1,3-Dicyanobenzene supplier

Name
1,3-Dicyanobenzene
EINECS 210-933-7
CAS No. 626-17-5
Article Data138
CAS DataBase
Density 1.16 g/cm³
Solubility 0.7 g/L (20 °C) in water
Melting Point 163-165 °C(lit.)
Formula C₈H₄N₂
Boiling Point 239 °C at 760 mmHg
Molecular Weight 128.133
Flash Point 106.4 °C
Transport Information UN 2811
Appearance off-white to light brown solid
Safety 22-24/25
Risk Codes 22-20/22
Molecular Structure
Hazard Symbols Xn
Synonyms Isophthalonitrile(8CI);1,3-Benzodinitrile;1,3-Bis(cyano)benzene;3-Cyanobenzonitrile;Meta-dicyanobenzene;NSC 87880;m-Benzenedinitrile;m-Cyanobenzonitrile;m-Dicyanobenzene;1,3-Benzenedicarbonitrile;
PSA 47.58000
LogP 1.42996

Synthetic route

: 626-18-6
1,3-dimethanol benzene

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
Stage #1: 1,3-dimethanol benzene 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%

: 24964-64-5
3-Cyanobenzaldehyde

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide at 100℃;	98%
With hydroxylamine hydrochloride; zinc(II) oxide for 0.0166667h; Microwave irradiation; neat (no solvent);	91%
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride 2: 19 percent Chromat. / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / acetonitrile / 0.5 h / Photolysis View Scheme

: 108-38-3
m-xylene

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 3441-01-8
3-cyanobenzamide

C: 620-22-4
3-Methylbenzonitrile

Conditions

Conditions	Yield
With ammonia; oxygen; B0.5CrK0.02Mo0086Na0009P0.007V at 350 - 420℃; under 1500.15 Torr; Gas phase; Heating / reflux;	A 98% B n/a C n/a

...Expand

: 626-19-7
Isophthalaldehyde

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With aluminum oxide; hydroxylamine hydrochloride; methanesulfonyl chloride at 100℃; for 0.5h;	97%
With hydroxylamine hydrochloride; pyrographite; methanesulfonyl chloride at 100℃; for 1h;	94%
With hydroxylamine hydrochloride; 2,4,6-triphenylpyrylium tetrafluoroborate In acetonitrile at 40℃; under 750.075 Torr; for 24h; Molecular sieve; Irradiation; Inert atmosphere;	78%

: N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide

: 4612-28-6
1,3-phenylenediboronic acid

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 16937-03-4
4-nitro-N-(4-chlorophenyl)benzenesulfonamide

Conditions

Conditions	Yield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 14h; Catalytic behavior; Reflux;	A 95% B n/a

...Expand

: 121-91-5
isophthalic acid

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With aluminum oxide; aminosulfonic acid; urea for 0.116667h; Irradiation;	93%
With ammonia at 310 - 400℃;
With diammonium phosphate at 370℃;
Multi-step reaction with 2 steps 1: ammonium / 0.5 h / Heating 2: phosphorus pentoxide / 1 h / 15 - 37.5 Torr / Heating View Scheme

: 4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

: 4612-28-6
1,3-phenylenediboronic acid

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 6295-97-2
4-bromo-benzenesulfonic acid-(4-chloro-anilide)

Conditions

Conditions	Yield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 15h; Catalytic behavior; Reflux;	A 93% B n/a

...Expand

: 1477-55-0
1,3-di(aminomethyl)benzene

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With nickel(II) sulphate; sodium hydroxide; dipotassium peroxodisulfate In dichloromethane for 24h; Ambient temperature;	92%
With Dess-Martin periodane In dichloromethane at 25℃; for 0.25h;	90%
With ammonium hydroxide; iodine at 60℃; for 2h;	90%

: potassiumhexacyanoferrate(II) trihydrate

: 6952-59-6
3-cyanobromobenzene

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In N,N-dimethyl acetamide at 120℃; for 1h;	92%

: potassiumhexacyanoferrate(II) trihydrate

: 108-36-1
1,3-dibromobenzene

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; Schlenk technique;	92%
With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In N,N-dimethyl acetamide at 120℃; for 5h;	89%

: 119986-58-2
N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide

: 4612-28-6
1,3-phenylenediboronic acid

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 2903-34-6
4-methyl-N-(4-chlorophenyl)benzenesulfonamide

