Benzoic acid,4,5-bis(2-methoxyethoxy)-2-nitro-, ethyl ester
- CAS Number:179688-26-7
- Molecular Formula:C15H21NO8
- Molecular Weight:343.334
- Mol File:179688-26-7.mol
Synonyms:4,5-Bis(2-methoxyethoxy)-2-nitrobenzoic acid ethyl ester;
Physicochemical Properties
- Melting Point:N/A
- Boiling Point:467.8 °C at 760 mmHg
- Density:1.215 g/cm3
- Solubility:N/A
- Flash Point:185.6 °C
- Vapor Density:N/A
- Refractive Index:1.51
- Sensitive:N/A
- Storage Temp.:N/A
- Appearance/Colour:N/A
Benzoic acid,4,5-bis(2-methoxyethoxy)-2-nitro-, ethyl ester Safety information and MSDS
·Hazard identification:
| Pictogram(s) | No symbol. |
|---|---|
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
·Composition/information on ingredients:
| Chemical name | Common names and synonyms | CAS number | EC number | Concentration |
|---|---|---|---|---|
| Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate | Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate | 179688-26-7 | 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.
Benzoic acid,4,5-bis(2-methoxyethoxy)-2-nitro-, ethyl ester Relevant articles
All total 25 Articles be found
All total 25 Articles be foundSynthetic method of erlotinib
-
Paragraph 0080-0082, (2020/07/12)
The invention relates to a synthetic method of erlotinib, and belongs to the technical field of chemical synthesis. The preparation method comprises the following synthesis steps: (1) reacting a compound I with 2-chloroethyl methyl ether to generate a compound II; (2) oxidizing the compound II through peracetic acid to generate a compound III; (3) reacting the compound III with benzene sulfonyl chloride to generate a compound IV; (4) carrying out a ring closing reaction on the compound IV, ammonium chloride and formamide to generate a compound V; (5) reacting the compound V with phosphorus oxychloride to generate a compound VI; and (6) reacting the compound VI with m-aminophenylacetylene to generate a compound VII erlotinib. The invention provides a new synthetic route, and the used raw materials are common materials, are simple and easily available, can adapt to production of various scales, and the synthetic method has good industrial production prospects.
Synthesis and evaluation of novel 18F-labeled quinazoline derivatives with low lipophilicity for tumor PET imaging
Chong, Yan,Chang, Jin,Zhao, Wenwen,He, Yong,Li, Yuqiao,Zhang, Huabei,Qi, Chuanmin
, p. 42 - 53 (2018/02/06)
Four novel 18F-labeled quinazoline derivatives with low lipophilicity, [18F]4-(2-fluoroethoxy)-6,7-dimethoxyquinazoline ([18F]I), [18F]4-(3-((4-(2-fluoroethoxy)-7-methoxyquinazolin-6-yl)oxy)propyl)morpholine ([18F]II), [18F]4-(2-fluoroethoxy)-7-methoxy-6-(2-methoxyethoxy)quinazoline ([18F]III), and [18F]4-(2-fluoroethoxy)-6,7-bis(2-methoxyethoxy)quinazoline ([18F]IV), were synthesized via a 2-step radiosynthesis procedure with an overall radiochemical yield of 10% to 38% (without decay correction) and radiochemical purities of >98%. The lipophilicity and stability of labeled compounds were tested in vitro. The log P values of the 4 radiotracers ranged from 0.52 to 1.07. We then performed ELISA to measure their affinities to EGFR-TK; ELISA assay results indicated that each inhibitor was specifically bounded to EGFR-TK in a dose-dependent manner. The EGFR-TK autophosphorylation IC50 values of [18F]I, [18F]II, [18F]III, and [18F]IV were 7.732, 0.4698, 0.1174, and 0.1176?μM, respectively. All labeled compounds were evaluated via cellular uptake and blocking studies in HepG2 cell lines in vitro. Cellular uptake and blocking experiment results indicated that [18F]I and [18F]III had excellent cellular uptake at 120-minute postinjection in HepG2 carcinoma cells (51.80?±?3.42%ID/mg protein and 27.31?±?1.94%ID/mg protein, respectively). Additionally, biodistribution experiments in S180 tumor-bearing mice in vivo indicated that [18F]I had a very fast clearance in blood and a relatively high uptake ratio of tumor to blood (4.76) and tumor to muscle (1.82) at 60-minute postinjection. [18F]III had a quick clearance in plasma, and its highest uptake ratio of tumor to muscle was 2.55 at 15-minute postinjection. These experimental results and experiences were valuable for the further exploration of novel radiotracers of quinazoline derivatives.
