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139152-08-2

139152-08-2

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139152-08-2 Usage

Chemical Properties

Off-white powder

Uses

4,5-Dichlorophthalonitrile is suitable as a reactant in the synthesis of 4,5-bis(3,4-dimethoxyphenyl) phthalonitrile and 4,5-bis(2,6-dimethoxyphenoxy) phthalonitrile. It may be used in the synthesis of 4,5-diphenoxyphthalonitrile.

General Description

4,5-Dichlorophthalonitrile (4,5-dichloro-1,2-dicyanobenzene) is a phthalonitrile derivative. It has been synthesized from 4,5-dichloro-1,2-benzenedicarboxamide and characterized by 1H ,13C-NMR and IR. 4,5-dichlorophthalonitrile undergoes base catalyzed nucleophilic aromatic substitution reaction with O-, S- nucleophiles and acidic -CH containing compounds to form corresponding phthalonitrile derivatives, which are the precursors in the synthesis of phthalocyanines.

Check Digit Verification of cas no

The CAS Registry Mumber 139152-08-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,9,1,5 and 2 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 139152-08:
(8*1)+(7*3)+(6*9)+(5*1)+(4*5)+(3*2)+(2*0)+(1*8)=122
122 % 10 = 2
So 139152-08-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H2Cl2N2/c9-7-1-5(3-11)6(4-12)2-8(7)10/h1-2H

139152-08-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,5-Dichlorophthalonitrile

1.2 Other means of identification

Product number -
Other names 1,2-Dichloro-4,5-dicyanobenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:139152-08-2 SDS

139152-08-2Synthetic route

4,5-dichloro-1,2-benzenedicarboxamide
147699-62-5

4,5-dichloro-1,2-benzenedicarboxamide

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

Conditions
ConditionsYield
With trichlorophosphate In pyridine; methanol; water86%
With thionyl chloride; N,N-dimethyl-formamide 1) 0 - 5 deg C, 5 h, 2) r.t., 24 h;75%
With thionyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 29h;50%
With thionyl chloride In N,N-dimethyl-formamide at 0℃; for 12h; Inert atmosphere;50%
With thionyl chloride In N,N-dimethyl-formamide at 0℃; Inert atmosphere;1.48 g
phosgene
75-44-5

phosgene

4.5-dichloro-phthalic acid diamide

4.5-dichloro-phthalic acid diamide

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

Conditions
ConditionsYield
With N,N-dimethyl-aniline; chlorobenzene
4,5-dichlorophthalic anhydride
942-06-3

4,5-dichlorophthalic anhydride

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / formamide / 3 h / Heating
2: 72 percent / 25-33percent NH4OH / 48 h / Ambient temperature
3: 75 percent / SOCl2, DMF / 1) 0 - 5 deg C, 5 h, 2) r.t., 24 h
View Scheme
Multi-step reaction with 3 steps
1: formamide / 3 h / Reflux
2: ammonium hydroxide / 48 h / 20 °C
3: thionyl chloride / N,N-dimethyl-formamide / 29 h / 0 - 20 °C
View Scheme
4,5-dichlorophthalimide
15997-89-4

4,5-dichlorophthalimide

hydrazine hydrate (1 mol)

hydrazine hydrate (1 mol)

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / 25-33percent NH4OH / 48 h / Ambient temperature
2: 75 percent / SOCl2, DMF / 1) 0 - 5 deg C, 5 h, 2) r.t., 24 h
View Scheme
4,5-dichlorophthalic acid
56962-08-4

4,5-dichlorophthalic acid

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 93 percent / acetic anhydride / 5 h / Heating
2: 98 percent / formamide / 3 h / Heating
3: 72 percent / 25-33percent NH4OH / 48 h / Ambient temperature
4: 75 percent / SOCl2, DMF / 1) 0 - 5 deg C, 5 h, 2) r.t., 24 h
View Scheme
Multi-step reaction with 4 steps
1: acetic anhydride / 5 h / Reflux
2: formamide / 3 h / Reflux
3: ammonium hydroxide / 48 h / 20 °C
4: thionyl chloride / N,N-dimethyl-formamide / 29 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: formamide / 4 h / 140 - 180 °C
2: ammonium hydroxide / dimethyl sulfoxide / 6 h / 0 - 20 °C
3: thionyl chloride / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: formamide / 4 h / 140 - 180 °C
2: ammonia / dimethyl sulfoxide / 6 h / 25 °C / Cooling with ice
3: thionyl chloride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere
View Scheme
4,5-dichlorophthalimide
15997-89-4

