613-73-0

Usage

Chemical Properties

white to yellow-beige crystals, crystalline

Uses

1,2-Phenylenediacetonitrile is used as API and intermediate.

InChI:InChI=1/C10H8N2/c11-7-5-9-3-1-2-4-10(9)6-8-12/h1-4H,5-6H2

Synthetic route

phenylacetonitrile (140-29-4) + acetonitrile (75-05-8) → 1,2-phenylenediacetonitrile (613-73-0)

Conditions	Yield
for 3h; Irradiation;	0.05%

2-methylbenzyl bromide (89-92-9) → 1,2-phenylenediacetonitrile (613-73-0)

tetraethylammoniumcyanide (13435-20-6) + α,α'-dibromo-o-xylene (91-13-4) → 1,2-phenylenediacetonitrile (613-73-0)

Conditions	Yield
In dichloromethane

potassium cyanide (151-50-8) + α,α'-dibromo-o-xylene (91-13-4) → 1,2-phenylenediacetonitrile (613-73-0)

potassium cyanide (151-50-8) + o-xylylene dibromide → 1,2-phenylenediacetonitrile (613-73-0)

Conditions	Yield
With ethanol; water

o-xylene (95-47-6) → 1,2-phenylenediacetonitrile (613-73-0)

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

sodium cyanide (773837-37-9) + α,α'-dibromo-o-xylene (91-13-4) → 1,2-phenylenediacetonitrile (613-73-0)

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

N-cyanomorpholine (1530-89-8) + 1,2-phenylenediacetonitrile (613-73-0) → 2-morpholino-9H-indeno[2,1-d]pyrimidin-4-amine (1616963-14-4)

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

1,10-phenanthroline-5,6-dione (27318-90-7) + 1,2-phenylenediacetonitrile (613-73-0) → Naphtho[2,3-f][1,ω]phenanthroline-9,14-dicarbonitrile

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

bis(acetonitrile)diiodotricarbonyltungsten(II) (113350-36-0, 102382-37-6) + 1,2-phenylenediacetonitrile (613-73-0) + triphenylphosphine (603-35-0) → [WI2(CO)3(C6H4(CH2CN)2)(P(C6H5)3)]

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%

C36H22O2 + 1,2-phenylenediacetonitrile (613-73-0) → C46H26N2

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

MoI2(CO)3(MeCN)2 (102349-56-4) + 1,2-phenylenediacetonitrile (613-73-0) + triphenylphosphine (603-35-0) → [MoI2(CO)3(C6H4(CH2CN)2)(P(C6H5)3)]

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%

bis(acetonitrile)diiodotricarbonyltungsten(II) (113350-36-0, 102382-37-6) + triphenyl-arsane (603-32-7) + 1,2-phenylenediacetonitrile (613-73-0) → [WI2(CO)3(C6H4(CH2CN)2)(As(C6H5)3)]

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%

[WI(CO)(NCMe)(P(OiPr)3)2(η2-MeC2Me)][BPh4] + 1,2-phenylenediacetonitrile (613-73-0) → [WI(CO)(1,2-C6H4(NCCH2)2)(P(OiPr)3)2(η2-MeC2Me)][BPh4]

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%

ethanol (64-17-5) + 1,2-phenylenediacetonitrile (613-73-0) → ethyl 2-[2-(2-ethoxy-2-oxoethyl)phenyl]acetate (17532-66-0)

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%

1,4-di-tert-butyl-1,4-diazabutadiene (28227-42-1, 30834-74-3) + 1,2-phenylenediacetonitrile (613-73-0) → naphthalene-1,4-dicarbonitrile (3029-30-9) + tert-butylamine (75-64-9)

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

N,N'-Bis(2,4-dimethylphenyl)glyoxaldiimin (76509-14-3) + 1,2-phenylenediacetonitrile (613-73-0) → naphthalene-1,4-dicarbonitrile (3029-30-9) + 2,4-Xylidine (95-68-1)

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

triphenyl phosphite (101-02-0) + MoI2(CO)3(MeCN)2 (102349-56-4) + 1,2-phenylenediacetonitrile (613-73-0) → [MoI2(CO)3(C6H4(CH2CN)2)(P(OC6H5)3)]

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%

MoI2(CO)3(MeCN)2 (102349-56-4) + triphenyl-arsane (603-32-7) + 1,2-phenylenediacetonitrile (613-73-0) → [MoI2(CO)3(C6H4(CH2CN)2)(As(C6H5)3)]

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%

MoI2(CO)3(MeCN)2 (102349-56-4) + triphenylantimony (603-36-1) + 1,2-phenylenediacetonitrile (613-73-0) → [MoI2(CO)3(C6H4(CH2CN)2)(Sb(C6H5)3)]

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%

1,2-phenylenediacetonitrile (613-73-0) + 3,6-dibromo-phenanthrene-9,10-dione (53348-05-3) → 3,6-dibromo-9,14-dicyanobenzo[f]tetraphene

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

1,2-phenylenediacetonitrile (613-73-0) → o-xylylenediamide (7500-54-1)

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

ethanol (64-17-5) + 1,2-phenylenediacetonitrile (613-73-0) → 2-Amino-3-ethyl-3H-indene-1-carbonitrile (80900-31-8)

