1,2-Bis(cyanomethyl)benzene supplier

Name
1,2-Bis(cyanomethyl)benzene
EINECS 210-351-3
CAS No. 613-73-0
Article Data10
CAS DataBase
Density 1.101g/cm³
Solubility Insoluble in water.
Melting Point 58-61 ºC
Formula C10H8 N2
Boiling Point 325.4°C at 760 mmHg
Molecular Weight 156.187
Flash Point 157.7°C
Transport Information
Appearance white to yellow-beige crystals, crystalline
Safety 510075
Risk Codes R20/21/22;R36/37/38
Molecular Structure
Hazard Symbols
Synonyms o-Benzenediacetonitrile(7CI,8CI); (2-(Cyanomethyl)phenyl)acetonitrile; 1,2-Bis(cyanomethyl)benzene;1,2-Phenylenediacetonitrile; NSC 5170; o-Bis(cyanomethyl)benzene;o-Phenylenediacetonitrile; o-Xylylene dicyanide; a,a'-Dicyano-o-xylene
PSA 47.58000
LogP 1.81876

Synthetic route

: 140-29-4
phenylacetonitrile

: 75-05-8
acetonitrile

: 613-73-0
1,2-phenylenediacetonitrile

Conditions

Conditions	Yield
for 3h; Irradiation;	0.05%

: 89-92-9
2-methylbenzyl bromide

: 613-73-0
1,2-phenylenediacetonitrile

: 13435-20-6
tetraethylammoniumcyanide

: 91-13-4
α,α'-dibromo-o-xylene

: 613-73-0
1,2-phenylenediacetonitrile

Conditions

Conditions	Yield
In dichloromethane

: 151-50-8
potassium cyanide

: 91-13-4
α,α'-dibromo-o-xylene

: 613-73-0
1,2-phenylenediacetonitrile

: 151-50-8
potassium cyanide

o-xylylene dibromide: o-xylylene dibromide

: 613-73-0
1,2-phenylenediacetonitrile

Conditions

Conditions	Yield
With ethanol; water

: 95-47-6
o-xylene

: 613-73-0
1,2-phenylenediacetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine / water / UV-irradiation 2: ethanol; water / 2 h / Reflux View Scheme

: 773837-37-9
sodium cyanide

: 91-13-4
α,α'-dibromo-o-xylene

: 613-73-0
1,2-phenylenediacetonitrile

Conditions

Conditions	Yield
In ethanol; water for 2h; Reflux;

: 1530-89-8
N-cyanomorpholine

: 613-73-0
1,2-phenylenediacetonitrile

: 1616963-14-4
2-morpholino-9H-indeno[2,1-d]pyrimidin-4-amine

Conditions

Conditions	Yield
With potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 2h; Inert atmosphere;	96%

: 27318-90-7
1,10-phenanthroline-5,6-dione

: 613-73-0
1,2-phenylenediacetonitrile

: Naphtho[2,3-f][1,ω]phenanthroline-9,14-dicarbonitrile

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 20℃; for 36h; Condensation;	90%

: 113350-36-0, 102382-37-6
bis(acetonitrile)diiodotricarbonyltungsten(II)

: 613-73-0
1,2-phenylenediacetonitrile

: 603-35-0
triphenylphosphine

: [WI2(CO)3(C6H4(CH2CN)2)(P(C6H5)3)]

Conditions

Conditions	Yield
In dichloromethane byproducts: NCCH3; addn. of PPh3, 1 min. stirring, addn. of 1,2-C6H4(CH2CN)2, 1 h, room temp., molar ratio: 1:1:1; filtration, vac. evapn., recrystn.(CH2CL2-Et2O), elem. anal.;	89%

...Expand

: C36H22O2

: 613-73-0
1,2-phenylenediacetonitrile

: C46H26N2

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 35℃; for 8h; Inert atmosphere;	88%

: 102349-56-4
MoI2(CO)3(MeCN)2

: 613-73-0
1,2-phenylenediacetonitrile

: 603-35-0
triphenylphosphine

: [MoI2(CO)3(C6H4(CH2CN)2)(P(C6H5)3)]

Conditions

Conditions	Yield
In dichloromethane byproducts: NCCH3; addn. of PPh3, 1 min. stirring, addn. of 1,2-C6H4(CH2CN)2, 1 h, room temp., molar ratio: 1:1:1; filtration, vac. evapn., recrystn.(CH2CL2-Et2O), elem. anal.;	86%