4,5-dichlorophthalimide

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium hydroxide / 48 h / 20 °C
2: thionyl chloride / N,N-dimethyl-formamide / 29 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: ammonium hydroxide / dimethyl sulfoxide / 6 h / 0 - 20 °C
2: thionyl chloride / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: ammonia / dimethyl sulfoxide / 6 h / 25 °C / Cooling with ice
2: thionyl chloride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere
View Scheme
1-Adamantanethiol
34301-54-7

1-Adamantanethiol

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

C28H32N2S2
1417158-52-1

C28H32N2S2

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h;99%
n-Heptyl Resorcinol
18979-76-5

n-Heptyl Resorcinol

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4,5-bis(3-heptyloxyphenoxy)phthalonitrile

4,5-bis(3-heptyloxyphenoxy)phthalonitrile

Conditions
ConditionsYield
Stage #1: n-Heptyl Resorcinol With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.166667h; Inert atmosphere;
Stage #2: 4,5-dichlorophthalonitrile In N,N-dimethyl-formamide at 100℃; for 1.83h; Inert atmosphere;		98.7%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4-t-butylbenzenethiol
2396-68-1

4-t-butylbenzenethiol

3,6-bis[(tert-butylphenyl)sulfanyl]phthalonitrile
1130308-49-4

3,6-bis[(tert-butylphenyl)sulfanyl]phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 20h;98%
2,3-dihydroxytriptycene
928880-37-9

2,3-dihydroxytriptycene

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4,5-(1,2-dioxytriptycene)phthalonitrile

4,5-(1,2-dioxytriptycene)phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;98%
ethyl-3-hydroxybenzoate
7781-98-8

ethyl-3-hydroxybenzoate

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4,5-bis(3-ethoxycarbonylphenoxy)phthalonitrile

4,5-bis(3-ethoxycarbonylphenoxy)phthalonitrile

Conditions
ConditionsYield
With potassium carbonate97%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4-aminotiophenol
1193-02-8

4-aminotiophenol

4,5-bis((4-aminophenyl)thio)phthalonitrile

4,5-bis((4-aminophenyl)thio)phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 12h; Inert atmosphere;97%
5-Hydroxy-2-methylpyridine
1121-78-4

5-Hydroxy-2-methylpyridine

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4,5-bis(4′-methylpyridin-3′-yloxy)phthalonitrile

4,5-bis(4′-methylpyridin-3′-yloxy)phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;97%
3-(9H-carbazol-9-yl)phenylboronic acid
864377-33-3

3-(9H-carbazol-9-yl)phenylboronic acid

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

3,3’’-di(9H-carbazol-9-yl)-[1,1’:2′ ,1’’-terphenyl]-4′,5′-dicarbonitrile

3,3’’-di(9H-carbazol-9-yl)-[1,1’:2′ ,1’’-terphenyl]-4′,5′-dicarbonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Reflux; Inert atmosphere;97%
4-tritylphenol
978-86-9

4-tritylphenol

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

bis{4,5-[4-(triphenylmethyl)phenoxy]}-1,2-dicyanobenzene
356098-74-3

bis{4,5-[4-(triphenylmethyl)phenoxy]}-1,2-dicyanobenzene

Conditions
ConditionsYield
Stage #1: 4-tritylphenol With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.166667h; Inert atmosphere;
Stage #2: 4,5-dichlorophthalonitrile In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;		96%
2-aminopyridine
504-29-0

2-aminopyridine

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

1,3-bis(2-pyridylimino)-5,6-dichloroisoindole
1386999-76-3

1,3-bis(2-pyridylimino)-5,6-dichloroisoindole

Conditions
ConditionsYield
With calcium chloride In butan-1-ol for 48h; Reflux; Inert atmosphere;96%
4-mercaptobenzoic acid
1074-36-8

4-mercaptobenzoic acid

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4,4′-((4,5-dicyano-1,2-phenylene)bis(sulfanediyl))dibenzoic acid

4,4′-((4,5-dicyano-1,2-phenylene)bis(sulfanediyl))dibenzoic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;96%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

3-(n-octyloxy)thiophenol
162557-60-0

3-(n-octyloxy)thiophenol

4,5-bis((3-(octyloxy)phenyl)thio)phthalonitrile

4,5-bis((3-(octyloxy)phenyl)thio)phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 7h; Inert atmosphere;95.1%
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4-chloro-5-[4-(hydroxymethyl)phenoxy]phthalonitrile
649553-05-9

4-chloro-5-[4-(hydroxymethyl)phenoxy]phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In acetone for 24h; Heating;95%
4-sulfanylphenol
637-89-8

