1897-41-2

Basic information

• Product Name: Tetrachloroterephthalonitrile
• Synonyms: tetrachloro-p-phthalodinitril;Tetrachloroterephthalonitrile,98%;Tetrachloro-terephthalodinitrile(TCTPN);Tetrachloro- terephthalodinitrile;1,4-Benzenedicarbonitrile, 2,3,5,6-tetrachloro-;TETRACHLOROTERTPHTHALONITRILE;1,4-Dicyano-2,3,5,6-tetra-chloro-benzene;2,3,5,6-Tetrachloro-1,4-benzenedicarbonitrile
• CAS NO: 1897-41-2
• Molecular Formula: C₈Cl₄N₂
• Molecular Weight: 265.91
• EINECS: 401-550-8
• Product Categories: C8 to C9;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 1897-41-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 308-312 °C(lit.)
• Boiling Point: 370.1 °C at 760 mmHg
• Flash Point: 166.8 °C
• Appearance: /
• Density: 1.71 g/cm³
• Vapor Pressure: 1.13E-05mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Tetrachloroterephthalonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrachloroterephthalonitrile(1897-41-2)
• EPA Substance Registry System: Tetrachloroterephthalonitrile(1897-41-2)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-53-50/53
• Safety Statements: 24-37-61-60
• RIDADR: 3077
• WGK Germany: 1
• RTECS: TI8275000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 1897-41-2(Hazardous Substances Data)

Usage

Uses

Tetrachloroterephthalonitrile may be used to synthesize 2-aminotrifluoroterephthalonitriles.

General Description

Tetrachloroterephthalonitrile (TCTPN), a dinitrile derivative, is an isomer of chloranil. The halogen bond of TCTPN has been studied using 35Cl solid-state NMR.

InChI:InChI=1/C8Cl4N2/c9-5-3(1-13)6(10)8(12)4(2-14)7(5)11

Synthetic route

2,3,5,6-tetrachloro-1,4-benzenecarboxamide (1786-85-2) → 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2)

Conditions	Yield
With trichlorophosphate at 135℃; for 6h;	89%

1,2,4,5-tetrachloro-3,6-dinitrobenzene (20098-38-8) + potassium cyanide (151-50-8) → 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + 2,3,5,6-Tetrachloro-4-nitro-benzonitrile

Conditions	Yield
With cetyltrimethylammonim bromide In chloroform; water for 2h; Product distribution; Heating; various substituted nitrobenzenes;	A 79% B 4%
With cetyltrimethylammonim bromide In diethyl ether; chloroform for 2h; Heating;	A 79% B 4%

tetrachloroterephthaloyl dichloride (719-32-4) → 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / NH3 / diethyl ether / 8 h / 0 - 20 °C 2: 89 percent / POCl3 / 6 h / 135 °C View Scheme

terephthaloyl chloride (100-20-9) + 2.5-diethoxy-aniline hydrochloride → 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / Fe; Cl2 / 24 h / 180 °C 2: 91 percent / NH3 / diethyl ether / 8 h / 0 - 20 °C 3: 89 percent / POCl3 / 6 h / 135 °C View Scheme

1,2,4,5-tetrachloro-3,6-dinitrobenzene (20098-38-8) + cetyltrimethylammonim bromide (57-09-0) → 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2)

Conditions	Yield
In chloroform; water

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + 4-mercaptobenzoic acid (1074-36-8) → 4,4',4'',4'''-((3,6-dicyanobenzene-1,2,4,5-tetrayl)tetrakis(sulfanediyl))-tetrabenzoic acid

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;	99%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; Inert atmosphere;	35%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → Dactal (2136-79-0)

Conditions	Yield
With sulfuric acid	97%
With sulfuric acid	97%
With sulfuric acid; water; acetic acid at 190℃; for 72h;	91.2%
With sulfuric acid In water at 75 - 163℃; for 8.5h; Temperature; Solvent; Flow reactor;	1609 g

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + 4-aminotiophenol (1193-02-8) → 2,3,5,6-tetrakis((4-aminophenyl)thio)terephthalonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 5h; Inert atmosphere;	97%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → 2,3,5,6-tetrachloro-1,4-benzenecarboxamide (1786-85-2)

