13001-40-6

Basic information

• Product Name: 1,4-Bis(4-cyanostyryl)benzene
• Synonyms: optical brightener 199;C.I.199;Fluorescent Brightener 199;1,4-BIS(4-CYANOSTYRYL)BENZENE;4,4'-(p-phenylenediethene-2,1-diyl)bisbenzonitrile;Optical Brightening Agent ER C. I. 199;Benzonitrile, 4,4-(1,4-phenylenedi-2,1-ethenediyl)bis-;1,4-BIS(2-CYANO STYRYL)BENZENE 99+%
• CAS NO: 13001-40-6
• Molecular Formula: C₂₄H₁₆N₂
• Molecular Weight: 332.4
• EINECS: 235-836-7
• Mol File: 13001-40-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 230-234°C
• Boiling Point: 571.3 °C at 760 mmHg
• Flash Point: 272.8 °C
• Appearance: Light yellow
• Density: 1.18 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Very Slightly)
• Stability: Incompatible with strong oxidizing agents. Combustible.
• CAS DataBase Reference: 1,4-Bis(4-cyanostyryl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Bis(4-cyanostyryl)benzene(13001-40-6)
• EPA Substance Registry System: 1,4-Bis(4-cyanostyryl)benzene(13001-40-6)

Safety Data

• Hazardous Substances Data: 13001-40-6(Hazardous Substances Data)

Usage

Chemical Properties

solid

Synthetic route

diethyl [(4-cyanophenyl)methyl]phosphonate (1552-41-6) + terephthalaldehyde, (623-27-8) → 1,4-bis(p-cyanostyryl)benzene (13001-40-6)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;	52%

terephthalaldehyde, (623-27-8) + para-methylbenzonitrile (104-85-8) → 1,4-bis(p-cyanostyryl)benzene (13001-40-6)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 45℃; for 5h;	18%

terephthalaldehyde, (623-27-8) + (p-cyanobenzyl)triphenylphosphonium bromide (26104-68-7) → 1,4-bis(p-cyanostyryl)benzene (13001-40-6)

Conditions	Yield
With sodium ethanolate In ethanol for 3.5h;	17%

diethyl [(4-cyanophenyl)methyl]phosphonate (1552-41-6) + 4-[(E)-2-(4-Formyl-phenyl)-vinyl]-benzonitrile (72436-40-9) → 1,4-bis(p-cyanostyryl)benzene (13001-40-6)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide Yield given;

4-[(E)-2-(4-Cyano-phenyl)-vinyl]-benzoic acid → 1,4-bis(p-cyanostyryl)benzene (13001-40-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 2: H2 / 5 percent Pd/BaSO4, "quinoline S" / xylene / Heating 3: KOH / dimethylformamide View Scheme

4-[(E)-2-(4-Cyano-phenyl)-vinyl]-benzoyl chloride (73755-13-2) → 1,4-bis(p-cyanostyryl)benzene (13001-40-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / 5 percent Pd/BaSO4, "quinoline S" / xylene / Heating 2: KOH / dimethylformamide View Scheme

4-ethenylbenzonitrile (3435-51-6) + para-diiodobenzene (624-38-4) → 1,4-bis(p-cyanostyryl)benzene (13001-40-6)

Conditions	Yield
With triphenyl phosphite; triethylamine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 120℃; Heck Reaction;

4-cyanobenzaldehyde (105-07-7) → 1,4-bis(p-cyanostyryl)benzene (13001-40-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Alkaline conditions 2: bis(dibenzylideneacetone)-palladium(0); triphenyl phosphite; triethylamine / N,N-dimethyl-formamide / 120 °C View Scheme

1,4-bis(p-cyanostyryl)benzene (13001-40-6) → 2,13-dicyano[5]helicene

Conditions	Yield
With iodine; methyloxirane In benzene Dehydrogenation; photocyclization; Irradiation;	32%

1,4-bis(p-cyanostyryl)benzene (13001-40-6) → 1,4-bis<2-(4-cyanophenyl)ethyl>benzene (81919-21-3)

