Product Name

  • Name

    1,4-Dicyanobenzene

  • EINECS 210-783-2
  • CAS No. 623-26-7
  • Article Data334
  • CAS DataBase
  • Density 1.164 g/cm3
  • Solubility 0.08 g/L (23 °C) in water
  • Melting Point 221-225 °C(lit.)
  • Formula C8H4N2
  • Boiling Point 289.6 °C at 760 mmHg
  • Molecular Weight 128.133
  • Flash Point 142.8 °C
  • Transport Information
  • Appearance biege powder
  • Safety 26-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 623-26-7 (1,4-Dicyanobenzene)
  • Hazard Symbols IrritantXi
  • Synonyms Terephthalonitrile(8CI);1,4-Benzodinitrile;1,4-Bis(cyano)benzene;
  • PSA 47.58000
  • LogP 1.42996

Synthetic route

1,4-benzenedicarboxaldehyde bis(dimethylhydrazone)
20114-65-2

1,4-benzenedicarboxaldehyde bis(dimethylhydrazone)

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With dihydrogen peroxide; acetonitrile at 55℃; for 60h;100%
With HOF* CH3CN at 0℃;98%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
Stage #1: para-methylbenzonitrile With hydrogen bromide; dihydrogen peroxide In tetrachloromethane; water at 20℃; for 1h; Irradiation;
Stage #2: With ammonia; iodine In tetrachloromethane; water; acetonitrile at 20 - 60℃; for 18h;		99%
With 1,10-Phenanthroline; ammonium acetate; dihydrogen peroxide; oxygen In N,N-dimethyl acetamide at 180℃; under 11400.8 Torr; for 24h; Autoclave;66%
With tert.-butylnitrite; N-hydroxyphthalimide; palladium diacetate In acetonitrile at 80℃; for 24h; Inert atmosphere; Sealed tube;64%
terephthalaldehyde,
623-27-8

terephthalaldehyde,

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With ammonium iodide In dimethyl sulfoxide at 20℃; for 4h; Electrolysis;99%
With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride In 1,2-dichloro-ethane at 20 - 50℃; for 16h;98%
With hexamethylene bis(N-methylimidazolium)bis(dichloroiodate); ammonia In water; acetonitrile at 20℃; for 1h;92%
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With ammonium iodide In dimethyl sulfoxide at 20℃; for 4h; Electrolysis;99%
With trifluorormethanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester In dichloromethane at 23℃; for 24h; Inert atmosphere;99%
With hydroxylamine hydrochloride; FeOO280 In toluene for 5h; Condensation; dehydration; Heating;98%
p-xylylene glycol
589-29-7

p-xylylene glycol

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With ammonium hydroxide; iodine at 60℃; for 2h;99%
With ammonium hydroxide; iodine at 60℃; for 2h;99%
Stage #1: p-xylylene glycol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;		99%
4-cyanobenzaldehyde oxime
52707-54-7, 52707-59-2, 64847-77-4

4-cyanobenzaldehyde oxime

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With gallium(III) trichloride In acetonitrile at 80℃; for 36h; Reagent/catalyst; Inert atmosphere;99%
With acetonitrile for 1h; Reflux; Green chemistry;95%
With 4-nitro-1-((trifluoromethyl)sulfonyl)-1H-imidazole; triethylamine In acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Sealed tube;69%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

potassium ferrocyanide

potassium ferrocyanide

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Schlenk technique;99%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Schlenk technique;97%
With copper(II) acetate monohydrate; sodium carbonate; 1,3-phenylene-bis-(1H)-tetrazole; potassium iodide In N,N-dimethyl-formamide at 130℃; for 8h; Inert atmosphere;93%
potassium hexacyanoferrate(II) trihydrate

potassium hexacyanoferrate(II) trihydrate

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere;99%
With tetrabutylammomium bromide; copper(II) acetate monohydrate; potassium iodide In water at 20 - 140℃; Microwave irradiation;73%
With sodium carbonate In N,N-dimethyl-formamide at 110℃; for 20h; Catalytic behavior; Sealed tube;100 %Chromat.
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

potassium hexacyanoferrate(II) trihydrate

potassium hexacyanoferrate(II) trihydrate

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere;99%
With sodium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Catalytic behavior; Sealed tube;93 %Chromat.
potassium hexacyanoferrate(II)

potassium hexacyanoferrate(II)

