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88-99-3

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88-99-3 Usage

Description

Phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2. It is an isomer of isophthalic acid and terephthalic acid. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale.

Chemical Properties

PHTHALIC ACID,C6H4(COOH)2, mp 208 °C (ortho), 330 °C (meta and iso), the ortho form sublimes and the meta and iso forms decompose with heat, sp gr 1.593 (ortho). Phthalic acid is very slightly soluble in H2O, soluble in alcohol, and slightly soluble in ether. The solid form is colorless, crystalline

Uses

Different sources of media describe the Uses of 88-99-3 differently. You can refer to the following data:
1. Phthalic Acid (Phenyl-13C6, D4) is labelled Phthalic Acid (P384480) which is an organic reagent used to synthesize phthalates.
2. It is a dibasic acid, with pKa's of 2.89 and 5.51. The mono potassium salt, potassium hydrogen phthalate is a standard acid in analytical chemistry. Typically phthalate esters are prepared from the widely available phthalic anhydride. Reduction of phthalic acid with sodium amalgam in the presence of water gives the 1,3- cyclohexadiene derivative.
3. Organic reagent used to synthesize phthalates.

Definition

Different sources of media describe the Definition of 88-99-3 differently. You can refer to the following data:
1. ChEBI: A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.
2. phthalic acid: colourlesscrystalline dicarboxylic acid,C6H4(COOH)2; r.d. 1.6; m.p. 207°C.The two –COOH groups are substitutedon adjacent carbon atoms ofthe ring, the technical name beingbenzene-1,2-dicarboxylic acid. Theacid is made from phthalic anhydride(benzene-1,2-dicarboxylic anhydride,C8H4O3), which is made by the catalyticoxidation of naphthalene. Theanhydride is used in making plasticizersand polyester resins.

Production Methods

Phthalic acid is produced by the catalytic oxidation of naphthalene directly to phthalic anhydride and a subsequent hydrolysis of the anhydride. Phthalic acid was first obtained by French chemist Auguste Laurent in 1836 by oxidizing naphthalene tetrachloride. Believing the resulting substance to be a naphthalene derivative, he named it "naphthalic acid". After the Swiss chemist Jean Charles Galissard de Marignac determined its correct formula, Laurent gave it its present name. Manufacturing methods in the nineteenth century included oxidation of naphthalene tetrachloride with nitric acid, or, better, oxidation of the hydrocarbon with fuming sulfuric acid, using mercury or mercury(II) sulfate as a catalyst.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 2414, 1965 DOI: 10.1021/jo01018a074

General Description

White crystals or fine white powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Phthalic acid is a carboxylic acid. Phthalic acid is sensitive to exposure to extreme heat. Phthalic acid reacts violently with nitric acid. Phthalic acid is incompatible with sodium nitrite. Phthalic acid is also incompatible with oxidizers. .

Fire Hazard

Phthalic acid is combustible.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. A skin and mucous membrane irritant. Combustible when heated. In the form of dust (anhydride) it can explode. Mixtures with sodmm nitrite explode when heated. Violent reaction with HNO3. When heated to decomposition it emits acrid smoke and irritating fumes. Used in synthesis of dyes and dyestuffs, in medcines and perfumes.

Safety

The toxicity of phthalic acid is low with LD50 (mouse) of 550 mg/kg. However, many phthalate esters have been implicated as endocrine disruptors.

Purification Methods

Crystallise phthalic acid from water. [Beilstein 9 IV 3167.]

Isomers

Phthalic acid is one of three isomers of benzene dicarboxylic acid, the others being iso phthalic acid and terephthalic acid. Sometimes the term "phthalic acids" is used to refer to this family of isomers, but in the singular, "phthalic acid", refers exclusively to the ortho- isomer.