Conditions

Conditions	Yield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 16h; Catalytic behavior; Reflux;	A 92% B n/a

...Expand

: 108-38-3
m-xylene

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With oxygen; ammoxidation catalyst containing 10.2wtpercent V2O5, 8.5wtpercent Cr2O3, 76.2wtpercent TiO2, 0.4wtpercent B2O3, 4.8wtpercent natural diamond at 130 - 380℃; for 24h; Product distribution / selectivity; Inert atmosphere;	91%
With ammonia at 425 - 450℃; under 760.051 Torr; for 2h; Reagent/catalyst; Temperature;	85.4%
With ammonium hydroxide at 370℃; Flow reactor;	77%

: 126-33-0
sulfolane

: 121-91-5
isophthalic acid

: 506-77-4
cyanogen chloride

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
	91%

...Expand

: 1740-57-4
isophthalamide

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With 3 A molecular sieve at 280 - 500℃; under 0.003 Torr; for 0.25h; Pyrolysis;	90%
With phosphorus pentoxide
With phosphorus pentoxide under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating;

: 64847-76-3
3-(hydroxyimino)methylbenzonitrile

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With trichloro(trifluoromethanesulfonato)titanium(IV) at 80℃; for 10h; Dehydration;	89%
With thionyl chloride; polyvinylpyrrolidone In dichloromethane at 20℃; for 0.25h; Dehydration;	84%
Multi-step reaction with 3 steps 1: Cl(gas) / CHCl3 2: 63 percent 3: cyclohexane / 25 °C / Irradiation View Scheme
With fluorosulfonyl fluoride; sodium carbonate In dimethyl sulfoxide at 20℃; for 12h;	251 mg
With fluorosulfonyl fluoride; potassium carbonate at 20℃; for 12h;	212 mg

: 626-00-6
1,3-Diiodobenzene

: potassium ferrocyanide

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With copper(l) iodide at 80℃; for 0.333333h; Inert atmosphere; Sonication; chemoselective reaction;	89%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; Green chemistry;
With sodium carbonate In N,N-dimethyl-formamide at 120℃;

: potassium hexacyanoferrate(II) trihydrate

: 6952-59-6
3-cyanobromobenzene

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With dichloro(2,2-bis(diphenylphosphino)diphenyl ether)palladium(II); potassium acetate In 1,4-dioxane; water at 90℃; for 1.33333h; Sealed tube;	89%

: 874-97-5
3-(hydroxymethyl)benzonitrile

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With potassium phosphate; ammonium formate In acetonitrile at 115℃; for 16h; Sealed tube; Green chemistry;	88%
Multi-step reaction with 3 steps 1: potassium carbonate; fluorosulfonyl fluoride; dimethyl sulfoxide / 12 h / 20 °C 2: hydroxylamine hydrochloride; potassium carbonate / 20 °C 3: potassium carbonate; fluorosulfonyl fluoride / 12 h / 20 °C View Scheme

: 46133-07-7
3-((hydroxyimino)methyl)benzaldoxime

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With acetyl chloride; zinc(II) oxide for 0.5h; Heating;	87%
With pyrographite; methanesulfonyl chloride at 100℃; for 0.25h;	85%

: 557-21-1
zinc(II) cyanide

: 6952-59-6
3-cyanobromobenzene

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In tetrahydrofuran; water at 20℃; for 18h; Inert atmosphere;	84%

: 626-16-4
3-(chloromethyl)benzyl chloride

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With ammonia; iodine In water at 60℃; for 4h;	81%

: 108-38-3
m-xylene

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 620-22-4
3-Methylbenzonitrile

Conditions

Conditions	Yield
With ammonia; oxygen; silica-supported catalyst with 50percentweight silica and V, Cr, Mo and B in a ratio of 1:1:0.1:0.2 at 400℃; under 1125.11 Torr; Product distribution / selectivity; Gas phase;	A 80.2% B 3.7%
vanadia; zirconium(IV) oxide at 339.85℃; Kinetics;
With ammonia; oxygen In water at 470℃; Product distribution / selectivity;
With ammonia; oxygen; V4Sb3.1W0.66Cs0.74Ox at 430℃; Steatite spheres; Inert atmosphere;
With ammonia at 380℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature;

: 4553-62-2
2-methylglutaronitrile

: 121-91-5
isophthalic acid

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 29553-51-3
3-methyl-piperidine-2,6-dione

