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632-58-6

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632-58-6 Usage

Chemical Properties

colourless crystals

Uses

Dyes, intermediates.

General Description

Colorless plates.

Air & Water Reactions

Sparingly water soluble.

Reactivity Profile

A chlorinated organic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Tetrachlorophthalic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Fire Hazard

Flash point data for Tetrachlorophthalic acid are not available; Tetrachlorophthalic acid is probably combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 632-58-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 2 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 632-58:
(5*6)+(4*3)+(3*2)+(2*5)+(1*8)=66
66 % 10 = 6
So 632-58-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H2Cl4O4/c9-3-1(7(13)14)2(8(15)16)4(10)6(12)5(3)11/h(H,13,14)(H,15,16)

632-58-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetrachlorophthalic Acid

1.2 Other means of identification

Product number -
Other names Tetrachlorophthalic acid

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:632-58-6 SDS

632-58-6Synthetic route

phthalic anhydride
85-44-9

phthalic anhydride

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
With antimonypentachloride; chlorine at 200℃;
With sulfuric acid; iodine; chlorine at 50 - 60℃; schliesslich bei 200grad;
octachloronaphthalene
2234-13-1

octachloronaphthalene

A

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

B

hexachloronaphthoquinone-(1,4)
58852-12-3

hexachloronaphthoquinone-(1,4)

Conditions
ConditionsYield
With nitric acid at 90℃;
1,2,3,4,5,6,8-heptachloronaphthalene
58863-15-3

1,2,3,4,5,6,8-heptachloronaphthalene

A

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

B

2,5,6,7,8-pentachloro-[1,4]naphthoquinone

2,5,6,7,8-pentachloro-[1,4]naphthoquinone

Conditions
ConditionsYield
With nitric acid at 100℃; im geschlossenen Rohr;
With nitric acid at 100℃; im Druckrohr;
1,2,3,4,5-Pentachloronaphthalene
67922-25-2

1,2,3,4,5-Pentachloronaphthalene

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
With nitric acid at 180 - 200℃; im geschlossenen Rohr;
2,5,6,7,8-pentachloro-[1,4]naphthoquinone

2,5,6,7,8-pentachloro-[1,4]naphthoquinone

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
With chromic acid
With nitric acid
2,3,4,5-tetrachloro-6-trichloroacetyl-benzoic acid

2,3,4,5-tetrachloro-6-trichloroacetyl-benzoic acid

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
With sodium hydroxide
2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

A

pentachlorobenzene
608-93-5

pentachlorobenzene

B

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
With sulfuric acid at 200 - 250℃;
Phthaloyl dichloride
88-95-9

Phthaloyl dichloride

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
With chlorine; iron at 120 - 170℃;
tetrachlorophthalic anhydride
117-08-8

tetrachlorophthalic anhydride

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
With sodium hydroxide; water for 0.75h; Hydrolysis; Heating;
tetrachlorophthalic anhydride
117-08-8

tetrachlorophthalic anhydride

water
7732-18-5

water

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

antimonypentachloride
7647-18-9

antimonypentachloride

iodine
7553-56-2

iodine

9,10-phenanthrenequinone
84-65-1

9,10-phenanthrenequinone

A

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

B

1,2,3,4,5,6,8-heptachloro-anthraquinone
26529-50-0

1,2,3,4,5,6,8-heptachloro-anthraquinone

C

1,2,3,4,5,6,7-heptachloro-anthraquinone
861526-53-6

1,2,3,4,5,6,7-heptachloro-anthraquinone

D

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

Conditions
ConditionsYield
Kochen des Reaktionsproduktes mit Salzsaeure;
2-Benzoylbenzoic acid
85-52-9

