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552-30-7

Basic Information
CAS No.: 552-30-7
Name: 1,2,4-Benzenetricarboxylic anhydride
Molecular Structure:
Molecular Structure of 552-30-7 (1,2,4-Benzenetricarboxylic anhydride)
Formula: C9H4O5
Molecular Weight: 192.13
Synonyms: Trimellitic acid anhydride;1, 3-Dioxo-5-phthalancarboxylic acid;Epon 9150;1,3-Dihydro-1, 3-dioxo-5-isobenzofurancarboxylic acid;4-Carboxyphthalic anhydride;5-Isobenzofurancarboxylic acid,1,3-dihydro-1,3-dioxo-;Trimellitic acid, cyclic 1,2-anhydride;Anhydrotrimellic acid;Trimellic acid anhydride;Trimellic acid 1, 2-anhydride;5-Isobenzofurancarboxylic acid, 1,3-dihydro-1,3-dioxo-;1,3-dioxoisobenzofuran-5-carboxylic acid;1, 2,4-Benzenetricarboxylic acid 1,2-anhydride;Trimellitic acid 1, 2-anhydride;Trimellitic Anhydride(TMA);benzene-1,2,4-tricarboxylic acid 1,2-anhydride;
EINECS: 209-008-0
Density: 1.669 g/cm3
Melting Point: 163-166 °C(lit.)
Boiling Point: 470.6 °C at 760 mmHg
Flash Point: 201.3 °C
Solubility: decomposes in water
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 37-41-42/43
Safety: 22-26-36/37/39
Transport Information:
PSA: 80.67000
LogP: 0.69540
Synthetic route
528-44-9

1,2,4-benzene tricarboxylic acid

552-30-7

trimellitic Anhydride

13940-95-9

benzene-1,2,4-tricarboxylic acid-2-methyl ester

552-30-7

trimellitic Anhydride

Conditions
ConditionsYield
at 200℃;
13912-71-5

benzene-1,2,4-tricarboxylic acid-1-methyl ester

552-30-7

trimellitic Anhydride

Conditions
ConditionsYield
at 200℃;
6051-66-7

2,5-dimethylterephthalic acid

A

108-31-6

maleic anhydride

B

89-32-7

Pyromellitic dianhydride

C

528-44-9

1,2,4-benzene tricarboxylic acid

D

552-30-7

trimellitic Anhydride

Conditions
ConditionsYield
With vanadia at 400℃; Product distribution; effect of temperature on gas-phase oxidation;
18190-63-1

2,4-dimethylisophthalic acid

A

89-32-7

Pyromellitic dianhydride

B

528-44-9

1,2,4-benzene tricarboxylic acid

C

552-30-7

trimellitic Anhydride

Conditions
ConditionsYield
With vanadia at 400℃; Product distribution; effect of temperature on gas-phase oxidation of methyl-substituted carboxylic acids and anhydrides;
95-63-6

1,2,4-Trimethylbenzene

552-30-7

trimellitic Anhydride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
2: sulfuric acid
3: aqueous-methanolic KOH-solution
5: 200 °C
View Scheme
Multi-step reaction with 5 steps
2: sulfuric acid
3: aqueous-methanolic KOH-solution
5: 200 °C
View Scheme
Multi-step reaction with 2 steps
1: KMnO4; water; NaOH-solution / man macht schwefelsauer, behandelt mit SO2, saettigt mit Na2SO4
2: 200 - 220 °C / im Vakuum
View Scheme
With 1,1,2,2-tetrabromoethane; cobalt(II) acetate; manganese(II) acetate; acetic acid at 220℃; under 15001.5 - 17251.7 Torr; Reagent/catalyst; Temperature; Pressure; Inert atmosphere; Large scale;1360 g
54699-35-3

1,2-dimethyl 1,2,4-benzenetricarboxylate

552-30-7

trimellitic Anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 200 °C
View Scheme
Multi-step reaction with 2 steps
2: 200 °C
View Scheme
2459-10-1

benzene-1,2,4-tricarboxylic acid trimethyl ester

552-30-7

trimellitic Anhydride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous-methanolic KOH-solution
3: 200 °C
View Scheme
Multi-step reaction with 3 steps
1: aqueous-methanolic KOH-solution
3: 200 °C
View Scheme
22572-84-5

diethyl 4-aminophthalate

552-30-7

trimellitic Anhydride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous HCl; aqueous NaNO2
2: aqueous NaOH
3: 180 °C / 0.5 Torr
View Scheme
105903-40-0