Conditions	Yield
With toluene-4-sulfonic acid hydrazide In 2-methoxy-ethanol for 16h; Heating;

1,4-bis(p-cyanostyryl)benzene (13001-40-6) → 1,4-bis(4'-guanylphenylethyl)benzene dihydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: p-toluenesulfohydrazide / 2-methoxy-ethanol / 16 h / Heating 2: HCl gas / 72 h / Ambient temperature 3: 63 percent / NH3 / 72 h / Ambient temperature View Scheme

1,4-bis(p-cyanostyryl)benzene (13001-40-6) → C28H32N2O2*ClH

Conditions	Yield
Multi-step reaction with 2 steps 1: p-toluenesulfohydrazide / 2-methoxy-ethanol / 16 h / Heating 2: HCl gas / 72 h / Ambient temperature View Scheme

1,4-bis(p-cyanostyryl)benzene (13001-40-6) → 1,4-bis<4-(2-imidazolinyl)phenylethyl>benzene

Conditions	Yield
Multi-step reaction with 3 steps 1: p-toluenesulfohydrazide / 2-methoxy-ethanol / 16 h / Heating 2: HCl gas / 72 h / Ambient temperature 3: 78 percent / ethanol / 16 h / Heating View Scheme

1,4-bis(p-cyanostyryl)benzene (13001-40-6) → 1,4-bis<4-(1,4,5,6-tetrahydro-2-pyrimidinyl)phenylethyl>benzene

Conditions	Yield
Multi-step reaction with 3 steps 1: p-toluenesulfohydrazide / 2-methoxy-ethanol / 16 h / Heating 2: HCl gas / 72 h / Ambient temperature 3: 61 percent / ethanol / Heating View Scheme

1,4-dibromotetrafluorobenzene (344-03-6) + 1,4-bis(p-cyanostyryl)benzene (13001-40-6) → C6Br2F4*C24H16N2

Conditions	Yield
In chloroform for 0.5h;

para-diiodobenzene (624-38-4) + 1,4-bis(p-cyanostyryl)benzene (13001-40-6) → C6H4I2*C24H16N2

Conditions	Yield
In chloroform for 0.5h;

2,3,4,5,6-pentafluorophenol (771-61-9) + 1,4-bis(p-cyanostyryl)benzene (13001-40-6) → 2C6HF5O*C24H16N2

Conditions	Yield
In chloroform for 0.5h;

4-bromotetrafluorobenzenecarboxylic acid (4707-24-8) + 1,4-bis(p-cyanostyryl)benzene (13001-40-6) → C7HBrF4O2*C24H16N2

Conditions	Yield
In chloroform for 0.5h;

1,4-diiodo-2,3,5,6-tetrafluorobenzene (392-57-4) + 1,4-bis(p-cyanostyryl)benzene (13001-40-6) → C6F4I2*C24H16N2

Conditions	Yield
In chloroform for 0.5h;

1,4-bis(p-cyanostyryl)benzene (13001-40-6) + recorcinol (108-46-3) → 2C6H6O2*3C24H16N2

Conditions	Yield
In chloroform for 0.5h;

[(zinc)4O(1,4-benzenedicarboxylate)3] + 1,4-bis(p-cyanostyryl)benzene (13001-40-6) → 1,4-bis-p-cyanostyrylbenzene(at)MOF-5

Conditions	Yield
In N,N-dimethyl-formamide for 12h;

Upstream product

• 1552-41-6 diethyl [(4-cyanophenyl)methyl]phosphonate 
• 623-27-8 terephthalaldehyde, 
• 105-07-7 4-cyanobenzaldehyde 
• 3435-51-6 4-ethenylbenzonitrile 
• 624-38-4 para-diiodobenzene 
• 73755-13-2 4-[(E)-2-(4-Cyano-phenyl)-vinyl]-benzoyl chloride 
• 104-85-8 para-methylbenzonitrile 
• 26104-68-7 (p-cyanobenzyl)triphenylphosphonium bromide 
• 72436-40-9 4-[(E)-2-(4-Formyl-phenyl)-vinyl]-benzonitrile 

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