2-Benzoylbenzoic acid

antimonypentachloride
7647-18-9

antimonypentachloride

A

hexachlorobenzene
118-74-1

hexachlorobenzene

B

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

C

1,2,3,4,5,6,7-heptachloro-anthraquinone
861526-53-6

1,2,3,4,5,6,7-heptachloro-anthraquinone

D

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

1,2,3,4-tetrachloronaphthalene
20020-02-4

1,2,3,4-tetrachloronaphthalene

nitric acid
7697-37-2

nitric acid

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
at 210 - 215℃;
octachloronaphthalene
2234-13-1

octachloronaphthalene

nitric acid
7697-37-2

nitric acid

A

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

B

hexachloro-naphthoquinone-(1.4)

hexachloro-naphthoquinone-(1.4)

Conditions
ConditionsYield
at 90℃;
hexachloronaphthoquinone-(1,4)
58852-12-3

hexachloronaphthoquinone-(1,4)

nitric acid
7697-37-2

nitric acid

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

1,2,3,4-tetrachloro-9,10-anthraquinone
2841-29-4

1,2,3,4-tetrachloro-9,10-anthraquinone

nitric acid
7697-37-2

nitric acid

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
at 140 - 150℃;
1,4,5,8-tetrachloroanthraquinone
81-58-3

1,4,5,8-tetrachloroanthraquinone

antimonypentachloride
7647-18-9

antimonypentachloride

A

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

B

1,2,3,4,5,6,8-heptachloro-anthraquinone
26529-50-0

1,2,3,4,5,6,8-heptachloro-anthraquinone

C

1,2,3,4,5,6,7-heptachloro-anthraquinone
861526-53-6

1,2,3,4,5,6,7-heptachloro-anthraquinone

D

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

1,2,3,4,5,6,8-heptachloronaphthalene
58863-15-3

1,2,3,4,5,6,8-heptachloronaphthalene

nitric acid
7697-37-2

nitric acid

A

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

B

pentachloronaphthoquinone-(1.4)

pentachloronaphthoquinone-(1.4)

p-chloranil

p-chloranil

nitric acid
7697-37-2

nitric acid

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

1,2,3,4,5-Pentachloronaphthalene
67922-25-2

1,2,3,4,5-Pentachloronaphthalene

nitric acid
7697-37-2

nitric acid

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
at 180 - 200℃;
2,5,6,7,8-pentachloro-[1,4]naphthoquinone

2,5,6,7,8-pentachloro-[1,4]naphthoquinone

CrO3

CrO3

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

sulfuric acid
7664-93-9

sulfuric acid

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

A

pentachlorobenzene
608-93-5

pentachlorobenzene

B

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
at 200 - 250℃;
2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

antimonypentachloride
7647-18-9

antimonypentachloride

A

hexachlorobenzene
118-74-1

hexachlorobenzene

B

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

1,2,3,4,5,6,7-heptachloro-anthraquinone
861526-53-6

1,2,3,4,5,6,7-heptachloro-anthraquinone

antimonypentachloride
7647-18-9

antimonypentachloride

A

hexachlorobenzene
118-74-1

hexachlorobenzene

B

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

C

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

2,3,4,5-tetrachloro-6-pentachlorobenzoyl-benzoic acid

2,3,4,5-tetrachloro-6-dichloroacetyl-benzoic acid
875846-61-0

2,3,4,5-tetrachloro-6-dichloroacetyl-benzoic acid

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: natrium carbonate; chlorine
2: diluted NaOH-solution
View Scheme
1,2,3,4,5,6,8-heptachloronaphthalene
58863-15-3

1,2,3,4,5,6,8-heptachloronaphthalene

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitric acid / 100 °C / im Druckrohr
2: nitric acid
View Scheme
p-chloranil

p-chloranil

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: PCl5 / 250 °C / im Druckrohr
2: nitric acid / 100 °C / im Druckrohr
3: nitric acid
View Scheme
2-amino-4,5,6,7-tetrachloroisoindoline-1,3-dione
6641-31-2

2-amino-4,5,6,7-tetrachloroisoindoline-1,3-dione

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

Conditions
ConditionsYield
With sodium hydroxide In water
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

pentaphenylantimony
2170-05-0

pentaphenylantimony

bis(tetraphenylantimony) tetrachlorophthalate

bis(tetraphenylantimony) tetrachlorophthalate

Conditions
ConditionsYield
In toluene at 90℃; for 1h;91%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