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; Green chemistry;98%
With CHF3O3S*C52H45NO2P2Pd; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.116667h; Microwave irradiation;92%
copper(l) iodide In various solvent(s) at 160℃; for 16h;75%
potassium hexacyanoferrate(III) trihydrate

potassium hexacyanoferrate(III) trihydrate

para-diiodobenzene
624-38-4

para-diiodobenzene

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With potassium phosphate In N,N-dimethyl-formamide at 120℃; for 2h;98%
4-aminobenzyl cyanide
10406-25-4

4-aminobenzyl cyanide

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With ammonium hydroxide; trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; ammonium bromide at 20℃; for 1.5h; Green chemistry;98%
With copper(l) iodide; oxygen In dichloromethane at 20℃; under 760.051 Torr; for 6h; Sealed tube;21 %Spectr.
Multi-step reaction with 2 steps
1: N-chloro-succinimide / 0.17 h / 20 °C / Milling
2: triethylamine / 0.33 h / 20 °C / Milling
View Scheme
potassium cyanide

potassium cyanide

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
Stage #1: potassium cyanide With acetic acid In ethylene glycol at 20℃; Sealed tube;
Stage #2: 4-bromobenzenecarbonitrile With P(t-Bu)3 Palladacycle Gen. 3; potassium acetate In 1,4-dioxane; water at 60℃; for 16h; Sealed tube;		98%
terephthalaldehyde oxime
69386-99-8, 18705-39-0

terephthalaldehyde oxime

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; triphenylphosphine In acetonitrile at 20℃; for 0.166667h; Reagent/catalyst;97%
With Polyethylene glycol supported phosphorus chloride In dichloromethane for 0.5h; Reflux; Molecular sieve;97%
With S,S-dimethyl dithiocarbonate; triethylamine In 1,4-dioxane at 90℃;92%
4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

potassium ferrocyanide

potassium ferrocyanide

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With copper(l) iodide; per-6-amino-β-cyclodextrin; sodium carbonate; potassium iodide In N,N-dimethyl-formamide at 130℃; for 18h; Microwave irradiation;97%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Catalytic behavior;96%
With sodium carbonate In N,N-dimethyl-formamide at 120℃;96%
terephthalaldehyde bisoxime

terephthalaldehyde bisoxime

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With poly(ethylene glycol)-bound sulfonyl chloride In dichloromethane for 1h; Reflux;97%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

N-cyano-N-phenyl-p-toluenesulfonamide
55305-43-6

N-cyano-N-phenyl-p-toluenesulfonamide

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With silver hexafluoroantimonate; bis(1,5-cyclooctadiene)iridium(I) tetrafluoroborate; ammonium cerium (IV) nitrate; lanthanum(lll) triflate; XPhos at 90℃; for 10h;95.7%
Stage #1: 4-bromobenzenecarbonitrile With [CoBr2(bpy)]; 3-chloroprop-1-ene; trifluoroacetic acid; zinc In acetonitrile at 20℃; Knochel Zinc Vinyl Coupling;
Stage #2: N-cyano-N-phenyl-p-toluenesulfonamide With zinc In acetonitrile at 0 - 50℃; Inert atmosphere;		0.1 g
4-cyanophenyl trifluoromethanesulfonate
66107-32-2

4-cyanophenyl trifluoromethanesulfonate

potassium cyanide
151-50-8

potassium cyanide

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In various solvent(s) at 60℃; for 2h;95%
1,4-bis((E)-(2,2-dimethylhydrazono)methyl)benzene
20114-65-2

1,4-bis((E)-(2,2-dimethylhydrazono)methyl)benzene

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With dihydrogen peroxide; 2-nitrobenzeneseleninic acid In methanol at 20℃; for 0.5h;95%
With pyridine; dihydrogen peroxide; acetic acid; methyltrioxorhenium(VII) In water; acetonitrile for 0.25h;94%
N-tert-octyl-4-cyanobenzamide
860682-30-0