...Expand

: 113350-36-0, 102382-37-6
bis(acetonitrile)diiodotricarbonyltungsten(II)

: 603-32-7
triphenyl-arsane

: 613-73-0
1,2-phenylenediacetonitrile

: [WI2(CO)3(C6H4(CH2CN)2)(As(C6H5)3)]

Conditions

Conditions	Yield
In dichloromethane byproducts: NCCH3; addn. of AsPh3, 3 min. stirring, addn. of 1,2-C6H4(CH2CN)2, 1 h, room temp., molar ratio: 1:1:1; filtration, vac. evapn., recrystn.(CH2CL2-Et2O), elem. anal.;	85%

...Expand

: [WI(CO)(NCMe)(P(OiPr)3)2(η2-MeC2Me)][BPh4]

: 613-73-0
1,2-phenylenediacetonitrile

: [WI(CO)(1,2-C6H4(NCCH2)2)(P(OiPr)3)2(η2-MeC2Me)][BPh4]

Conditions

Conditions	Yield
In dichloromethane ligand was added to soln. of W-complex in CH2Cl2, stirred for 20 h in Schlenk apparatus; filtered, vol. was reduced in vacuo, layered with Et2O, cooled to -17°C for 5 ds; elem. anal.;	85%

: 64-17-5
ethanol

: 613-73-0
1,2-phenylenediacetonitrile

: 17532-66-0
ethyl 2-[2-(2-ethoxy-2-oxoethyl)phenyl]acetate

Conditions

Conditions	Yield
With sulfuric acid for 7h; Heating;	84%
With sulfuric acid for 7h; Heating;	73%
With sulfuric acid for 6h; Heating / reflux;	70.6%

: 28227-42-1, 30834-74-3
1,4-di-tert-butyl-1,4-diazabutadiene

: 613-73-0
1,2-phenylenediacetonitrile

A: 3029-30-9
naphthalene-1,4-dicarbonitrile

B: 75-64-9
tert-butylamine

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120℃; for 1h;	A 82% B n/a

...Expand

: 76509-14-3
N,N'-Bis(2,4-dimethylphenyl)glyoxaldiimin

: 613-73-0
1,2-phenylenediacetonitrile

A: 3029-30-9
naphthalene-1,4-dicarbonitrile

B: 95-68-1
2,4-Xylidine

Conditions

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide at 20℃; for 15h; Mechanism; var. glyoxaldiimines;	A 82% B n/a
With potassium hydroxide In N,N-dimethyl acetamide at 20℃; for 15h;	A 82% B n/a

...Expand

: 101-02-0
triphenyl phosphite

: 102349-56-4
MoI2(CO)3(MeCN)2

: 613-73-0
1,2-phenylenediacetonitrile

: [MoI2(CO)3(C6H4(CH2CN)2)(P(OC6H5)3)]

Conditions

Conditions	Yield
In dichloromethane byproducts: NCCH3; addn. of POPh3, 5 min. stirring, addn. of 1,2-C6H4(CH2CN)2, 1 h, room temp., molar ratio: 1:1:1; filtration, vac. evapn., recrystn.(CH2CL2-Et2O), elem. anal.;	82%

...Expand

: 102349-56-4
MoI2(CO)3(MeCN)2

: 603-32-7
triphenyl-arsane

: 613-73-0
1,2-phenylenediacetonitrile

: [MoI2(CO)3(C6H4(CH2CN)2)(As(C6H5)3)]

Conditions

Conditions	Yield
In dichloromethane byproducts: NCCH3; addn. of AsPh3, 3 min. stirring, addn. of 1,2-C6H4(CH2CN)2, 1 h, room temp., molar ratio: 1:1:1; filtration, vac. evapn., recrystn.(CH2CL2-Et2O), elem. anal.;	80%

...Expand

: 102349-56-4
MoI2(CO)3(MeCN)2

: 603-36-1
triphenylantimony

: 613-73-0
1,2-phenylenediacetonitrile

: [MoI2(CO)3(C6H4(CH2CN)2)(Sb(C6H5)3)]

Conditions

Conditions	Yield
In dichloromethane byproducts: NCCH3; addn. of SbPh3, 5 min. stirring, addn. of 1,2-C6H4(CH2CN)2, 1 h, room temp., molar ratio: 1:1:1; filtration, vac. evapn., recrystn.(CH2CL2-Et2O), elem. anal.;	80%