Check Digit Verification of cas no

The CAS Registry Mumber 88-99-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 8 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 88-99:
(4*8)+(3*8)+(2*9)+(1*9)=83
83 % 10 = 3
So 88-99-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)/p-2

88-99-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (A14450)  Phthalic acid, 99%   

  • 88-99-3

  • 250g

  • 307.0CNY

  • Detail
  • Alfa Aesar

  • (A14450)  Phthalic acid, 99%   

  • 88-99-3

  • 1000g

  • 455.0CNY

  • Detail
  • Alfa Aesar

  • (A14450)  Phthalic acid, 99%   

  • 88-99-3

  • 5000g

  • 1932.0CNY

  • Detail
  • Alfa Aesar

  • (41770)  Phthalic acid, ACS, 99.5+%   

  • 88-99-3

  • 100g

  • 290.0CNY

  • Detail
  • Alfa Aesar

  • (41770)  Phthalic acid, ACS, 99.5+%   

  • 88-99-3

  • 500g

  • 1160.0CNY

  • Detail
  • Sigma-Aldrich

  • (80010)  Phthalicacid  puriss. p.a., ≥99.5% (T)

  • 88-99-3

  • 80010-100G

  • 522.99CNY

  • Detail
  • Sigma-Aldrich

  • (80010)  Phthalicacid  puriss. p.a., ≥99.5% (T)

  • 88-99-3

  • 80010-1KG

  • 2,213.64CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000766)  Phthalicacid  European Pharmacopoeia (EP) Reference Standard

  • 88-99-3

  • Y0000766

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (79255)  Phthalicacid  analytical standard

  • 88-99-3

  • 79255-100MG

  • 458.64CNY

  • Detail
  • USP

  • (1535899)  Phthalicacid  United States Pharmacopeia (USP) Reference Standard

  • 88-99-3

  • 1535899-50MG

  • 4,647.24CNY

  • Detail
  • Vetec

  • (V900011)  Phthalicacid  Vetec reagent grade, 98%

  • 88-99-3

  • V900011-500G

  • 129.87CNY

  • Detail
  • Sigma-Aldrich

  • (402915)  Phthalicacid  ACS reagent, ≥99.5%

  • 88-99-3

  • 402915-25G

  • 398.97CNY

  • Detail

88-99-3SDS

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 phthalic acid

1.2 Other means of identification

Product number -
Other names 1,2-Benzenedicarboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Metabolite
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:88-99-3 SDS

88-99-3Synthetic route

o-xylene
95-47-6

o-xylene

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With zinc(II) oxide In N,N-dimethyl-formamide for 0.0833333h; microwave irradiation;89%
With manganese(II) bromide; dihydrogen peroxide; oxygen In supercritical water at 380℃; under 172517 - 180018 Torr;78%
With dihydrogen peroxide; sodium carbonate; acetic acid at 100℃; under 7500.75 Torr; for 12h; Reagent/catalyst; Green chemistry;78%
o-xylene
95-47-6

o-xylene

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

C

benzoic acid
65-85-0

benzoic acid

D

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 380℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B 72%
C n/a
D n/a
With oxygen; manganese(II) bromide; hydrogen bromide In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B 65%
C n/a
D n/a
With dihydrogen peroxide; manganese(II) bromide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B 63%
C n/a
D n/a
o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 50h; Heating;93%
With potassium hydroxide; sodium tetrahydroborate; air; palladium on activated charcoal In methanol at 20℃; for 7h;90%
With tert.-butylhydroperoxide; copper(l) chloride In acetonitrile at 20℃; for 2.5h;84%
o-xylene
95-47-6

o-xylene

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B 66%
C n/a
With dihydrogen peroxide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B 66%
C n/a
With oxygen; manganese(II) bromide; hydrogen bromide In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B 66%
C n/a
With oxygen; hydrogen bromide; manganese(II) acetate In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B 63%
C n/a
o-xylene
95-47-6