N-tert-octyl-4-cyanobenzamide

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate for 3h; Heating / reflux;95%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With C20H28Br2N2O4Pd2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.166667h; Inert atmosphere; Microwave irradiation;95%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Catalytic behavior; Temperature; Inert atmosphere; Schlenk technique;95%
With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In N,N-dimethyl acetamide at 120℃; for 1h;91%
4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

2,3-dicyano-5,6-dichloro-p-benzoquinone
84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With silver (II) carbonate; copper(II) bis(trifluoromethanesulfonate); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 20h;95%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With C42H58NO3PPdS(2-); potassium acetate; tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube;94%
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; sodium carbonate; triethylamine In water; acetonitrile at 70℃; for 18h;75%
With palladium diacetate; potassium carbonate; XPhos In 1,4-dioxane; water at 100℃; for 10h; sealed tube; Inert atmosphere;69 %Chromat.
With palladium diacetate; sodium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 10 - 12h; Inert atmosphere; Schlenk technique;
4-chlorophenyl thiocyanate
3226-37-7

4-chlorophenyl thiocyanate

4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With N,N,N-trimethyl-2-(sulfooxy)ethanaminium palladium(II) chloride; sodium carbonate In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; water for 2h;94%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere;93%
With tetrabutylammomium bromide; copper(II) acetate monohydrate In water at 180℃; for 22h;67%
With nano Fe3O4 coated TiO2/Cu2O core-shell magnetic composite In N,N-dimethyl-formamide at 120℃;
para-diiodobenzene
624-38-4

para-diiodobenzene

potassium ferrocyanide

potassium ferrocyanide

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.116667h; Microwave irradiation;93%
With mesoporous silica SBA-15 supported Cu2O nanoparticles In N,N-dimethyl-formamide at 120℃; for 8h; Green chemistry;91%
With copper(l) iodide at 80℃; for 0.333333h; Inert atmosphere; Sonication;83%
4-cyano-N-isopropylbenzamide
70380-44-8

4-cyano-N-isopropylbenzamide

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0 - 30℃; for 1h; chemoselective reaction;93%
potassium hexacyanoferrate(II) trihydrate

potassium hexacyanoferrate(II) trihydrate

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With dichloro(2,2-bis(diphenylphosphino)diphenyl ether)palladium(II) In 1,4-dioxane at 90℃; Inert atmosphere; Sealed tube;93%
para-xylene
106-42-3

para-xylene

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With ammonia; oxygen; ammoxidation catalyst containing 10.2wtpercent V2O5, 8.5wtpercent Cr2O3, 76.2wtpercent TiO2, 0.4wtpercent B2O3, 4.8wtpercent natural diamond at 130 - 370℃; for 24h; Product distribution / selectivity;92%
With ammonia at 425℃; under 750.075 Torr; Temperature; Pressure; Reagent/catalyst;87.3%
With ammonia; oxygen; V-Cr-O; silica gel atmospheric pressure;85%
E,E-terephthalaldoxime

E,E-terephthalaldoxime

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With Burgess Reagent In tetrahydrofuran for 1h; Dehydration; Heating;92%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4 A molecular sieve In acetonitrile at 80℃; for 0.25h;80%
terephthalonitrile
623-26-7

terephthalonitrile

5-(4-cyanophenyl)tetrazole
14389-10-7

5-(4-cyanophenyl)tetrazole

Conditions
ConditionsYield
With sodium azide; copper(II) sulfate In dimethyl sulfoxide at 140℃; for 0.5h;100%
With sodium azide In N,N-dimethyl-formamide at 120℃; for 3h;99%
With sodium azide In dimethyl sulfoxide at 110℃; for 0.3h; Green chemistry;98%
terephthalonitrile
623-26-7

terephthalonitrile

[(μ(2)-(1,4-(Ph2PCH2CH2O)2-2,3,5,6-((CH3)4C6)))2(CO)6Rh2][BF4]2

[(μ(2)-(1,4-(Ph2PCH2CH2O)2-2,3,5,6-((CH3)4C6)))2(CO)6Rh2][BF4]2

[(μ(2)-(1,4-(Ph2PCH2CH2O)2-2,3,5,6-(C6(CH3)4)))2(CO)2(μ(2)-1,4-(-NC)2C6H4)2Rh2][BF4]2

[(μ(2)-(1,4-(Ph2PCH2CH2O)2-2,3,5,6-(C6(CH3)4)))2(CO)2(μ(2)-1,4-(-NC)2C6H4)2Rh2][BF4]2

Conditions
ConditionsYield
In dichloromethane-d2 N2-atmosphere; detd by NMR spectroscopy;100%
terephthalonitrile
623-26-7

terephthalonitrile

2AsF6(1-)*C8H4N2*2H(1+)

