Methyl 1H-Pyrrole-1-carboxylate supplier

Name
METHYL PYRROLE-1-CARBOXYLATE
EINECS 224-281-6
CAS No. 4277-63-8
Article Data18
CAS DataBase
Density 1.09 g/cm³
Solubility
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
Hazard Symbols Xi
Synonyms Pyrrole-1-carboxylicacid, methyl ester (6CI,7CI,8CI);Methyl 1-pyrrolecarboxylate;Methyl1H-pyrrole-1-carboxylate;N-(Methoxycarbonyl)pyrrole;N-Carbomethoxypyrrole;
PSA 31.23000
LogP 1.10260

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

Conditions	Yield
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;

...Expand

: 109-97-7
pyrrole

: 616-38-6
carbonic acid dimethyl ester

: 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%

: 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

Conditions	Yield
In chloroform-d1 at 19.84℃; for 56h;	A 78% B n/a

...Expand

: 124-41-4
sodium methylate

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

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 20671-52-7
lithium pyrrolide

: 79-22-1
methyl chloroformate

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

Conditions

Conditions	Yield
In diethyl ether; hexane for 2h; Heating;	40%

: 186581-53-3, 908094-01-9
diazomethane

: 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

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

...Expand

: 109-97-7
pyrrole

: 79-22-1
methyl chloroformate

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

Conditions

Conditions	Yield
With potassium hydride In tetrahydrofuran at 0℃;
With sodium hydride

: 186581-53-3, 908094-01-9
diazomethane

: 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

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

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 18276-53-4
1-(trimethylsilyl)-1H-pyrrole

: 124-38-9
carbon dioxide

A: 1193-62-0
methyl Pyrrole-2-carboxylate

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

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

Conditions

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 18276-53-4
1-(trimethylsilyl)-1H-pyrrole

: 124-38-9
carbon dioxide

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

Conditions

Conditions	Yield
Yield given. Multistep reaction;

...Expand

: 21972-99-6
pyrrole-1-carboxylic acid

: 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 View Scheme

: 56475-80-0
N-(methoxycarbonyl)pyrrolidine

: 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 View Scheme

: 109-97-7
pyrrole

: 13509-27-8
methyl phenyl carbonate

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

B: 56880-01-4
1-phenoxycarbonyl pyrrole

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 119.84℃; for 24h; Product distribution; Further Variations:; Temperatures; reaction time;	A 47 % Chromat. B 12 % Chromat.

...Expand

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

: 762-42-5
dimethyl acetylenedicarboxylate

: 19169-19-8
trimethyl 7-azabicyclo[2.2.1]hepta-2,5-diene-2,3,7-tricarboxylate

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane at 40℃; for 1h;	90%

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

: 1408320-94-4
N-chloro-N-(phenylmethoxy)-N'-(phenylmethyl)urea

: methyl (5RS,1SR)-3-oxo-2-(phenylmethoxy)-4-(phenylmethyl)-2,4,8-triazabicyclo[3.2.1]oct-6-en-8-carboxylate

Conditions

Conditions	Yield
With sodium 2,2,3,3-tetrafluoropropan-1-olate In acetonitrile at 0℃; Inert atmosphere;	90%

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

: 82853-93-8
N,N′-dibenzyloxyurea

: (±)-(5R,1S)-methyl-3-oxo-2,4-bis(phenylmethoxy)-2,4,8-triazabicyclo[3.2.1]oct-6-en-8-carboxylate

Conditions

Conditions	Yield
With 2,2,3,3-tetrafluoropropanol; [bis(acetoxy)iodo]benzene; sodium 2,2,3,3-tetrafluoropropan-1-olate In acetonitrile at 0℃; for 3.5h; Inert atmosphere;	86%

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

: 13894-21-8
ethynyl p-tolyl sulfone

: 83060-74-6
(1S,4R)-2-(Toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hepta-2,5-diene-7-carboxylic acid methyl ester

