cis-Stilbene (HCID 5356785)

Überblick

Cis-stilbene is an oily yellow liquid. Freezing point 5 °C. Insoluble in water. Soluble in ethanol. Unstable relative to the trans isomer, which is a solid with a melting point of 122-124 °C.

Namen und Bezeichner

Bevorzugter Name: cis-Stilbene
IUPAC: (Z)-stilbene
Lokaler Name: cis-Stilben
Englischer Name: cis-Stilbene
Summenformel: C14H12
Molmasse: 180.25

Namen und Synonyme

cis-Stilbene(Z)-1,2-Diphenylethene(Z)-Stilbene645-49-8cis-1,2-DiphenylethyleneIsostilbenecis-DiphenyletheneStilbene, (Z)-Z-stilbene[(Z)-2-Phenylethenyl]benzene(Z)-1,2-DiphenylethyleneCCRIS 5932

Weitere Namen anzeigen

cis-1,2-DiphenyletheneStilbebeNsc66424CIS-BIBENZALCIS-STILBEBEDibenzal(cis)

DTXSID5026049Benzene, 1,1'-(1,2-ethenediyl)bis-, (Z)-HSDB 4270Stilbene, cis-EINECS 211-445-7NSC 66424TTG5048Y3KBenzene, 1,1'-(1Z)-1,2-ethenediylbis-

Datenbank-Bezeichner

CAS: 645-49-8
PubChem CID: 5356785
DTXSID: DTXSID5026049
ChEMBL: CHEMBL393702
ChEBI: CHEBI:36008
UNII: TTG5048Y3K
EC Number: 211-445-7
Nikkaji: J7.069F

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 4,8
Polarare Oberfläche (TPSA): 0 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 0
Frei drehbare Bindungen: 2
Schwere Atome: 14
Formalladung: 0
Komplexität: 148

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Aromatic Hydrocarbons

SpringerMaterials Properties13C nuclear magnetic resonance spectrum

Color/Form · 2 Einträge

LIQUID

YELLOW OIL

SolubilityCOMPLETELY SOL IN COLD ABSOLUTE ALCOHOL

Boiling Point · 2 Einträge

293 °F at 13 mmHg (NTP, 1992)

135 DEG @ 10 MM HG

Melting Point · 2 Einträge

41 to 43 °F (NTP, 1992)

1 °C

Physikochemische Eigenschaften

Schmelzpunkt: -5 °C · -5°C
Siedepunkt: 82 · 82-84 °C0.4 mm Hg(lit.)
Dichte: 1.011 g/mL · 1.011 g/mL at 25 °C(lit.)
Brechungsindex: 20 · n20/D 1.622(lit.)
Flammpunkt: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
Aggregatzustand: clear liquid
Farbe: Colorless to Yellow to Green
Wasserlöslichkeit: Immiscible with water. Miscible with ethanol.
Merck: 14 · 14,8817
BRN: 1616739 · 1616739
Stabilität: Stable. Combustible. Incompatible with strong oxidizing agents.
InChI: 1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11-
InChIKey: PJANXHGTPQOBST-QXMHVHEDSA-N
SMILES: c1ccc(cc1)\C=C/c2ccccc2
LogP: 4.83 · 4.830 (est)
CAS Datenbank: 645 · 645-49-8(CAS DataBase Reference)
EPA chemische Informationen: cis-Stilbene (645-49-8)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (88.4%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: Benzene, 1,1'-(1,2-ethenediyl)bis-, (Z)-

Benzene, 1,1'-(1Z)-1,2-ethenediylbis-: Does not have an individual approval but may be used under an appropriate group standard

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

Hazards SummaryEffects after intraperitoneal injection of rats include liver changes; TDLo = 361 mg/kg; [RTECS] An irritant; [MSDSonline] See trans-1,2-Diphenylethylene.

Reactive GroupHydrocarbons, Aromatic

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

Air and Water ReactionsSensitive to prolonged exposure to air and light [Lancaster]. Insoluble in water.

Sicherheit und Schutzausrüstung

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

First Aid · 1 Eintrag

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.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill 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 ethanol 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.

Personal Protective Equipment (PPE) · 1 Eintrag

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)

Toxikologische Informationen

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Sicherheitsdaten

wgk: 3
hs_code: 29029090
RTECS-Nr.: DA0513600
risk_code: 36/38
hazard_code: Xi
safety_code: 26-36
Speicherklasse: 10 - Combustible liquids
Giftige Stoffe Daten: 645-49-8(Hazardous Substances Data)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 3 Einträge

CIS-STILBENE IS CONVERTED VIA THE CIS-EPOXIDE BY RABBIT-LIVER MICROSOMES INTO THREO-1,2-DIPHENYL-1,2-ETHANEDIOL, & TRANS-STILBENE VIA THE TRANS-EPOXIDE INTO THE CORRESPONDING MESO-ISOMER. A SOL FRACTION FROM RABBIT LIVER CATALYZED INTERCONVERSION OF THESE ISOMERIC DIOLS VIA BENZOIN FORMATION.

CIS-STILBENE IS OXYGENATED BY RABBIT-LIVER MICROSOMES TO CIS-STILBENE OXIDE... OBSERVED ONLY AFTER VERY SHORT INCUBATION TIMES. RATIO OF OXYGENASE TO HYDRATASE ACTIVITIES DECR RAPIDLY WITH TIME SO THAT THREO-STILBENE GLYCOL IS MAJOR...PRODUCT.

INCUBATION OF CIS-STILBENE WITH RABBIT LIVER MICROSOMES IN PRESENCE OF NADPH YIELDED THREO-STILBENE GLYCOL & A TRACE OF MESOSTILBENE GLYCOL.

Verwendung und Herstellung

Uses · 2 Einträge

Used as a research chemical; [HSDB]

RESEARCH CHEMICAL

U.S. Exports · 2 Einträge

(1977) No Data

(1979) No Data

U.S. Imports · 2 Einträge

(1977) No Data

(1979) No Data

U.S. Production · 2 Einträge

(1977) NOT COMMERCIALLY PRODUCED IN US

(1979) NOT COMMERCIALLY PRODUCED IN US

Methods of Manufacturing · 1 Eintrag

...CIS-FORM BY COPPER-CHROMITE DECARBOXYLATION OF ALPHA-PHENYLCINNAMIC ACID: BUCKLES, WHEELER, ORG SYN COLL VOL IV, 857 (1963). SYNTH OF CIS...FORMS BY WITTIG REACTION & BY DECARBOXYLATION OF PHENYLCINNAMIC ACIDS: WHEELER, BATLLE DE PABON, J ORG CHEM 30, 1473 (1965).

Anwendungen

Verwendencis-Stilbene: stilbene and its natural derivatives such as resveratrol and vitisins inhibits Staphylococcus aureus hemolytic activity and biofilm formation without affecting its bacterial growth