4-sulfanylphenol

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4,5-bis((4-hydroxyphenyl)thio)phthalonitrile
1210049-82-3

4,5-bis((4-hydroxyphenyl)thio)phthalonitrile

Conditions
ConditionsYield
Stage #1: 4-sulfanylphenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Inert atmosphere;
Stage #2: 4,5-dichlorophthalonitrile In N,N-dimethyl-formamide for 24h; Inert atmosphere;		95%
Stage #1: 4-sulfanylphenol With potassium carbonate In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 4,5-dichlorophthalonitrile In dimethyl sulfoxide at 90℃; for 12h; Inert atmosphere;		91%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;75%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

Quinoline-2-thiol
2637-37-8

Quinoline-2-thiol

4,5-[2-mercaptoquinoline]phthalonitrile

4,5-[2-mercaptoquinoline]phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2.5h; Inert atmosphere;95%
1-methyl-2-(1-thiohex-6-yl)-1,2-closo-dodecaborane

1-methyl-2-(1-thiohex-6-yl)-1,2-closo-dodecaborane

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

C26H52B20N2S2

C26H52B20N2S2

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 45℃; for 4h;95%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

triethyl phosphite
122-52-1

triethyl phosphite

tetraethyl (4,5-dicyano-1,2-phenylene)bisphosphonate

tetraethyl (4,5-dicyano-1,2-phenylene)bisphosphonate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) at 230℃; under 5171.62 Torr; for 0.75h; Microwave irradiation;95%
1-(3-mercapto)propyl-3,5,7,9,11,13,15-isobutylpentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane
480438-85-5

1-(3-mercapto)propyl-3,5,7,9,11,13,15-isobutylpentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4,5-bis(mercaptopropylisobutyl-POSS)phthalonitrile
1035113-11-1

4,5-bis(mercaptopropylisobutyl-POSS)phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran for 48h; Heating;94%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4-methoxy-phenol
150-76-5

4-methoxy-phenol

4,5-bis(4-methoxyphenoxy)phthalonitrile
147699-64-7

4,5-bis(4-methoxyphenoxy)phthalonitrile

Conditions
ConditionsYield
Stage #1: 4-methoxy-phenol With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.25h; Inert atmosphere;
Stage #2: 4,5-dichlorophthalonitrile In N,N-dimethyl acetamide at 110℃; for 3h; Inert atmosphere;		93.4%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 0.5h;72%
1-butanethiol
109-79-5

1-butanethiol

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

1,2-dibutylthio-4,5-dicyanobenzene
165284-85-5

1,2-dibutylthio-4,5-dicyanobenzene

Conditions
ConditionsYield
With copper(I) oxide; sodium hydride In N,N-dimethyl-formamide for 3h; Condensation; Heating;93%
With N,N-dimethyl acetamide; potassium carbonate at 90℃; for 8h; Inert atmosphere;72%
With potassium carbonate In N,N-dimethyl acetamide at 90℃; for 12h; Inert atmosphere;
15-thiol-13,17-dioxa nonacosane
309275-22-7

15-thiol-13,17-dioxa nonacosane

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

1,2-di(13,17-dioxa nonacosane-15-sulfanyl) phthalonitrile
309275-24-9

1,2-di(13,17-dioxa nonacosane-15-sulfanyl) phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 50℃; for 48h;93%
morpholine
110-91-8

morpholine

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4-chloro-5-morpholinophthalonitrile
309735-19-1

4-chloro-5-morpholinophthalonitrile

Conditions
ConditionsYield
at 20℃; for 24h; Inert atmosphere;93%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

4,5-bis[3-(dimethylamino)phenoxy]phthalonitrile

4,5-bis[3-(dimethylamino)phenoxy]phthalonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere;93%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 18h;93%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

2-methoxy-phenol
90-05-1

2-methoxy-phenol

4,5-bis(2-methoxyphenoxy)phthalonitrile

4,5-bis(2-methoxyphenoxy)phthalonitrile

Conditions
ConditionsYield
Stage #1: 2-methoxy-phenol With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.25h; Inert atmosphere;
Stage #2: 4,5-dichlorophthalonitrile In N,N-dimethyl acetamide at 110℃; for 3h; Inert atmosphere;		92.8%
5-chloro-2-pyridylamine
1072-98-6

