Product Name

  • Name

    2,4-Dimethyl-3-ethyl-1H-pyrrole

  • EINECS 208-234-7
  • CAS No. 517-22-6
  • Article Data39
  • CAS DataBase
  • Density 0.925 g/cm3
  • Solubility
  • Melting Point 63.75°C (estimate)
  • Formula C8H13N
  • Boiling Point 199.1 °C at 760 mmHg
  • Molecular Weight 123.198
  • Flash Point 71.7 °C
  • Transport Information
  • Appearance clear yellow to red-brown liquid
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 517-22-6 (2,4-Dimethyl-3-ethyl-1H-pyrrole)
  • Hazard Symbols IrritantXi
  • Synonyms Pyrrole,3-ethyl-2,4-dimethyl- (6CI,7CI,8CI);2,4-Dimethyl-3-ethylpyrrole;3-Ethyl-2,4-dimethyl-1H-pyrrole;3-Ethyl-2,4-dimethylpyrrole;Cryptopyrrole;Kryptopyrrol;Kryptopyrrole;NSC 62025;
  • PSA 15.79000
  • LogP 2.19390

Synthetic route

ethyl 3,5-dimethyl-4-ethylpyrrole-2-carboxylate
2199-47-5

ethyl 3,5-dimethyl-4-ethylpyrrole-2-carboxylate

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With sodium hydroxide In ethylene glycol for 1h; Heating;100%
With potassium hydroxide In ethylene glycol for 5h; Heating;80%
With ethylene glycol; potassium hydroxide; hydrazinium sulfate In tetrahydrofuran for 2h; Reflux;76%
With sodium hydroxide In methanol; water for 2h; Heating;17%
With ethylene glycol; potassium hydroxide
ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate
2386-26-7

ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate In diethylene glycol for 3h; Heating;82%
With potassium hydroxide; hydrazine hydrate In diethylene glycol Heating;75%
With sodium ethanolate; hydrazine hydrate at 165 - 170℃; im Autoklaven;
2,4-dimethyl-3-acetylpyrrole
2386-25-6

2,4-dimethyl-3-acetylpyrrole

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With lithium aluminium tetrahydride81%
With lithium aluminium tetrahydride In tetrahydrofuran for 4.5h; Heating;75%
With lithium aluminium tetrahydride In tetrahydrofuran at 85℃; for 4h;60%
4-ethyl-3,5-dimethylpyrrole-2-carbaldehyde
1500-91-0

4-ethyl-3,5-dimethylpyrrole-2-carbaldehyde

A

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

B

2-hydroxyethyl acetate
542-59-6

2-hydroxyethyl acetate

Conditions
ConditionsYield
With ethylene glycol; toluene-4-sulfonic acid In benzene for 0.25h; Heating;A 35%
B n/a
1-(2,4-dimethyl-pyrrol-3-yl)-ethanone-hydrazone

1-(2,4-dimethyl-pyrrol-3-yl)-ethanone-hydrazone

sodium ethanolate
141-52-6

sodium ethanolate

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
at 150 - 160℃;
hemin

hemin

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With hydrogen iodide; acetic acid
ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate
2386-26-7

ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate

A

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

B

3-ethyl-2,4-dimethyl-pyrrol-1-ylamine

3-ethyl-2,4-dimethyl-pyrrol-1-ylamine

Conditions
ConditionsYield
With sodium ethanolate; hydrazine hydrate
benzyl 4-ethyl-3,5-dimethylpyrrole-2-carboxylate
1925-61-7

benzyl 4-ethyl-3,5-dimethylpyrrole-2-carboxylate

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With methanol; nickel at 120℃; under 73550.8 Torr; Hydrogenation;
2-(4-ethyl-3,5-dimethyl-pyrrole-2-carbonyl)-benzoic acid

2-(4-ethyl-3,5-dimethyl-pyrrole-2-carbonyl)-benzoic acid

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With hydrogen iodide; acetic acid
bilirubin
635-65-4

bilirubin

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With hydrogen iodide; acetic acid
4-ethyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid
17106-07-9

4-ethyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
at 100 - 102℃; under 20 - 22 Torr; Yield given;
γ-phylloporphyrin-XV
2644-60-2

