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Cas Database

4376-18-5

4376-18-5

Identification

  • Molecular Formula:C9H8O4

  • EINECS:224-476-6

Synonyms:1,2-Benzenedicarboxylicacid, monomethyl ester (9CI);Phthalic acid, methyl ester (6CI,7CI);Phthalicacid, monomethyl ester (8CI);2-(1-Methoxycarbonyl)benzoic acid;2-(Methoxycarbonyl)benzoic acid;D 3;D 3 (ester);Methyl 2-carboxybenzoate;Methyl hydrogen phthalate;Methyl phthalate;Monomethyl phthalate;NSC 8281;o-(Methoxycarbonyl)benzoic acid;

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Safety information and MSDS

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:

  • Hazard Statement:

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:AHH
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  • Product Description:2-(Methoxycarbonyl)benzoicacid
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Relevant articles and documentsAll total 59 Articles be found

Synthesis of New Dialkyl 2,2′-[Carbonyl bis (azanediyl)]dibenzoates via Curtius Rearrangement

Yassine, Hasna,Bouali, Jamila,Oumessaoud, Asmaa,Ourhzif, El Mahdi,Hamri, Salha,Hafid, Abderrafia,Khouili, Mostafa,Pujol, Maria Dolors

, p. 1971 - 1979 (2021/01/21)

The 2-(alkylcarbonyl)benzoic acids obtained by esterification of phthalic anhydride are converted into azide derivatives: alkyl 2-[(azidocarbonyl)amino]benzoates and to ureas: dialkyl 2,2′-[carbonyl bis (azanediyl)]dibenzoates. These transformations were carried out using classical Curtius rearrangement conditions in the presence of diphenylphosphoryl azide (DPPA) in a basic medium, followed by hydrolysis. Subsequently, a final condensation reaction of these urea derivatives enabled us to obtain, for the first time, the new alkyl derivatives, alkyl 2-[2,4-dioxo-1,2-dihydroquinazolin-3(4 H)-yl]benzoates. All the new compounds obtained in satisfactory yields were characterized by 1H and 13C NMR, and by X-ray crystallographic analysis.

Selective Synthesis in Microdroplets of 2-Phenyl-2,3-dihydrophthalazine-1,4-dione from Phenyl Hydrazine with Phthalic Anhydride or Phthalic Acid

Gao, Dan,Jin, Feng,Yan, Xin,Zare, Richard N.

supporting information, p. 1466 - 1471 (2019/01/04)

Pyridazine derivatives are privileged structures because of their potential biological and optical properties. Traditional synthetic methods usually require acid or base as a catalyst under reflux conditions with reaction times ranging from hours to a few days or require microwave assistance to induce the reaction. Herein, this work presents the accelerated synthesis of a pyridazine derivative, 2-phenyl-2,3-dihydrophthalazine-1,4-dione (PDHP), in electrosprayed microdroplets containing an equimolar mixture of phenyl hydrazine and phthalic anhydride or phthalic acid. This reaction occurred on the submillisecond timescale with good yield (over 90 % with the choice of solvent) without using an external catalyst at room temperature. In sharp contrast to the bulk reaction of obtaining a mixture of two products, the reaction in confined microdroplets yields only the important six-membered heterocyclic product PDHP. Results indicated that surface reactions in microdroplets with low pH values cause selectivity, acceleration, and high yields.

Carbonylative Suzuki-Miyaura couplings of sterically hindered aryl halides: Synthesis of 2-aroylbenzoate derivatives

Bayer, Annette,Ismael, Aya,Skrydstrup, Troels

supporting information, p. 1754 - 1759 (2020/03/17)

We have developed a carbonylative approach to the synthesis of diversely substituted 2-aroylbenzoate esters featuring a new protocol for the carbonylative coupling of aryl bromides with boronic acids and a new strategy to favour carbonylative over non-carbonylative reactions. Two different synthetic pathways-(i) the alkoxycarbonylation of 2-bromo benzophenones and (ii) the carbonylative Suzuki-Miyaura coupling of 2-bromobenzoate esters-were evaluated. The latter approach provided a broader substrate tolerance, and thus was the preferred pathway. We observed that 2-substituted aryl bromides were challenging substrates for carbonylative chemistry favouring the non-carbonylative pathway. However, we found that carbonylative Suzuki-Miyaura couplings can be improved by slow addition of the boronic acid, suppressing the unwanted direct Suzuki coupling and, thus increasing the yield of the carbonylative reaction.