4-cyano-phthalic acid diethyl ester

552-30-7

trimellitic Anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous NaOH
2: 180 °C / 0.5 Torr
View Scheme
243968-20-9

2-amino-5-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester

552-30-7

trimellitic Anhydride

330193-56-1

2-(2-amino-3-tert-butoxycarbonyl-4,7-dihydro-5H-thieno[2,3-c]pyran-5-ylmethyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 24h;100%
In N,N-dimethyl-formamide at 100℃; for 24h;100%
In N,N-dimethyl-formamide at 100℃; for 24h;100%
83-07-8

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one

552-30-7

trimellitic Anhydride

292870-53-2

2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 20℃; for 72h;100%
With dmap In N,N-dimethyl-formamide at 110℃; for 12h;46%
153-94-6

D-tryptophan

552-30-7

trimellitic Anhydride

(R)-2-(1-carboxy-2-(1H-indol-3-yl)ethyl)-1,3-dioxoisoindoline-5-carboxylic acid

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 200℃; for 0.166667h; microwave irradiation;99%
13822-56-5

3-(trimethoxysilyl)propan-1-amine

552-30-7

trimellitic Anhydride

1204776-58-8

C15H21NO8Si

Conditions
ConditionsYield
In tetrahydrofuran at -5 - 5℃; for 6h; Inert atmosphere;99%
919-30-2

3-aminopropyltriethoxysilane

552-30-7

trimellitic Anhydride

1204776-59-9

C18H27NO8Si

Conditions
ConditionsYield
In tetrahydrofuran at -5 - 5℃; Inert atmosphere;99%
99-31-0

5-aminoisophthalic acid

552-30-7

trimellitic Anhydride

51222-09-4

C17H9NO8

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 6h; Heating;98%

chromium dichloride

1707-03-5

diphenyl-phosphinic acid

10025-73-7

chromium(III) chloride

552-30-7

trimellitic Anhydride

[Cr(OP(CH3)(C6H5)O)2(OOCC6H3C2O3)]x

Conditions
ConditionsYield
With trimethylamine In tetrahydrofuran byproducts: (CH3)3NHCl; N2-atmosphere; shaking CrCl3 with trace of CrCl2, refluxing with 2 equiv. of phosphinic acid and 2.5 equiv. NMe3 (1 h), cooling to room temp., addn. of 1 equiv. C9H4O5 and excess NMe3, refluxing (0.5 h); filtration, evapn. to dryness, drying (140°C, several days); elem. anal.;98%

C53H86N4O15

552-30-7

trimellitic Anhydride

C62H90N4O20

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 20℃; for 12 - 15h;98%
100-01-6

4-nitro-aniline

552-30-7

trimellitic Anhydride

2-(4-nitrophenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Conditions
ConditionsYield
With acetic acid at 130℃; for 16h; Condensation;97%
In acetic acid for 20h; Reflux;95%
24313-88-0

3,4,5-Trimethoxyaniline

552-30-7

trimellitic Anhydride

[2-(3,4,5-trimethoxy)phenyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Conditions
ConditionsYield
With acetic acid at 130℃; for 16h; Condensation;97%
826-81-3

2-methyl-8-quinolinol

552-30-7

trimellitic Anhydride

C19H11NO5

Conditions
ConditionsYield
In nitrobenzene at 175 - 180℃; for 3h;97%
837-11-6

2-(4'-hydroxyphenyl)-2-(4'-aminophenyl)-propane

552-30-7

trimellitic Anhydride

N-{4-[2-(4-hydroxyphenyl)isopropyl]phenyl}trimellitimide

Conditions
ConditionsYield
Stage #1: 2-(4'-hydroxyphenyl)-2-(4'-aminophenyl)-propane; trimellitic Anhydride In 1-methyl-pyrrolidin-2-one at 20℃; for 6h; Inert atmosphere;
Stage #2: In 1-methyl-pyrrolidin-2-one; toluene at 120℃; for 10h; Dean-Stark;
97%
α,ω-Diisocyanato-polybutadiene, isocyanate group conc. 719 mmol/g, Mw/Mn = 1.3, structure units 1,2- : 1,4-trans : 1,4-cis = 60 : 25 : 15