γ-phylloporphyrin-XV

A

2,3-dimethyl-1H-pyrrole
600-28-2

2,3-dimethyl-1H-pyrrole

B

2,4-dimethyl-1H-pyrrole
625-82-1

2,4-dimethyl-1H-pyrrole

C

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

D

4-ethyl-2,3-dimethyl-1H-pyrrole
491-18-9

4-ethyl-2,3-dimethyl-1H-pyrrole

E

3-(4,5-dimethyl-pyrrol-3-yl)-propionic acid methyl ester
53365-83-6

3-(4,5-dimethyl-pyrrol-3-yl)-propionic acid methyl ester

F

methyl 2,4-dimethyl-3-pyrrolepropionate
54474-51-0

methyl 2,4-dimethyl-3-pyrrolepropionate

Conditions
ConditionsYield
With hydrogen iodide Product distribution; structural analysis by degradative techniques;
meso-porphyrin-II-dimethyl ester
62222-14-4

meso-porphyrin-II-dimethyl ester

A

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

B

4-ethyl-2,3-dimethyl-1H-pyrrole
491-18-9

4-ethyl-2,3-dimethyl-1H-pyrrole

C

3-(4,5-dimethyl-pyrrol-3-yl)-propionic acid methyl ester
53365-83-6

3-(4,5-dimethyl-pyrrol-3-yl)-propionic acid methyl ester

D

methyl 2,4-dimethyl-3-pyrrolepropionate
54474-51-0

methyl 2,4-dimethyl-3-pyrrolepropionate

Conditions
ConditionsYield
With hydrogen iodide Product distribution; structural analysis by degradative techniques;
etioporphyrin III
26608-34-4

etioporphyrin III

A

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

B

4-ethyl-2,3-dimethyl-1H-pyrrole
491-18-9

4-ethyl-2,3-dimethyl-1H-pyrrole

Conditions
ConditionsYield
With hydrogen iodide Product distribution; structural analysis by degradative techniques;
ethioporphyrin I
448-71-5

ethioporphyrin I

A

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

B

4-ethyl-2,3-dimethyl-1H-pyrrole
491-18-9

4-ethyl-2,3-dimethyl-1H-pyrrole

Conditions
ConditionsYield
With hydrogen iodide Product distribution; structural analysis by degradative technique;
mesoporphyrin IX DME
1263-63-4

mesoporphyrin IX DME

A

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

B

4-ethyl-2,3-dimethyl-1H-pyrrole
491-18-9

4-ethyl-2,3-dimethyl-1H-pyrrole

C

3-(4,5-dimethyl-pyrrol-3-yl)-propionic acid methyl ester
53365-83-6

3-(4,5-dimethyl-pyrrol-3-yl)-propionic acid methyl ester

D

methyl 2,4-dimethyl-3-pyrrolepropionate
54474-51-0

methyl 2,4-dimethyl-3-pyrrolepropionate

Conditions
ConditionsYield
With hydrogen iodide Product distribution; structural analysis by degradative techniques;
3.5-dimethyl-4-vinyl-pyrrole-carboxylic acid-(2)

3.5-dimethyl-4-vinyl-pyrrole-carboxylic acid-(2)

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With methanol; platinum Hydrogenation;
4-methyl-3-ethyl-pyrrol-aldehyde-(2)

4-methyl-3-ethyl-pyrrol-aldehyde-(2)

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With sodium ethanolate; hydrazine hydrate at 160 - 165℃; unter Druck;
bilirubinic acid

bilirubinic acid

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
With hydrogen iodide; acetic acid
5-bromo-5'-bromomethyl-3,4'-diethyl-4,3'-dimethyl-1H,2'H-2,2'-methanylylidene-bis-pyrrole

5-bromo-5'-bromomethyl-3,4'-diethyl-4,3'-dimethyl-1H,2'H-2,2'-methanylylidene-bis-pyrrole

hydrogen iodide
10034-85-2

hydrogen iodide

acetic acid
64-19-7

acetic acid

A

3-ethyl-4-methyl-1H-pyrrole
488-92-6

3-ethyl-4-methyl-1H-pyrrole

B

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

C

3-ethyl-2,4,5-trimethyl-1H-pyrrole
520-69-4

3-ethyl-2,4,5-trimethyl-1H-pyrrole

hydrogen iodide
10034-85-2

hydrogen iodide

(3-ethyl-5-bromo-4-methyl-pyrrol-2-yl)-(4-ethyl-3,5-dimethyl-pyrrol-2-ylidene)-methane; tribromoide
49619-17-2

