1,2-Benzenedicarbonitrile,4,5-dichloro- supplier

Name
4,5-DICHLOROPHTHALONITRILE
EINECS
CAS No. 139152-08-2
Article Data6
CAS DataBase
Density 1.48g/cm³
Solubility
Melting Point 180-184 °C(lit.)
Formula C₈H₂Cl₂N₂
Boiling Point 312.4 °C at 760 mmHg
Molecular Weight 197.023
Flash Point 141.1 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn； Xi
Synonyms 1,2-Dichloro-4,5-dicyanobenzene;1,2-Dicyano-4,5-dichlorobenzene;4,5-Dichloro-1,2-dicyanobenzene;4,5-Dichlorobenzene-1,2-dicarbonitrile;4,5-Dichlorophthalonitrile;
PSA 47.58000
LogP 2.73676

Synthetic route

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

: 139152-08-2
4,5-dichlorophthalonitrile

Conditions

Conditions	Yield
With trichlorophosphate In pyridine; methanol; water	86%
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

: 75-44-5
phosgene

4.5-dichloro-phthalic acid diamide: 4.5-dichloro-phthalic acid diamide

: 139152-08-2
4,5-dichlorophthalonitrile

Conditions

Conditions	Yield
With N,N-dimethyl-aniline; chlorobenzene

: 942-06-3
4,5-dichlorophthalic anhydride

: 139152-08-2
4,5-dichlorophthalonitrile

Conditions

Conditions	Yield
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

: 15997-89-4
4,5-dichlorophthalimide

hydrazine hydrate (1 mol): hydrazine hydrate (1 mol)

: 139152-08-2
4,5-dichlorophthalonitrile

Conditions

Conditions	Yield
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

: 56962-08-4
4,5-dichlorophthalic acid

: 139152-08-2
4,5-dichlorophthalonitrile

Conditions

Conditions	Yield
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

: 15997-89-4
4,5-dichlorophthalimide

: 139152-08-2
4,5-dichlorophthalonitrile

Conditions

Conditions	Yield
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

: 34301-54-7
1-Adamantanethiol

: 139152-08-2
4,5-dichlorophthalonitrile

: 1417158-52-1
C28H32N2S2

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h;	99%

: 18979-76-5
n-Heptyl Resorcinol

: 139152-08-2
4,5-dichlorophthalonitrile

: 4,5-bis(3-heptyloxyphenoxy)phthalonitrile

Conditions

Conditions	Yield
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%

: 139152-08-2
4,5-dichlorophthalonitrile

: 2396-68-1
4-t-butylbenzenethiol

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

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 20h;	98%

: 928880-37-9
2,3-dihydroxytriptycene

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;	98%

: 7781-98-8
ethyl-3-hydroxybenzoate

: 139152-08-2
4,5-dichlorophthalonitrile

: 4,5-bis(3-ethoxycarbonylphenoxy)phthalonitrile

Conditions

Conditions	Yield
With potassium carbonate	97%

: 139152-08-2
4,5-dichlorophthalonitrile

: 1193-02-8
4-aminotiophenol

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

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 12h; Inert atmosphere;	97%

: 1121-78-4
5-Hydroxy-2-methylpyridine

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;	97%

: 864377-33-3
3-(9H-carbazol-9-yl)phenylboronic acid

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 12h; Reflux; Inert atmosphere;	97%

: 978-86-9
4-tritylphenol

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
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%

: 504-29-0
2-aminopyridine

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
With calcium chloride In butan-1-ol for 48h; Reflux; Inert atmosphere;	96%

: 1074-36-8
4-mercaptobenzoic acid

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;	96%

: 139152-08-2
4,5-dichlorophthalonitrile

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

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

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 7h; Inert atmosphere;	95.1%

: 623-05-2
(4-hydroxyphenyl)methanol

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;	95%

: 637-89-8
4-sulfanylphenol

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
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%

: 139152-08-2
4,5-dichlorophthalonitrile

: 2637-37-8
Quinoline-2-thiol

: 4,5-[2-mercaptoquinoline]phthalonitrile

Conditions

Conditions	Yield
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

: 139152-08-2
4,5-dichlorophthalonitrile

: C26H52B20N2S2

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 45℃; for 4h;	95%

: 139152-08-2
4,5-dichlorophthalonitrile

: 122-52-1
triethyl phosphite

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

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) at 230℃; under 5171.62 Torr; for 0.75h; Microwave irradiation;	95%

: 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

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 48h; Heating;	94%

: 139152-08-2
4,5-dichlorophthalonitrile

: 150-76-5
4-methoxy-phenol

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

Conditions

Conditions	Yield
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%

: 109-79-5
1-butanethiol

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
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;