o-xylene

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

C

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

D

benzoic acid
65-85-0

benzoic acid

E

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 380℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 71%
D n/a
E n/a
With oxygen; hydrogen bromide; manganese(II) acetate In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 60%
D n/a
E n/a
With oxygen; hydrogenchloride; manganese(II) acetate In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 17%
D n/a
E n/a
With oxygen; manganese(II) acetate In water at 380℃; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 8%
D n/a
E n/a
naphthalene
91-20-3

naphthalene

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With zinc(II) oxide In N,N-dimethyl-formamide for 0.125h; microwave irradiation;78%
With sodium hypochlorite; ruthenium(III) chloride trihydrate; sulfuric acid; tetrabutylammomium bromide In water; 1,2-dichloro-ethane at 23℃; for 0.5h; pH=9; Green chemistry;58%
With silica gel at -196.1℃; Irradiation;49%
o-xylene
95-47-6

o-xylene

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: o-xylene With manganese(IV) oxide; C32H16N8O4Ru; C46H39CrN12O2; oxygen at 195℃; under 14251.4 Torr; for 0.2h;
Stage #2: With manganese(IV) oxide; C32H16N8O4Ru; C46H39CrN12O2; oxygen; acetic acid at 150℃; under 4500.45 Torr; for 4h; Temperature; Pressure; Reagent/catalyst;
A 89.3%
B 10.6%
Stage #1: o-xylene With N-acetylphthalimide; Cr(4+)*4NO3(1-); C36H24N8NiO4; C52H44FeN4O8; oxygen at 120℃; under 2250.23 Torr; for 1.5h;
Stage #2: With N-acetylphthalimide; Cr(4+)*4NO3(1-); C36H24N8NiO4; C52H44FeN4O8; oxygen; acetic acid at 170℃; under 12001.2 Torr; for 0.6h; Temperature; Pressure; Reagent/catalyst;
A 14.4%
B 85.3%
With zinc(II) oxide In N,N-dimethyl-formamide for 0.133333h; microwave irradiation;A 80%
B 5 % Spectr.
carbon monoxide
201230-82-2

carbon monoxide

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 12h; Irradiation;78%
2,4,5-trimethylbenzaldehyde
5779-72-6

2,4,5-trimethylbenzaldehyde

A

1,2,4,5-benzenetetracarboxylic acid
89-05-4

1,2,4,5-benzenetetracarboxylic acid

B

5-methyl-1,2,4-benzenetricarboxylic acid
34240-10-3

5-methyl-1,2,4-benzenetricarboxylic acid

C

1,2,4-benzene tricarboxylic acid
528-44-9

1,2,4-benzene tricarboxylic acid

D

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: 2,4,5-trimethylbenzaldehyde With oxygen at 210℃; under 24002.4 Torr;
Stage #2: With oxygen; hydrogen bromide In water at 210℃; under 21752.2 Torr;
Stage #3: With hydrogen; 0.5% Pd/C at 150℃; under 7500.75 Torr;
o-xylene
95-47-6

o-xylene

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

C

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

D

benzoic acid
65-85-0

benzoic acid

E

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 380℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 74%
D n/a
E n/a
With dihydrogen peroxide In water at 380℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 71%
D n/a
E n/a
With dihydrogen peroxide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 52%
D n/a
E n/a
With dihydrogen peroxide; cobalt(II) bromide In water at 380℃; under 172517 - 180018 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C 51%
D n/a
E n/a
inden-1-one
83-33-0

inden-1-one

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate In acetic acid at 120℃; under 760.051 Torr; for 15h;82%
With KO2; 18-crown-6 ether In N,N-dimethyl-formamide for 20h; Ambient temperature;61 % Chromat.
o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide; sodium tetrahydroborate; air; palladium on activated charcoal In methanol at 20℃; for 3h;86%
With tetrakis(pyridine)silver(II) peroxodisulfate In water; acetonitrile for 5h; Ambient temperature;80%
With potassium permanganate In water; acetonitrile
carbon monoxide
201230-82-2

carbon monoxide

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

C

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 18h; Irradiation;A 4%
B 85%
C 3%
2-Iodobenzoic acid
88-67-5