α,ω-Diisocyanato-polybutadiene, isocyanate group conc. 719 mmol/g, Mw/Mn = 1.3, structure units 1,2- : 1,4-trans : 1,4-cis = 60 : 25 : 15

552-30-7

trimellitic Anhydride

Poly(α,ω-diisocyanato-polybutadiene-co-trimellitic anhydride), LBD-3000 content 42 wt percent

Poly(α,ω-diisocyanato-polybutadiene-co-trimellitic anhydride), LBD-3000 content 42 wt percent

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one at 70 - 180℃; for 9h; Polymerization;96%
3454-24-8

bis(4-aminophenyl)diphenylsilane

552-30-7

trimellitic Anhydride

1357585-01-3

2-(4-((4-(5-carboxy-1,3-dioxoisoindolin-2-yl)phenyl)diphenylsilyl)phenyl)-1,3-dioxoisoindoline-5-carboxylic acid

Conditions
ConditionsYield
With acetic acid at 20℃; for 15h; Reflux;96%

O-(4-methoxybenzyl)-hydroxylamine HCl

552-30-7

trimellitic Anhydride

863990-91-4

2-(4-methoxybenzyloxy)-1,3-dioxoisoindoline-5-carboxylic acid

Conditions
ConditionsYield
With pyridine at 90℃; for 24h;95%
552-30-7

trimellitic Anhydride

42972-13-4

1,4-dihydroxy-phthalazine-6-carboxylic acid

Conditions
ConditionsYield
Stage #1: trimellitic Anhydride With hydrazine In isopropyl alcohol for 5h; Heating / reflux;
Stage #2: With hydrogenchloride; water In isopropyl alcohol at 20℃; for 1h;
95%
1374879-15-8

2,6-diamino-4-trifluoromethyl-40-phenoxydiphenyl ether

552-30-7

trimellitic Anhydride

1374879-16-9

2,6-bis(N-trimellitimido)-4-trifluoromethyl-40-phenoxydiphenyl ether

Conditions
ConditionsYield
With acetic acid for 15h; Inert atmosphere; Reflux;95%
591-27-5

m-Hydroxyaniline

552-30-7

trimellitic Anhydride

82811-05-0

N-(3-hydroxyphenyl)trimellitimide

Conditions
ConditionsYield
Stage #1: m-Hydroxyaniline; trimellitic Anhydride In 1-methyl-pyrrolidin-2-one at 20℃; for 6h; Inert atmosphere;
Stage #2: In 1-methyl-pyrrolidin-2-one; toluene at 120℃; for 10h; Dean-Stark;
95%
83-55-6

5-amino-1-naphthol

552-30-7

trimellitic Anhydride

N-(5-hydroxynaphthyl)trimellitimide

Conditions
ConditionsYield
Stage #1: 5-amino-1-naphthol; trimellitic Anhydride In 1-methyl-pyrrolidin-2-one at 20℃; for 6h; Inert atmosphere;
Stage #2: In 1-methyl-pyrrolidin-2-one; toluene at 120℃; for 10h; Dean-Stark;
95%
101-68-8

di(4-isocyanatophenyl)methane

552-30-7

trimellitic Anhydride

Poly(4,4\-methylenedi(phenylisocyanate)-trimellitic anhydride)

Poly(4,4\-methylenedi(phenylisocyanate)-trimellitic anhydride)

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one at 70 - 180℃; for 9h; Polymerization;94%
38945-21-0