: 309275-22-7
15-thiol-13,17-dioxa nonacosane

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 50℃; for 48h;	93%

: 110-91-8
morpholine

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
at 20℃; for 24h; Inert atmosphere;	93%

: 139152-08-2
4,5-dichlorophthalonitrile

: 99-07-0
3-Dimethylaminophenol

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

Conditions

Conditions	Yield
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%

: 139152-08-2
4,5-dichlorophthalonitrile

: 90-05-1
2-methoxy-phenol

: 4,5-bis(2-methoxyphenoxy)phthalonitrile

Conditions

Conditions	Yield
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%

: 1072-98-6
5-chloro-2-pyridylamine

: 139152-08-2
4,5-dichlorophthalonitrile

: 1109281-07-3
C18H9Cl4N5

Conditions

Conditions	Yield
With calcium chloride In hexan-1-ol for 18h; Reflux; Inert atmosphere;	92%

: 139152-08-2
4,5-dichlorophthalonitrile

: 98-80-6
phenylboronic acid

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

Conditions

Conditions	Yield
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%

: 331-39-5
caffeic acid

: 139152-08-2
4,5-dichlorophthalonitrile

: 1446888-26-1
C17H8N2O4

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 48h; Inert atmosphere;	92%

: 1138-52-9
3,5-Di-tert-butylphenol

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 0.5h;	91%
With potassium carbonate In dimethyl sulfoxide at 90℃; Inert atmosphere;	90%

: 98-29-3
4-tert-Butylcatechol

: 139152-08-2
4,5-dichlorophthalonitrile

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

Conditions

Conditions	Yield
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%

: 139152-08-2
4,5-dichlorophthalonitrile

: 108-98-5
thiophenol

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

Conditions

Conditions	Yield
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%

1,2-Benzenedicarbonitrile,4,5-dichloro- Specification

The 1,2-Benzenedicarbonitrile,4,5-dichloro-, with CAS registry number 139152-08-2, belongs to the following product categories: (1)Functional Materials; (2)Phthalonitriles & Naphthalonitriles; (3)Phthalonitriles (Building Blocks for Phthalocyanines); (4)C8 to C9; (5)Cyanides/Nitriles; (6)Nitrogen Compounds. It has the systematic name of 4,5-dichlorobenzene-1,2-dicarbonitrile. And the chemical formula fo this chemical is C₈H₂Cl₂N₂.

Physical properties of 1,2-Benzenedicarbonitrile,4,5-dichloro-: (1)ACD/LogP: 2.23; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 0; (6)Polar Surface Area: 47.58 Å²; (7)Index of Refraction: 1.603; (8)Molar Refractivity: 45.54 cm³; (9)Molar Volume: 132.4 cm³; (10)Polarizability: 18.05×10^-24cm³; (11)Surface Tension: 64.2 dyne/cm; (12)Density: 1.48 g/cm³; (13)Flash Point: 141.1 °C; (14)Enthalpy of Vaporization: 55.34 kJ/mol; (15)Boiling Point: 312.4 °C at 760 mmHg; (16)Vapour Pressure: 0.000529 mmHg at 25°C.

Preparation: this chemical can be prepared by 4,5-dichloro-1,2-benzenedicarboxamide. This reaction will need reagents SOCl₂, DMF. The yield is about 75%.

Uses of 1,2-Benzenedicarbonitrile,4,5-dichloro-: it can be used to produce 5,6-dichloro-isoindoline-1,3-dione-diimine. This reaction will need reagents formamide, sodium amide. The reaction temperature is 0 ℃.

When you are using this chemical, please be cautious about it as the following:
The 1,2-Benzenedicarbonitrile,4,5-dichloro- irritates to eyes, respiratory system and skin. And it is harmful by inhalation, in contact with skin and if swallowed. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cc(C#N)c(C#N)cc1Cl
(2)InChI: InChI=1/C8H2Cl2N2/c9-7-1-5(3-11)6(4-12)2-8(7)10/h1-2H
(3)InChIKey: SRIJSZQFAMLVQV-UHFFFAOYAE
(4)Std. InChI: InChI=1S/C8H2Cl2N2/c9-7-1-5(3-11)6(4-12)2-8(7)10/h1-2H
(5)Std. InChIKey: SRIJSZQFAMLVQV-UHFFFAOYSA-N

Product Name

4,5-DICHLOROPHTHALONITRILE

Synthetic route

1,2-Benzenedicarbonitrile,4,5-dichloro- Specification

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