2-Iodobenzoic acid

carbon monoxide
201230-82-2

carbon monoxide

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With potassium carbonate; potassium tetrachloropalladate(II) In water at 50℃; under 760 Torr; for 20h;95%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

A

2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

B

phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

C

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 18h; Irradiation;A 4%
B 85%
C 3%
o-xylene
95-47-6

o-xylene

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

2-(hydroxymethyl)benzoic acid
612-20-4

2-(hydroxymethyl)benzoic acid

C

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

D

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

Conditions
ConditionsYield
Stage #1: o-xylene With N-hydroxyphthalimide; air; cobalt(II) acetate; manganese(II) acetate In acetic acid at 150℃; under 22801.5 Torr; for 3h;
Stage #2: With sodium hydroxide at 90℃; Further stages.;
A 6%
B 8%
C 73%
D 3%
aqueous potassium hydroxide

aqueous potassium hydroxide

2-(2-chlorobenzyl)isoindoline-1,3-dione
74805-32-6

2-(2-chlorobenzyl)isoindoline-1,3-dione

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In iced-water; water98%
2-carboxycinnamic acid
612-40-8

2-carboxycinnamic acid

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With Oxone In water; acetonitrile for 22h; Reflux;85%
phthaloyl peroxide
4733-52-2

phthaloyl peroxide

A

N,N'-diphenyl-1,4-phenylenediamine
6246-98-6, 73334-88-0, 73334-89-1

N,N'-diphenyl-1,4-phenylenediamine

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With N,N'-diphenyl-1,4-phenylenediamine In tetrahydrofuran at 25℃;A 88%
B 98%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

A

N,N'-diphenyl-1,4-phenylenediamine
6246-98-6, 73334-88-0, 73334-89-1

N,N'-diphenyl-1,4-phenylenediamine

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With monoperoxyphthalic acid In tetrahydrofuran at 25℃;A 88%
B 98%
o-xylene
95-47-6

o-xylene

para-xylene
106-42-3

para-xylene

A

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; oxygen; manganese(II) bromide In water at 400℃; under 187519 Torr; Product distribution / selectivity;A 46%
B n/a
2-(3-bromopropyl)isoindole-1,3-dione
5460-29-7

2-(3-bromopropyl)isoindole-1,3-dione

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

bis(3-aminopropyl)methylbenzylammonium trihydrochloride

bis(3-aminopropyl)methylbenzylammonium trihydrochloride

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; hydrogenchlorideA 90%
B n/a
carbon monoxide
201230-82-2

carbon monoxide

benzoic acid
65-85-0

benzoic acid

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With sodium acetate; palladium diacetate; silver carbonate In 1,4-dioxane at 150℃; under 760.051 Torr; for 48h;41%
1,3-dimethylnaphthalene
575-41-7

1,3-dimethylnaphthalene

A

1,3-naphthalenedicarboxylic acid
2089-93-2

1,3-naphthalenedicarboxylic acid

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With oxygen; cobalt acetate; hydrogen bromide; manganese(II) acetate In water; acetic acid at 180 - 200℃; under 12001.2 Torr; for 1.08333h; Product distribution / selectivity;A 30%
B 0.1%
o-xylene
95-47-6

o-xylene

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

C

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

D

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

E

benzoic acid
65-85-0

benzoic acid

F

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 380℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;A n/a
B n/a
C n/a
D 70%
E n/a
F n/a
2-Methylacetophenone
577-16-2, 122382-54-1

