1720-32-7

Basic information

• Product Name: 1,6-DIPHENYL-1,3,5-HEXATRIENE
• Synonyms: DPH;DICINNAMYL;1,6-DIPHENYL-1,3,5-HEXATRIENE;1,6-DIPHENYLHEXATRIENE;[(1E,3E,5E)-6-Phenyl-1,3,5-hexatrienyl]benzene;1,1’-(1,3,5-hexatriene-1,6-diyl)bis-benzen;1,3,5-Hexatriene, 1,6-diphenyl-;1,3,5-hexatriene,1,6-diphenyl-
• CAS NO: 1720-32-7
• Molecular Formula: C₁₈H₁₆
• Molecular Weight: 232.32
• EINECS: 217-011-3
• Product Categories: AcyclicStains and Dyes;Alkenes;D;Organic Building Blocks;Stains&Dyes, A to
• Mol File: 1720-32-7.mol
• Article Data: 28

Chemical Properties

• Melting Point: 199-203 °C(lit.)
• Boiling Point: 309.49°C (rough estimate)
• Flash Point: 221 °C
• Appearance: Yellow/Crystalline Powder or Crystals
• Density: 1.0479 (estimate)
• Vapor Pressure: 4.44E-05mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly)
• BRN: 1907440
• CAS DataBase Reference: 1,6-DIPHENYL-1,3,5-HEXATRIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-DIPHENYL-1,3,5-HEXATRIENE(1720-32-7)
• EPA Substance Registry System: 1,6-DIPHENYL-1,3,5-HEXATRIENE(1720-32-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 1720-32-7(Hazardous Substances Data)

Usage

Description

1,6-Diphenyl-1,3,5-hexatriene is a yellow crystalline powder or crystals that is known for its fluorescent properties. It is commonly used as a fluorescence probe in various applications, particularly in the study of membranes and lipid droplets.

Uses

1. Used in Membrane Studies:
1,6-Diphenyl-1,3,5-hexatriene is used as a fluorescence probe for membrane studies, specifically in the investigation of fluorescence depolarisation and membrane fluidity by flow cytometry. Its fluorescent properties allow researchers to gain insights into the structure and dynamics of biological membranes.
2. Used in Lipid Droplet Detection:
1,6-Diphenyl-1,3,5-hexatriene serves as an alternative to Nile red for the fluorescent detection of lipid droplets. This application is particularly useful in the study of lipid metabolism and storage, as well as in the development of new methods for detecting and analyzing lipid droplets in cells.

Synthesis Reference(s)

Synthesis, p. 731, 1990 DOI: 10.1055/s-1990-26998

Purification Methods

Crystallise the hexatriene from CHCl3 or EtOH/CHCl3 (1:1). [Beilstein 5 H 691, 5 IV 2425.]

InChI:InChI=1/C18H16/c1-2-3-6-15-18(16-11-7-4-8-12-16)17-13-9-5-10-14-17/h2-15H,1H2

Upstream product

• 110-86-1 pyridine 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 17338-03-3 1,6-diphenylhexa-2,4-diyne-1,6-diol 
• 29268-75-5 (E)-1-(3,3-dichloroprop-1-en-1-yl)benzene 
• 58463-02-8 (1E,5E)-1,6-diphenyl-1,5-hexadiene 
• 4403-20-7 1,6-diphenyl-hexa-1,5-diene-3,4-diol 
• 879124-86-4 1,6-diphenyl-hexa-2,4-diene-1,6-diol 
• 102957-66-4 4,6-diethoxy-1,6-diphenyl-hexan-2-ol 
• 844901-89-9 1,2,3,4,5,6-hexabromo-1,6-diphenyl-hexane 
• 96465-09-7 1,3,5-triethoxy-1,6-diphenyl-hexane 
• 109-89-7 diethylamine 
• 110-89-4 piperidine 
• 108-86-1 bromobenzene 
• 2235-12-3 1,3,5-hexatriene 

Downstream Products

• 38557-34-5 cis,trans,trans-1,6-Diphenyl-1,3,5-hexatriene 
• 1087-49-6 1,6-diphenylhexane 
• 1720-32-7 1,6-diphenylhexa-(1E,3Z,5E)-triene 
• 1610-23-7 1,6-dicyclohexylhexane 
• 205808-71-5 cis,cis,trans-1,6-diphenyl-1,3,5-hexatriene 
• 105230-99-7 1,4-dibenzyl-1,3-butadiene 
• 125341-43-7 C₁₈H₁₆^(1-)*C₁₆H₃₆N⁽¹⁺⁾ 
• 133786-85-3 (1R,2S,3S,4S,5S,6R)-1,6-Diphenyl-hexane-1,2,3,4,5,6-hexaol 
• 133786-85-3 (1R,2S,3R,4R,5S,6R)-1,6-Diphenyl-hexane-1,2,3,4,5,6-hexaol 
• 133786-85-3 (1S,2R,3R,4R,5S,6R)-1,6-Diphenyl-hexane-1,2,3,4,5,6-hexaol 
• 1720-32-7 all-trans-1,6-Diphenyl-1,3,5-hexatriene radical anion 
• 125341-49-3 C₁₈H₁₆^(1-)*Na⁽¹⁺⁾ 
• 22147-26-8 2,7-Diphenyl-heptatrien-(2cis,4trans,6trans)-al-⁽¹⁾ 
• 844901-89-9 1,2,3,4,5,6-hexabromo-1,6-diphenyl-hexane 

Relevant articles and documents

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Synthesis of diphenylhexatriene by the Pd-catalyzed dimerization of cinnamyl acetate

A mild and operationally simple method to synthesize diphenylhexatriene (DPH) is reported. The method relies on the Pd-catalyzed dimerization of cinnamyl acetate and provides efficient access to DPH in a single step.

Palladium-Catalyzed Three-Component Reaction of 3-(Tri-n- butylstannyl)allyl Acetates, Aldehydes, and Triorganoboranes: An Alternative to the Carbonyl Allylation Using α,γ-Substituted Allylic Tin Reagents

A three-component reaction of 3-(tri-n-butylstannyl)allyl acetates, aldehydes, and triorganoboranes in the presence of a palladium-Xantphos catalyst system predominately gave (E)-anti-homoallylic alcohols with high diastereoselectivity and good to high levels of alkene stereocontrol. An efficient chirality transfer was observed when an enantioenriched substrate was employed. The reaction was initiated by the formation of an allylic gem-palladium/stannyl intermediate, which subsequently underwent allylation of the aldehyde by an allyltributyltin followed by a coupling reaction of the in-situ-generated (E)-vinylpalladium acetate with the triorganoborane.

Z-selective metathesis homocoupling of 1,3-dienes by molybdenum and tungsten monoaryloxide pyrrolide (MAP) complexes

Molybdenum or tungsten monoaryloxide pyrrolide (MAP) complexes that contain OHIPT as the aryloxide (hexaisopropylterphenoxide) are effective catalysts for homocoupling of simple (E)-1,3-dienes to give (E,Z,E)-trienes in high yield and with high Z selectivities. A vinylalkylidene MAP species was shown to have the expected syn structure in an X-ray study. MAP catalysts that contain OHMT (hexamethylterphenoxide) are relatively inefficient.