O-allylhydroxylamine hydrochloride

552-30-7

trimellitic Anhydride

863990-92-5

2-(allyloxy)-1,3-dioxoisoindoline-5-carboxylic acid

Conditions
ConditionsYield
With pyridine at 90℃; for 24h;94%
123-30-8

4-amino-phenol

552-30-7

trimellitic Anhydride

22005-25-0

2-(4-hydroxyphenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: 4-amino-phenol; trimellitic Anhydride In 1-methyl-pyrrolidin-2-one at 20℃; for 6h; Inert atmosphere;
Stage #2: In 1-methyl-pyrrolidin-2-one; toluene at 120℃; for 10h; Dean-Stark;
93%
With acetic acid at 130℃; for 16h; Condensation;85%
104-76-7

2-Ethylhexyl alcohol

552-30-7

trimellitic Anhydride

3319-31-1

Hatcol 200

Conditions
ConditionsYield
With methanesulfonic acid In water at 180 - 208℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere;93%
α,ω-Diisocyanato-polybutadiene, isocyanate group conc. 719 mmol/g, Mw/Mn = 1.3, structure units 1,2- : 1,4-trans : 1,4-cis = 60 : 25 : 15

α,ω-Diisocyanato-polybutadiene, isocyanate group conc. 719 mmol/g, Mw/Mn = 1.3, structure units 1,2- : 1,4-trans : 1,4-cis = 60 : 25 : 15

552-30-7

trimellitic Anhydride

Poly(α,ω-diisocyanato-polybutadiene-co-trimellitic anhydride), LBD-3000 content 94 wt percent

Poly(α,ω-diisocyanato-polybutadiene-co-trimellitic anhydride), LBD-3000 content 94 wt percent

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one at 70 - 180℃; for 9h; Polymerization;92%
106-47-8

4-chloro-aniline

552-30-7

trimellitic Anhydride

2-(4-chlorophenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Conditions
ConditionsYield
With acetic acid at 130℃; for 16h; Condensation;92%
With acetic acid In diethyl ether Reflux;
101-54-2

N-phenylphenylene-1,4-diamine

552-30-7

trimellitic Anhydride

330217-26-0

C21H14N2O4

Conditions
ConditionsYield
In acetic acid for 10h; Inert atmosphere; Reflux;92%

1,4-(4-amino-2-trifluoromethylphenoxy)-2-(3'-trifluoromethylphenyl)benzene

552-30-7

trimellitic Anhydride

2,2'-(4,4'-(3'-(trifluoromethyl)biphenyl-2,5-diyl)bis(oxy)bis(3-(trifluoromethyl)-4,1-phenylene))bis(1,3-dioxoisoindoline-5-carboxylic acid)

Conditions
ConditionsYield
With acetic acid at 120℃; for 13h;92%
α,ω-Diisocyanato-polybutadiene, isocyanate group conc. 719 mmol/g, Mw/Mn = 1.3, structure units 1,2- : 1,4-trans : 1,4-cis = 60 : 25 : 15

α,ω-Diisocyanato-polybutadiene, isocyanate group conc. 719 mmol/g, Mw/Mn = 1.3, structure units 1,2- : 1,4-trans : 1,4-cis = 60 : 25 : 15

552-30-7

trimellitic Anhydride

Poly(α,ω-diisocyanato-polybutadiene-co-trimellitic anhydride), LBD-3000 content 16 wt percent

Poly(α,ω-diisocyanato-polybutadiene-co-trimellitic anhydride), LBD-3000 content 16 wt percent

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one at 70 - 180℃; for 9h; Polymerization;91%
108-42-9

3-chloro-aniline

552-30-7

trimellitic Anhydride

2-(3-chlorophenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Conditions
ConditionsYield
With acetic acid at 130℃; for 16h; Condensation;91%
95-76-1

m,p-dichloroaniline

552-30-7

trimellitic Anhydride

[2-(3,4-dichloro)phenyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid

Conditions
ConditionsYield
With acetic acid at 130℃; for 16h; Condensation;91%
With acetic acid In diethyl ether Reflux;
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    1,2,4-Benzenetricarboxylic anhydride CAS 552-30-7

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    552-30-7 1,2,4-Benzenetricarboxylic anhydride

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    1,2,4-Benzenetricarboxylic anhydride

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    Product Name 1,2,4-Benzenetricarboxylic anhydride CAS No. 552-30-7 Appearance White solid Assay ≥99% Appearance:White powder Storage