Conditions	Yield
Stage #1: 2,3,5,6-tetrachloroterephthalonitrile With acetamide; acetic acid at 50℃; under 760.051 Torr; for 0.5h; Stage #2: With tetrakis(acetonitrile)palladium(II) tetrafluoroborate at 50℃; under 2 Torr; for 2h;	96%

4-sulfanylphenol (637-89-8) + 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → 2,3,5,6-tetrakis(4-hydroxyphenylthio)benzene-1,4-dinitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 6h; Inert atmosphere;	94%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → tetrafluoroterephthalonitrile (1835-49-0)

Conditions	Yield
With potassium fluoride; 18-crown-6 ether In N,N-dimethyl-formamide at 140℃; for 6h;	92%
With potassium fluoride In N,N-dimethyl-formamide at 110℃; for 10h; Product distribution / selectivity;	90%
With potassium fluoride; tetra-n-propylammonium bromide In N,N-dimethyl-formamide at 130℃; for 7h; Product distribution / selectivity;	90%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + 1,2,3,4,7,8,9,10-octahydro-[1,2,3]benzodiazaphospholo[2,1-a][1,2,3]benzodiazaphosphole (1570321-40-2) + chlorobenzene (108-90-7) → C32H32Cl4N6P4*C6H5Cl

Conditions	Yield
at 20℃; for 1h; Schlenk technique; Inert atmosphere;	91%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + benzene-1,2-diol (120-80-9) → C14H4Cl2N2O2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;	90%

potassium fluoride + 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → tetrafluoroterephthalonitrile (1835-49-0)

Conditions	Yield
heating to 300°C, 5 h;	74.4%
heating to 300°C, 5 h;	74.4%
heating to 250°C, 5 h;	68.7%

tetrahydrofuran (109-99-9) + 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + 5,6,13,14-tetrahydro-7λ2,15λ2-naphtho[2,1-d]naphtho[2',1':4,5][1,2,3]diazaphospholo[2,1-a][1,2,3]diazaphosphole → C48H32Cl4N6P4*2C4H8O

Conditions	Yield
at 20℃; for 2h; Schlenk technique; Inert atmosphere;	74%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + thiophenol (108-98-5) → 2,3,5,6-tetrakis(phenylthio)terephthalonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere;	66%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + 1,2-benzenedithiole (17534-15-5) → C20H8N2S4

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 72h;	62%

pyridine-4-thiol (4556-23-4) + 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → 2,3,5,6-tetrakis(pyridin-4-ylthio)terephthalonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 5h; Inert atmosphere;	56%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + 2,6-dichloro-4-(trifluoromethyl)aniline (24279-39-8) → 2,3,5-trichloro-6-(2,6-dichloro-4-(trifluoromethyl)phenylamino)terephthalonitrile (1416421-46-9)

Conditions	Yield
Stage #1: 2,6-dichloro-4-(trifluoromethyl)aniline With sodium hydroxide In N,N-dimethyl-formamide for 0.166667h; Stage #2: 2,3,5,6-tetrachloroterephthalonitrile In N,N-dimethyl-formamide at 60℃; for 2h;	55%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + diethyl 2,6-dimethyl-4-benzyl-1,4-dihydropyridine-3,5-dicarboxylate (1539-57-7) → C14H7Cl4N

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); sodium acetate at 25℃; for 18h; Irradiation;	54%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) + 1,2-benzenedithiole (17534-15-5) → C14H4Cl2N2S2

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;	43%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → C8H2Cl4N8 (1244467-05-7)

Conditions	Yield
Stage #1: 2,3,5,6-tetrachloroterephthalonitrile With sodium azide; pyridine hydrochloride In N,N-dimethyl-formamide at 120℃; for 24h; Stage #2: With water; sodium hydroxide In N,N-dimethyl-formamide at 20℃;	32%

ortho-mercaptophenol (1121-24-0) + 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → C14H4Cl2N2OS

