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Cas Database

4277-63-8

4277-63-8

Identification

  • Product Name:1H-Pyrrole-1-carboxylicacid, methyl ester

  • CAS Number: 4277-63-8

  • EINECS:224-281-6

  • Molecular Weight:125.127

  • Molecular Formula: C6H7NO2

  • HS Code:2933990090

  • Mol File:4277-63-8.mol

Synonyms:Pyrrole-1-carboxylicacid, methyl ester (6CI,7CI,8CI);Methyl 1-pyrrolecarboxylate;Methyl1H-pyrrole-1-carboxylate;N-(Methoxycarbonyl)pyrrole;N-Carbomethoxypyrrole;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi,Xn

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH302 Harmful if swallowed

  • 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

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:N-Carbomethoxypyrrole
  • Packaging:2.5g
  • Price:$ 180
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Methyl 1H-pyrrole-1-carboxylate 97%
  • Packaging:25 g
  • Price:$ 768
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Methyl 1H-pyrrole-1-carboxylate 97%
  • Packaging:5 g
  • Price:$ 192
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Methyl 1-pyrrolecarboxylate 98%
  • Packaging:5g
  • Price:$ 99
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Methyl 1H-Pyrrole-1-carboxylate 97%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Methyl 1H-Pyrrole-1-carboxylate 97%
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Methyl 1H-Pyrrole-1-carboxylate 97%
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  • Manufacture/Brand:Crysdot
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Relevant articles and documentsAll total 14 Articles be found

Changes in Regioselectivity of H Atom Abstraction during the Hydroxylation and Cyclization Reactions Catalyzed by Hyoscyamine 6β-Hydroxylase

Ushimaru, Richiro,Ruszczycky, Mark W.,Liu, Hung-Wen

supporting information, p. 1062 - 1066 (2019/01/23)

Hyoscyamine 6β-hydroxylase (H6H) is an αKG-dependent nonheme iron oxidase that catalyzes the oxidation of hyoscyamine to scopolamine via two separate reactions: hydroxylation followed by oxidative cyclization. Both of these reactions are expected to involve H atom abstraction from each of two adjacent carbon centers (C6 vs C7) in the substrate. During hydroxylation, there is a roughly 85:1 preference for H atom abstraction from C6 versus C7; however, this inverts to a 1:16 preference during cyclization. Furthermore, 18O incorporation experiments in the presence of deuterated substrate are consistent with the catalytic iron(IV)-oxo complex being able to support the coordination of an additional ligand during hydroxylation. These observations suggest that subtle differences in the substrate binding configuration can have significant consequences for the catalytic cycle of H6H.

Anion exchange: A novel way of preparing hierarchical porous structure in poly(ionic liquid)s

Qin, Li,Wang, Binshen,Zhang, Yongya,Chen, Li,Gao, Guohua

supporting information, p. 3785 - 3788 (2017/04/04)

Hierarchical porous poly(ionic liquid)s (PILs) with high specific surface area were firstly synthesized via anion exchange. The exchange of bulky salicylate and its dimers/clusters in PILs by other smaller anions increased the specific surface area and fa

Solventless selective phosgene-free N-carbonylation of N-heteroaromatics (pyrrole, indole, carbazole) under mild conditions

Carafa, Marianna,Iannone, Francesco,Mele, Valentina,Quaranta, Eugenio

, p. 3377 - 3385 (2013/01/16)

N-Heteroaromatics HetNH, such as pyrrole (1), indole (2) and carbazole (3), have been selectively N-carbonylated by a direct reaction with diphenyl carbonate (DPC), used as an environmental friendly carbonyl active species in place of toxic and hazardous phosgene. The carbonylation reaction can be effectively catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), which can act as a base catalyst by activating the HetNH substrate, and as a nucleophile catalyst by activating the organic carbonate. The influence of reaction parameters (temperature, reaction time, DBU load, DPC/HetNH molar ratio) on the productivity of the process has been also investigated. The synthetic methodology does not require severe temperature conditions, is solventless, simple (only one step), efficient and selective, and offers a new solution to the synthesis of synthetically versatile HetNCO2Ph derivatives through a route alternative to the current traditional phosgenation methods.

Green N-methylation of electron deficient pyrroles with dimethylcarbonate

Laurila, Michael L.,Magnus, Nicholas A.,Staszak, Michael A.

experimental part, p. 1199 - 1201 (2010/04/22)

The N-methylation of electron-deficient pyrroles was affected using dimethyl carbonate in the presence of DMF and catalytic DABCO. This alkylation methodology has proven useful for the alkylation of a variety of pyrroles in 72-98% yields and is considered to be green chemistry relative to the more common use of methyl halides or dimethyl sulfate.

