Law constant of 7.2X10-4 atm-cu m/mole(SRC), determined from a water solubility of 0.29 mg/l(4) and a vapor pressure of 8.8X10-4 at 25 °C(5), however, adsorption to soil may attenuate this process(SRC). trans-1,2-Diphenylethylene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9,850(SRC), determined from a measured log Kow of 4.81(2) and a regression-derived equation(3), indicates that trans-1,2-diphenylethylene is expected to adsorb to suspended solids and sediment(SRC). trans-1,2-Diphenylethylene is expected to volatilize from water surfaces(3) based on an estimated Henry's Law constant of 7.2X10-4 atm-cu m/mole(SRC), determined from a water solubility of 0.29 mg/l(4) and a vapor pressure of 8.8X10-4 at 25 °C(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 140 hours, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment. The estimated volatilation half-life from a model pond is 90 days if adsorption is considered(6). According to a classification scheme(7), an estimated BCF of 1,000(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is very high(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trans-1,2-diphenylethylene, which has a vapor pressure of 8.81X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase trans-1,2-diphenylethylene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules(SRC). The half-life for the reaction in air with hydroxyl radicals is estimated to be 6 hours(SRC), calculated from its rate constant of 6.8X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). The half-life for the reaction in air with ozone is estimated to be 1 hour(SRC), calculated from its rate constant of 2.5X10-16 cu cm/molecule-sec(SRC), estimated with a structure estimation method(3).

The rate constant for the vapor-phase reaction of trans-1,2-diphenylethylene with photochemically-produced hydroxyl radicals has been estimated as 6.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of trans-1,2-diphenylethylene with ozone molecules has been estimated as 2.5X10-16 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of 1 hour at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). trans-1,2-Diphenylethylene was converted to trans-1,2-diphenylethylene oxide (ratio of conversion was 44%) after 1 hour of irradiation with a xenon lamp (operating through a Pyrex filter) in the presence of nitrogen dioxide in air(2). trans-1,2-Diphenylethylene is not expected to undergo hydrolysis(SRC) due to the lack of functional groups to hydrolyze(3).

An estimated BCF of 1,000 was calculated for trans-1,2-diphenylethylene(SRC), using a log Kow of 4.81(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(SRC).

The Koc of trans-1,2-diphenylethylene is estimated as 9,850(SRC), using a log Kow of 4.81(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that trans-1,2-diphenylethylene is expected to be immobile in soil.

The Henry's Law constant for trans-1,2-diphenylethylene is estimated as 7.2X10-4 atm-cu m/mole(SRC) based upon its vapor pressure, 8.81X10-4 mm Hg(1), and water solubility, 0.29 mg/l(2). This Henry's Law constant indicates that trans-1,2-diphenylethylene is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 140 hours(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 90 days if adsorption is considered(4). trans-1,2-Diphenylethylene's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC), however, adsorption to soil may attenuate this process(SRC). trans-1,2-Diphenylethylene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

DRINKING WATER: Trans-1,2-diphenylethylene was detected in drinking water samples from Ottawa in January and February, 1978(1). Trans-1,2-diphenylethylene was quantitatively detected in drinking water in Poplarville, Mississippi in March 1989; Philadelphia, PA in February 1976; and in Ottumwa, Iowa in September 1976(2).

Occupational exposure to trans-1,2-diphenylethylene may occur through inhalation of dust particles and dermal contact with this compound at workplaces where it is produced or used. Limited monitoring data indicate that non-occupational exposure can occur from the ingestion of contaminated drinking water. (SRC)

Drug Information

TRANS-STILBENE GIVES 4-HYDROXY-TRANS-STILBENE IN RABBIT & GUINEA PIG. /FROM TABLE/|STUDY OF RING-HYDROXYLATED METABOLITES OF TRANS-STILBENE /SHOWS/...URINE CONTAINS RANGE OF POLYHYDROXYLATED BIBENZYL DERIVATIVES. ...EVIDENCE /SUGGESTS/ THAT BIBENZYL COMPD ARE FORMED BY MICROFLORAL REDUCTION OF STILBENES.|IN GUINEA PIGS & RABBITS, /TRANS-STILBENE/ BIOTRANSFORMATION INTO 4-HYDROXY-, 4,4'-DIHYDROXY-, 3-HYDROXY-4-METHOXY-, & 3-METHOXY-4-HYDROXYSTILBENES OCCURS... HOWEVER, IN MOUSE ONLY LIMITED CONVERSION TO 4,4'-DIHYDROXY- TAKES PLACE.|SCHEME FOR OXIDATIVE CLEAVAGE OF ETHYLENIC LINKAGE OF STILBENE IS PRESENTED.|For more Metabolism/Metabolites (Complete) data for TRANS-1,2-DIPHENYLETHYLENE (6 total), please visit the HSDB record page.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Derivative, Stilbene

trans-Stilbene Use and Manufacturing

Methods of Manufacturing

Trans-form prepd by Clemmensen redn of benzoin: Shriner, Berger, Org Syn Coll Vol III, 786 (1955); cis-form by copper-chromite decarboxylation of alpha-phenylcinnamic acid: Buckles, Wheeler, Org Synth Coll Vol IV, 857 (1963).|Synthesis of cis- and trans-forms by Wittig reaction and decarboxylation of phenylcinnamic acids: Wheeler, Batlle de Pabon, J Org Chem 30, 1473 (1965).|By passing toluene over hot lead oxide. Method of purification: crystallization; zone melting used for very pure crystals.

Uses

Mfr of dyes and optical bleaches; crystals are used as phosphors and scintillators

Production

(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US

Grades: technical; pure.

Benzene, 1,1'-(1E)-1,2-ethenediylbis-: ACTIVE

Computed Properties

Molecular Weight:180.24
XLogP3:4.8
Rotatable Bond Count:2
Exact Mass:180.093900383
Monoisotopic Mass:180.093900383
Heavy Atom Count:14
Complexity:149
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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