Automated on-line monitoring of the TiO2-based photocatalytic degradation of dimethyl phthalate and diethyl phthalate

Salazar-Beltrán, Daniel,Hinojosa-Reyes, Laura,Maya-Alejandro, Fernando,Turnes-Palomino, Gemma,Palomino-Cabello, Carlos,Hernández-Ramírez, Aracely,Guzmán-Mar, Jorge Luis

, p. 863 - 870 (2019/04/17)

A fully automated on-line system for monitoring the TiO2-based photocatalytic degradation of dimethyl phthalate (DMP) and diethyl phthalate (DEP) using sequential injection analysis (SIA) coupled to liquid chromatography (LC) with UV detection was proposed. The effects of the type of catalyst (sol-gel, Degussa P25 and Hombikat), the amount of catalyst (0.5, 1.0 and 1.5 g L-1), and the solution pH (4, 7 and 10) were evaluated through a three-level fractional factorial design (FFD) to verify the influence of the factors on the response variable (degradation efficiency, %). As a result of FFD evaluation, the main factor that influences the process is the type of catalyst. Degradation percentages close to 100% under UV-vis radiation were reached using the two commercial TiO2 materials, which present mixed phases (anatase/rutile), Degussa P25 (82%/18%) and Hombikat (76%/24%). 60% degradation was obtained using the laboratory-made pure anatase crystalline TiO2 phase. The pH and amount of catalyst showed minimum significant effect on the degradation efficiencies of DMP and DEP. Greater degradation efficiency was achieved using Degussa P25 at pH 10 with 1.5 g L-1 catalyst dosage. Under these conditions, complete degradation and 92% mineralization were achieved after 300 min of reaction. Additionally, a drastic decrease in the concentration of BOD5 and COD was observed, which results in significant enhancement of their biodegradability obtaining a BOD5/COD index of 0.66 after the photocatalytic treatment. The main intermediate products found were dimethyl 4-hydroxyphthalate, 4-hydroxy-diethyl phthalate, phthalic acid and phthalic anhydride indicating that the photocatalytic degradation pathway involved the hydrolysis reaction of the aliphatic chain and hydroxylation of the aromatic ring, obtaining products with lower toxicity than the initial molecules.

A Br?nsted acidic, ionic liquid containing, heteropolyacid functionalized polysiloxane network as a highly selective catalyst for the esterification of dicarboxylic acids

Rajabi, Fatemeh,Wilhelm, Christian,Thiel, Werner R.

supporting information, p. 4438 - 4444 (2020/08/10)

A Br?nsted acidic, ionic liquid containing, heteropolyanion functionalized polysiloxane network was formed by self-condensation of dodecatungstophosphoric acid and a zwitterionic organosilane precursor containing both imidazolinium and sulfonate groups. The resulting hybrid material POS-HPA-IL was investigated as a catalyst for the selective esterification of dicarboxylic acids.

Process route upstream and downstream products

Process route

<i>N</i>-<i>tert</i>-butyl-<i>N</i>-[(methyl-phenyl-carbamoyl)-methyl]-phthalamic acid

N-tert-butyl-N-[(methyl-phenyl-carbamoyl)-methyl]-phthalamic acid

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; diethyl ether / 24 h / 20 °C
2: sodium isopropoxide / propan-2-ol / 0.5 h / Heating
Withsodium isopropylate;Inmethanol; diethyl ether; isopropyl alcohol;2: Dieckmann condensation;
phthalic anhydride
85-44-9

phthalic anhydride

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / tetrahydrofuran / 1 h / 20 °C
2: methanol; diethyl ether / 24 h / 20 °C
3: sodium isopropoxide / propan-2-ol / 0.5 h / Heating
methanol
67-56-1

methanol

phthalic anhydride
85-44-9

phthalic anhydride

nitromethane
75-52-5

nitromethane

sodium methylate
124-41-4

sodium methylate

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
methanol
67-56-1

methanol

phthalic anhydride
85-44-9

phthalic anhydride

potassium cyanide
151-50-8

potassium cyanide

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
methanol
67-56-1

methanol

phthalic anhydride
85-44-9

phthalic anhydride

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
Reflux;
98%
for 5h; Reflux;
97%
at 60 - 80 ℃;
96.7%
95%
Withboron trifluoride diethyl etherate; for 0.00833333h; further reagents;
95%
for 8h; Reflux; Inert atmosphere;
92%
90%
for 8h; Heating;
88%
for 1h; Heating;
85%
Incarbon dioxide;at 50 ℃; under 73130.8 Torr; Rate constant; var. pressures;
Withpotassium cyanide; for 2h; Heating;
at 100 ℃; for 6h;
Reflux;
at 120 ℃; Autoclave;
Withpotassium hydroxide; at 20 ℃; for 0.5h;
for 3h; Schlenk technique; Inert atmosphere; Reflux;
phthalic anhydride
85-44-9