(3-ethyl-5-bromo-4-methyl-pyrrol-2-yl)-(4-ethyl-3,5-dimethyl-pyrrol-2-ylidene)-methane; tribromoide

acetic acid
64-19-7

acetic acid

A

3-ethyl-4-methyl-1H-pyrrole
488-92-6

3-ethyl-4-methyl-1H-pyrrole

B

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

C

3-ethyl-2,4,5-trimethyl-1H-pyrrole
520-69-4

3-ethyl-2,4,5-trimethyl-1H-pyrrole

3-ethyl-2,4-pentanedione
1540-34-7

3-ethyl-2,4-pentanedione

selenacetylacetone

selenacetylacetone

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / Zn, AcOH / 1 h / Heating
2: 80 percent / KOH / ethane-1,2-diol / 5 h / Heating
View Scheme
benzyl 4-ethyl-3,5-dimethylpyrrole-2-carboxylate
1925-61-7

benzyl 4-ethyl-3,5-dimethylpyrrole-2-carboxylate

A

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

B

<4-ethyl-5-formyl-3-methyl-pyrrol-2-yl>-carbamic acid ethyl ester

<4-ethyl-5-formyl-3-methyl-pyrrol-2-yl>-carbamic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2, triethylamine / 10percent Pd/C / ethanol / 2 h
2: 100 - 102 °C / 20 - 22 Torr
View Scheme
acetylacetone
123-54-6

acetylacetone

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) NaNO2, AcOH 2) Zn dust, AcOH / 1) H2O, 25 deg C, overnight 2) reflux, 24 h
2: 82 percent / KOH, NH2NH2*H2O / bis-(2-hydroxy-ethyl) ether / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: zinc; acetic acid
2: diborane
3: ethylene glycol; potassium hydroxide
View Scheme
Multi-step reaction with 3 steps
1.1: sodium nitrite; acetic acid / water / 4 h / 20 °C / Cooling with ice
1.2: 1 h / 60 °C / Cooling with ice
2.1: potassium hydroxide / ethylene glycol / 4 h / 160 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 85 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid; sodium nitrite / water / 12 h / 0 - 25 °C
1.2: 1 h / 60 °C / Cooling with ice
2.1: potassium hydroxide / 1,2-dimethoxyethane / 4 h / 160 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / Cooling with ice; Reflux
View Scheme
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

methyl 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoate
18818-25-2

methyl 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoate

(Z)-methyl 3-(5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)-2,4-dimethyl-1H-pyrrol-3-yl)propanoate hydrobromide

(Z)-methyl 3-(5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)-2,4-dimethyl-1H-pyrrol-3-yl)propanoate hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In tetrahydrofuran; methanol; water at 20℃; for 3h; Inert atmosphere;99%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

C15H5BBr6F2N2
1350764-68-9

C15H5BBr6F2N2

C31H29BBr4F2N4

C31H29BBr4F2N4

Conditions
ConditionsYield
In toluene at 20℃; for 0.5h; Inert atmosphere;98%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate
2199-59-9

ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate

(Z)-ethyl 5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate hydrobromide

(Z)-ethyl 5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In tetrahydrofuran; methanol at 20℃; Inert atmosphere;98%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

3-ethyl-2,4-dimethyl-5-((trifluoromethyl)thio)-1H-pyrrole

3-ethyl-2,4-dimethyl-5-((trifluoromethyl)thio)-1H-pyrrole

Conditions
ConditionsYield
With chloro-trimethyl-silane In dichloromethane at 20℃; for 0.5h; Schlenk technique;97%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

2,4-dimethyl-3-ethyl-5-trifluoromethylpyrrole

2,4-dimethyl-3-ethyl-5-trifluoromethylpyrrole

Conditions
ConditionsYield
With chloro-trimethyl-silane In dichloromethane at 20℃; for 0.5h; Green chemistry;97%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

2-(1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile
117506-45-3

2-(1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile

2-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)malononitrile
137123-51-4

2-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)malononitrile

Conditions
ConditionsYield
In acetic acid for 2h; Ambient temperature;95%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

C18H25NO2S
1128076-99-2

C18H25NO2S

C18H33NS
1128077-15-5

C18H33NS

Conditions
ConditionsYield
With N,N-dimethyl acetamide; magnesium bromide at 90℃; for 1h;95%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