2AsF6(1-)*C8H4N2*2H(1+)

Conditions
ConditionsYield
With arsenic pentafluoride; hydrogen fluoride at -196 - 20℃; for 0.5h; Sealed tube;100%
terephthalonitrile
623-26-7

terephthalonitrile

terephthalamide
3010-82-0

terephthalamide

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; water; 1-benzyl-1-azonia-3,5-diaza-7-phosphaadamantyl chloride for 1h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Reflux; Green chemistry;99%
With [RuH(tBu-PNP(-))(CO)]; water In tetrahydrofuran; tert-butyl alcohol at 20℃; for 24h;99%
With 1,3-dimethyl-1H-imidazol-3-ium hydrogen carbonate; water In ethanol at 80℃; for 6.5h; Catalytic behavior; Green chemistry; chemoselective reaction;95%
terephthalonitrile
623-26-7

terephthalonitrile

p-xylylidenediamine
539-48-0

p-xylylidenediamine

Conditions
ConditionsYield
With sodium tetrahydroborate In water at 25℃; for 3h; pH=5.5;99%
With ammonia; hydrogen; nickel In methanol at 60℃; under 30002.4 Torr; for 0.533333h;98%
With hydrogen; Ni(NO3)2, Cu(NO3)2, Cr(NO3)3, Na2CO3; calcined at 380 deg C for 18 h; pretreatment is given in full text In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24h; Product distribution / selectivity;98.7%
terephthalonitrile
623-26-7

terephthalonitrile

5,5'-(1,4-phenylene)bis(1H-tetrazole)
6926-49-4

5,5'-(1,4-phenylene)bis(1H-tetrazole)

Conditions
ConditionsYield
With sodium azide; triethylamine hydrochloride In N,N-dimethyl-formamide at 130℃; for 2h; Microwave irradiation; Inert atmosphere;99%
Stage #1: terephthalonitrile With sodium azide; pyridine hydrochloride In N,N-dimethyl-formamide at 120℃; for 18h;
Stage #2: With water; sodium hydroxide In N,N-dimethyl-formamide at 20℃;		92%
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 126.84℃; for 2h; Microwave irradiation; Sealed tube;90%
terephthalonitrile
623-26-7

terephthalonitrile

dichloromethane
75-09-2

dichloromethane

[(Rh2(CH3OC6H4NCHNC6H4OCH3)2)2(OOCCH2COO)2]

[(Rh2(CH3OC6H4NCHNC6H4OCH3)2)2(OOCCH2COO)2]

4Rh(2+)*4CH(NC6H4OCH3)2(1-)*2CH2(CO2)2(2-)*2C6H4(CN)2*4CH2Cl2=Rh4(CH(NC6H4OCH3)2)4(CH2(CO2)2)2(C6H4(CN)2)2*4CH2Cl2

4Rh(2+)*4CH(NC6H4OCH3)2(1-)*2CH2(CO2)2(2-)*2C6H4(CN)2*4CH2Cl2=Rh4(CH(NC6H4OCH3)2)4(CH2(CO2)2)2(C6H4(CN)2)2*4CH2Cl2

Conditions
ConditionsYield
In ethanol; dichloromethane a CH2Cl2 soln. of Rh comp. carefully layered with CH2Cl2-EtOH soln. of ligand; lefted for a several d;99%
...Expand
pyridine
110-86-1

pyridine

terephthalonitrile
623-26-7

terephthalonitrile

cadmium(II) perchlorate hexahydrate

cadmium(II) perchlorate hexahydrate

Cd(2+)*C5H5N*C6H4(COO)2(2-) = [Cd(C5H5N)(C6H4(COO)2)]
238734-76-4

Cd(2+)*C5H5N*C6H4(COO)2(2-) = [Cd(C5H5N)(C6H4(COO)2)]