4,5,6,7-tetrachloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran
20687-94-9

4,5,6,7-tetrachloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran

Conditions
ConditionsYield
With sulfur tetrafluoride at 190 - 200℃; for 16h; Heating;89.3%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

1,2,3,4-tetrachloro-1,3-cyclohexadiene-5,6-dicarboxylic acid
49578-22-5

1,2,3,4-tetrachloro-1,3-cyclohexadiene-5,6-dicarboxylic acid

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane at 25℃; electroreduction (divided cells, lead plates, 0.20 A);86%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

C7H10N2*C8H2Cl4O4

C7H10N2*C8H2Cl4O4

Conditions
ConditionsYield
In methanol for 432h;82.15%
4,4'-bipyridine
553-26-4

4,4'-bipyridine

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

water
7732-18-5

water

cobalt(II) perchlorate hexahydrate

cobalt(II) perchlorate hexahydrate

C8Cl4O4(2-)*Co(2+)*C10H8N2*2H2O

C8Cl4O4(2-)*Co(2+)*C10H8N2*2H2O

Conditions
ConditionsYield
With potassium hydroxide at 20 - 120℃; for 72h; Autoclave;81%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

C4H5N3*C8H2Cl4O4

C4H5N3*C8H2Cl4O4

Conditions
ConditionsYield
In ethanol; water at 20℃; for 0.25h;80%
ethanol
64-17-5

ethanol

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

water
7732-18-5

water

cadmium(II) chloride
10108-64-2

cadmium(II) chloride

{[Cd(tetrachlorophthalate)(H2O)2]·EtOH}n

{[Cd(tetrachlorophthalate)(H2O)2]·EtOH}n

Conditions
ConditionsYield
for 0.5h;75%
N-Methylformamide
123-39-7

N-Methylformamide

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

water
7732-18-5

water

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

Mn(3,4,5,6-tetrachloro-1,2-benzenedicarboxylic acid)(N-methylformamide)2(H2O)2

Mn(3,4,5,6-tetrachloro-1,2-benzenedicarboxylic acid)(N-methylformamide)2(H2O)2

Conditions
ConditionsYield
for 0.5h;70%
N-Methylformamide
123-39-7

N-Methylformamide

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

Mn(3,4,5,6-tetrachloro-1,2-benzenedicarboxylic acid)(N-methylformamide)2(H2O)2

Mn(3,4,5,6-tetrachloro-1,2-benzenedicarboxylic acid)(N-methylformamide)2(H2O)2

Conditions
ConditionsYield
In water for 0.5h;70%
In water for 0.5h;70%
copper(II) choride dihydrate

copper(II) choride dihydrate

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

[Cu(1,2-HBDC-Cl4)2(DMF)2]

[Cu(1,2-HBDC-Cl4)2(DMF)2]

Conditions
ConditionsYield
In water at 20℃; for 0.25h;70%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

tris(4-N,N-dimethylaminophenyl)antimony
201742-17-8

tris(4-N,N-dimethylaminophenyl)antimony

[(4-N,N-dimethylaminophenyl)3Sb(OC(O)C6Cl4C(O)O)]

[(4-N,N-dimethylaminophenyl)3Sb(OC(O)C6Cl4C(O)O)]

Conditions
ConditionsYield
With hydrogen peroxide In diethyl ether; water byproducts: water; addn. of aq. 30.0% soln. of H2O2 to mixt. of tris(4-N,N-dimethylaminophenyl)antimony and HOC(O)C6Cl4C(O)OH in ether, standing at 20°C for18.0 h; filtration, drying;69%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

ethylenediamine hydrochloride
18299-54-2

ethylenediamine hydrochloride

2C8H2Cl4O4*C2H8N2

2C8H2Cl4O4*C2H8N2

Conditions
ConditionsYield
In acetone at 20℃; for 0.25h;68%
3(5)-amino-1,2,4-triazole
61-82-5

