SciFinder®
Page 1
1. 3 Steps
1
Step
1
Stages
1.1
Notes
Yield
literature preparation, Reactants: 1,
Reagents: 1, Steps: 1, Stages: 1
R:O=C(NH2)2, 170°C
2
Step
2
Stages
2.1
Notes
Yield
literature preparation, Reactants: 1,
Reagents: 2, Steps: 1, Stages: 1
R:NH3, R:NH4OH
3
Step
3
Stages
3.1
R:SOCl2, C:DMF
Notes
Yield
literature preparation, Reactants: 1,
Reagents: 1, Catalysts: 1, Steps: 1,
Stages: 1
SciFinder®
Page 2
Source
Dielectric Response in the First
Silicon Phthalocyanine Network
Polymer
Darwish, Wael; Turky, Gamal
Journal of Inorganic and
Organometallic Polymers and
Materials
Volume 24
Issue 2
Pages 347-354
Journal; Online Computer File
2014
Company/Organization
Department of Polymers and
Pigments
National Research Centre
Giza, Egypt 12622
Number of Steps
3
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
2. 2 Steps
1
Step
1
Stages
1.1
Notes
Yield
literature preparation, Reactants: 1,
Reagents: 2, Steps: 1, Stages: 1
R:NH3, R:NH4OH
2
Step
Stages
Notes
Yield
SciFinder®
2
2.1
Page 3
literature preparation, Reactants: 1,
Reagents: 1, Catalysts: 1, Steps: 1,
Stages: 1
R:SOCl2, C:DMF
Source
Dielectric Response in the First
Silicon Phthalocyanine Network
Polymer
Darwish, Wael; Turky, Gamal
Journal of Inorganic and
Organometallic Polymers and
Materials
Volume 24
Issue 2
Pages 347-354
Journal; Online Computer File
2014
Company/Organization
Department of Polymers and
Pigments
National Research Centre
Giza, Egypt 12622
Number of Steps
2
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
3. Single Step
Step
1
Stages
1.1
R:SOCl2, C:DMF
Notes
Yield
literature preparation, Reactants: 1,
Reagents: 1, Catalysts: 1, Steps: 1,
Stages: 1
Transformation:
1. Dehydration of (Thio)amides to
Nitriles/ von Braun Reaction
SciFinder®
Page 4
Source
Dielectric Response in the First
Silicon Phthalocyanine Network
Polymer
Darwish, Wael; Turky, Gamal
Journal of Inorganic and
Organometallic Polymers and
Materials
Volume 24
Issue 2
Pages 347-354
Journal; Online Computer File
2014
Company/Organization
Department of Polymers and
Pigments
National Research Centre
Giza, Egypt 12622
Number of Steps
1
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
4. Single Step
Step
1
Stages
Notes
1.1
R:Poly(methyl siloxane), S:AcNMe2, rt →
1.2
100°C
C:Pd2(dba)3, C:(Ph2P)2-ferrocene, 4 h, 100°C
Yield
Rosenmund-von Braun reaction,
73%
Reactants: 2, Reagents: 1, Catalysts: 2,
Solvents: 1, Steps: 1, Stages: 2
Transformation:
Uncategorized
Experimental Procedure
General/Typical Procedure: Synthesis of Substituted Phthalonitriles - General Procedure A 25 mL
two-neck round-bottom flask was charged with 1 mmol of o-dibromobenzene in DMAC (2 mL) and
PMHS (20 mg) was added at r.t. The reaction mixture was heated to the required temperature (Table
1) and Pd2 (dba)3 (20 mg, 2 mol%) and DPPF (15 mg, 2.7 mol%) were added. Afterwards, Zn(CN)2
(117 mg, 1 mmol) was added in 4-5 portions during the time mentioned in Table 1 till TLC indicated
completion of the reaction. The reaction mixture was cooled, diluted with EtOAc and filtered. Filtrate
was washed with H2O, dried with MgSO4, and concentrated in vacuo. The crude product was purified
by column chromatography using CH2Cl2 as eluent. 11b, yield 62%.