Conditions
ConditionsYield
In water 140°C, 1 d; elem. anal.;99%
...Expand
terephthalonitrile
623-26-7

terephthalonitrile

toluene(cyclopentadienyl)iron(II) hexafluorophosphate

toluene(cyclopentadienyl)iron(II) hexafluorophosphate

1,2-bis-(diphenylphosphino)ethane
1663-45-2

1,2-bis-(diphenylphosphino)ethane

(((C5H5)Fe((C6H5)2PC2H4P(C6H5)2))2(NCC6H4CN))(2+)*2PF6(1-)=(((C5H5)Fe((C6H5)2PCH2CH2P(C6H5)2))2(NCC6H4CN))(PF6)2

(((C5H5)Fe((C6H5)2PC2H4P(C6H5)2))2(NCC6H4CN))(2+)*2PF6(1-)=(((C5H5)Fe((C6H5)2PCH2CH2P(C6H5)2))2(NCC6H4CN))(PF6)2

Conditions
ConditionsYield
In dichloromethane Irradiation (UV/VIS); soln. Fe complex, dppe, and nitrile ligand in CH2Cl2 was irradiated withvisible light (ordinary lamp, 100 W) for 18 h at 20°C; solvent was removed in vacuo; elem. anal.;99%
...Expand
terephthalonitrile
623-26-7

terephthalonitrile

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

4-(5,6-dihydro-4H-1,3-oxazine-2-yl)benzonitrile
41527-01-9

4-(5,6-dihydro-4H-1,3-oxazine-2-yl)benzonitrile

Conditions
ConditionsYield
With Montmorillonite KSF at 125℃; for 1h; chemoselective reaction;99%
With montmorillonite KSF at 30℃; for 0.25h; Sonication; chemoselective reaction;96%
With phosphotungstic acid for 0.0583333h; Microwave irradiation; chemoselective reaction;95%
With sulfur; cobalt(II) nitrate In neat (no solvent) at 90℃; for 0.0333333h; Time; Microwave irradiation;90%
With sulfur In neat (no solvent) at 100℃; for 3h; Reagent/catalyst;82%
terephthalonitrile
623-26-7

terephthalonitrile

benzyl methyl ether
538-86-3

benzyl methyl ether

4-(methoxy(phenyl)methyl)benzonitrile

4-(methoxy(phenyl)methyl)benzonitrile

Conditions
ConditionsYield
With fac-tris(2-(4,6-difluorophenyl)pyridinato,N,C(2'))iridium(III); N-[3,5-bis(trifluoromethyl)phenyl]-2,4,6-triisopropylbenzenesulfonamide; potassium carbonate In acetone at 40℃; for 24h; Sealed tube; Inert atmosphere; Irradiation;99%
With tris[2-phenylpyridinato-C2,N]iridium(III); dipotassium hydrogenphosphate; Octanal; Methyl thioglycolate In N,N-dimethyl acetamide at -78 - 23℃; for 12h; Reagent/catalyst; Solvent; Irradiation; Inert atmosphere;77%
With thiobenzoic acid; potassium phosphate In N,N-dimethyl acetamide at 20℃; for 6h; Irradiation;55%
terephthalonitrile
623-26-7

terephthalonitrile

ethyl 5-(4-bromophenyl)-1,2,3-thiadiazole-4-carboxylate

ethyl 5-(4-bromophenyl)-1,2,3-thiadiazole-4-carboxylate

ethyl 5-(4-bromophenyl)-3-(4-cyanophenyl)isothiazole-4-carboxylate

ethyl 5-(4-bromophenyl)-3-(4-cyanophenyl)isothiazole-4-carboxylate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; chloro(1,5-cyclooctadiene)rhodium(I) dimer In chlorobenzene at 130℃; for 1h; Glovebox;99%
terephthalonitrile
623-26-7