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h;	12%

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → 2,3,5,6-tetrafluoro-1,4-benzenedimethanol (92339-07-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / KF; 18-crown-6 / dimethylformamide / 6 h / 140 °C 2: 80 percent / H2; H2SO4 / Ni / 48 h / 30 °C 3: 87 percent / aq. H2SO4 / 2 h / 20 °C 4: 52 percent / LiAlH4 / diethyl ether / 2 h / Heating View Scheme

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → 2,3,5,6-tetrafluoroterephthalaldehyde (3217-47-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / KF; 18-crown-6 / dimethylformamide / 6 h / 140 °C 2: 80 percent / H2; H2SO4 / Ni / 48 h / 30 °C 3: 87 percent / aq. H2SO4 / 2 h / 20 °C View Scheme

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → 2,3,5,6-tetrafluoroterephthalaldehyde dimethylacetal (306739-72-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / KF; 18-crown-6 / dimethylformamide / 6 h / 140 °C 2: 80 percent / H2; H2SO4 / Ni / 48 h / 30 °C View Scheme

2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → C20H12F4N2

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / KF; 18-crown-6 / dimethylformamide / 6 h / 140 °C 2: 80 percent / H2; H2SO4 / Ni / 48 h / 30 °C 3: 87 percent / aq. H2SO4 / 2 h / 20 °C 4: 75 percent / 16 h / 120 °C View Scheme

potassium fluoride + 2,3,5,6-tetrachloroterephthalonitrile (1897-41-2) → dichlorodifluoro-1,4-phenylene dicyanide (60341-41-5) + 2-chloro-3,5,6-trifluoro-1,4-phenylene dicyanide (1929-68-6)

Conditions	Yield
evidently an isomeric mixture is obtained;
evidently an isomeric mixture is obtained;

Upstream product

• 20098-38-8 1,2,4,5-tetrachloro-3,6-dinitrobenzene 
• 57-09-0 cetyltrimethylammonim bromide 
• 151-50-8 potassium cyanide 
• 100-20-9 terephthaloyl chloride 
• 719-32-4 tetrachloroterephthaloyl dichloride 
• 1786-85-2 2,3,5,6-tetrachloro-1,4-benzenecarboxamide 

Downstream Products

• 1835-49-0 tetrafluoroterephthalonitrile 
• 1861-32-1 Dacthal 
• 887-54-7 methyl tetrachlorophthalate 
• 1786-85-2 2,3,5,6-tetrachloro-1,4-benzenecarboxamide 
• 1416422-05-3 C₁₃H₄BrCl₃N₄ 
• 1416421-34-5 C₁₆H₄Cl₃F₃N₄ 
• 1416422-14-4 C₁₃H₃Cl₅N₄ 
• 1416422-20-2 C₁₃H₃Cl₅N₄ 
• 1416421-36-7 C₁₄H₃Cl₅N₄O₂ 
• 1416421-46-9 2,3,5-trichloro-6-(2,6-dichloro-4-(trifluoromethyl)phenylamino)terephthalonitrile 
• 652-36-8 2,3,5,6-tetrafluoroterephthalic acid 
• 1244467-05-7 C₈H₂Cl₄N₈ 
• 60341-41-5 dichlorodifluoro-1,4-phenylene dicyanide 
• 1929-68-6 2-chloro-3,5,6-trifluoro-1,4-phenylene dicyanide 

Relevant articles and documents

A new route to 2,3,5,6-tetrafluoroterephthal aldehyde and its chemical transformation

The title compound was prepared from commercial available and cheaper starting material terephthalolyl chloride by six-step reaction sequence in total 40% yield. Its chemical transformations were also studied.

Process for the preparation of cyanotetrachlorobenzenes

Cyanotetrachlorobenzenes, especially ortho- and para- dicyanotetrachlorobenzenes, are prepared by reacting in a liquid medium at 20°-100° C. a corresponding nitrotetrachlorobenzene with, in solution, an inorganic cyanide. Preferably the liquid medium is a two-phase water/water-immiscible organic solvent system, e.g. water/chloroform, a phase transfer catalyst is present and the inorganic cyanide is an alkali metal or alkaline earth metal cyanide.The compounds are useful chemical intermediates in the synthesis of, for instance, pesticidal compounds.