phthalic anhydride

Dimethyl ether
115-10-6,157621-61-9

Dimethyl ether

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
Withsulfuric acid; at 175 ℃;
phthalic acid dimethyl ester
131-11-3,64441-70-9

phthalic acid dimethyl ester

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
Withpotassium hydroxide;Inwater; dimethyl sulfoxide;at 0 ℃; for 0.666667h; Solvent; Reagent/catalyst;
94%
Withwater; potassium hydroxide;Indimethyl sulfoxide;at 0 ℃; for 0.666667h; Solvent;
94%
Withsodium hydroxide; phosphate buffer; for 8h; Ambient temperature; pig liver esterase;
90%
Withsodium hydroxide;In1,4-dioxane; water;at 20 ℃; Kinetics; EA, ΔH(excit.), ΔS(excit.), isodielectric activation energy, other solvents: acetone - water and DMSO - water;
Withsodium hydroxide; potassium chloride;Inmethanol; water;at 25 ℃; Thermodynamic data; Kinetics; Mechanism; further solvents; ΔF, ΔH, ΔS, Ea, log A;
Multistep reaction; (i) Me2NCH2CH2OH, (ii) aq. HCl;
Withwater; at 40 ℃; pH=3;
2-Methoxycarbonyl-benzoateN,N,N-trimethyl-hydrazinium;
36933-83-2

2-Methoxycarbonyl-benzoateN,N,N-trimethyl-hydrazinium;

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
benzene-1,2-dicarboxylic acid
88-99-3,73607-73-5

benzene-1,2-dicarboxylic acid

phthalic acid dimethyl ester
131-11-3,64441-70-9

phthalic acid dimethyl ester

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
Withaluminum oxide;Incyclohexane; N,N-dimethyl-formamide;Product distribution; study of selectivity of methylation on alumina surface;
methyl o-formylbenzoate
4122-56-9

methyl o-formylbenzoate

Monomethyl phthalate
4376-18-5

Monomethyl phthalate

Conditions
ConditionsYield
Withperchloric acid; N-Chlorourethan; acetic acid;Inwater;at 29.9 ℃; for 10h; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔG(excit.);
Withperchloric acid; mercury(II) diacetate; N-bromoacetamide;Inacetic acid;at 24.9 ℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔG(excit.), ΔH(excit.), ΔS(excit.);
Withperchloric acid; bis(2,2'-bipyridyl) copper(II) permanganate;Inwater; acetic acid;at 14.9 ℃; Rate constant; Kinetics; Thermodynamic data; other temperatures; ΔH, ΔS, ΔG; kinetics and mechanism of the oxidation of monosubstituted benzaldehydes by bis(2,2'-bipyridyl)copper(II) permanganate (BBCP); formation and decomposition of benzaldehyde-BBCP complexes;
WithHABR;Inwater; acetic acid;at 14.85 - 44.85 ℃; pH=2.04; Kinetics;
Withpyridinium hydrobromide perbromide;Inwater; acetic acid;at 44.85 ℃; Further Variations:; Temperatures; Activation energy; Kinetics; Thermodynamic data;
Withbenzyltrimethylammonium tribromide; potassium bromide;Inwater; acetic acid;at 44.85 ℃; for 10h; Further Variations:; Temperatures; Kinetics;
Withbenzyltrimethylammonium chlorobromate;Inwater; acetic acid;at 24.84 ℃; pH=2.04; Further Variations:; Temperatures; Kinetics; Thermodynamic data;
Withtetra-N-butylammonium tribromide; acetic acid; at 14.84 ℃; Further Variations:; Temperatures; Kinetics;
With2,2'-bipyridinium chlorochromate;Indimethyl sulfoxide;at 24.84 ℃; Temperature; Kinetics;
Withmorpholinium chlorochromate;Indimethyl sulfoxide;at 44.84 ℃; Temperature; Kinetics;
Withtetraethylammonium chlorochromate(VI);Indimethyl sulfoxide;at 24.84 ℃; Temperature; Kinetics;
Withhydrogenchloride;Temperature; Kinetics;

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