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Dimethyl isophthalate

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Name

Dimethyl isophthalate

EINECS 215-951-9
CAS No. 1459-93-4 Density 1.175 g/cm3
PSA 52.60000 LogP 1.25980
Solubility insoluble in water Melting Point 64-68 °C
Formula C10H10O4 Boiling Point 285 °C at 760 mmHg
Molecular Weight 194.20 Flash Point 148 °C
Transport Information Appearance white to off-white flakes or crystalline powder
Safety 26-36 Risk Codes 36
Molecular Structure Molecular Structure of 1459-93-4 (Dimethyl isophthalate) Hazard Symbols IrritantXi
Synonyms

1,3-Benzenedicarboxylicacid, dimethyl ester (9CI);Isophthalic acid, dimethyl ester (6CI,8CI);1,3-Di(methoxycarbonyl)benzene;Dimethyl 1,3-benzenedicarboxylate;Dimethyl m-phthalate;Methyl 3-carbomethoxybenzoate;Morflex 1129;NSC 15313;

 

Dimethyl isophthalate Synthetic route

67-56-1

methanol

121-91-5

isophthalic acid

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With thionyl chloride at 20℃; for 72h;95.7%
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride for 3h;92%
75-44-5

phosgene

121-91-5

isophthalic acid

A

1459-93-4

dimethyl Isophthalate

B

99-63-8

benzene-1,3-dicarbonyl dichloride

Conditions
ConditionsYield
With pyridine In dichloromethaneA n/a
B 100%
1283160-97-3

dimethyl 5-pivaloxyisophthalate

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); (dimethoxy)methylsilane; tricyclohexylphosphine In toluene at 80℃; for 12h; Inert atmosphere;99%
67-56-1

methanol

881-99-2

1,3-bis-trichloromethyl-benzene

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
at 20℃; for 6h; UV-irradiation;99%
51839-15-7

5-iodo-isophthalic acid dimethyl ester

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With Ac-Cys-OMe; bismuth(III) oxide; N-ethyl-N,N-diisopropylamine In dichloromethane for 48h; Irradiation;96%
51760-21-5

dimethyl 5-bromoisophthalate

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With formic acid; tributyl-amine; 10-phenyl-10H-phenothiazine In acetonitrile at 20℃; for 24h; Inert atmosphere; UV-irradiation;94%
67-56-1

methanol

201230-82-2

carbon monoxide

141694-38-4

3-Fluorosulfonyloxy-benzoic acid methyl ester

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With triethylamine; palladium diacetate; 1,3-bis-(diphenylphosphino)propane In dimethyl sulfoxide under 760 Torr; a) room temperature, 15 min, b) 60 deg C, 2 h;92%
67-56-1

methanol

626-19-7

Isophthalaldehyde

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With Oxone; indium(III) triflate for 1.5h; Reflux;92%
With Oxone at 60℃; for 0.666667h; Sonication;90%
Stage #1: methanol; Isophthalaldehyde With pyridine at 20℃; for 0.0833333h;
Stage #2: With N-Bromosuccinimide at 20℃; for 9h;
100 %Chromat.
585524-77-2

3-(5,5-dimethyl-1,3,2-dioxaborinanyl)-1-methoxycarbonylbenzene

24424-99-5

di-tert-butyl dicarbonate

74-88-4

methyl iodide

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
Stage #1: 3-(5,5-dimethyl-1,3,2-dioxaborinanyl)-1-methoxycarbonylbenzene; di-tert-butyl dicarbonate With 4,4'-dimethyl-2,2'-bipyridines; lithium methanolate; copper(l) chloride In N,N-dimethyl acetamide at 30℃; for 6h; Inert atmosphere; Schlenk technique;
Stage #2: methyl iodide In N,N-dimethyl acetamide at 30℃; for 2h; Schlenk technique;
91%
67-56-1

methanol

626-19-7

Isophthalaldehyde

A

1459-93-4

dimethyl Isophthalate

B

619-21-6

m-formylphenyl benzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide at 20 - 70℃; for 15h; Green chemistry;A 90%
B 8%
121-91-5

isophthalic acid

616-38-6

carbonic acid dimethyl ester

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction;89%
With dimanganese decacarbonyl at 180℃; for 1h; Sealed tube;
1634-04-4

tert-butyl methyl ether

1877-71-0

benzene 1,3-dicarboxylic acid monomethyl ester

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate at 90℃; Schlenk technique;88%
922-67-8

propynoic acid methyl ester

187808-48-6

methyl 5-(N,N-dimethylamino)-2,4-pentadienoate

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
In xylene for 12h; Heating;87.3%
67-56-1

methanol

108-37-2

1-bromo-3-chlorobenzene

201230-82-2

carbon monoxide

A

1459-93-4

dimethyl Isophthalate

B

2905-65-9

methyl 3-chlorobenzoate

C

535-80-8

3-chlorobenzoate

Conditions
ConditionsYield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 8h; Irradiation;A 2.5%
B 86%
C 9.5%
67-56-1

methanol

201230-82-2

carbon monoxide

108-36-1

1,3-dibromobenzene

A

121-91-5

isophthalic acid

B

1459-93-4

dimethyl Isophthalate

C

618-89-3

methyl 3-bromobenzoate

Conditions
ConditionsYield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 14h; Irradiation;A 5%
B 86%
C 8%
108-37-2

