1,2-Benzenedicarboxylicacid, 1-methyl ester
- CAS Number:4376-18-5
- Molecular Formula:C9H8O4
- Molecular Weight:180.16
- Mol File:4376-18-5.mol
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;
Physicochemical Properties
- Melting Point:82-84 °C(lit.)
- Boiling Point:328.9 °C at 760 mmHg
- Density:1.288 g/cm3
- Solubility:N/A
- Flash Point:134.7 °C
- Vapor Density:N/A
- Refractive Index:N/A
- Sensitive:N/A
- Storage Temp.:Refrigerator
- Appearance/Colour:white to off-white crystalline powder
Xi1,2-Benzenedicarboxylicacid, 1-methyl ester Safety information and MSDS
·Hazard identification:
| Pictogram(s) |  |
|---|---|
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/…if you feel unwell. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
·Composition/information on ingredients:
| Chemical name | Common names and synonyms | CAS number | EC number | Concentration |
|---|---|---|---|---|
| METHYL HYDROGEN PHTHALATE | METHYL HYDROGEN PHTHALATE | 4376-18-5 | none | 100% |
·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.
1,2-Benzenedicarboxylicacid, 1-methyl ester Relevant articles
All total 59 Articles be found
All total 59 Articles be foundSynthesis 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.
1,2-Benzenedicarboxylicacid, 1-methyl ester Synthetic route And Reaction conditions
![<i>N</i>-<i>tert</i>-butyl-<i>N</i>-[(methyl-phenyl-carbamoyl)-methyl]-phthalamic acid](/Databaselist/images/loading.webp)
- 4376-18-5
Monomethyl phthalate
| Conditions | Yield |
|---|---|
Multi-step reaction with 2 steps 1: methanol; diethyl ether / 24 h / 20 °C 2: sodium isopropoxide / propan-2-ol / 0.5 h / Heating |
| Conditions | Yield |
|---|---|
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 Withsodium isopropylate;
triethylamine;Intetrahydrofuran;
methanol;
diethyl ether;
isopropyl alcohol;3: Dieckmann condensation; |
- 67-56-1
methanol
- 85-44-9
phthalic anhydride
- 75-52-5
nitromethane
- 124-41-4
sodium methylate
- 4376-18-5
Monomethyl phthalate
| Conditions | Yield |
|---|---|
| Conditions | Yield |
|---|---|
| Conditions | Yield |
|---|---|
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% |
With1-hydro-3-(3-sulfopropyl)-imidazolium 4-methyl-benzenesulfonate;
at 60 ℃;
Heating; | 90% |
for 8h;
Heating; | 88% |
for 1h;
Heating; | 85% |
Withsodium hydroxide; | |
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; |
| Conditions | Yield |
|---|---|
Withsulfuric acid;
at 175 ℃; |
- 131-11-3,64441-70-9
phthalic acid dimethyl ester
- 4376-18-5
Monomethyl phthalate
| Conditions | Yield |
|---|---|
Withpotassium hydroxide;Inwater;
dimethyl sulfoxide;at 0 ℃;
for 0.666667h;
Solvent;
Reagent/catalyst; | 94% |
| 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; |
- 36933-83-2
2-Methoxycarbonyl-benzoateN,N,N-trimethyl-hydrazinium;
- 4376-18-5
Monomethyl phthalate
| Conditions | Yield |
|---|---|
Withhydrogenchloride; |
- 186581-53-3,908094-01-9,334-88-3
diazomethane
- 88-99-3,73607-73-5
benzene-1,2-dicarboxylic acid
- 131-11-3,64441-70-9
phthalic acid dimethyl ester
- 4376-18-5
Monomethyl phthalate
| Conditions | Yield |
|---|---|
Withaluminum oxide;Incyclohexane;
N,N-dimethyl-formamide;Product distribution;
study of selectivity of methylation on alumina surface; |
| Conditions | Yield |
|---|---|
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; | |
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; | |
Withpotassium permanganate;Inwater;
acetonitrile; | |
methyl o-formylbenzoate;Withbis(pyridine)silver(I) permanganate;
acetic acid;Inwater;at 24.84 ℃;
for 10h;
Darkness; Withhydrogenchloride;Temperature;
Kinetics; |
1,2-Benzenedicarboxylicacid, 1-methyl ester Raw materials
- 67-56-1
methanol
- 85-44-9
phthalic anhydride
- 75-52-5
nitromethane
- 124-41-4
sodium methylate
- 151-50-8
potassium cyanide
1,2-Benzenedicarboxylicacid, 1-methyl ester Target Products
Business Type:
- Lab/Research institutionsTrading CompanyManufacturers
Certificate:
- Product LicenseEnterprise AuthenticationISOGMPFDAHALAL
Country :
China (Mainland)(47)
United Kingdom(2)
India(2)
United States(2)
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