13280-61-0

Basic information

• Product Name: 1,4-BIS(2-METHYLSTYRYL)BENZENE
• Synonyms: 1,4-DI(2-METHYLSTYRYL)BENZENE;1,4-BIS(2-METHYLSTYRYL)BENZENE;BIS(MSB);1,4-bis[2-(2-methylphenyl)ethenyl]-benzen;1,4-Bis(2-methylstyryl)benzene, 99+%;Bis(msb), 99.50%, scintillation grade;Bis(MSB), scintillation grade;2,2'-[1,4-Phenylenebis(ethene-1,2-diyl)]bistoluene
• CAS NO: 13280-61-0
• Molecular Formula: C₂₄H₂₂
• Molecular Weight: 310.43
• EINECS: 236-285-5
• Product Categories: Scintillators;Stilbenes
• Mol File: 13280-61-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 180-182 °C(lit.)
• Boiling Point: 385.59°C (rough estimate)
• Flash Point: 231.3°C
• Appearance: Light green to yellow-green/Crystalline Powder
• Density: 1.0591 (estimate)
• Refractive Index: 1.9130 (estimate)
• Storage Temp.: −20°C
• Sensitive: Light Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 2375845
• CAS DataBase Reference: 1,4-BIS(2-METHYLSTYRYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BIS(2-METHYLSTYRYL)BENZENE(13280-61-0)
• EPA Substance Registry System: 1,4-BIS(2-METHYLSTYRYL)BENZENE(13280-61-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 13280-61-0(Hazardous Substances Data)

Usage

Uses

Absolute fluorescence emission in cyclohexane (max): 420nm. Utilized as a scintillator reagent.

Synthetic route

dimethyl 2-methylbenzylphosphonate (17105-62-3) + terephthalaldehyde, (623-27-8) → 1,4-bis[2-(2-methyl-phenyl)ethenyl]-benzene (13280-61-0)

Conditions	Yield
With potassium hydroxide In ethanol; N,N-dimethyl-formamide at 60℃; for 0.5h;	35%

1-chloromethyl-2-methylbenzene (552-45-4) → 1,4-bis[2-(2-methyl-phenyl)ethenyl]-benzene (13280-61-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: CH3ONa / methanol; benzene / 0.5 h / Heating 2: 35 percent / KOH / ethanol; dimethylformamide / 0.5 h / 60 °C View Scheme

1,4-bis(bromomethyl)benzene (623-24-5) + 2-methylphenyl aldehyde (529-20-4) → 1,4-bis[2-(2-methyl-phenyl)ethenyl]-benzene (13280-61-0)

Conditions	Yield
Stage #1: 1,4-bis(bromomethyl)benzene With triphenylphosphine at 20℃; for 3h; Reflux; Large scale; Stage #2: 2-methylphenyl aldehyde With potassium isopropoxide at 20℃; Reagent/catalyst; Large scale;	133.6 kg

diethyl 2-methylbenzylphosphonate (62778-16-9) + terephthalaldehyde, (623-27-8) → 1,4-bis[2-(2-methyl-phenyl)ethenyl]-benzene (13280-61-0)

Conditions	Yield
Stage #1: diethyl 2-methylbenzylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Stage #2: terephthalaldehyde, In tetrahydrofuran; mineral oil at 0℃; for 1h;

1,4-bis[2-(2-methyl-phenyl)ethenyl]-benzene (13280-61-0) → terephthalaldehyde, (623-27-8) + 2-methylphenyl aldehyde (529-20-4)

Conditions	Yield
With oxygen at 130℃; for 12h; Sealed tube;	A 83% B 82%
With oxygen at 130℃; for 12h; Sealed tube; Overall yield = 89.7 percent;
With oxygen at 110℃; for 12h; Green chemistry;

silver perchlorate monohydrate (14242-05-8) + 1,4-bis[2-(2-methyl-phenyl)ethenyl]-benzene (13280-61-0) → [silver(I)2(1,4-bis(methylstyryl)benzene)(ClO4)2]

Conditions	Yield
In toluene under Ar; soln. of Ag salt in toluene added to ligand; stirred for 10 min; layered with n-pentane; sealed under Ar; wrapped with tin foil; crystd. at room temp. in the dark for 3 d; elem. anal.;	31%

silver tetrafluoroborate (14104-20-2) + 1,4-bis[2-(2-methyl-phenyl)ethenyl]-benzene (13280-61-0) → [silver(I)2(1,4-bis(methylstyryl)benzene)(H2O)4](BF4)2

Conditions	Yield
In 1,3,5-trimethyl-benzene under Ar; soln. of Ag salt in mesitylene added to ligand; stirred for 5 min; filtered; filtrate layered with n-pentane; sealed under Ar; wrapped withtin foil; crystd. at room temp. in the dark for 3 d; elem. anal.;	28%

Upstream product

• 623-24-5 1,4-bis(bromomethyl)benzene 
• 529-20-4 2-methylphenyl aldehyde 
• 62778-16-9 diethyl 2-methylbenzylphosphonate 
• 623-27-8 terephthalaldehyde, 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 17105-62-3 dimethyl 2-methylbenzylphosphonate 

Downstream Products

• 623-27-8 terephthalaldehyde, 
• 529-20-4 2-methylphenyl aldehyde 

Relevant articles and documents

Preparation method of 1,4-bis(2-methylstyryl)benzene

The invention relates to a preparation method of 1,4-bis(2-methylstyryl)benzene. The 1,4-bis(2-methylstyryl)benzene is prepared from diethyl methylbenzylphosphonate and terephthalaldehyde through a reaction. Compared with the prior art, the preparation me

SYMMETRICAL AND UNSYMMETRICAL DERIVATIVES OF DISTYRYLBENZENE

The symmetrically substituted derivatives I-V of 1,4-distyrylbenzene have been prepared via the Horner reaction.A modification of the latter enabled preparation of unsymmetrical derivatives of 1,4-distyrylbenzene.