N-phenylthiophthalimide
14204-27-4

N-phenylthiophthalimide

3-ethyl-2,4-dimethyl-5-(phenylthio)-1H-pyrrole
1128077-07-5

3-ethyl-2,4-dimethyl-5-(phenylthio)-1H-pyrrole

Conditions
ConditionsYield
With N,N-dimethyl acetamide; magnesium bromide at 90℃; for 1h;95%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

2-((4-methoxyphenyl)thio)isoindoline-1,3-dione
88683-45-8

2-((4-methoxyphenyl)thio)isoindoline-1,3-dione

C15H19NOS
1128077-18-8

C15H19NOS

Conditions
ConditionsYield
With N,N-dimethyl acetamide; magnesium bromide at 90℃; for 1h;95%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

C22H23IN2O2
1227204-45-6

C22H23IN2O2

1-(5-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)(4-iodophenyl)methyl)-2,4-dimethyl-1H-pyrrol-3-yl)ethanone
1227204-48-9

1-(5-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)(4-iodophenyl)methyl)-2,4-dimethyl-1H-pyrrol-3-yl)ethanone

Conditions
ConditionsYield
With acetyl chloride In methanol at -78 - 0℃; Inert atmosphere;95%
With methanol; acetyl chloride at -78 - 0℃; for 1.5h;95%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

ethylenesulfonyl fluoride
677-25-8

ethylenesulfonyl fluoride

2-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)ethane-1-sulfonyl fluoride

2-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)ethane-1-sulfonyl fluoride

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.0833333h;95%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

4-(prop-2-ynyloxy)benzaldehyde
5651-86-5

4-(prop-2-ynyloxy)benzaldehyde

4,4-difluoro-8-(prop-2-ynyloxy)benzene-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene

4,4-difluoro-8-(prop-2-ynyloxy)benzene-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene

Conditions
ConditionsYield
Stage #1: 2,4-dimethyl-3-ethyl-pyrrole; 4-(prop-2-ynyloxy)benzaldehyde With trifluoroacetic acid In dichloromethane at 20℃; Inert atmosphere;
Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere;
Stage #3: boron trifluoride diethyl etherate With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
94%
Stage #1: 2,4-dimethyl-3-ethyl-pyrrole; 4-(prop-2-ynyloxy)benzaldehyde With trifluoroacetic acid In dichloromethane at 25℃; for 12h; Inert atmosphere;
Stage #2: In dichloromethane at 25℃; Inert atmosphere;
Stage #3: boron trifluoride diethyl etherate With triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere;
22%
Stage #1: 2,4-dimethyl-3-ethyl-pyrrole; 4-(prop-2-ynyloxy)benzaldehyde
Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone
Stage #3: boron trifluoride diethyl etherate Alkaline conditions;
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene
87751-69-7

rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene

(E)-4-ethyl-3,5-dimethyl-2-(1,3-diphenyl-2-propenyl)pyrrole

(E)-4-ethyl-3,5-dimethyl-2-(1,3-diphenyl-2-propenyl)pyrrole

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); C34H23P; potassium carbonate In toluene; acetonitrile at -20℃; for 38h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;93%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

1-methyl-5-pyrrol-2-ylpyrrole-2-carbaldehyde
105235-04-9

1-methyl-5-pyrrol-2-ylpyrrole-2-carbaldehyde

3-ethyl-2,4,12-trimethylprodigiosene hydrochloride
105256-97-1, 105257-09-8

3-ethyl-2,4,12-trimethylprodigiosene hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 5℃; for 0.333333h;92%
1-{5-[(benzyl-hydroxy-amino)-phenyl-methyl]-2,4-dimethyl-1H-pyrrol-3-yl}-ethanone

1-{5-[(benzyl-hydroxy-amino)-phenyl-methyl]-2,4-dimethyl-1H-pyrrol-3-yl}-ethanone

2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

1-(5-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)(phenyl)methyl)-2,4-dimethyl-1H-pyrrol-3-yl)ethanone

1-(5-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)(phenyl)methyl)-2,4-dimethyl-1H-pyrrol-3-yl)ethanone

Conditions
ConditionsYield
With acetyl chloride In methanol at -78 - 0℃; Inert atmosphere;92%
With methanol; acetyl chloride at -78 - 0℃; for 1.5h;92%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

3,7-bis(N,N-dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-one
1290536-55-8

3,7-bis(N,N-dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-one

C27H36N3Si(1+)