Conditions

Conditions	Yield
With aluminum (III) chloride at 270℃; for 4h;	A 69% B 76%

...Expand

: 10442-39-4
tetra-n-butylammonium cyanide

: 114650-55-4
C13H9N3S

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 108697-88-7
3-cyanophenyl phenyl sulfide

Conditions

Conditions	Yield
In dimethyl sulfoxide at 25℃; for 1h; Irradiation;	A 75% B 17%

...Expand

: 114650-55-4
C13H9N3S

A: 626-17-5
benzene-1,3-dicarbonitrile

B: 108697-88-7
3-cyanophenyl phenyl sulfide

Conditions

Conditions	Yield
With tetra-n-butylammonium cyanide In dimethyl sulfoxide at 25℃; for 1h; Irradiation;	A 75% B 17%

: 626-15-3
1,3-bis-(bromomethyl)benzene

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; ammonia In water at 60℃; for 4h;	75%

: potassiumhexacyanoferrate(II) trihydrate

: 1235553-97-5
naphthalen-2-yl 4-methylbenzene-1-sulfonate

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; potassium carbonate In water at 80℃; for 18h; Inert atmosphere;	72%

: 6952-59-6
3-cyanobromobenzene

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
Stage #1: 3-cyanobromobenzene; N,N-dimethyl-formamide With magnesium In tetrahydrofuran at 20℃; Stage #2: With ammonia; iodine In tetrahydrofuran; water at 20℃;	71%

: 6952-59-6
3-cyanobromobenzene

: 626-17-5
benzene-1,3-dicarbonitrile

Conditions

Conditions	Yield
Stage #1: 3-cyanobromobenzene With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -15℃; for 0.25h; Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2h; Stage #3: With ammonia; iodine In tetrahydrofuran; water at 20℃; for 2h;	71%

: 626-17-5
benzene-1,3-dicarbonitrile

: 1477-55-0
1,3-di(aminomethyl)benzene

Conditions

Conditions	Yield
With ammonia; hydrogen In methanol at 100℃; under 22502.3 Torr; for 2h; Pressure; Reagent/catalyst; Temperature;	99%
With hydrogen; cobalt/diatomaceous earth catalyst "G67", cobalt content=56percent; pretreatment is given in full text In 1,2,4-Trimethylbenzene; ammonia at 100℃; for 50h; Product distribution / selectivity;	96.2%
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;	95.2%

: 626-17-5
benzene-1,3-dicarbonitrile

: 1740-57-4
isophthalamide

Conditions

Conditions	Yield
With dihydrogen peroxide; potassium carbonate In dimethyl sulfoxide for 0.166667h; Ambient temperature;	99%
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 dihydrogen peroxide; sodium carbonate In dimethyl sulfoxide at 60℃; for 3h; Reagent/catalyst; Temperature;	98.7%

: 626-17-5
benzene-1,3-dicarbonitrile

: 38442-51-2
tert-butylmercury chloride

: 139100-52-0
2,4-dicyano-1,5-bis(1,1-dimethylethyl)benzene

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In dimethyl sulfoxide at 35℃; for 4.5h; Irradiation;	99%

: 626-17-5
benzene-1,3-dicarbonitrile

: 89379-02-2
tert-butylmercury iodide

: 139100-52-0
2,4-dicyano-1,5-bis(1,1-dimethylethyl)benzene

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium iodide In dimethyl sulfoxide at 25℃; for 19h; Irradiation;	99%

: 626-17-5
benzene-1,3-dicarbonitrile

: 50907-33-0
3-(1H-tetrazole-5-yl)benzonitrile

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 120℃; for 3h;	99%
With sodium azide In N,N-dimethyl-formamide for 24h; Reflux;	95%
With sodium azide In N,N-dimethyl-formamide at 110 - 120℃; for 24h;	95%

: 626-17-5
benzene-1,3-dicarbonitrile

: 1,3-phenylenedimethanamine dihydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen In propan-1-ol; water at 60℃; under 375.038 Torr; for 18h; Flow reactor;	99%
Stage #1: benzene-1,3-dicarbonitrile With ammonia; hydrogen In water; isopropyl alcohol at 110℃; under 15001.5 Torr; for 24h; Autoclave; Stage #2: With hydrogenchloride In methanol; ethyl acetate Cooling with ice;	66%
Multi-step reaction with 2 steps 1: tris(pentafluorophenyl)borate / chloroform-d1 / 4 h / 25 °C / Inert atmosphere 2: hydrogenchloride; water / diethyl ether / 1 h / 20 °C View Scheme