...Expand

: 613-73-0
1,2-phenylenediacetonitrile

: 53348-05-3
3,6-dibromo-phenanthrene-9,10-dione

: 3,6-dibromo-9,14-dicyanobenzo[f]tetraphene

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 20℃;	80%

: 613-73-0
1,2-phenylenediacetonitrile

: 7500-54-1
o-xylylenediamide

Conditions

Conditions	Yield
Stage #1: 1,2-phenylenediacetonitrile With acetamide; acetic acid at 50℃; under 760.051 Torr; for 0.5h; Stage #2: With tetrakis(acetonitrile)palladium(II) tetrafluoroborate at 50℃; under 1 - 3 Torr; for 2h;	79%
With sulfuric acid

: 64-17-5
ethanol

: 613-73-0
1,2-phenylenediacetonitrile

: 80900-31-8
2-Amino-3-ethyl-3H-indene-1-carbonitrile

Conditions

Conditions	Yield
rhodium(III) chloride; sodium carbonate; triphenylphosphine for 24h; Heating;	78%

: 613-73-0
1,2-phenylenediacetonitrile

: 189242-48-6
2-amino-1H-indene-1-carbonitrile

Conditions

Conditions	Yield
With carbonylhydridotris(triphenylphosphine)iridium(I) In tetrahydrofuran at 30℃; for 12h;	76%
With ethanol; sodium ethanolate

: 113350-36-0, 102382-37-6
bis(acetonitrile)diiodotricarbonyltungsten(II)

: 613-73-0
1,2-phenylenediacetonitrile

: [WI2(CO)3(C6H4(CH2CN)2)2]

Conditions

Conditions	Yield
In dichloromethane byproducts: NCCH3; 1h, room temp., molar ratio: 1:2; filtration, vac. evapn., recrystn.(CH2CL2-Et2O), elem. anal.;	75%

: 101-02-0
triphenyl phosphite

: 113350-36-0, 102382-37-6
bis(acetonitrile)diiodotricarbonyltungsten(II)

: 613-73-0
1,2-phenylenediacetonitrile

: [WI2(CO)3(C6H4(CH2CN)2)(P(OC6H5)3)]

Conditions

Conditions	Yield
In dichloromethane byproducts: NCCH3; addn. of POPh3, 5 min. stirring, addn. of 1,2-C6H4(CH2CN)2, 1 h, room temp., molar ratio: 1:1:1; filtration, vac. evapn., recrystn.(CH2CL2-Et2O), elem. anal.;	73%

...Expand

: 102349-56-4
MoI2(CO)3(MeCN)2

: 613-73-0
1,2-phenylenediacetonitrile

: [MoI2(CO)3(C6H4(CH2CN)2)2]

Conditions

Conditions	Yield
In dichloromethane byproducts: NCCH3; 1h, room temp., molar ratio: 1:2; filtration, vac. evapn., recrystn.(CH2CL2-Et2O), elem. anal.;	72%

: 13716-10-4
di(tert-butyl)chlorophosphine

: 613-73-0
1,2-phenylenediacetonitrile

: 1395070-51-5
N-[2,2-di-tert-butyl-2λ5-indeno[1,2-d][1,2]azaphosphol-3(8H)-ylidene]-P,P-di-tert-butylphosphinous amide

Conditions

Conditions	Yield
Stage #1: 1,2-phenylenediacetonitrile With sodium hydride In tetrahydrofuran Inert atmosphere; Stage #2: di(tert-butyl)chlorophosphine In tetrahydrofuran Inert atmosphere;	70%

: 79-16-3
N-methyl-acetamide

N-(tertiary)-butylamine-glyoxalbisaldimine: N-(tertiary)-butylamine-glyoxalbisaldimine

: 613-73-0
1,2-phenylenediacetonitrile

: 3029-30-9
naphthalene-1,4-dicarbonitrile

Conditions

Conditions	Yield
	68.5%

...Expand

: 32155-34-3
9,10-dioxo-9,10-dihydrophenanthrene-3-carboxylic acid

: 613-73-0
1,2-phenylenediacetonitrile

: 1185274-48-9
9,14-dicyanobenzo[b]triphenylene-3-carboxylic acid

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 40℃; for 6h;	68%

: 51479-97-1
N1,N2-bis(o-tolyl)ethane-1,2-diimine

: 613-73-0
1,2-phenylenediacetonitrile

A: 3029-30-9
naphthalene-1,4-dicarbonitrile

B: 95-53-4
o-toluidine

Conditions

Conditions	Yield
With sodium methylate In N,N-dimethyl acetamide at 25℃; for 15h;	A 67% B n/a