Conditions

Conditions	Yield
at 85℃; for 24h;	85%
at 80 - 85℃; for 24h;	60%
at 80 - 85℃; for 48h; Yield given;

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

: 90388-37-7
N-(2,4-dichloro-6-oxo-2,4-cyclohexadien-1-ylidene)-4-nitrobenzamide

: 1-carbomethoxy-6,8-dichloro-3a,9a-dihydro-9-(4-nitrobenzoyl)-9H-pyrrolo<3,2-b><1,4>benzoxazine

Conditions

Conditions	Yield
In dichloromethane for 17h; Ambient temperature;	83%

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

: 13894-21-8
ethynyl p-tolyl sulfone

: 83060-74-6
7-methoxycarbonyl-2-p-toluenesulfonyl-7-azanorbornadiene

Conditions

Conditions	Yield
In dichloromethane under 9000720 Torr;	81%
at 85 - 90℃;	72%
at 85℃; for 26h;	67%

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

: 815-60-1
2,4-dibromo-3-pentanone

A: 53406-52-3
methyl 2α,4α-dimethyl-3-oxo-8-azabicyclo<3.2.1>oct-6-ene-8-carboxylate

B: methyl 2β,4β-dimethyl-3-oxo-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate

Conditions

Conditions	Yield
With diethylzinc In hexane; toluene	A 81% B 6%
With zinc; 1,1-dibromomethane In acetonitrile at 20℃; for 1h; ultrasonification; Title compound not separated from byproducts;

...Expand

: 75-77-4
chloro-trimethyl-silane

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

: 1199553-52-0
methyl 2,5-bis(trimethylsilyl)-1H-pyrrole-1-carboxylate

Conditions

Conditions	Yield
Stage #1: methyl 1H-pyrrole-1-carboxylate With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Inert atmosphere;	80%

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

: 359779-60-5
4-bromo-1,1,1-trifluorobut-3-yn-2-one

: 2-(4,4,4-trifluoro-3-oxobut-1-ynyl)-1-methoxycarbonyl-1H-pyrrole

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃; Inert atmosphere;	78%
	76%

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

: 126554-35-6
methyl 2-diazobut-3-enoate

: 126554-31-2
Methyl N-(methoxycarbonyl)-8-azabicyclo<3.2.1>octa-2,6-diene-2-carboxylate

Conditions

Conditions	Yield
With rhodium(II) hexanoate In hexane for 12h; Heating;	75%
rhodium(II) acetate	21%

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

: 152328-56-8
phenylsulfonyl 6-chloro-3-pyridyl acetylene

: 163299-82-9
2-Benzenesulfonyl-3-(6-chloro-pyridin-3-yl)-7-aza-bicyclo[2.2.1]hepta-2,5-diene-7-carboxylic acid methyl ester

Conditions

Conditions	Yield
at 80 - 85℃; for 24h;	70%

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

: 227454-51-5
1-((bromoethynyl)sulfonyl)-4-methylbenzene

: 227454-64-0
N-methoxycarbonyl-7-aza-2-bromo-3-p-tolylsulfonylbicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In toluene at 90℃; for 24h;	70%

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

: 38651-07-9
1,3-dibromo-1-phenylbutan-2-one

: methyl 2β-methyl-3-oxo-4β-phenyl-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate

: methyl 2α-methyl-3-oxo-4α-phenyl-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate

Conditions

Conditions	Yield
With diethylzinc In hexane; toluene	A 5% B 69%

...Expand

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

: 619-44-3
methyl 4-iodobenzoate

: C14H13NO4

Conditions

Conditions	Yield
With tris(4-anisyl)amine; 2-butyl-4,7-bis(1-methyl-1H-pyrrol-2-yl)-2H-benzo[d][1,2,3]triazole In dimethyl sulfoxide at 20℃; for 24h; Irradiation; Schlenk technique; Inert atmosphere;	69%