: 626-17-5
benzene-1,3-dicarbonitrile

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

: 1235527-98-6
3-(5,6-dihydro-4H-1,3-oxazine-2-yl)benzonitrile

Conditions

Conditions	Yield
With Montmorillonite KSF for 2h; Microwave irradiation; chemoselective reaction;	98%
With phosphotungstic acid for 0.0333333h; Microwave irradiation; chemoselective reaction;	98%
With montmorillonite KSF at 30℃; for 0.25h; Sonication; chemoselective reaction;	98%
With sulfur; cobalt(II) nitrate In neat (no solvent) at 90℃; for 0.0333333h; Time; Microwave irradiation;	89%

: 626-17-5
benzene-1,3-dicarbonitrile

: 107428-05-7
dimethyl 2,2-di(but-2-yn-1-yl)malonate

: 1381967-57-2
tetramethyl 1,1',4,4'-tetramethyl-3,3'-(1,3-phenylene)bis(6,7-dihydro-5H-cyclopenta[c]pyridine-6,6-dicarboxylate)

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride In benzene for 3h; Inert atmosphere; Reflux;	98%

: 214360-44-8
2-(4-cyanophenyl)-5,5-dimethyl[1,3,2]dioxaborinane

: 626-17-5
benzene-1,3-dicarbonitrile

: C15H7N3

Conditions

Conditions	Yield
With 4-(diphenylphosphino)morpholine; bis(triphenylphosphine)nickel(II) chloride; copper(II) bis(trifluoromethanesulfonate) at 85℃; for 7h; Reagent/catalyst; Solvent; Inert atmosphere;	97.8%

: 626-17-5
benzene-1,3-dicarbonitrile

: 213596-33-9
2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane

: 4’-methoxy-[1,1’-biphenyl]-2,6-dicarbonitrile

Conditions

Conditions	Yield
With 4-(diphenylphosphino)morpholine; bis(triphenylphosphine)nickel(II) chloride; copper(II) bis(trifluoromethanesulfonate) In 1,4-dioxane at 90℃; for 7h; Reagent/catalyst; Solvent; Inert atmosphere;	97.6%

: 626-17-5
benzene-1,3-dicarbonitrile

: 5123-13-7
5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane

: 2,6-dicyano-1,1′-biphenyl

Conditions

Conditions	Yield
With 4-(diphenylphosphino)morpholine; bis(triphenylphosphine)nickel(II) chloride; copper(II) bis(trifluoromethanesulfonate); N-fluorobis(benzenesulfon)imide In 1,4-dioxane at 80℃; for 8h; Reagent/catalyst; Solvent; Inert atmosphere;	97.4%

: 626-17-5
benzene-1,3-dicarbonitrile

: 502622-85-7
5,5-dimethyl-2-(4-nitrophenyl)-1,3,2-dioxaborinane

: 4’-nitrobiphenyl-2,6-dicarbonitrile

Conditions

Conditions	Yield
With 4-(diphenylphosphino)morpholine; bis(triphenylphosphine)nickel(II) chloride; copper(II) bis(trifluoromethanesulfonate) In 1,4-dioxane at 100℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere;	97.3%

: 626-17-5
benzene-1,3-dicarbonitrile

: stannic chloride (diethyl malonate)

: 137737-09-8
(SnCl4)2(((C2H5OCO)2CC(NH2))2C6H4)

Conditions

Conditions	Yield
In 1,2-dichloro-ethane react. at 80°C for 5 h, all operations in dry atmosphere; filtn., washing with C2H4Cl2 or CCl4, drying in vacuum, elem. anal.;	97%

: 626-17-5
benzene-1,3-dicarbonitrile

: 107-15-3
ethylenediamine

: 1016927-51-7
3-(4,5-dihydro-1H-imidazol-2-yl)benzonitrile

Conditions

Conditions	Yield
With bis(2-hydroxy-κO-2-phenylacetato)copper(II); iodine; sodium acetate In toluene at 90℃; for 0.25h; Time; Microwave irradiation; chemoselective reaction;	97%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 110℃; for 2.5h; chemoselective reaction;	96%
With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 0.333333h; chemoselective reaction;	92%