5-chloro-2-pyridylamine

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

C18H9Cl4N5
1109281-07-3

C18H9Cl4N5

Conditions
ConditionsYield
With calcium chloride In hexan-1-ol for 18h; Reflux; Inert atmosphere;92%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

phenylboronic acid
98-80-6

phenylboronic acid

1,2-dicyano-4,5-diphenylbenzene
36360-44-8

1,2-dicyano-4,5-diphenylbenzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; sodium bromide In 1,4-dioxane; water for 6h; Suzuki-Miyaura cross coupling; Inert atmosphere; Heating;92%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; sodium bromide In 1,4-dioxane; water for 5.5h; Inert atmosphere; Heating;75%
caffeic acid
331-39-5

caffeic acid

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

C17H8N2O4
1446888-26-1

C17H8N2O4

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 48h; Inert atmosphere;92%
3,5-Di-tert-butylphenol
1138-52-9

3,5-Di-tert-butylphenol

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

4,5-bis(3,5-di-tert-butylphenoxy)-1,2-dicyanobenzene
405066-84-4

4,5-bis(3,5-di-tert-butylphenoxy)-1,2-dicyanobenzene

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 0.5h;91%
With potassium carbonate In dimethyl sulfoxide at 90℃; Inert atmosphere;90%
4-tert-Butylcatechol
98-29-3

4-tert-Butylcatechol

4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

7-tert-butyldibenzo [b,e] [1,4] dioxine-2,3-dicarbonitrile

7-tert-butyldibenzo [b,e] [1,4] dioxine-2,3-dicarbonitrile

Conditions
ConditionsYield
Stage #1: 4-tert-Butylcatechol; 4,5-dichlorophthalonitrile With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
Stage #2: In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;		91%
4,5-dichlorophthalonitrile
139152-08-2

4,5-dichlorophthalonitrile

thiophenol
108-98-5

thiophenol

4,5-bis(phenylthio)-1,2-dicyanobenzene
147699-67-0

4,5-bis(phenylthio)-1,2-dicyanobenzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 15h;90%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere;82%
With potassium carbonate In dimethyl sulfoxide for 12h; Inert atmosphere;75%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 0.5h;51%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 0.5h;46%

139152-08-2Relevant articles and documents

A facile reprecipitation method for the preparation of polyimide hollow spheres with controllable morphologies and permeable shell

Liu, Junzhi,Yan, Yuzhi,Chen, Zhihua,Gu, Yi,Liu, Xikui

, p. 1194 - 1196 (2010)

We present our preliminary work on the fabrication of polyimide hollow sphere by reprecipitation. Through fine-tuning the PAA concentration, many intriguing shapes, including deflated capsules, bowl-shaped and dimple-like hollow spheres can be obtained. Adding salt to the PAA solution helps the formation of PI hollow spheres with complete shells. The morphologies can be fixed through imidization, thus obtaining a controllable and reproducible method to prepare high-performance polyimide hollow spheres with various morphologies.

Surface modified polymer hollow nanocapsules, and method for preparing the same

-

, (2018/05/05)

The present invention relates to surface-modified polymer hollow nanocapsules in which polymer hollow nanocapsules, formed via polymerization of a composition containing a compound represented by chemical formula 1, are surface-modified to have a positive zeta potential when dispersed in water; and a method of preparing the same. In the chemical formula 1: X is subphthalocyanine, phthalocyanine, or porphyrin; L_1 is -OR_1- or -SR_2-, wherein the R_1 and R_2 are each independently a direct bond, an alkylene group having 1-10 carbon atoms, an alkenylene group having 2-10 carbon atoms, a cycloalkylene group having 6-20 carbon atoms, a cycloalkenylene group having 6-20 carbon atoms, or an arylene group having 6-20 carbon atoms; Y_1 is a vinyl group, an acryl group, a methacryl group, a thiol group, or an amine group; and m is an integer of 3-10.COPYRIGHT KIPO 2018

A simple synthesis of 4,5-disubstituted 1,2-dicyanobenzenes and 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines

Wohrle,Eskes,Shigehara,Yamada

, p. 194 - 196 (2007/10/02)

4,5-Dichloro-1,2-dicyanobenzene (5) was prepared in an overall yield of 49% from 4,5-dichloro-1,2-benzenedicarboxylic acid (1). The reactions of 5 with phenols, thiophenol and 1-propanethiol led in a nucleophilic displacement reaction to the 4,5-bis(aryloxy)-, 4,5-bis(phenylthio)- and 4,5-bis(propylthio)-1,2-dicyanobenzenes 6 which were converted in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene in high yields to octasubstituted phthalocyanines (tetrabenzoporphyrazines) 7. Some compounds 7 contain eight free phenolic, carboxylic acid or pyridyl groups.

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