2-Methylacetophenone

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With oxygen; zirconyl acetate; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate; acetic anhydride; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione In acetic acid at 120℃; under 760.051 Torr; for 15h;73%
phthalyl alcohol
612-14-6

phthalyl alcohol

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With C15H27Br2CoN3; potassium hydroxide In toluene at 140℃; for 16h; Cannizzaro Reaction; Inert atmosphere; Sealed tube;80%
With potassium permanganate
o-xylene
95-47-6

o-xylene

A

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With sodium hydroxide; water; dihydrogen peroxide; manganese(II) bromide at 380℃; under 172517 Torr;A 46%
B n/a
With manganese(II) bromide; dihydrogen peroxide; oxygen; sodium bromide In supercritical water at 380℃; under 172517 - 180018 Torr;
o-xylene
95-47-6

o-xylene

para-xylene
106-42-3

para-xylene

m-xylene
108-38-3

m-xylene

A

isophthalic acid
121-91-5

isophthalic acid

B

terephthalic acid
100-21-0

terephthalic acid

C

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

D

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; oxygen; manganese(II) bromide In water at 400℃; under 187519 Torr; Product distribution / selectivity;A 86.3%
B 66.7%
C 61.5%
D n/a
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

acetylacetonatocobalt(III) Co(AA)3

acetylacetonatocobalt(III) Co(AA)3

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With acetic acid In o-xyleneA 71%
B n/a
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

phthalic anhydride
85-44-9

phthalic anhydride

Conditions
ConditionsYield
(2-(pyridin-2-yl)phenyl)boronic acid In nonane for 5.5h; Product distribution / selectivity; 3 Å Molecular sieve; Reflux;100%
With 2,6-dimethylpyridine; tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide; N,N-dimethyl-formamide at 25 - 30℃; for 12h; Inert atmosphere; Photolysis;99%
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 1h;98%
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

ortho-phthalic acid bis(trimethylsilyl) ester
2078-22-0

ortho-phthalic acid bis(trimethylsilyl) ester

Conditions
ConditionsYield
With saccharin at 125℃; for 1h; Inert atmosphere;100%
98%
With iodine In neat (no solvent) at 20℃; for 52h; Green chemistry;46%
2-(vinyloxy)ethyl isothiocyanate
59565-09-2

2-(vinyloxy)ethyl isothiocyanate

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

phthalic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

phthalic acid bis-[1-(2-isothiocyanato-ethoxy)-ethyl] ester

Conditions
ConditionsYield
Stage #1: 2-(vinyloxy)ethyl isothiocyanate; benzene-1,2-dicarboxylic acid at 120℃;
Stage #2: With trifluoroacetic acid at 70 - 80℃; for 1h;
100%
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Hexamethylphosphorous triamide
1608-26-0

Hexamethylphosphorous triamide

N,N,N',N'-tetramethyl-phthalamide
6329-16-4

N,N,N',N'-tetramethyl-phthalamide

Conditions
ConditionsYield
In benzene for 0.5h; Heating;100%
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

3,4,5,6-tetradeuterophtaloyl dicarboxylic acid
87976-26-9

3,4,5,6-tetradeuterophtaloyl dicarboxylic acid

Conditions
ConditionsYield
With hydrogen; water-d2; platinum on activated charcoal at 180℃; for 24h;100%
Stage #1: benzene-1,2-dicarboxylic acid With platinum on carbon; hydrogen; water-d2 at 180℃; under 3420.23 Torr; for 24h;
Stage #2: With water In diethyl ether
51%
[(η(5)-C5H5)2Co][OH]

[(η(5)-C5H5)2Co][OH]

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

4((C5H5)2Co)(1+)*2(C6H4COOHCOO)(1-)*C6H4(COO)2(2-) = [(C5H5)2Co]4[(C6H4COOHCOO)2][C6H4(COO)2]

4((C5H5)2Co)(1+)*2(C6H4COOHCOO)(1-)*C6H4(COO)2(2-) = [(C5H5)2Co]4[(C6H4COOHCOO)2][C6H4(COO)2]

Conditions
ConditionsYield
In water mixing; filtn., solvent evpn.;100%
bis(benzene)chromium hydroxide

bis(benzene)chromium hydroxide

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

((C6H6)2Cr)(1+)*C6H4COOHCOO(1-)*C6H4(COOH)2 = [(C6H6)2Cr][(C6H4COOHCOO)][C6H4(COOH)2]