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

: 104525-94-2
diethyl (E)-4-diazopent-2-enedioate

: 126554-26-5, 126554-39-0
(1S,4R,5R)-8-Aza-bicyclo[3.2.1]octa-2,6-diene-2,4,8-tricarboxylic acid 2,4-diethyl ester 8-methyl ester

Conditions

Conditions	Yield
rhodium(II) acetate	62%

: 872885-13-7
4-chloro-1,1,1-trifluorobut-3-yn-2-one

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

A: 2-(4,4,4-trifluoro-3-oxobut-1-ynyl)-1-methoxycarbonyl-1H-pyrrole

: 2-chloro-3-trifluoroacetyl-7-methoxycarbonyl-7-azabicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In 1,4-dioxane at 20℃; for 6h; Diels-Alder Cycloaddition; Inert atmosphere;	A 19% B 62%

...Expand

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

: 126554-33-4
ethyl (E)-2-diazo-4-(phenylsulfonyl)-3-butenoate

: 126554-29-8, 126554-42-5
(1S,4R,5R)-4-Benzenesulfonyl-8-aza-bicyclo[3.2.1]octa-2,6-diene-2,8-dicarboxylic acid 2-ethyl ester 8-methyl ester

Conditions

Conditions	Yield
rhodium(II) acetate	61%

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

: 115419-61-9
N-[2,2,2-trichloro-1-(trimethylsilyloxy)ethyl]-N-(trimethylsilyl)amine

: 1-(1-carbomethoxy-pyrrol-2-yl)-2,2,2-trichloroethylamine

Conditions

Conditions	Yield
Stage #1: methyl 1H-pyrrole-1-carboxylate; N-[2,2,2-trichloro-1-(trimethylsilyloxy)ethyl]-N-(trimethylsilyl)amine With chloro-trimethyl-silane In dichloromethane at 20℃; for 0.05h; Stage #2: With hafnium tetrakis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 10h; Further stages.;	61%

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

: 54210-98-9
1,3-dibromo-1-phenyl-2-propanone

: methyl 3-oxo-2β-phenyl-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate

: methyl 3-oxo-2α-phenyl-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate

Conditions

Conditions	Yield
With diethylzinc In hexane; toluene	A 15% B 59%

...Expand

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

: 141-32-2
acrylic acid n-butyl ester

: methyl (E)-2-(3-butoxy-3-oxoprop-1-en-1-yl)-1H-pyrrole-1-carboxylate

Conditions

Conditions	Yield
With sodium 3-{(4-methoxyphenyl)thio}propane-1-sulfonate; copper diacetate; palladium diacetate; toluene-4-sulfonic acid In N,N-dimethyl-formamide at 70℃; for 18h;	59%

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

: 23680-40-2
methyl 3-bromopropiolate

: 208177-19-9
3-Bromo-7-aza-bicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
at 90 - 95℃; for 33h;	56%

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

: 23680-40-2
methyl 3-bromopropiolate

: methyl 3-bromo-7-methoxycarbonyl-7-azabicyclo[2.2.1]hepta-2,5-diene-2-carboxylate

Conditions

Conditions	Yield
at 90 - 95℃; for 30h; Cycloaddition;	56%

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

: 815-60-1
2,4-dibromo-3-pentanone

: 53406-52-3
methyl 2α,4α-dimethyl-3-oxo-8-azabicyclo<3.2.1>oct-6-ene-8-carboxylate

Conditions

Conditions	Yield
With diethylzinc In hexane; benzene a) 0 deg C, 3 h, b) r.t., 17 h;	55%

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

: 55591-23-6
1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonyl chloride

A: methyl 2-(tridecafluorohexyl)pyrrole-1-carboxylate

B: methyl 3-(tridecafluorohexyl)pyrrole-1-carboxylate

Conditions

Conditions	Yield
With dichlorotris(triphenylphosphine)ruthenium(II) In pentane at 120℃; for 24h;	A 55% B 1%

...Expand

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

Product Name

METHYL PYRROLE-1-CARBOXYLATE

Synthetic route

Methyl 1H-Pyrrole-1-carboxylate Specification

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