terephthalonitrile

benzaldehyde
100-52-7

benzaldehyde

4-cyanobenzhydrol
13391-47-4

4-cyanobenzhydrol

Conditions
ConditionsYield
With pentanal; tetrabutylammonium acetate In dimethyl sulfoxide at 50℃; for 6h; Reagent/catalyst; Solvent; Electrochemical reaction;99%
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 12h; Solvent; Reagent/catalyst; Irradiation; Inert atmosphere; Sealed tube;83%
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 6h; Sealed tube; Electrochemical reaction;79%
With methanol; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; triethylamine at -78 - 20℃; for 5h; Catalytic behavior; Reagent/catalyst; Irradiation; Inert atmosphere;55%
terephthalonitrile
623-26-7

terephthalonitrile

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

4-[hydroxy(4-methylphenyl)methyl]benzonitrile

4-[hydroxy(4-methylphenyl)methyl]benzonitrile

Conditions
ConditionsYield
With pentanal; tetrabutylammonium acetate In dimethyl sulfoxide at 50℃; for 6h; Electrochemical reaction;99%
With methanol; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; triethylamine at -78 - 20℃; for 6h; Irradiation; Inert atmosphere;81%
terephthalonitrile
623-26-7

terephthalonitrile

methyl 2-naphthyl ketone
93-08-3

methyl 2-naphthyl ketone

4-(1-hydroxy-1-(naphthalen-2-yl)ethyl)benzonitrile

4-(1-hydroxy-1-(naphthalen-2-yl)ethyl)benzonitrile

Conditions
ConditionsYield
With pentanal; tetrabutylammonium acetate In dimethyl sulfoxide at 50℃; for 6h; Electrochemical reaction;99%
With methanol; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; triethylamine at -78 - 20℃; for 72h; Irradiation; Inert atmosphere;81%
terephthalonitrile
623-26-7

terephthalonitrile

4-methoxy-N-[(E)-phenylmethylidene]aniline
1613-90-7

4-methoxy-N-[(E)-phenylmethylidene]aniline

4-(((4-methoxyphenyl)amino)(phenyl)methyl)benzonitrile

4-(((4-methoxyphenyl)amino)(phenyl)methyl)benzonitrile

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube;99%
terephthalonitrile
623-26-7

terephthalonitrile

ethylenediamine
107-15-3

ethylenediamine

1,4-bis<2-(4,5-dihydro-1H-imidazol-2-yl)>benzene
3617-11-6

1,4-bis<2-(4,5-dihydro-1H-imidazol-2-yl)>benzene

Conditions
ConditionsYield
With tetraphosphorus decasulfide for 0.0333333h; microwave irradiation;98%
With cupric indole-3-acetate at 80℃; for 0.333333h; Neat (no solvent); Microwave irradiation;90%
With Cu(II) immobilized on Fe3O4-agarose nanomagnetic catalyst functionalized with ethanolamine phosphate-salicylaldehyde Schiff base at 100℃; for 2h;90%
terephthalonitrile
623-26-7

terephthalonitrile

ethylenediamine
107-15-3

ethylenediamine

4-(4,5-dihydro-1H-imidazol-2-yl)benzonitrile
850786-33-3

4-(4,5-dihydro-1H-imidazol-2-yl)benzonitrile

Conditions
ConditionsYield
With bis(2-hydroxy-κO-2-phenylacetato)copper(II); iodine; sodium acetate In toluene at 90℃; for 0.25h; Time; Microwave irradiation; chemoselective reaction;98%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 110℃; for 3h; chemoselective reaction;95%
With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 0.5h; chemoselective reaction;95%
terephthalonitrile
623-26-7

terephthalonitrile

Trimethylenediamine
109-76-2

Trimethylenediamine

4-(2-(1,4,5,6-tetrahydropyrimidinyl))benzonitrile
1235528-01-4

4-(2-(1,4,5,6-tetrahydropyrimidinyl))benzonitrile

Conditions
ConditionsYield
With Montmorillonite K-10 for 7h; Microwave irradiation; chemoselective reaction;98%
With bis(2-hydroxy-κO-2-phenylacetato)copper(II); iodine; sodium acetate In toluene at 90℃; for 0.333333h; Time; Microwave irradiation; chemoselective reaction;98%
With C37H38Cu2O11; sodium acetate In toluene for 4h; Reflux;95%
With phosphotungstic acid at 125℃; for 1.5h; chemoselective reaction;86%
With Co2(5,5′-(pentane-1,2-diyl)-bis(oxy)diisophthalate)(CH3CN)(H2O)3 In toluene for 4h; Catalytic behavior; Reagent/catalyst; Reflux;45%