1-bromo-3-chlorobenzene

201230-82-2

carbon monoxide

A

1459-93-4

dimethyl Isophthalate

B

2905-65-9

methyl 3-chlorobenzoate

C

535-80-8

3-chlorobenzoate

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 8h; Irradiation;A 2.5%
B 86%
C 9.5%
201230-82-2

carbon monoxide

108-36-1

1,3-dibromobenzene

A

121-91-5

isophthalic acid

B

1459-93-4

dimethyl Isophthalate

C

618-89-3

methyl 3-bromobenzoate

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 14h; Irradiation;A 5%
B 86%
C 8%
67-56-1

methanol

126717-94-0, 126786-51-4

(1S,4S,8R)-8-(2-Chloro-ethoxy)-3-oxo-2-oxa-bicyclo[2.2.2]oct-5-ene-6-carboxylic acid methyl ester

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 6h; Heating;83%
6018-41-3

methyl coumalate

5788-17-0

methyl (2E)-3-methoxy-2-propenoate

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
In toluene at 200℃; for 16h; Diels-Alder Cycloaddition; Inert atmosphere; Sealed tube;83%

methyl 8-butoxy-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-6-carboxylate

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 65℃; for 18h; Catalytic behavior; Reagent/catalyst; Temperature;82%
67-56-1

methanol

1877-71-0

benzene 1,3-dicarboxylic acid monomethyl ester

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With oxygen; potassium carbonate In hexane at 20℃; for 14h; Sonication;72%
67-56-1

methanol

121-91-5

isophthalic acid

A

1459-93-4

dimethyl Isophthalate

B

51760-21-5

dimethyl 5-bromoisophthalate

Conditions
ConditionsYield
Stage #1: isophthalic acid With sulfuric acid; sulfur trioxide; bromine at 150℃; for 7h;
Stage #2: methanol With sulfuric acid at 120℃;
A 26.8%
B 65.1%
177913-48-3

4-amino-1-hydroxycyclohexa-3,5-diene-1,3-dicarboxylic acid dimethyl ester

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With BF3 etherate; sodium hydrogencarbonate In dichloromethane; benzene62%
67-56-1

methanol

108-38-3

m-xylene

A

1459-93-4

dimethyl Isophthalate

B

99-36-5

1-methoxycarbonyl-3-methylbenzene

C

99-04-7

m-Toluic acid

Conditions
ConditionsYield
Stage #1: m-xylene With manganese(IV) oxide; oxygen; cobalt(II) diacetate tetrahydrate at 156℃; under 7500.75 Torr;
Stage #2: methanol Reagent/catalyst; Temperature; Pressure;
A 8.3%
B 57.7%
C 24.9%
67-56-1

methanol

95536-87-1, 126786-50-3

(1S,4S,8R)-8-Ethoxy-3-oxo-2-oxa-bicyclo[2.2.2]oct-5-ene-6-carboxylic acid methyl ester

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 6h; Heating;51%
67-56-1

methanol

121-91-5

isophthalic acid

A

1459-93-4

dimethyl Isophthalate

B

1877-71-0

benzene 1,3-dicarboxylic acid monomethyl ester

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 65℃;A n/a
B 42%
96600-64-5

4-methoxycarbonyl-3a,4-dihydrophthalide

922-67-8

propynoic acid methyl ester

A

65399-15-7

4-methoxycarbonyl-phthalide

B

131-11-3

phthalic acid dimethyl ester

C

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
In xylene for 40h; Heating;A 37%
B 10%
C 41%
121-91-5

isophthalic acid

1459-93-4

dimethyl Isophthalate

Conditions
ConditionsYield
With diethyl ether
67-56-1

methanol

99-63-8

benzene-1,3-dicarbonyl dichloride

1459-93-4

dimethyl Isophthalate

57664-97-8, 64803-72-1

isophthalic acid ; disilver (I)-compound

74-88-4

methyl iodide

1459-93-4

dimethyl Isophthalate

1459-93-4

dimethyl Isophthalate

2760-98-7

isophthalic dihydrazide

Conditions
ConditionsYield
With hydrazine hydrate In methanol at 70℃; for 4h;100%
With hydrazine hydrate In methanol91%
With hydrazine hydrate In ethanol Reflux;86%
1459-93-4