3(5)-amino-1,2,4-triazole

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

C2H4N4*C8H2Cl4O4

C2H4N4*C8H2Cl4O4

Conditions
ConditionsYield
In tetrahydrofuran; water for 0.25h;67%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

C16H18Cl8Mn2O17*H2O

C16H18Cl8Mn2O17*H2O

Conditions
ConditionsYield
In ethanol; water for 0.5h;65%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

1,4-bis[(1,2,4-triazole-1-yl)methyl]-2,3,5,6-tetrafluorobenzene
1515870-17-3

1,4-bis[(1,2,4-triazole-1-yl)methyl]-2,3,5,6-tetrafluorobenzene

water
7732-18-5

water

cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

{[Co(tcpa)(Fbtx)(H2O)2]·0.5H2O}n

{[Co(tcpa)(Fbtx)(H2O)2]·0.5H2O}n

Conditions
ConditionsYield
at 20 - 140℃; for 48.96h; High pressure; Autoclave;65%
methanol
67-56-1

methanol

1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

2C8H2Cl4O4*C12H8N2*CH4O

2C8H2Cl4O4*C12H8N2*CH4O

Conditions
ConditionsYield
In water for 0.25h;64%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

2-amino-6-methylpyrimidin-4-ol
3977-29-5

2-amino-6-methylpyrimidin-4-ol

2C5H7N3O*C8H2Cl4O4*2H2O

2C5H7N3O*C8H2Cl4O4*2H2O

Conditions
ConditionsYield
With water In ethanol for 0.25h;62%
1,2-bis((2-methyl-1H-imidazol-1-yl)methyl)benzene
177428-71-6

1,2-bis((2-methyl-1H-imidazol-1-yl)methyl)benzene

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

C16H18N4*C8H2Cl4O4*2H2O

C16H18N4*C8H2Cl4O4*2H2O

Conditions
ConditionsYield
With water In ethanol62%
benzoimidazole
51-17-2

benzoimidazole

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

C8H2Cl4O4*C7H6N2*H2O

C8H2Cl4O4*C7H6N2*H2O

Conditions
ConditionsYield
With water In ethanol; water at 20℃; for 0.25h;53%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

water
7732-18-5

water

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

{[Ni(1,2-BDC-Cl4)(H2O)5]*DMF*H2O}

{[Ni(1,2-BDC-Cl4)(H2O)5]*DMF*H2O}

Conditions
ConditionsYield
at 20℃; for 0.25h;50%
copper(II) acetate tetrahydrate

copper(II) acetate tetrahydrate

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

trans-1,2-bis(4-pyridyl)ethylene
1135-32-6

trans-1,2-bis(4-pyridyl)ethylene

{[Cu(tetrachlorophthalic acid(-2H))(1,2-di(4-pyridyl)ethylene)]}n

{[Cu(tetrachlorophthalic acid(-2H))(1,2-di(4-pyridyl)ethylene)]}n

Conditions
ConditionsYield
In water at 120℃; for 96h; Autoclave; High pressure;45%
lanthanum(III) nitrate hexahydrate

lanthanum(III) nitrate hexahydrate

ethanol
64-17-5

ethanol

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

{[La2(3,4,5,6-tetrachloro-1,2-benzenedicarboxylate)3(H2O)4]·ethanol}n

{[La2(3,4,5,6-tetrachloro-1,2-benzenedicarboxylate)3(H2O)4]·ethanol}n

Conditions
ConditionsYield
With sodium hydroxide In water; N,N-dimethyl-formamide at 85℃; for 72h; Sealed tube;42%
N-formyldiethylamine
617-84-5

N-formyldiethylamine

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

water
7732-18-5

water

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

[Mn2(3,4,5,6-tetrachloro-1,2-benzenedicarboxylic acid)2(N,N-diethylformamide)2(H2O)6]*2H2O

[Mn2(3,4,5,6-tetrachloro-1,2-benzenedicarboxylic acid)2(N,N-diethylformamide)2(H2O)6]*2H2O