1,4-Dicyanobenzene Chemical Properties

Molecule structure of 1,4-Dicyanobenzene (CAS NO.623-26-7):
 

IUPAC Name: Benzene-1,4-dicarbonitrile
Molecular Weight: 128.13076 g/mol
Molecular Formula: C8H4N2
Density: 1.16 g/cm3 
Melting Point: 221-225 °C(lit.)
Boiling Point: 289.6 °C at 760 mmHg
Flash Point: 142.8 °C    
Index of Refraction: 1.565 
Molar Refractivity: 35.88 cm3  
Molar Volume: 110 cm3
Polarizability: 14.22×10-24 cm3
Surface Tension: 55.6 dyne/cm
Enthalpy of Vaporization: 52.9 kJ/mol  
Vapour Pressure: 0.00217 mmHg at 25 °C
Water Solubility: 0.08 g/L (23 °C)
XLogP3: 0.9
H-Bond Acceptor: 2
Exact Mass: 128.037448
MonoIsotopic Mass: 128.037448
Topological Polar Surface Area: 47.6
Heavy Atom Count: 10 
Canonical SMILES: C1=CC(=CC=C1C#N)C#N
InChI: InChI=1S/C8H4N2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H
InChIKey: BHXFKXOIODIUJO-UHFFFAOYSA-N
EINECS: 210-783-2
Product Categories: Aromatic Nitriles; C8 to C9; Cyanides/Nitriles; Nitrogen Compounds

1,4-Dicyanobenzene Uses

 1,4-Dicyanobenzene is used in organic synthesis and aim to produce medicine.

1,4-Dicyanobenzene Toxicity Data With Reference

1.    

eye-rbt 500 mg/24H MLD

     28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,159.
2.    

orl-rat LD50:>6400 mg/kg

     ZAARAM    Zentralblatt fuer Arbeitsmedizin und Arbeitsschutz, 19 (1969),225.
3.    

ipr-rat LD50:4004 mg/kg

     APFRAD    Annales Pharmaceutiques Francaises, 48 (1990),23.
4.    

orl-mus LD50:>300 mg/kg

     JMCMAR    Journal of Medicinal Chemistry, 21 (1978),906.
5.    

ipr-mus LD50:699 mg/kg

     INHEAO    Industrial Health, 4 (1966),11.

1,4-Dicyanobenzene Consensus Reports

Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

1,4-Dicyanobenzene Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-24/25 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S24/25:Avoid contact with skin and eyes.
RIDADR: 3439
WGK Germany: 2
RTECS: CZ1925000
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29269095
Moderately toxic by ingestion and intraperitoneal routes. An eye irritant. When heated to decomposition it emits toxic fumes of CN− and NOx. See also NITRILES.

1,4-Dicyanobenzene Specification

 1,4-Dicyanobenzene (CAS NO.623-26-7) is also named as 1,4-Benzendikarbonitril ; 1,4-Benzendikarbonitril [Czech] ; 1,4-Benzodinitrile ; 4-Cyanobenzonitrile ; NSC 144977 ; NSC 78439 ; Nitril kyseliny tereftalove ; Nitril kyseliny tereftalove [Czech] ; Tereftalodinitril ; Tereftalodinitril [Czech] ; Tereftalonitril ; Tereftalonitril [Czech] ; Terephthalic acid dinitrile ; Terephthalodinitril ; Terephthalodinitril [German] ; Terephthalodinitrile ; Terephthalonitrile ; p-Benzenedinitrile ; p-Dicyanobenzene ; p-Pdn ; p-Phthalodinitrile . 1,4-Dicyanobenzene (CAS NO.623-26-7) is white needle crystal or powder. It is insoluble in water, slightly soluble in ethanol, acetone and hot ether, soluble in hot benzene and hot acetic acid. 1,4-Dicyanobenzene is stable and incompatible with strong acids, strong bases, strong oxidizing agents, strong reducing agents. It is toxic and flammable. It will produce toxic nitrogen oxide and cyanide fumes when buring. So the storage environment should be ventilate, low-temperature and dry.

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