C27H36N3Si(1+)

Conditions
ConditionsYield
Stage #1: 3,7-bis(N,N-dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-one With trifluoromethylsulfonic anhydride In acetonitrile at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 2,4-dimethyl-3-ethyl-pyrrole In acetonitrile at 0 - 25℃; for 0.166667h; Inert atmosphere;
90.1%
Stage #1: 3,7-bis(N,N-dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-one With trifluoromethylsulfonic anhydride
Stage #2: 2,4-dimethyl-3-ethyl-pyrrole
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

2-ethylthioisoindoline-1,3-dione
17796-70-2

2-ethylthioisoindoline-1,3-dione

C10H17NS
1128077-89-3

C10H17NS

Conditions
ConditionsYield
With N,N-dimethyl acetamide; magnesium bromide at 90℃; for 1h;90%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

bis(4-(methoxycarbonyl)phenyl)iodonium trifluoromethanesulfonate
1416276-96-4

bis(4-(methoxycarbonyl)phenyl)iodonium trifluoromethanesulfonate

methyl 4-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)benzoate

methyl 4-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)benzoate

Conditions
ConditionsYield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate In acetonitrile at 25℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique;90%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

2-((difluoromethyl)thio)isoindoline-1,3-dione

2-((difluoromethyl)thio)isoindoline-1,3-dione

2-((difluoromethyl)thio)-4-ethyl-3,5-dimethyl-1H-pyrrole

2-((difluoromethyl)thio)-4-ethyl-3,5-dimethyl-1H-pyrrole

Conditions
ConditionsYield
With chloro-trimethyl-silane In 1,2-dichloro-ethane at 80 - 120℃; for 16h; Schlenk technique;90%
With chloro-trimethyl-silane In dichloromethane at 80 - 120℃; Inert atmosphere; Sealed tube;90%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 3-ethyl-2,4-dimethylpyrrole-1-carboxylate

tert-butyl 3-ethyl-2,4-dimethylpyrrole-1-carboxylate

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 1h;90%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

benzyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate
37059-18-0

benzyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate

(Z)-benzyl 5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate hydrobromide

(Z)-benzyl 5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In tetrahydrofuran; methanol at 20℃; Inert atmosphere;90%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

N-(benzylthio)phthalimide
14204-26-3

N-(benzylthio)phthalimide

C15H19NS
1128077-10-0

C15H19NS

Conditions
ConditionsYield
With N,N-dimethyl acetamide; magnesium bromide at 90℃; for 1h;89%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

C15H13ClN2
1391852-14-4

C15H13ClN2

C23H25N3
1402649-93-7

C23H25N3

Conditions
ConditionsYield
With trichlorophosphate In dichloromethane at 20℃; for 12h; Cooling with ice; Inert atmosphere;89%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

4-ethyl-3,5,N,N-tetramethylpyrrole-2-carboxamide
13219-74-4

4-ethyl-3,5,N,N-tetramethylpyrrole-2-carboxamide

bis(4-ethyl-3,5-dimethyl-pyrrol-2-yl)ketone
13228-22-3

bis(4-ethyl-3,5-dimethyl-pyrrol-2-yl)ketone

Conditions
ConditionsYield
Stage #1: 4-ethyl-3,5,N,N-tetramethylpyrrole-2-carboxamide With trichlorophosphate at 50℃; for 0.25h;
Stage #2: 2,4-dimethyl-3-ethyl-pyrrole In dichloromethane for 1.5h; Reflux;
Stage #3: With sodium carbonate In dichloromethane; water for 2h; Reflux;
89%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

3-acetoxy-1,3-diphenylpropene
73930-97-9

3-acetoxy-1,3-diphenylpropene

C23H25N

C23H25N

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); C37H40NO4PSi2; potassium carbonate; N-Trimethylsilylacetamide In dichloromethane at 23℃; for 2h; Inert atmosphere; Schlenk technique;89%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

3-methoxypyrrole-2-carboxaldehyde
54764-96-4

3-methoxypyrrole-2-carboxaldehyde

A

3,5-dimethyl-4-ethyl-2-(3-methoxypyrrolyl-2-methylene)-2H-pyrrole
1233087-60-9

3,5-dimethyl-4-ethyl-2-(3-methoxypyrrolyl-2-methylene)-2H-pyrrole

B

3,5-dimethyl-4-ethyl-2-(3-methoxypyrrolyl-2-methylene)-2H-pyrrolium dichlorophosphate
1233087-61-0

