Conditions | Yield |
---|---|
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% |
phosgene
isophthalic acid
A
dimethyl Isophthalate
B
benzene-1,3-dicarbonyl dichloride
Conditions | Yield |
---|---|
With pyridine In dichloromethane | A n/a B 100% |
dimethyl 5-pivaloxyisophthalate
dimethyl Isophthalate
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); (dimethoxy)methylsilane; tricyclohexylphosphine In toluene at 80℃; for 12h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
at 20℃; for 6h; UV-irradiation; | 99% |
5-iodo-isophthalic acid dimethyl ester
dimethyl Isophthalate
Conditions | Yield |
---|---|
With Ac-Cys-OMe; bismuth(III) oxide; N-ethyl-N,N-diisopropylamine In dichloromethane for 48h; Irradiation; | 96% |
dimethyl 5-bromoisophthalate
dimethyl Isophthalate
Conditions | Yield |
---|---|
With formic acid; tributyl-amine; 10-phenyl-10H-phenothiazine In acetonitrile at 20℃; for 24h; Inert atmosphere; UV-irradiation; | 94% |
methanol
carbon monoxide
3-Fluorosulfonyloxy-benzoic acid methyl ester
dimethyl Isophthalate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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. |
3-(5,5-dimethyl-1,3,2-dioxaborinanyl)-1-methoxycarbonylbenzene
di-tert-butyl dicarbonate
methyl iodide
dimethyl Isophthalate
Conditions | Yield |
---|---|
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% |
methanol
Isophthalaldehyde
A
dimethyl Isophthalate
B
m-formylphenyl benzoic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide at 20 - 70℃; for 15h; Green chemistry; | A 90% B 8% |
Conditions | Yield |
---|---|
With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction; | 89% |
With dimanganese decacarbonyl at 180℃; for 1h; Sealed tube; |
tert-butyl methyl ether
benzene 1,3-dicarboxylic acid monomethyl ester
dimethyl Isophthalate
Conditions | Yield |
---|---|
With iron(III) trifluoromethanesulfonate at 90℃; Schlenk technique; | 88% |
propynoic acid methyl ester
methyl 5-(N,N-dimethylamino)-2,4-pentadienoate
dimethyl Isophthalate
Conditions | Yield |
---|---|
In xylene for 12h; Heating; | 87.3% |
methanol
1-bromo-3-chlorobenzene
carbon monoxide
A
dimethyl Isophthalate
B
methyl 3-chlorobenzoate
C
3-chlorobenzoate
Conditions | Yield |
---|---|
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% |
methanol
carbon monoxide
1,3-dibromobenzene
A
isophthalic acid
B
dimethyl Isophthalate
C
methyl 3-bromobenzoate
Conditions | Yield |
---|---|
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% |
1-bromo-3-chlorobenzene
carbon monoxide
A
dimethyl Isophthalate
B
methyl 3-chlorobenzoate
C
3-chlorobenzoate
Conditions | Yield |
---|---|
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% |
carbon monoxide
1,3-dibromobenzene
A
isophthalic acid
B
dimethyl Isophthalate
C
methyl 3-bromobenzoate
Conditions | Yield |
---|---|
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% |
methanol
(1S,4S,8R)-8-(2-Chloro-ethoxy)-3-oxo-2-oxa-bicyclo[2.2.2]oct-5-ene-6-carboxylic acid methyl ester
dimethyl Isophthalate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 6h; Heating; | 83% |
methyl coumalate
methyl (2E)-3-methoxy-2-propenoate
dimethyl Isophthalate
Conditions | Yield |
---|---|
In toluene at 200℃; for 16h; Diels-Alder Cycloaddition; Inert atmosphere; Sealed tube; | 83% |
dimethyl Isophthalate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol at 65℃; for 18h; Catalytic behavior; Reagent/catalyst; Temperature; | 82% |
methanol
benzene 1,3-dicarboxylic acid monomethyl ester
dimethyl Isophthalate
Conditions | Yield |
---|---|
With oxygen; potassium carbonate In hexane at 20℃; for 14h; Sonication; | 72% |
methanol
isophthalic acid
A
dimethyl Isophthalate
B
dimethyl 5-bromoisophthalate