Superbase-promoted direct N-carbonylation of pyrrole with carbonic acid diesters

Carafa, Marianna,Distaso, Monica,Mele, Valentina,Trani, Francesca,Quaranta, Eugenio

, p. 3691 - 3696 (2008/09/20)

Carbonic acid diesters have been investigated as carbonylating agents in the direct reaction with pyrrole (HetNH). In the presence of superbases (DBU, P1-t-Bu, BTPP) as catalysts, the heteroaromatic substrate can be N-carbonylated by direct reaction with carbonic acid diesters under not-severe experimental conditions. The carbonylation reaction makes accessible pyrrole N-carbonyl derivatives (HetNC(O)OR, (HetN)2CO) selectively through a simple straightforward way, which offers a safe eco-friendly alternative to the traditional synthetic methods based on hazardous phosgene or phosgene-derivatives.

Process route upstream and downstream products

Process route

methyl 1,8-diazabicyclo[5.4.0]undec-6-ene-8-carboxylate
1309041-52-8

methyl 1,8-diazabicyclo[5.4.0]undec-6-ene-8-carboxylate

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

1,8-diazabicyclo[5.4.0]undec-7-ene
6674-22-2,83329-50-4

1,8-diazabicyclo[5.4.0]undec-7-ene

Conditions
Conditions Yield
In chloroform-d1; at 19.84 ℃; for 56h;
78%
1-(trimethylsilyl)-1H-pyrrole
18276-53-4

1-(trimethylsilyl)-1H-pyrrole

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

methyl Pyrrole-2-carboxylate
1193-62-0

methyl Pyrrole-2-carboxylate

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

1H-pyrrole-2,5-dicarboxylic acid dimethyl ester
1757-29-5

1H-pyrrole-2,5-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
Yield given. Multistep reaction. Yields of byproduct given;
1-(trimethylsilyl)-1H-pyrrole
18276-53-4

1-(trimethylsilyl)-1H-pyrrole

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

methyl Pyrrole-2-carboxylate
1193-62-0

methyl Pyrrole-2-carboxylate

methyl 1H-pyrrole-3-carboxylate
2703-17-5

methyl 1H-pyrrole-3-carboxylate

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

1H-pyrrole-2,5-dicarboxylic acid dimethyl ester
1757-29-5

1H-pyrrole-2,5-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
Product distribution; other time, other temperature; lithiations of 1-trialkylsilylpyrroles in multistep reactions;
Yield given. Multistep reaction. Yields of byproduct given;
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

N-Methylpyrrole
96-54-8

N-Methylpyrrole

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
Conditions Yield
tetrabutylammomium bromide; at 110 ℃; atmospheric pressure;
92%
4%
tetrabutylammomium bromide; at 120 ℃; for 24h; atmospheric pressure;
36%
51%
With tert-butylimino-tri(pyrrolidino)phosphorane; at 119.84 ℃; for 6.5h; Further Variations:; Reagents; Temperatures; reaction time; Product distribution;
68 % Chromat.
With 1,4-diaza-bicyclo[2.2.2]octane; In N,N-dimethyl-formamide; at 90 - 92 ℃; for 24h;
N-methoxycarbonyl-2,5-dimethoxypyrrolidine
66893-74-1

N-methoxycarbonyl-2,5-dimethoxypyrrolidine

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
Conditions Yield
With toluene-4-sulfonic acid; In benzene; for 4h; Heating;
62%
sodium methylate
124-41-4

sodium methylate

pyrrole-1-carboxylic acid anhydride
107962-24-3

pyrrole-1-carboxylic acid anhydride

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
Conditions Yield
In tetrahydrofuran; at -20 ℃; for 0.25h;
69%
N-(methoxycarbonyl)pyrrolidine
56475-80-0

N-(methoxycarbonyl)pyrrolidine

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 77 percent / anodic oxidation in the tetraethylammonium p-toluenesulfonate
2: 62 percent / TsOH / benzene / 4 h / Heating
With toluene-4-sulfonic acid; In benzene;
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
Conditions Yield
With porous poly(ionic liquid) prepared by the anion exchange of poly(bisvinylimidazolium-base disalicylate) and NaCl; at 110 ℃; for 9h; Reagent/catalyst;
87%
methyl chloroformate
79-22-1

methyl chloroformate

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
Conditions Yield
With potassium hydride; In tetrahydrofuran; at 0 ℃;
With sodium hydride;
pyrrole-1-carboxylic acid
21972-99-6

pyrrole-1-carboxylic acid

methyl 1H-pyrrole-1-carboxylate
4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 87 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDCl*HCl) / CH2Cl2 / 0.25 h / 25 °C
2: 69 percent / tetrahydrofuran / 0.25 h / -20 °C
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

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