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

1,2-phenylenediacetonitrile (613-73-0) → 2-amino-1H-indene-1-carbonitrile (189242-48-6)

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

bis(acetonitrile)diiodotricarbonyltungsten(II) (113350-36-0, 102382-37-6) + 1,2-phenylenediacetonitrile (613-73-0) → [WI2(CO)3(C6H4(CH2CN)2)2]

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

triphenyl phosphite (101-02-0) + bis(acetonitrile)diiodotricarbonyltungsten(II) (113350-36-0, 102382-37-6) + 1,2-phenylenediacetonitrile (613-73-0) → [WI2(CO)3(C6H4(CH2CN)2)(P(OC6H5)3)]

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%

MoI2(CO)3(MeCN)2 (102349-56-4) + 1,2-phenylenediacetonitrile (613-73-0) → [MoI2(CO)3(C6H4(CH2CN)2)2]

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

di(tert-butyl)chlorophosphine (13716-10-4) + 1,2-phenylenediacetonitrile (613-73-0) → N-[2,2-di-tert-butyl-2λ5-indeno[1,2-d][1,2]azaphosphol-3(8H)-ylidene]-P,P-di-tert-butylphosphinous amide (1395070-51-5)

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%

N-methyl-acetamide (79-16-3) + N-(tertiary)-butylamine-glyoxalbisaldimine + 1,2-phenylenediacetonitrile (613-73-0) → naphthalene-1,4-dicarbonitrile (3029-30-9)

Conditions	Yield
	68.5%

9,10-dioxo-9,10-dihydrophenanthrene-3-carboxylic acid (32155-34-3) + 1,2-phenylenediacetonitrile (613-73-0) → 9,14-dicyanobenzo[b]triphenylene-3-carboxylic acid (1185274-48-9)

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

N1,N2-bis(o-tolyl)ethane-1,2-diimine (51479-97-1) + 1,2-phenylenediacetonitrile (613-73-0) → naphthalene-1,4-dicarbonitrile (3029-30-9) + o-toluidine (95-53-4)

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

1,2-phenylenediacetonitrile (613-73-0) → 2-Cyanmethyl-phenylessigsaeure (56066-94-5) + o-xylylenediamide (7500-54-1)

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

1,2-phenylenediacetonitrile (613-73-0) → o-xylylenediamide (7500-54-1) + 2-(2-Cyanomethyl-phenyl)-acetamide

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

N-o-toluidine-glyoxalbisaldimine + 1,2-phenylenediacetonitrile (613-73-0) → naphthalene-1,4-dicarbonitrile (3029-30-9)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide	63%

1,2-phenylenediacetonitrile (613-73-0) + 4,5,6,7-tetrahydrocyclobuta[b]naphthalene-1,2-dione (273733-05-4) → 7,8,9,10-tetrahydrodibenzo[b,h]biphenylene-5,12-dicarbonitrile

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

C36H20O4 + 1,2-phenylenediacetonitrile (613-73-0) → C56H28N4

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

C36H20O4 + 1,2-phenylenediacetonitrile (613-73-0) → C56H28N4

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

Upstream product

• 89-92-9 2-methylbenzyl bromide 
• 13435-20-6 tetraethylammoniumcyanide 
• 91-13-4 α,α'-dibromo-o-xylene 
• 151-50-8 potassium cyanide 
• 95-47-6 o-xylene 
• 773837-37-9 sodium cyanide 
• 140-29-4 phenylacetonitrile 
• 75-05-8 acetonitrile 

Downstream Products

• 122679-47-4 phthalan-1,3-dione-bis-(4-dimethylamino-phenylimine) 
• 72851-41-3 7,12-dicyano-benzofluoranthene 
• 4424-20-8 2,3,4,5-tetrahydro-1H-3-benzazepine 
• 42988-81-8 2,2'-o-phenylene-bis-ethylamine 
• 7500-53-0 1,2-Phenylenediacetic acid 
• 7500-54-1 o-xylylenediamide 
• 100255-99-0 o-phenylene-di-acetaldehyde-disemicarbazone 
• 3029-30-9 naphthalene-1,4-dicarbonitrile 
• 75-64-9 tert-butylamine 
• 75-31-0 isopropylamine 
• 108-91-8 cyclohexylamine 
• 76509-15-4 2,3-Bis(2,4-dimethylphenylamino)-1,2,3,4-tetrahydronaphthalin-1,4-dicarbonitril 
• 76509-16-5 2,3,9,10-Tetrakis(2,4-dimethylphenylamino)-1,2,3,4-tetrahydro-1,4-ethanonaphthalin-1,4-dicarbonitril 
• 95-68-1 2,4-Xylidine 

Relevant academic research and scientific papers

A heterogeneous palladium catalyst hybridised with a titanium dioxide photocatalyst for direct C-C bond formation between an aromatic ring and acetonitrile

A palladium catalyst hybridised with a titanium dioxide photocatalyst can promote cyanomethylation of an aromatic ring by using acetonitrile, where the photocatalyst activates acetonitrile to form a cyanomethyl radical before the C-C bond formation using the palladium catalyst.

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A new strong photochromic solid compound, a 3-ketone of the 2,3-diphenylindenone oxide, has been prepared for first time.The new compound exhibits very strong photochromic and thermochromic phenomena.