((C6H6)2Cr)(1+)*C6H4COOHCOO(1-)*C6H4(COOH)2 = [(C6H6)2Cr][(C6H4COOHCOO)][C6H4(COOH)2]

Conditions
ConditionsYield
In water mixing; filtn., solvent evpn.;100%
5-(3-chloropyridin-2-yl)-7-(2-pyridin-2-ylethoxy)-1H-indazole-3-amine
1093966-48-3

5-(3-chloropyridin-2-yl)-7-(2-pyridin-2-ylethoxy)-1H-indazole-3-amine

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

2-[5-(3-chloropyridin-2-yl)-7-(2-pyridin-2-ylethoxy)-1H-indazol-3-yl]-1H-isoindole-1,3(2H)-dione
1093966-58-5

2-[5-(3-chloropyridin-2-yl)-7-(2-pyridin-2-ylethoxy)-1H-indazol-3-yl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
Stage #1: 5-(3-chloropyridin-2-yl)-7-(2-pyridin-2-ylethoxy)-1H-indazole-3-amine; benzene-1,2-dicarboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20 - 50℃; for 2h;
Stage #2: With sodium hydrogencarbonate In water; N,N-dimethyl-formamide
100%
5-Aminouracil
932-52-5

5-Aminouracil

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

5-phthalimidopyrimidine-2,4(1H,3H)-dione
59007-52-2

5-phthalimidopyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With pyridine at 150℃; for 0.5h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube; Microwave irradiation;100%
2,6-diisopropylbenzenamine
24544-04-5

2,6-diisopropylbenzenamine

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

(E)-2-(((2,6-diisopropylphenyl)imino)methyl)benzoic acid

(E)-2-(((2,6-diisopropylphenyl)imino)methyl)benzoic acid

Conditions
ConditionsYield
In methanol at 20℃; for 2h; Inert atmosphere; Reflux;100%
methanol
67-56-1

methanol

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

Conditions
ConditionsYield
With boron trifluoride at 95℃; for 1h; Product distribution; other reaction time: 15, 20, 30 min;99.9%
With boron trifluoride at 95℃; for 1h;99.9%
With sulfuric acid for 24h; Reflux;96%
Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Diethyl phthalate
84-66-2

Diethyl phthalate

Conditions
ConditionsYield
In various solvent(s) at 80℃; for 2h;99%
2-amino-4-methylbenzophenone
4937-62-6

2-amino-4-methylbenzophenone

water
7732-18-5

water

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

2-(N-isopropylamino)-4-methylbenzophenone
23070-81-7

2-(N-isopropylamino)-4-methylbenzophenone

Conditions
ConditionsYield
With sodium hydroxide; sodium borohydrid In acetone99%
trimethylaluminum
75-24-1

trimethylaluminum

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

[(AlMe2)2(μ-phthalate)]2

[(AlMe2)2(μ-phthalate)]2

Conditions
ConditionsYield
In not given addn. of AlMe3 (2 equiv.) to phthalic acid; according to J. Lewinski et al. Inorg. Chem. 1998, 37, 2575;99%
In toluene byproducts: CH4; N2-atmosphere; addn. of 2 equiv. AlMe3 to ligand at -78°C, warming to room temp., standing for 1 h; evapn. (vac.); elem. anal.;95%
3-Bromo-4-methoxyphenethylamine
159465-27-7

3-Bromo-4-methoxyphenethylamine

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

N-(3-bromo-4-methoxy-phenethyl)-phthalimide

N-(3-bromo-4-methoxy-phenethyl)-phthalimide

Conditions
ConditionsYield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In dichloromethane at 20℃; for 12h;99%
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

bis(pyridin-2-yl)methylamine
58088-50-9

bis(pyridin-2-yl)methylamine

1-(pyridin-2-yl)-3-(2-(1-(pyridin-2-yl)imidazo[1,5-a]pyridin-3-yl)phenyl)imidazo[1,5-a]pyridine