Preparation method of erlotinib intermediate
-
Paragraph 0020-0027, (2018/03/01)
The invention belongs to the field of chemical synthesis and relates to a preparation method of an erlotinib intermediate 6,7-di(methoxyethoxy)quinazoline-4-one. According to the invention, by screening reaction conditions, a preparation technology of the
Method for synthesizing erlotinib intermediate with microchannel reactor
-
Paragraph 0048-0050; 0060; 0070; 0080; 0089-0093; 0101; 0132, (2018/09/08)
The invention discloses a method for synthesizing an erlotinib intermediate with a microchannel reactor, belongs to the field of synthesis of anti-tumor drugs in organic synthesis and solves the problems of low yield, poor purity, high energy consumption,
A method for preparing environmental protection of erlotinib hydrochloride
-
Paragraph 0072-0074, (2017/09/26)
The invention discloses an environment-friendly method for preparing high-yield erlotinib hydrochloride. The method comprises the following steps: directly performing cyclic condensation by taking 2-amino-4,5-di(2-methoxy ethyoxyl) ethyl benzoate hydrochloride as a key intermediate, reacting with aminophenylacetylene to generate erlotinib hydrochloride after performing chlorination, and refining to obtain the high-purity erlotinib hydrochloride. The process route provided by the invention is mild in reaction condition and high in yield; the first-class reagent and other reagents harmful to the environment and the operators are not used, the byproduct is few, the aftertreatment is simple and the commercial process can be easily processed.
Benzoic acid,4,5-bis(2-methoxyethoxy)-2-nitro-, ethyl ester Synthetic route And Reaction conditions
- 179688-27-8
ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
| Conditions | Yield |
|---|---|
- 3943-89-3
Ethyl protocatechuate
- 7732-18-5
water
- 584-08-7
potassium carbonate
- 6482-24-2
2-Bromoethyl methyl ether
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
| Conditions | Yield |
|---|---|
- 3943-89-3
Ethyl protocatechuate
- 6482-24-2
2-Bromoethyl methyl ether
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
| Conditions | Yield |
|---|---|
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
| Conditions | Yield |
|---|---|
| 94% | |
|
81% |
- 3943-89-3
Ethyl protocatechuate
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
| Conditions | Yield |
|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; tetrabutylammonium iodide / acetone / 120 h / Heating 2: acetic acid; nitric acid / 24 h / 20 °C | |
Multi-step reaction with 2 steps 1: potassium carbonate; tetrabutylammonium iodide / acetone 2: acetic acid; nitric acid / 24 h / 20 °C | |
Multi-step reaction with 2 steps 1: 68 percent / potassium carbonate; tetrabutylammonium iodide / acetone / 72 h / Heating 2: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C | |
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 6 h / Reflux 2: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water | |
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 6 h / Reflux 2: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice | |
Multi-step reaction with 2 steps 1: potassium carbonate; tetrabutylammomium bromide / acetonitrile 2: acetic acid; nitric acid / 0 °C | |
Multi-step reaction with 2 steps 1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetone / 64 h / Inert atmosphere; Reflux 2: acetic acid; nitric acid / 24 h / 5 °C | |
Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C 2.1: acetic acid; nitric acid / 24 h / 5 - 20 °C 3.1: sodium carbonate / methanol; water / 1.5 h / 65 °C 3.2: 2 h | |