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    Trimellitic Anhydride Basic information Product Name: Trimellitic Anhydride Synonyms: 1,2,4-Benzenetricarboxylic acid anhydride;1,2,4-Benzenetricarboxylic acid anhydride-1,2;1,2,4-Benzenetricarboxylic acid, cyclic 1,2-anhy

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Chemistry

Molecular Structure of 1,2,4-Benzenetricarboxylic anhydride (CAS NO.552-30-7):

IUPAC Name: 1,3-dioxo-2-benzofuran-5-carboxylic acid
Molecular Formula: C9H4O5
Formula Weight: 192.13
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 69.67 Å2
Index of Refraction: 1.662
Molar Refractivity: 42.61 cm3
Molar Volume: 115 cm3
Surface Tension: 79.4 dyne/cm
Density: 1.669 g/cm3
Flash Point: 201.3 °C
Enthalpy of Vaporization: 77.24 kJ/mol
Boiling Point: 470.6 °C at 760 mmHg
Melting point: 163-166 °C(lit.)
Vapour Pressure: 1.17E-09 mmHg at 25°C
Sensitive: Moisture Sensitive
EINECS: 209-008-0
Merck: 14,9703
BRN: 9394
Stability: Stable. Moisture sensitive.
InChI
InChI=1/C9H4O5/c10-7(11)4-1-2-5-6(3-4)9(13)14-8(5)12/h1-3H,(H,10,11)
Smiles
c12c(C(=O)OC2=O)ccc(c1)C(O)=O
Product Categories: Industrial/Fine Chemicals; Fluorenes, etc. (reagent for high-performance polymer research); Functional Materials; Reagent for High-Performance Polymer Research

Uses

  1,2,4-Benzenetricarboxylic anhydride (CAS NO.552-30-7) is used as an embossing agent for vinyl flooring and as a curing agent for epoxy resins. It is also used as an intermediate for the synthesis of surface coatings chemicals, polymers, dyes printing inks, adhesives, pharmaceuticals . It is mainly used as raw material for polyimide resin, polyester resin, plasticizer TOTM and also be used for producing heatproof & insulating, paint, adhesive,surfactant, synthesize dye materials etc.

Production

1,2,4-trimethylbenzene as raw material, TRIMELLITIC ANHYDRIDE (552-30-7) is synthesized by liquid nitric acid oxidation or cobalt(manganese) catalytic air oxidation.

Toxicity Data With Reference

1.    

orl-mus LD50:1900 mg/kg

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 18 (7)(1974),57.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by ingestion. Has caused pulmonary edema from inhalation. Irritant to lungs and air passages. May be a powerful allergen. Typical attack consists of breathlessness, wheezing, cough, running nose, immunological sensitization, and asthma symptoms. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.
Hazard Codes: HarmfulXn
Risk Statements: 37-41-42/43
R37:Irritating to respiratory system 
R41:Risk of serious damage to the eyes. 
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements: 22-26-36/37/39
S22:Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 1
RTECS: DC2050000
F: 10-21
HS Code: 29173980

Standards and Recommendations

OSHA PEL: TWA 0.005 ppm
ACGIH TLV: TWA CL 0.04 mg/m3
DFG MAK: 0.04 mg/m3
NIOSH REL: (Trimellitic Anhydride): handle as extremely toxic

Analytical Methods

For occupational chemical analysis use NIOSH: Trimethyllitic Anhydride, P&CAM 322.

Specification

 1,2,4-Benzenetricarboxylic anhydride , with CAS number of 552-30-7, can be called 1,2, 4-Benzenetricarboxylic acid, cyclic 1,2-anhydride ; 5-Phthalanacarboxylic acid, 1,3-dioxo- ; 5-Isobenzofurancarboxylic acid,1,3-dihydro-1,3-dioxo- ; Trimellitic acid, cyclic 1,2-anhydride ; 5-Isobenzofurancarboxylic acid, 1,3-dihydro-1,3-dioxo- . 1,2,4-Benzenetricarboxylic anhydride (CAS NO.552-30-7) is a needle-shaped crystal. Dissolved in water, 2-butanone, acetone, dimethyl formamide and ethyl acetate, cyclohexanone, and soluble in ethanol reacts slightly soluble in carbon tetrachloride, toluene.