1-(pyridin-2-yl)-3-(2-(1-(pyridin-2-yl)imidazo[1,5-a]pyridin-3-yl)phenyl)imidazo[1,5-a]pyridine

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In acetic acid butyl ester; ethyl acetate at 20℃; for 17h; Reflux;99%
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
With 5 wt percent zeolite NaY-Bf at 180℃; for 5h; Autoclave; Green chemistry;99%
2-propylheptan-1-ol
10042-59-8

2-propylheptan-1-ol

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

di(2-propylheptyl) phthalate
53306-54-0

di(2-propylheptyl) phthalate

Conditions
ConditionsYield
With titanium(IV) isopropylate at 170 - 220℃; under 760.051 Torr; for 4.5h; Inert atmosphere; Large scale;99%
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 6h; Reagent/catalyst; Solvent; Temperature;
1-ethyl-2,3-dimethylimidazolin-3-ium methyl carbonate

1-ethyl-2,3-dimethylimidazolin-3-ium methyl carbonate

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

1-ethyl-2,3-dimethylimidazolinium hydrogen phthalate salt

1-ethyl-2,3-dimethylimidazolinium hydrogen phthalate salt

Conditions
ConditionsYield
In methanol at 20 - 30℃; for 4h;99%
triphenylarsineoxide
1153-05-5, 856568-31-5

triphenylarsineoxide

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

2C18H15AsO*C8H6O4

2C18H15AsO*C8H6O4

Conditions
ConditionsYield
In benzene Heating;98%
benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

benzylamine
100-46-9

benzylamine

N,N'-dibenzylphthalamide
38228-99-8

N,N'-dibenzylphthalamide

Conditions
ConditionsYield
In xylene for 7.5h; Heating;98%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

2-(2-carboxyphenyl)benzimidazole
16529-06-9

2-(2-carboxyphenyl)benzimidazole

Conditions
ConditionsYield
at 200℃; under 187519 Torr; for 3h; Temperature; Autoclave; Inert atmosphere;98%
With hydrogenchloride at 80℃; for 4h;79%
at 150℃; for 2h;75%
With polyphosphoric acid at 250℃; for 4h;71%
penta(p-tolyl)antimony(V)
13328-67-1, 51017-91-5

penta(p-tolyl)antimony(V)

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

tetraphenylantimony monophthalate
127948-08-7

tetraphenylantimony monophthalate

Conditions
ConditionsYield
In 1,4-dioxane; toluene sealed evacuated ampoule, soln. of Sb-compd. in toluene addn. to soln. of acid in dioxane, heating (90°C, 1 h); cooling, filtration, residue drying;98%
pentaphenylantimony
2170-05-0

pentaphenylantimony

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

tetraphenylantimony phthalate
127948-08-7

tetraphenylantimony phthalate

Conditions
ConditionsYield
In toluene byproducts: benzene; room temp., 0.5-1 h; elem. anal.;98%

88-99-3Relevant articles and documents

Negative correlations between cultivable and active-yet-uncultivable pyrene degraders explain the postponed bioaugmentation

Jiang, Bo,Chen, Yating,Xing, Yi,Lian, Luning,Shen, Yaoxin,Zhang, Baogang,Zhang, Han,Sun, Guangdong,Li, Junyi,Wang, Xinzi,Zhang, Dayi

, (2021/09/24)