Conditions
ConditionsYield
for 0.5h;40%
N-formyldiethylamine
617-84-5

N-formyldiethylamine

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

[Mn2(3,4,5,6-tetrachloro-1,2-benzenedicarboxylato)2(N,N-diethylformamide)(H2O)6]*2H2O

[Mn2(3,4,5,6-tetrachloro-1,2-benzenedicarboxylato)2(N,N-diethylformamide)(H2O)6]*2H2O

Conditions
ConditionsYield
In water for 0.5h;40%
N-formyldiethylamine
617-84-5

N-formyldiethylamine

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

[Mn2(3,4,5,6-tetrachloro-1,2-benzenedicarboxylic acid)2(N,N-diethylformamide)2(H2O)6]*2H2O

[Mn2(3,4,5,6-tetrachloro-1,2-benzenedicarboxylic acid)2(N,N-diethylformamide)2(H2O)6]*2H2O

Conditions
ConditionsYield
In water for 0.5h;40%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

potassium nitrate

potassium nitrate

Mn(2+)*2K(1+)*2C8Cl4O4(2-)*4H2O

Mn(2+)*2K(1+)*2C8Cl4O4(2-)*4H2O

Conditions
ConditionsYield
In ethanol; water for 0.5h;40%
tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

water
7732-18-5

water

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

cadmium(II) chloride
10108-64-2

cadmium(II) chloride

{[Cd(1,2-HBDC-Cl4)2(H2O)4]*2DMF}

{[Cd(1,2-HBDC-Cl4)2(H2O)4]*2DMF}

Conditions
ConditionsYield
at 20℃; for 0.25h;40%
1,1'-[1,4-phenylenebis(methylene)]bis(2-methyl-1H-imidazole)
82410-79-5

1,1'-[1,4-phenylenebis(methylene)]bis(2-methyl-1H-imidazole)

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

C16H18N4*2C8H2Cl4O4

C16H18N4*2C8H2Cl4O4

Conditions
ConditionsYield
With nickel(II) nitrate In 1-methyl-pyrrolidin-2-one; water at 120℃; for 72h;38%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

copper(II) choride dihydrate

copper(II) choride dihydrate

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

triaqua-bis(2,2′-bipyridine-N,N′)(μ2-tetrachlorophthalato-O,O″)(tetrachlorophthalato-O)dicopper(II)

triaqua-bis(2,2′-bipyridine-N,N′)(μ2-tetrachlorophthalato-O,O″)(tetrachlorophthalato-O)dicopper(II)

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 80℃; for 4h; pH=7.5;35%
methanol
67-56-1

methanol

tetrachlorophthalic acid
632-58-6

tetrachlorophthalic acid

dimethyl 3,4,5,6-tetrachlorophthalate
20098-41-3

dimethyl 3,4,5,6-tetrachlorophthalate

Conditions
ConditionsYield
With sulfuric acid for 18.1667h; Reflux;35%

632-58-6Relevant articles and documents

A large-scale synthesis of the bioreductive drug 1,4-bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione bis-N-oxide (AQ4N)

Lee, Ho H.,Denny, William A.

, p. 2755 - 2758 (2007/10/03)

A large-scale synthesis of the bis-bioreductive drug 1,4-bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxy-anthracene-9,10-dione bis-N-oxide (AQ4N) has been developed. This six-step synthesis provides AQ4N in 20% overall yield from readily available tetrachlorophthalic anhydride. The key step was a KF-NaF-mediated conversion of 3,6-dichlorophthalic anhydride to 3,6-difluorophthalic anhydride, which could be achieved in 77% yield on a 100 g scale. A trace impurity in AQ4N was determined (by LC-MS and independent synthesis) to be the mono-N-oxide 1-amino-4-[2-(dimethylamino)ethyl]amino-5,8-dihydroxyanthracene-9,10-dione N-oxide. This is formed spontaneously from AQ4N under a number of conditions, including during HPLC on reversed-phase columns. The Royal Society of Chemistry 1999.

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