SciFinder®
Page 5
Source
Synthesis of phthalonitriles using a
palladium catalyst
Iqbal, Zafar; Lyubimtsev, Alexey;
Hanack, Michael
Synlett
Issue 15
Pages 2287-2290
Journal
2008
Company/Organization
Institut fuer Organische Chemie
Universitaet Tuebingen
Tuebingen, Germany 72076
Number of Steps
1
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
5. Single Step
Step
1
Stages
Notes
1.1
R:Poly(methyl siloxane), S:AcNMe2, rt →
1.2
100°C
C:Pd2(dba)3, C:(Ph2P)2-ferrocene, 8 h, 100°C
Yield
Rosenmund-von Braun reaction,
72%
Reactants: 2, Reagents: 1, Catalysts: 2,
Solvents: 1, Steps: 1, Stages: 2
Transformation:
Uncategorized
Experimental Procedure
General/Typical Procedure: Synthesis of Substituted Phthalonitriles - General Procedure A 25 mL
two-neck round-bottom flask was charged with 1 mmol of o-dibromobenzene in DMAC (2 mL) and
PMHS (20 mg) was added at r.t. The reaction mixture was heated to the required temperature (Table
1) and Pd2 (dba)3 (20 mg, 2 mol%) and DPPF (15 mg, 2.7 mol%) were added. Afterwards, Zn(CN)2
(117 mg, 1 mmol) was added in 4-5 portions during the time mentioned in Table 1 till TLC indicated
completion of the reaction. The reaction mixture was cooled, diluted with EtOAc and filtered. Filtrate
was washed with H2O, dried with MgSO4, and concentrated in vacuo. The crude product was purified
by column chromatography using CH2Cl2 as eluent. 11b, yield 72%.
SciFinder®
Page 6
Source
Synthesis of phthalonitriles using a
palladium catalyst
Iqbal, Zafar; Lyubimtsev, Alexey;
Hanack, Michael
Synlett
Issue 15
Pages 2287-2290
Journal
2008
Company/Organization
Institut fuer Organische Chemie
Universitaet Tuebingen
Tuebingen, Germany 72076
Number of Steps
1
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
6. 2 Steps
1
Step
1
Stages
1.1
R:O=C(NH2)2
1.2
R:NH3, S:H2O
Notes
Yield
first step thermal, Reactants: 1,
Reagents: 2, Solvents: 1, Steps: 1,
Stages: 2
82%
2
Step
Stages
Notes
Yield
SciFinder®
2
2.1
Reactants: 1, Reagents: 1, Solvents: 1,
Steps: 1, Stages: 1
R:SOCl2, S:DMF
Page 7
86%
Source
Molecular structure of 1,2,4,5tetracyanobenzene from gas-phase
electron diffraction and theoretical
calculations
Schultz, Gyorgy; Szabados, Agnes;
Tarczay, Gyorgy; Zauer, Karoly
Structural Chemistry
Volume 10
Issue 2
Pages 149-155
Journal
1999
Company/Organization
Structural Chemistry Research Group
Hungarian Academy of Sciences
Eotvos University
Budapest, Hung. H-1431
Number of Steps
2
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
7. Single Step
Step
1
Stages
1.1
R:SOCl2, S:DMF
Notes
Yield
Reactants: 1, Reagents: 1, Solvents: 1,
Steps: 1, Stages: 1
Transformation:
1. Dehydration of (Thio)amides to
Nitriles/ von Braun Reaction
86%
SciFinder®
Page 8
Source
Molecular structure of 1,2,4,5tetracyanobenzene from gas-phase
electron diffraction and theoretical
calculations
Schultz, Gyorgy; Szabados, Agnes;
Tarczay, Gyorgy; Zauer, Karoly
Structural Chemistry
Volume 10
Issue 2
Pages 149-155
Journal
1999
Company/Organization
Structural Chemistry Research Group
Hungarian Academy of Sciences
Eotvos University
Budapest, Hung. H-1431
Number of Steps
1
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
8. 2 Steps
1
Step
Stages
1
1.1
Notes
Yield
Reactants: 2, Steps: 1, Stages: 1
2
Step
Stages
Notes
Yield
SciFinder®
2
Page 9
solid state, Reactants: 1, Steps: 1,
Stages: 1
2.1
Source
Synthesis and crystal structure of
tetracyanoformylpentadienylidenepho
sphorane. Transformation into
tetracyanobenzene
Rihs, Grety; Weis, Claus D.; Wieland,
Peter
Phosphorus, Sulfur and Silicon and
the Related Elements
Volume 48
Issue 1-4
Pages 27-32
Journal
1990
Company/Organization
Dyestuffs Chem. Dep.