: 626-17-5
benzene-1,3-dicarbonitrile

: 60-23-1
Cysteamine

: 1016928-35-0
1,3-bis(4,5-dihydrothiazol-2-yl)benzene

Conditions

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 110℃; for 0.15h; chemoselective reaction;	97%
With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 0.116667h; chemoselective reaction;	95%

: 626-17-5
benzene-1,3-dicarbonitrile

: 109-76-2
Trimethylenediamine

: 1235528-02-5
3-(2-(1,4,5,6-tetrahydropyrimidinyl))benzonitrile

Conditions

Conditions	Yield
With bis(2-hydroxy-κO-2-phenylacetato)copper(II); iodine; sodium acetate In toluene at 90℃; for 0.333333h; Time; Microwave irradiation; chemoselective reaction;	97%
With phosphotungstic acid for 0.116667h; Microwave irradiation; chemoselective reaction;	96%
With Montmorillonite K-10 at 125℃; for 5.8h; chemoselective reaction;	95%
With C37H38Cu2O11; sodium acetate In toluene for 4h; Reflux;	95%

: 626-17-5
benzene-1,3-dicarbonitrile

A: 1477-55-0
1,3-di(aminomethyl)benzene

B: 100-81-2
3-methyl-benzenemethanamine

Conditions

Conditions	Yield
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;	A 96.8% B 0.1%
With hydrogen; Ni(NO3)2, Cu(NO3)2, Cr(NO3)3, Na2CO3; calcined at 380 deg C for 18 h; activated with H2 In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24h; Product distribution / selectivity;	A 92.1% B 0.1%

: 626-17-5
benzene-1,3-dicarbonitrile

: 127099-85-8, 780722-26-1
N-Cyanoguanidine

: 5118-74-1
3-(4,6-diamino-1,3,5-triazin-2-yl)benzonitrile

Conditions

Conditions	Yield
With potassium hydroxide In isopropyl alcohol at 110℃; for 12h;	96.5%
With potassium hydroxide In butan-1-ol at 120℃; for 1h;	81%
at 230 - 250℃;

: 626-17-5
benzene-1,3-dicarbonitrile

: 38274-19-0
2,2'-di(prop-1-ynyl)biphenyl

: 1,3-bis(1,4-dimethyldibenzo[f,h]isoquinolin-3-yl)benzene

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride In benzene for 24h; Inert atmosphere; Reflux;	96%

: 626-17-5
benzene-1,3-dicarbonitrile

: 623-26-7
terephthalonitrile

: 58491-62-6
furan-2,5-dicarbonitrile

: 18853-40-2
2,5-thiophenedicarbonitrile

: 6508-04-9
4-(4'-cyanophenoxy)benzonitrile

: Thiophene-2,5-dicarboximidic acid-diethyl ester-dihydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; ethanol; 2-methoxy-ethanol; acetone	95.5%

...Expand

: 626-17-5
benzene-1,3-dicarbonitrile

: 1877-72-1
3-Cyanobenzoic acid

Conditions

Conditions	Yield
With water at 30℃; for 25h; bacterial hydrolysis with cells of Rhodococcus rhodochrous NCIB 11,216; 0.25 M phosphate buffer, pH 7;	95%
With water; nitrile hydratase SP361 at 30℃; for 48h; in potassium phosphate buffer (pH = 7);	91%
With water; nitrile hydratase SP361 at 30℃; for 48h; in potassium phosphate buffer (pH = 7);	91%
With sodium hydroxide; sulfuric acid; sodium nitrite In water	52%

: 626-17-5
benzene-1,3-dicarbonitrile

: 107-15-3
ethylenediamine

: 952-08-9
1,3-bis(4,5-dihydro-1H-imidazol-2-yl)benzene

Conditions

Conditions	Yield
With tetraphosphorus decasulfide for 0.025h; microwave irradiation;	95%
With cupric indole-3-acetate at 80℃; for 0.333333h; Neat (no solvent); Microwave irradiation;	89%
With toluene-4-sulfonic acid for 1.83333h; Reflux; neat (no solvent);	87%

: 626-17-5
benzene-1,3-dicarbonitrile

: 141-43-5
ethanolamine

: 3-(4,5-Dihydrooxazol-2-yl)benzonitrile

Conditions

Conditions	Yield
With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 0.166667h; chemoselective reaction;	95%
With tris(trifluoroacetato)bismuth(III) for 0.6h; Heating;	92%
With sulfur; cobalt(II) nitrate In neat (no solvent) at 90℃; for 0.05h; Time; Microwave irradiation;	83%
With sodium acetate at 100℃;