dimethyl Isophthalate

124-40-3

dimethyl amine

69383-71-7

N,N-dimethylisophthalamic acid methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; methanol at 20℃; for 2h;100%
1459-93-4

dimethyl Isophthalate

1877-71-0

benzene 1,3-dicarboxylic acid monomethyl ester

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 15h;99.2%
With sodium hydroxide In methanol; acetone at 20℃; for 24h; Substitution;98%
Stage #1: dimethyl Isophthalate With methanol; sodium hydroxide In acetone at 20℃; for 25h; Inert atmosphere;
Stage #2: With hydrogenchloride; water pH=1;
98%
1459-93-4

dimethyl Isophthalate

626-18-6

1,3-dimethanol benzene

Conditions
ConditionsYield
With C24H38Cl2N3PRu; hydrogen; sodium methylate In tetrahydrofuran at 25℃; under 38002.6 Torr; for 16h; Autoclave;99%
With C24H38Cl2N3PRu; hydrogen; sodium methylate In tetrahydrofuran at 25℃; under 37503.8 Torr; for 16h;99%
With lithium borohydride In tetrahydrofuran at 20℃; for 23h;95%
1459-93-4

dimethyl Isophthalate

73183-34-3

bis(pinacol)diborane

944392-68-1

dimethyl 5-(pinacolboryl)isophthalate

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole Inert atmosphere; Schlenk technique; Sealed tube;99%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole at 100℃; for 16h; Schlenk technique; Inert atmosphere;95%
Stage #1: bis(pinacol)diborane With C24H28ClIrN2O In n-heptane; isopropyl alcohol at 75℃; for 1h; Sealed tube; Inert atmosphere;
Stage #2: dimethyl Isophthalate In n-heptane; isopropyl alcohol Sealed tube; Inert atmosphere;
91%
36768-62-4

4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE

1459-93-4

dimethyl Isophthalate

42774-15-2

N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide

Conditions
ConditionsYield
With sodium methylate In methanol at 60 - 110℃; for 1.5h; Temperature; Inert atmosphere; Large scale;98.5%
In octane at 150 - 160℃; under 6750.68 - 8250.83 Torr; for 15h; Pressure; Solvent; Temperature; Autoclave; Inert atmosphere;97%
With solid supported catalyst C1 In acetonitrile at 20 - 70℃; for 15h; Reagent/catalyst;96.7%
at 190 - 230℃; for 7h; Large scale;93.5%
at 190 - 230℃; for 7h; Large scale;93.5%
854261-90-8

2-propynyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside

1459-93-4

dimethyl Isophthalate

854261-97-5

1,3-bis-[1,7-di-O-(2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl)hep-2,5-diyn-1,4,7-triol-4-yl]benzene

Conditions
ConditionsYield
Stage #1: 2-propynyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h;
Stage #2: dimethyl Isophthalate In tetrahydrofuran; hexane at 20℃; for 24h;
98%
1459-93-4

dimethyl Isophthalate

107-15-3

ethylenediamine

Conditions
ConditionsYield
In methanol at 25℃; for 12h;98%
In acetonitrile for 5h; Reflux;31.3%
1459-93-4

dimethyl Isophthalate

109-76-2

Trimethylenediamine

819883-45-9

1,3-bis-[N-((N'-3-aminopropyl)propyl-3-amine)methylamine]benzene

Conditions
ConditionsYield
In methanol at 25℃; for 12h;98%
1459-93-4

dimethyl Isophthalate

110-60-1

1,4-diaminobutane

1104610-46-9

C16H26N4O2

Conditions
ConditionsYield
In methanol at 25℃; for 12h;98%
1459-93-4

dimethyl Isophthalate

1067-55-6

dibutyldimethoxytin

22483-09-6

2,2-dimethoxyethylamine

N,N'-bis(2,2-dimethoxyethyl)isophthalamide

Conditions
ConditionsYield
94%
1459-93-4

dimethyl Isophthalate

13290-96-5

dimethyl 5-nitroisophthalate

Conditions
ConditionsYield
With iron(III) chloride; Nitrogen dioxide; ozone In 1,2-dichloro-ethane at 5℃; for 1.5h; Product distribution; Further Variations:; Solvents; Reagents;92%
With sulfur dioxide; dinitrogen pentoxide 1.) -78 to -11 deg C, 2 h, 2.) -11 deg C, 2 h;90%
With sulfuric acid; sulfur trioxide; nitric acid
1459-93-4

