ChemicalBook--->CAS DataBase List--->2199-51-1

2199-51-1

2199-51-1 Structure

2199-51-1 Structure
IdentificationMore
[Name]

Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate
[CAS]

2199-51-1
[Synonyms]

2,4-DIMETHYL-1H-PYRROLE-3-CARBOXYLIC ACID ETHYL ESTER
ETHYL 2,4-DIMETHYL-1H-PYRROLE-3-CARBOXYLATE
ETHYL 2,4-DIMETHYL-PYRROLE-3-CARBOXYLATE
ETHYL 2,4-DIMETHYLPYRROLE-3-CARBOXYLIC ACID
1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-, ethyl ester
Pyrrole-3-carboxylic acid, 2,4-dimethyl-, ethyl ester
Ethyl 2,4-dimethylpyrrole-3-carboxylate 98%
2,4-Dimethyl-1H-pyrrole-3-carboxylic acid ethyl
[EINECS(EC#)]

606-885-5
[Molecular Formula]

C9H13NO2
[MDL Number]

MFCD01365811
[Molecular Weight]

167.21
[MOL File]

2199-51-1.mol
Chemical PropertiesBack Directory
[Melting point ]

122-123°C
[Boiling point ]

162°C/11mmHg(lit.)
[density ]

1.1222 (rough estimate)
[refractive index ]

1.4680 (estimate)
[storage temp. ]

Inert atmosphere,2-8°C
[solubility ]

DMSO (Soluble), Chloroform (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

16.44±0.50(Predicted)
[color ]

Red to Very Dark Red
[λmax]

258nm(EtOH)(lit.)
[InChI]

InChI=1S/C9H13NO2/c1-4-12-9(11)8-6(2)5-10-7(8)3/h5,10H,4H2,1-3H3
[InChIKey]

QWSFDUPEOPMXCV-UHFFFAOYSA-N
[SMILES]

N1C=C(C)C(C(OCC)=O)=C1C
[CAS DataBase Reference]

2199-51-1(CAS DataBase Reference)
[NIST Chemistry Reference]

2,4-Dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester(2199-51-1)
Safety DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)Health Hazard (GHS08)Environment (GHS09)
GHS06,GHS08,GHS09
[Signal word ]

Danger
[Hazard statements ]

H301+H331-H315-H319-H360-H371-H373-H317-H334-H341-H350-H410
[Precautionary statements ]

P501-P273-P272-P260-P270-P202-P201-P271-P264-P280-P284-P302+P352-P391-P337+P313-P305+P351+P338-P308+P311-P362+P364-P333+P313-P301+P310+P330-P304+P340+P311-P403+P233-P405
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
[Hazard Note ]

Irritant
[HS Code ]

29337900
Hazard InformationBack Directory
[Chemical Properties]

White to light brown crystalline
[Uses]

ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate is used in the preparation of blue pyrrole dyes. It is also used as an intermediate in the synt hesis of receptor tyrosine kinase (RTK) inhibitors and their metabolites.
[Synthesis]

3,5-Dimethylpyrrole-2,4-dicarboxylic acid 2-t-butyl ester-4-ethyl ester

86770-31-2

Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate

2199-51-1

Step (ii): Preparation of 2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester In a 10-liter four-necked round-bottomed flask equipped with a mechanical stirrer, thermometer casing, gas introduction tube, and air condenser, 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester (II) (1.5 kg, 5.6 mol) and isopropanol (4.5 L) were added and stirred at 25-30 °C. Concentrated hydrochloric acid (2.2 L) was added slowly through the addition funnel. After addition, the reaction mixture was warmed up to 45-50 °C and maintained at this temperature until complete cessation of gas release. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solution was cooled to 25-30 °C and quenched in an ice-water bath. The product was separated by filtration and dried at 50 °C. A dried product of 721.3 g was obtained with 77.3% yield and >96% HPLC purity.

[References]

[1] Synlett, 2010, # 17, p. 2561 - 2564
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3062 - 3065
[3] Journal of the American Chemical Society,
[4] Journal of the American Chemical Society, 2009, vol. 131, p. 8578 - 8586
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 139 - 146
Spectrum DetailBack Directory
[Spectrum Detail]

Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate(2199-51-1)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

2199-51-1(sigmaaldrich)
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