: 626-17-5
benzene-1,3-dicarbonitrile

: 3544-13-6
5,5’-(1,3-phenylene)bis(1H-tetrazole)

Conditions

Conditions	Yield
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 120℃; for 14h; Inert atmosphere;	94%
With indium(III) chloride; sodium azide In water; isopropyl alcohol at 160℃; for 1h; Microwave irradiation;	86%
With sodium azide; triethylamine hydrochloride In N,N-dimethyl-formamide at 130℃; for 2h; Microwave irradiation; Inert atmosphere;	81%

: 626-17-5
benzene-1,3-dicarbonitrile

A: 1477-55-0
1,3-di(aminomethyl)benzene

B xylylene diamine condensation product: xylylene diamine condensation product

Conditions

Conditions	Yield
With ammonia; hydrogen; catalyst A In mata-xylene at 80 - 110℃; Conversion of starting material;	A 93.1% B 5.5%

1,3-Dicyanobenzene Consensus Reports

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

1,3-Dicyanobenzene Standards and Recommendations

OSHA PEL: TWA 5 mg/m³
ACGIH TLV: TWA 5 mg/m³

1,3-Dicyanobenzene Specification

1. Introduction of 1,3-Dicyanobenzene
1,3-Dicyanobenzene is also named as m-Phthalodinitrile;1,3-benzenedicarbonitrile;1,3-Benzodinitrile;3-Cyanobenzonitrile;Dinitrile of isophthalic acid;Isoftalonitril;Isophtalonitrile;m-Phthalodinitrile,and so on.m-Phthalodinitrile(626-17-5) is needle-like crystal with almond-like odor.

2. Properties of 1,3-Dicyanobenzene
Melting point: 163-165 °C(lit.)
Boiling point: 288 °C
Density: 0,992 g/cm³
Flash point: 288°C
Water Solubility: 0.7 g/L (20 °C)
BRN: 1072209

3. Structure Descriptors of 1,3-Dicyanobenzene
1,3-Dicyanobenzene is usually used as a chemical intermediate for amines like m-xylenediamine.

4. Toxicity of 1,3-Dicyanobenzene

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:>5 g/kg	ZAARAM Zentralblatt fuer Arbeitsmedizin und Arbeitsschutz. 19 (1969),225.
3.	orl-mus LD₅₀:178 mg/kg	JMCMAR Journal of Medicinal Chemistry. 21 (1978),906.
4.	ipr-mus LD₅₀:450 mg/kg	ZAARAM Zentralblatt fuer Arbeitsmedizin und Arbeitsschutz. 19 (1969),225.
5.	orl-rbt LD₅₀:250 mg/kg	ZAARAM Zentralblatt fuer Arbeitsmedizin und Arbeitsschutz. 19 (1969),225.
6.	orl-gpg LD₅₀:370 mg/kg	85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,77.

5. Safety Information of 1,3-Dicyanobenzene
Poison by ingestion. An eye irritant. When heated to decomposition it emits toxic fumes of NOx and CN−.
Hazard Codes: Xn
Risk Statements: 22-20/22 (20: Harmful by inhalation 20/22: Harmful by inhalation and if swallowed)
Safety Statements: 22-24/25 (22: Do not breathe dust 24/25: Avoid contact with skin and eyes)
RIDADR: 2811
WGK Germany: 1
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29269020

6. Hazards of 1,3-Dicyanobenzene
Air & Water Reactions
No rapid reaction with air No rapid reaction with water Insoluble in water
Fire Hazard
Excerpt from GUIDE 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For UN3171, if Lithium ion batteries are involved, also consult GUIDE 147. (ERG, 2012)
Health Hazard
Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact

Symptoms: Headache, nausea, confusion

Target Organs: Eyes, skin, central nervous system (NIOSH, 2003)
Reactivity Profile
m-PHTHALODINITRILE is a combustible solid. Emits toxic fumes of NOx and CN- when heated to decomposition. Incompatible with strong oxidizing agents.

7. Other details of 1,3-Dicyanobenzene
OSHA PEL: TWA 5 mg/m³ACGIH TLV: TWA 5 mg/m³

Product Name

1,3-Dicyanobenzene

Synthetic route

1,3-Dicyanobenzene Consensus Reports

1,3-Dicyanobenzene Standards and Recommendations

1,3-Dicyanobenzene Specification

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