Product Name

  • Name

    1,4-Bis(4-cyanostyryl)benzene

  • EINECS 235-836-7
  • CAS No. 13001-40-6
  • Article Data7
  • CAS DataBase
  • Density 1.18 g/cm3
  • Solubility
  • Melting Point 230-234 °C
  • Formula C24H16N2
  • Boiling Point 571.3 °C at 760 mmHg
  • Molecular Weight 332.404
  • Flash Point 272.8 °C
  • Transport Information
  • Appearance Light yellow
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 13001-40-6 (1,4-Bis(4-cyanostyryl)benzene)
  • Hazard Symbols
  • Synonyms 1,4-Bis(4-cyanostyryl)benzene;1,4-Bis(p-cyanostyryl)benzene;Blankophor ER;C.I. 40705;C.I. FluorescentBrightener 199;Fluorescent Brightener 199;Palanil Brilliant White R;Ultraphor RN;Benzonitrile,4,4'-(p-phenylenedivinylene)di- (7CI,8CI);
  • PSA 47.58000
  • LogP 5.77076

Synthetic route

diethyl [(4-cyanophenyl)methyl]phosphonate
1552-41-6

diethyl [(4-cyanophenyl)methyl]phosphonate

terephthalaldehyde,
623-27-8

terephthalaldehyde,

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;52%
terephthalaldehyde,
623-27-8

terephthalaldehyde,

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 45℃; for 5h;18%
terephthalaldehyde,
623-27-8

terephthalaldehyde,

(p-cyanobenzyl)triphenylphosphonium bromide
26104-68-7

(p-cyanobenzyl)triphenylphosphonium bromide

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 3.5h;17%
diethyl [(4-cyanophenyl)methyl]phosphonate
1552-41-6

diethyl [(4-cyanophenyl)methyl]phosphonate

4-[(E)-2-(4-Formyl-phenyl)-vinyl]-benzonitrile
72436-40-9

4-[(E)-2-(4-Formyl-phenyl)-vinyl]-benzonitrile

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide Yield given;
4-[(E)-2-(4-Cyano-phenyl)-vinyl]-benzoic acid

4-[(E)-2-(4-Cyano-phenyl)-vinyl]-benzoic acid

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

Conditions
ConditionsYield
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

4-[(E)-2-(4-Cyano-phenyl)-vinyl]-benzoyl chloride

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

Conditions
ConditionsYield
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

4-ethenylbenzonitrile

para-diiodobenzene
624-38-4

para-diiodobenzene

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

Conditions
ConditionsYield
With triphenyl phosphite; triethylamine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 120℃; Heck Reaction;
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

Conditions
ConditionsYield
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

1,4-bis(p-cyanostyryl)benzene

2,13-dicyano[5]helicene

2,13-dicyano[5]helicene

Conditions
ConditionsYield
With iodine; methyloxirane In benzene Dehydrogenation; photocyclization; Irradiation;32%
1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

1,4-bis<2-(4-cyanophenyl)ethyl>benzene
81919-21-3

1,4-bis<2-(4-cyanophenyl)ethyl>benzene

Conditions
ConditionsYield
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(p-cyanostyryl)benzene

1,4-bis(4'-guanylphenylethyl)benzene dihydrochloride

1,4-bis(4'-guanylphenylethyl)benzene dihydrochloride

Conditions
ConditionsYield
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

1,4-bis(p-cyanostyryl)benzene

C28H32N2O2*ClH

C28H32N2O2*ClH

Conditions
ConditionsYield
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(p-cyanostyryl)benzene

1,4-bis<4-(2-imidazolinyl)phenylethyl>benzene

1,4-bis<4-(2-imidazolinyl)phenylethyl>benzene

Conditions
ConditionsYield
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(p-cyanostyryl)benzene

1,4-bis<4-(1,4,5,6-tetrahydro-2-pyrimidinyl)phenylethyl>benzene

1,4-bis<4-(1,4,5,6-tetrahydro-2-pyrimidinyl)phenylethyl>benzene

Conditions
ConditionsYield
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-dibromotetrafluorobenzene

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

C6Br2F4*C24H16N2

C6Br2F4*C24H16N2

Conditions
ConditionsYield
In chloroform for 0.5h;
para-diiodobenzene
624-38-4

para-diiodobenzene

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

C6H4I2*C24H16N2

C6H4I2*C24H16N2

Conditions
ConditionsYield
In chloroform for 0.5h;
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

2C6HF5O*C24H16N2

2C6HF5O*C24H16N2

Conditions
ConditionsYield
In chloroform for 0.5h;
4-bromotetrafluorobenzenecarboxylic acid
4707-24-8

4-bromotetrafluorobenzenecarboxylic acid

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

C7HBrF4O2*C24H16N2

C7HBrF4O2*C24H16N2

Conditions
ConditionsYield
In chloroform for 0.5h;
1,4-diiodo-2,3,5,6-tetrafluorobenzene
392-57-4

1,4-diiodo-2,3,5,6-tetrafluorobenzene

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

C6F4I2*C24H16N2

C6F4I2*C24H16N2

Conditions
ConditionsYield
In chloroform for 0.5h;
1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

recorcinol
108-46-3

recorcinol

2C6H6O2*3C24H16N2

2C6H6O2*3C24H16N2

Conditions
ConditionsYield
In chloroform for 0.5h;
[(zinc)4O(1,4-benzenedicarboxylate)3]

[(zinc)4O(1,4-benzenedicarboxylate)3]

1,4-bis(p-cyanostyryl)benzene
13001-40-6

1,4-bis(p-cyanostyryl)benzene

1,4-bis-p-cyanostyrylbenzene(at)MOF-5

1,4-bis-p-cyanostyrylbenzene(at)MOF-5

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

1,4-Bis(4-cyanostyryl)benzene Specification

The Benzonitrile,4,4'-(1,4-phenylenedi-2,1-ethenediyl)bis- with the CAS number 13001-40-6 is also called 1,4-Bis(4-cyanostyryl)benzene. The IUPAC name is 4-[(E)-2-[4-[(E)-2-(4-cyanophenyl)ethenyl]phenyl]ethenyl]benzonitrile. Its molecular formula is C24H16N2. The EINECS registry number is 235-836-7.

The properties of the Benzonitrile,4,4'-(1,4-phenylenedi-2,1-ethenediyl)bis- are: (1)ACD/LogP: 6.58; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 2; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 47.58 Å2; (7)Index of Refraction: 1.66; (8)Molar Refractivity: 103.64 cm3; (9)Molar Volume: 280.4 cm3; (10)Polarizability: 41.08×10-24cm3; (11)Surface Tension: 59.9 dyne/cm; (12)Enthalpy of Vaporization: 85.67 kJ/mol; (13)Vapour Pressure: 4.61×10-13 mmHg at 25°C.

Uses: This chemical can prepare dibenzo[c,g]phenanthrene-9,12-dicarbonitrile. This reaction needs reagent I2, propylene oxide and solvent benzene. The yield is 32%. Tis reaction needs irradiation.

You can still convert the following datas into molecular structure:
(1)SMILES: N#Cc3ccc(\C=C\c2ccc(\C=C\c1ccc(C#N)cc1)cc2)cc3
(2)InChI: InChI=1/C24H16N2/c25-17-23-13-9-21(10-14-23)7-5-19-1-2-20(4-3-19)6-8-22-11-15-24(18-26)16-12-22/h1-16H/b7-5+,8-6+
(3)InChIKey: KIAAMJMIIHTGBH-KQQUZDAGBF

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