Bioaugmentation is an effective approach to remediate soils contaminated by polycyclic aromatic hydrocarbons (PAHs), but suffers from unsatisfactory performance in engineering practices, which is hypothetically explained by the complicated interactions between indigenous microbes and introduced degraders. This study isolated a cultivable pyrene degrader (Sphingomonas sp. YT1005) and an active pyrene degrading consortium (Gp16, Streptomyces, Pseudonocardia, Panacagrimonas, Methylotenera and Nitrospira) by magnetic-nanoparticle mediated isolation (MMI) from soils. Pyrene biodegradation was postponed in bioaugmentation with Sphingomonas sp. YT1005, whilst increased by 30.17% by the active pyrene degrading consortium. Pyrene dioxygenase encoding genes (nidA, nidA3 and PAH-RHDα-GP) were enriched in MMI isolates and positively correlated with pyrene degradation efficiency. Pyrene degradation by Sphingomonas sp. YT1005 only followed the phthalate pathway, whereas both phthalate and salicylate pathways were observed in the active pyrene degrading consortium. The results indicated that the uncultivable pyrene degraders were suitable for bioaugmentation, rather than cultivable Sphingomonas sp. YT1005. The negative correlations between Sphingomonas sp. YT1005 and the active-yet-uncultivable pyrene degraders were the underlying mechanisms of bioaugmentation postpone in engineering practices.

Method for treating 4-AA intermediate waste liquid

-

, (2022/03/17)

The invention belongs to the technical field of chemical synthesis, and discloses a method for treating 4-AA intermediate waste liquid. The method comprises the following three steps of: (1) heating N, N-bis (2-ethoxyl) phthalimide and a basic catalyst in an aqueous solution for reflux reaction to prepare a sodium phthalate feed liquid; (2) carrying out reduced pressure distillation on the sodium phthalate feed liquid in the step (1) to obtain ethanolamine, and preparing phthalic acid from residual residues through acid regulation; and (3) introducing ammonia gas or adding ammonia water into a reaction kettle containing the phthalic acid so as to perform heating reaction, performing cooling after the reaction is finished, adding water for washing, crystallizing, filtering and drying to obtain the phthalimide. According to the method disclosed by the invention, the byproduct hazardous wastes in the deprotection step of the enzymic method 4-AA are converted into the initial raw material of the enzymic method 4-AA, so that the hazardous wastes are turned into wealth, the raw material cost is effectively reduced, the storage, transportation and treatment expenses of the hazardous wastes are also effectively reduced, and the method has remarkable economic benefits and environmental benefits.

Chemical Modifications Induced by Phthalic Anhydride, a Respiratory Sensitizer, in Reconstructed Human Epidermis: A Combined HRMAS NMR and LC-MS/MS Proteomic Approach

Khong, Minh-Thuong,Berl, Valérie,Kuhn, Lauriane,Hammann, Philippe,Lepoittevin, Jean-Pierre

, p. 2087 - 2099 (2021/08/30)

Chemical skin and respiratory allergies are becoming a major health problem. To date our knowledge on the process of protein haptenation is still limited and mainly derived from studies performed in solution using model nucleophiles. In order to better understand chemical interactions between chemical allergens and the skin, we have investigated the reactivity of phthalic anhydride 1 (PA), a chemical respiratory sensitizer, toward reconstructed human epidermis (RHE). This study was performed using a new approach combining HRMAS NMR to investigate the in situ chemical reactivity and LC-MS/MS to identify modified epidermal proteins. In RHE, the reaction of PA appeared to be quite fast and the major product formed was phthalic acid. Two amide type adducts on lysine residues were observed and after 8h of incubation, we also observed the formation of an imide type cyclized adducts with lysine. In parallel, RHE samples topically exposed to phthalic anhydride (13C)-1 were analyzed using the shotgun proteomics method. Thus, 948 different proteins were extracted and identified, 135 of which being modified by PA, i.e., 14.2% of the extracted proteome. A total of 211 amino acids were modified by PA and validated by fragmentation spectra. We thus identified 154 modified lysines, 22 modified histidines, 30 modified tyrosines, and 5 modified arginines. The rate of modified residues, as a proportion of the total number of modifiable nucleophilic residues in RHE, was rather low (1%). At the protein level, modified proteins were mainly type I and type II keratins and other proteins which are abundant in the epidermis such as protein S100A, Caspase 14, annexin A2, serpin B3, fatty-acid binding protein 5, histone H2, H3, H4, etc. However, the most modified protein, mainly on histidine residues, was filaggrin, a protein that is of low abundance (0.0266 mol %) and rich in histidine.

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