...Expand

: 613-73-0
1,2-phenylenediacetonitrile

A: 56066-94-5
2-Cyanmethyl-phenylessigsaeure

B: 7500-54-1
o-xylylenediamide

Conditions

Conditions	Yield
With water for 24h; Rhodococcus rhodochrous AJ270;	A 11% B 65%

: 613-73-0
1,2-phenylenediacetonitrile

A: 7500-54-1
o-xylylenediamide

B: 2-(2-Cyanomethyl-phenyl)-acetamide

Conditions

Conditions	Yield
With potassium phosphate buffer; Rhodococcus sp. AJ270 at 30℃; for 24h;	A 65% B 11%

N-o-toluidine-glyoxalbisaldimine: N-o-toluidine-glyoxalbisaldimine

: 613-73-0
1,2-phenylenediacetonitrile

: 3029-30-9
naphthalene-1,4-dicarbonitrile

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide	63%

: 613-73-0
1,2-phenylenediacetonitrile

: 273733-05-4
4,5,6,7-tetrahydrocyclobuta[b]naphthalene-1,2-dione

: 7,8,9,10-tetrahydrodibenzo[b,h]biphenylene-5,12-dicarbonitrile

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 0.0833333h; Condensation; Heating;	62%

: C36H20O4

: 613-73-0
1,2-phenylenediacetonitrile

: C56H28N4

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 35℃; for 8h; Inert atmosphere;	62%

: C36H20O4

: 613-73-0
1,2-phenylenediacetonitrile

: C56H28N4

Conditions

Conditions	Yield
With sodium methylate In methanol; N,N-dimethyl-formamide at 35℃; for 8h; Inert atmosphere;	62%

1,2-Bis(cyanomethyl)benzene Chemical Properties

The Molecular Structure of o-Phenylenediacetonitrile (CAS NO.613-73-0):

Empirical Formula: C₁₀H₈N₂
Molecular Weight: 156.1839
IUPAC Name: 2-[2-(cyanomethyl)phenyl]acetonitrile
Appearance: white to yellow-beige crystals, crystalline
Nominal Mass: 156 Da
Average Mass: 156.1839 Da
Monoisotopic Mass: 156.068748 Da
Index of Refraction: 1.549
Molar Refractivity: 45.17 cm³
Molar Volume: 141.8 cm³
Surface Tension: 49.9 dyne/cm
Density: 1.101 g/cm³
Flash Point: 157.7 °C
Enthalpy of Vaporization: 56.75 kJ/mol
Boiling Point: 325.4 °C at 760 mmHg Vapour
Pressure: 0.000231 mmHg at 25°C
Product Categories: Benzene derivates
InChI
InChI=1/C10H8N2/c11-7-5-9-3-1-2-4-10(9)6-8-12/h1-4H,5-6H2
Smiles
c1ccc(CC#N)c(c1)CC#N

1,2-Bis(cyanomethyl)benzene Safety Profile

Hazard Codes: Harmful Xn Irritant Xi
Risk Statements: 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 36/37-36/37/39-26-36
S36/37:Wear suitable protective clothing and gloves
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing
RIDADR: 3276
WGK Germany: 1
HazardClass: 6.1
PackingGroup: III

1,2-Bis(cyanomethyl)benzene Specification

o-Phenylenediacetonitrile (CAS NO.613-73-0) is also called as EINECS 210-351-3 ; O-bis(cyanomethyl)benzene ; Alpha,alpha'-dicyano-o-xylene ; 1,2-Bis(cyanomethyl)benzene ; O-xylylene cyanide ; O-xylylene dicyanide ; O-benzenediacetonitrile ; O-xylylenedicyanide,97% ; O-phenylenediacetonitrile, 99+% .

Product Name

1,2-Bis(cyanomethyl)benzene

Synthetic route

1,2-Bis(cyanomethyl)benzene Chemical Properties

1,2-Bis(cyanomethyl)benzene Safety Profile

1,2-Bis(cyanomethyl)benzene Specification

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