Ciba-Geigy, Inc.
Basel, Switz.
Number of Steps
2
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
9. Single Step
Step
Stages
1
1.1
Notes
Yield
solid state, Reactants: 1, Steps: 1,
Stages: 1
Transformation:
Uncategorized
SciFinder®
Page 10
Source
Synthesis and crystal structure of
tetracyanoformylpentadienylidenepho
sphorane. Transformation into
tetracyanobenzene
Rihs, Grety; Weis, Claus D.; Wieland,
Peter
Phosphorus, Sulfur and Silicon and
the Related Elements
Volume 48
Issue 1-4
Pages 27-32
Journal
1990
Company/Organization
Dyestuffs Chem. Dep.
Ciba-Geigy, Inc.
Basel, Switz.
Number of Steps
1
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
10. Single Step
Step
1
Stages
1.1
R:SOCl2
Notes
Yield
Reactants: 1, Reagents: 1, Steps: 1,
Stages: 1
Transformation:
1. Dehydration of (Thio)amides to
Nitriles/ von Braun Reaction
Source
Syntheses and properties of some
polycyanobenzenes
Gibson, G. K. J.
Chemistry & Industry (London, United
Kingdom)
Issue 18
Pages 649-50
Journal
1981
SciFinder®
Page 11
Company/Organization
Div. Electr. Sci.
Natl. Phys. Lab.
Teddington, UK
Number of Steps
1
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
11. Single Step
Step
1
Stages
1.1
R:SOCl2, S:DMF
Notes
Yield
Classification: Elimination; Dehydration; 60%
# Conditions: SOCl2 DMF; 0 deg; 2
days 20 deg, Reactants: 1, Reagents: 1,
Solvents: 1, Steps: 1, Stages: 1
Transformation:
1. Dehydration of (Thio)amides to
Nitriles/ von Braun Reaction
Source
Thionyl chloride and
dimethylformamide as dehydrating
agents
Thurman, J. C.
Chemistry & Industry (London, United
Kingdom)
Issue 18
Pages 752
Journal
1964
Company/Organization
Natl. Chem. Lab.
Teddington, UK
Number of Steps
1
SciFinder®
Page 12
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
12. Single Step
Step
1
Stages
1.1
R:SOCl2, S:DMF
Notes
Yield
Classification: Elimination; Dehydration; 28%
# Conditions: SOCl2 DMF; 60 deg 7h;
SOCl2 DMF; heat 2h, Reactants: 1,
Reagents: 1, Solvents: 1, Steps: 1,
Stages: 1
Transformation:
1. Dehydration of (Thio)amides to
Nitriles/ von Braun Reaction
Source
Synthesis of pyromellitonitrile and
related compounds
Lawton, Emil A.; McRitchie, Donna D.
Journal of Organic Chemistry
Volume 24
Pages 26-8
Journal
1959
Company/Organization
Battelle Mem. Inst.
Columbus, O.
Number of Steps
1
CASREACT ®: Copyright © 2016 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.