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Methyl 1H-Pyrrole-1-carboxylate

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Name

Methyl 1H-Pyrrole-1-carboxylate

EINECS 224-281-6
CAS No. 4277-63-8 Density 1.09 g/cm3
PSA 31.23000 LogP 1.10260
Solubility N/A Melting Point 166-167°C
Formula C6H7NO2 Boiling Point 182.5 °C at 760 mmHg
Molecular Weight 125.127 Flash Point 64.2 °C
Transport Information UN 3272 3/PG 3 Appearance clear colorless to very slightly yellow liquid
Safety 24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 4277-63-8 (METHYL PYRROLE-1-CARBOXYLATE) Hazard Symbols IrritantXi
Synonyms

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

Article Data 18

Methyl 1H-Pyrrole-1-carboxylate Synthetic route

109-97-7

pyrrole

616-38-6

carbonic acid dimethyl ester

A

96-54-8

N-Methylpyrrole

B

4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
tetrabutylammomium bromide at 110℃; atmospheric pressure;A 4%
B 92%
tetrabutylammomium bromide at 120℃; for 24h; atmospheric pressure;A 36%
B 51%
With tert-butylimino-tri(pyrrolidino)phosphorane at 119.84℃; for 6.5h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time;A n/a
B 68 % Chromat.
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 90 - 92℃; for 24h;
109-97-7

pyrrole

616-38-6

carbonic acid dimethyl ester

4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
With porous poly(ionic liquid) prepared by the anion exchange of poly(bisvinylimidazolium-base disalicylate) and NaCl at 110℃; for 9h; Reagent/catalyst;87%
109-97-7

pyrrole

1309041-52-8

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

A

4277-63-8

methyl 1H-pyrrole-1-carboxylate

B

6674-22-2

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

Conditions
ConditionsYield
In chloroform-d1 at 19.84℃; for 56h;A 78%
B n/a
124-41-4

sodium methylate

107962-24-3

pyrrole-1-carboxylic acid anhydride

4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
In tetrahydrofuran at -20℃; for 0.25h;69%
66893-74-1

1-methoxycarbonyl-2,5-dimethoxypyrrolidine

4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 4h; Heating;62%
85684-89-5

1-triphenylmethylpyrrole

A

4277-63-8

methyl 1H-pyrrole-1-carboxylate

B

789-24-2

9-Phenylfluorene

C

5467-21-0

methyl 2,2,2-triphenylacetate

Conditions
ConditionsYield
With n-butyllithium In hexane; N,N-dimethyl-formamide for 2h; Ambient temperature;A 25%
B 31%
C 60%
20671-52-7

lithium pyrrolide

79-22-1

methyl chloroformate

4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
In diethyl ether; hexane for 2h; Heating;40%
85684-89-5

1-triphenylmethylpyrrole

124-38-9

carbon dioxide

A

4277-63-8

methyl 1H-pyrrole-1-carboxylate

B

789-24-2

9-Phenylfluorene

C

5467-21-0

methyl 2,2,2-triphenylacetate

Conditions
ConditionsYield
With n-butyllithium 1.) DMF, room temperature, 2 h; ether, 2.) ether, 0 deg C; Yield given. Multistep reaction. Yields of byproduct given;
109-97-7

pyrrole

79-22-1

methyl chloroformate

4277-63-8

methyl 1H-pyrrole-1-carboxylate

Conditions
ConditionsYield
With potassium hydride In tetrahydrofuran at 0℃;
With sodium hydride
18276-53-4

1-(trimethylsilyl)-1H-pyrrole

124-38-9

carbon dioxide

A

1193-62-0

methyl Pyrrole-2-carboxylate

B

2703-17-5

methyl 1H-pyrrole-3-carboxylate

C

4277-63-8

methyl 1H-pyrrole-1-carboxylate

D

1757-29-5

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

Conditions
ConditionsYield
Product distribution; other time, other temperature; lithiations of 1-trialkylsilylpyrroles in multistep reactions;
Yield given. Multistep reaction. Yields of byproduct given;

Methyl 1H-Pyrrole-1-carboxylate Specification

The cas register number of Methyl 1H-Pyrrole-1-carboxylate is 4277-63-8. It also can be called as 1H-Pyrrole-1-carboxylicacid, methyl ester and the IUPAC Name about this chemical is methyl pyrrole-1-carboxylate. It belongs to the following product categories, such as Carboxylic Acids, Pyrroles & Indoles, Carboxylic Acids, Pyrroles & Indoles, Building Blocks, Heterocyclic Building Blocks, Pyrroles and so on.

Physical properties about Methyl 1H-Pyrrole-1-carboxylate are: (1)ACD/LogP: 1.19; (2)ACD/LogD (pH 5.5): 1.19; (3)ACD/LogD (pH 7.4): 1.19; (4)ACD/BCF (pH 5.5): 4.75; (5)ACD/BCF (pH 7.4): 4.75; (6)ACD/KOC (pH 5.5): 106.16; (7)ACD/KOC (pH 7.4): 106.16; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 31.23Å2; (11)Index of Refraction: 1.501; (12)Molar Refractivity: 33.65 cm3; (13)Molar Volume: 114 cm3; (14)Polarizability: 13.34x10-24cm3; (15)Surface Tension: 37.7 dyne/cm; (16)Enthalpy of Vaporization: 41.87 kJ/mol; (17)Vapour Pressure: 0.809 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-methoxycarbonyl-2,5-dimethoxypyrrolidine. This reaction will need reagent TsOH and solvent benzene. The reaction time is 4 hour(s) at Heating. The yield is about 62%.

Uses of 1H-Pyrrole-1-carboxylate: it can be used to produce 3-oxo-nortrop-6-ene-8-carboxylic acid methyl ester with 1,1,3,3-tetrabromo-propan-2-one at temperature of -12 - 20 ℃. This reaction will need reagent ZnEt2 and solvent toluene with reaction time of 18 hours. The yield is about 40%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, please avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)n1cccc1
(2)InChI: InChI=1/C6H7NO2/c1-9-6(8)7-4-2-3-5-7/h2-5H,1H3
(3)InChIKey: MORALDOSFHZOQS-UHFFFAOYAL
(4)Std. InChI: InChI=1S/C6H7NO2/c1-9-6(8)7-4-2-3-5-7/h2-5H,1H3
(5)Std. InChIKey: MORALDOSFHZOQS-UHFFFAOYSA-N

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