dimethyl Isophthalate

62638-06-6

dimethyl cyclohexane-1,3-dicarboxylate

Conditions
ConditionsYield
With hydrogen; W-2 Raney nickel In tetrahydrofuran at 130℃; under 87915.2 Torr; for 30h;91%
With hydrogen; Rh/Al2O3 under 2585.7 Torr;85%
With hydrogen; tetra(n-butyl)ammonium hydrogensulfate; di-μ-chlorobis(norbornadiene)dirhodium(I) In phosphate buffer; cyclohexane at 60℃; under 2585.74 Torr; for 24h; pH=7.4; Catalytic hydrogenation;82.1%
With hydrogen; W 2 Raney nickel In tetrahydrofuran; methanol at 100 - 105℃; under 82743.7 Torr; for 15h;80%
With hydrogen; Rh/Al2O3
1459-93-4

dimethyl Isophthalate

51839-15-7

5-iodo-isophthalic acid dimethyl ester

Conditions
ConditionsYield
With sodium periodate; sulfuric acid; iodine at 36℃; for 12h; Inert atmosphere;91%
With sodium periodate; sulfuric acid; iodine at 20℃;76%
With sodium periodate; sulfuric acid; iodine at 30℃;61%
1459-93-4

dimethyl Isophthalate

156-87-6

propan-1-ol-3-amine

42089-95-2

N,N’-bis(3-hydroxypropyl)isophthalamide

Conditions
ConditionsYield
at 120 - 140℃; for 2.5h;90%
1459-93-4

dimethyl Isophthalate

54060-30-9

3-acetylenephenylamine

C17H13NO3

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;90%
1459-93-4

dimethyl Isophthalate

hexadecylmagnesium halogenide

hexadecylmagnesium halogenide

1350559-68-0

17,17'-(1,3-phenylene)ditritriacontan-17-ol

Conditions
ConditionsYield
In diethyl ether at 20℃; for 12h;89%

Dimethyl isophthalate Chemical Properties

Molecular Structure of Isophthalic acid dimethyl ester (CAS NO.1459-93-4):

Molecular Formula: C10H10O4
Molecular Weight: 194.184
IUPAC Name: Dimethyl benzene-1,3-dicarboxylate
Synonyms of Isophthalic acid dimethyl ester (CAS NO.1459-93-4): 1,3-Benzenedicarboxylic acid, dimethyl ester ; 4-09-00-03293 (Beilstein Handbook Reference) ; AI3-02247 ; BRN 1912251 ; Dimethyl 1,3-benzenedicarboxylate ; Dimethyl isophthalate ; Dimethyl m-phthalate ; Dimethylester kyseliny isoftalove ; Dimethylester kyseliny isoftalove [Czech] ; EINECS 215-951-9 ; HSDB 6138 ; Isophthalic acid dimethyl ester ; Methyl 3-(carbomethoxy)benzoate ; Methyl isophthalate ; Morflex 1129 ; NSC 15313 ; 1,3-Benzenedicarboxylic acid, 1,3-dimethyl ester
CAS NO: 1459-93-4
Classification Code: Skin / Eye Irritant
Melting point: 64-68 °C
Polar Surface Area: 52.6 Å2
Index of Refraction: 1.514
Molar Refractivity: 49.79 cm3
Molar Volume: 165.2 cm3
Surface Tension: 40.5 dyne/cm
Density of Isophthalic acid dimethyl ester (CAS NO.1459-93-4): 1.175 g/cm3
Flash Point: 148 °C
Enthalpy of Vaporization: 52.4 kJ/mol
Boiling Point: 285 °C at 760 mmHg
Vapour Pressure: 0.00288 mmHg at 25°C

Dimethyl isophthalate Uses

 Isophthalic acid dimethyl ester (CAS NO.1459-93-4) is synthesis of phthalates, as diphenyl-resistant polymer monomers PBT, other organic synthesis, for stationary liquid.

Dimethyl isophthalate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 971mg/kg (971mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Pharmaceutical Sciences. Vol. 56, Pg. 1446, 1967.

Dimethyl isophthalate Consensus Reports

Reported in EPA TSCA Inventory.

Dimethyl isophthalate Safety Profile

Hazard Codes of Isophthalic acid dimethyl ester (CAS NO.1459-93-4): IrritantXi
Risk Statements: 36 
R36: Irritating to eyes.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany: 3
RTECS: NT2540000
HS Code: 29173980
Hazardous Substances Data: 1459-93-4(Hazardous Substances Data)
Moderately toxic by intraperitoneal route. An eye irritant. When heated to decomposition it emits acrid smoke and fumes. See also ESTERS.

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