Conditions | Yield |
---|---|
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% |
4-amino-1-hydroxycyclohexa-3,5-diene-1,3-dicarboxylic acid dimethyl ester
dimethyl Isophthalate
Conditions | Yield |
---|---|
With BF3 etherate; sodium hydrogencarbonate In dichloromethane; benzene | 62% |
methanol
m-xylene
A
dimethyl Isophthalate
B
1-methoxycarbonyl-3-methylbenzene
C
m-Toluic acid
Conditions | Yield |
---|---|
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% |
methanol
(1S,4S,8R)-8-Ethoxy-3-oxo-2-oxa-bicyclo[2.2.2]oct-5-ene-6-carboxylic acid methyl ester
dimethyl Isophthalate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 6h; Heating; | 51% |
methanol
isophthalic acid
A
dimethyl Isophthalate
B
benzene 1,3-dicarboxylic acid monomethyl ester
Conditions | Yield |
---|---|
With sulfuric acid In tetrahydrofuran at 65℃; | A n/a B 42% |
4-methoxycarbonyl-3a,4-dihydrophthalide
propynoic acid methyl ester
A
4-methoxycarbonyl-phthalide
B
phthalic acid dimethyl ester
C
dimethyl Isophthalate
Conditions | Yield |
---|---|
In xylene for 40h; Heating; | A 37% B 10% C 41% |
Conditions | Yield |
---|---|
With diethyl ether |
isophthalic acid ; disilver (I)-compound
methyl iodide
dimethyl Isophthalate
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol at 70℃; for 4h; | 100% |
With hydrazine hydrate In methanol | 91% |
With hydrazine hydrate In ethanol Reflux; | 86% |
dimethyl Isophthalate
dimethyl amine
N,N-dimethylisophthalamic acid methyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; methanol at 20℃; for 2h; | 100% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
dimethyl Isophthalate
bis(pinacol)diborane
dimethyl 5-(pinacolboryl)isophthalate
Conditions | Yield |
---|---|
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% |
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE
dimethyl Isophthalate
N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide
Conditions | Yield |
---|---|
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% |
2-propynyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside
dimethyl Isophthalate
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 | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In methanol at 25℃; for 12h; | 98% |
In acetonitrile for 5h; Reflux; | 31.3% |
dimethyl Isophthalate
Trimethylenediamine
1,3-bis-[N-((N'-3-aminopropyl)propyl-3-amine)methylamine]benzene
Conditions | Yield |
---|---|
In methanol at 25℃; for 12h; | 98% |
Conditions | Yield |
---|---|
In methanol at 25℃; for 12h; | 98% |
Conditions | Yield |
---|---|
94% |
dimethyl Isophthalate
dimethyl 5-nitroisophthalate
Conditions | Yield |
---|---|
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 |
dimethyl Isophthalate
dimethyl cyclohexane-1,3-dicarboxylate
Conditions | Yield |
---|---|
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 |
dimethyl Isophthalate
5-iodo-isophthalic acid dimethyl ester
Conditions | Yield |
---|---|
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% |
dimethyl Isophthalate
propan-1-ol-3-amine
N,N’-bis(3-hydroxypropyl)isophthalamide
Conditions | Yield |
---|---|
at 120 - 140℃; for 2.5h; | 90% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; | 90% |
dimethyl Isophthalate
17,17'-(1,3-phenylene)ditritriacontan-17-ol
Conditions | Yield |
---|---|
In diethyl ether at 20℃; for 12h; | 89% |
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
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.
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. |
Reported in EPA TSCA Inventory.
Hazard Codes of Isophthalic acid dimethyl ester (CAS NO.1459-93-4): Xi
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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