Multi-step reaction with 2 steps 1: potassium tert-butylate; potassium iodide / N,N-dimethyl-formamide / 12 h / 100 °C 2: sulfuric acid; nitric acid / 1 h / 20 °C / Darkness | |
Multi-step reaction with 2 steps 1: potassium carbonate; tetrabutylammomium bromide / acetonitrile / Reflux 2: nitric acid / acetic acid / 0 °C | |
Multi-step reaction with 2 steps 1: ammonia; carbon dioxide / 0.5 h / 50 °C 2: acetic acid; nitric acid; sulfuric acid / 10 - 45 °C |
- 819813-71-3
3,4-bis(2-methoxyethoxy)-benzoic acid
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
| Conditions | Yield |
|---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / Cooling with ice; Reflux 2: nitric acid; acetic acid / 24.5 h / 0 - 20 °C Withsulfuric acid;
nitric acid;
acetic acid; |
- 627-42-9
2-chloroethyl methyl ether
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
| Conditions | Yield |
|---|---|
| 60 g |
- 99-50-3
3,4-Dihydroxybenzoic acid
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
| Conditions | Yield |
|---|---|
Multi-step reaction with 3 steps 1: sulfuric acid / 10 h / 40 - 80 °C 2: potassium tert-butylate; potassium iodide / N,N-dimethyl-formamide / 12 h / 100 °C 3: sulfuric acid; nitric acid / 1 h / 20 °C / Darkness |
- 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
| Conditions | Yield |
|---|---|
| 100% | |
| 100% | |
Withsulfuric acid;
nitric acid;
acetic anhydride;
acetic acid;
at 40 ℃;
for 2h;
Concentration;
Large scale; | 98.3% |
Withsulfuric acid;
nitric acid;Indichloromethane;at 5 ℃;
for 2h;
Solvent;
Temperature;
Green chemistry; | 98.4% |
Withnitric acid;
for 2h;
cooling; | 97.4% |
| 96% | |
Withnitric acid;
acetic acid;
at 0 - 20 ℃;
for 24.5h; | 96% |
Withsulfuric acid;
nitric acid;
acetic acid;
at 20 ℃;
for 18h; | 95% |
| 93% | |
Withsulfuric acid;
nitric acid;
acetic acid;
at 60 ℃;
for 0.0166667h;
Temperature; | 93.5% |
Withsulfuric acid;
nitric acid;
at 20 ℃;
for 1h;
Darkness; | 87% |
| 82.22% | |
Withnitric acid;
acetic acid;
at 20 ℃;
for 24h;
Cooling with ice; | 82.22% |
Withsulfuric acid;
nitric acid;
acetic acid;
at 10 - 45 ℃; | 63.2% |
Withnitric acid;
acetic acid;
at 20 ℃;
for 24h; | |
Withnitric acid;
acetic acid;
at 0 ℃; | |
Withnitric acid;
acetic acid;
at 5 ℃;
for 24h; | 54.3 g |
- 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester
- 179688-27-8
ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate
| Conditions | Yield |
|---|---|
Withhydrazine hydrate;InN,N-dimethyl-formamide;at 100 ℃;
for 3h;
chemoselective reaction;
Green chemistry; | 99% |
Withsodium tetrahydroborate;
ethanol;
at 30 - 40 ℃;
for 4h;
Green chemistry; | 98.1% |
| 95% | |
| 95.5% | |
| 94% | |
| 92% | |
| 92% | |
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester;Withpalladium 10% on activated carbon;Inethanol;for 0.166667h;
Autoclave; | 91.3% |
With10% Pt/activated carbon;
hydrogen;Inmethanol;at 90 ℃;
for 0.00972222h;
under 11251.1 Torr;
Reagent/catalyst;
Temperature;
Pressure; | 88.27% |
Withammonium hydroxide;
sodium dithionite;
sodium hydroxide;Intetrahydrofuran;
water;
ethyl acetate;for 2h;
Reflux; | 85.1% |
| 66% | |
Benzoic acid,4,5-bis(2-methoxyethoxy)-2-nitro-, ethyl ester Raw materials
- 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester
- 3943-89-3
Ethyl protocatechuate
- 7732-18-5
water
- 584-08-7
potassium carbonate
- 6482-24-2
2-Bromoethyl methyl ether
Benzoic acid,4,5-bis(2-methoxyethoxy)-2-nitro-, ethyl ester Target Products
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Country :
China (Mainland)(71)
India(3)
United Kingdom(1)
United States(1)
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