3,5-dimethyl-4-ethyl-2-(3-methoxypyrrolyl-2-methylene)-2H-pyrrolium dichlorophosphate

Conditions
ConditionsYield
With trichlorophosphate In dichloromethane; pentane for 1.01667h; Cooling;A n/a
B 86%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

10-chloro-5,5-difluoro-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
1414345-77-9

10-chloro-5,5-difluoro-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

C17H18BF2N3
1582309-41-8

C17H18BF2N3

Conditions
ConditionsYield
In toluene at 20℃; for 0.05h; Inert atmosphere;86%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

(3,5-dimethyl-1H-pyrrol-2-yl)(p-tolyl)methanone

(3,5-dimethyl-1H-pyrrol-2-yl)(p-tolyl)methanone

2-ethyl-4,4-difluoro-1,3,5,7-tetramethyl-8-(4-methylphenyl)-4-bora-3a,4a-diaza-s-indacene

2-ethyl-4,4-difluoro-1,3,5,7-tetramethyl-8-(4-methylphenyl)-4-bora-3a,4a-diaza-s-indacene

Conditions
ConditionsYield
Stage #1: 2,4-dimethyl-3-ethyl-pyrrole; boron trifluoride diethyl etherate; (3,5-dimethyl-1H-pyrrol-2-yl)-p-tolyl-methanone at 20℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: With N-ethyl-N,N-diisopropylamine at 20℃; for 4h; Schlenk technique; Inert atmosphere;
86%
2,4-dimethyl-3-ethyl-pyrrole
517-22-6

2,4-dimethyl-3-ethyl-pyrrole

benzyl 5-N,N-dimethylamido-3,4-dimethylpyrrole-2-carboxylate
16132-27-7

benzyl 5-N,N-dimethylamido-3,4-dimethylpyrrole-2-carboxylate

benzyl 8-ethyl-2,3,7,9-tetramethyl-5-dipyrroketone-1-carboxylate
16132-42-6

benzyl 8-ethyl-2,3,7,9-tetramethyl-5-dipyrroketone-1-carboxylate

Conditions
ConditionsYield
Stage #1: benzyl 5-N,N-dimethylamido-3,4-dimethylpyrrole-2-carboxylate With trichlorophosphate at 50℃; for 5h;
Stage #2: 2,4-dimethyl-3-ethyl-pyrrole In dichloromethane at 30℃; Inert atmosphere;
Stage #3: With water; sodium acetate In dichloromethane at 50℃; for 3h; Inert atmosphere;
85.7%

2,4-Dimethyl-3-ethylpyrrole Chemical Properties

Molecular Structure:Molecular Formula: C8H13N  
Molecular Weight: 123.2
IUPAC Name: 3-Ethyl-2,4-dimethyl-1H-pyrrole   
CAS No: 517-22-6
H bond acceptors: 1
H bond donors: 1
#Freely Rotating Bonds: 1
Polar Surface Area: 4.93 Å2
Index of Refraction: 1.511
Molar Refractivity: 39.88 cm3
Molar Volume: 133.1 cm3
Surface Tension: 32.8 dyne/cm
Density: 0.925 g/cm3
Flash Point: 71.7 °C
Enthalpy of Vaporization: 41.75 kJ/mol
Boiling Point: 199.1 °C at 760 mmHg
Vapour Pressure: 0.491 mmHg at 25°C
InChI: InChI=1/C8H13N/c1-4-8-6(2)5-9-7(8)3/h5,9H,4H2,1-3H3
InChIKey: ZEBBLOXDLGIMEG-UHFFFAOYAU
Std. InChI: InChI=1S/C8H13N/c1-4-8-6(2)5-9-7(8)3/h5,9H,4H2,1-3H3
Std. InChIKey: ZEBBLOXDLGIMEG-UHFFFAOYSA-N
Synonyms of 1H-Pyrrole,3-ethyl-2,4-dimethyl- (CAS No.517-22-6): Timtec-bb sbb004274 ; Kryptopyrrole ; Cryptopyrrole ; 'mauve factor' reagent ; 3-Ethyl-2,4-dimethylpyrrol ; 3-Ethyl-2,4-dimethylpyrrole ; 2,4-Dimethyl-3-ethyl-1H-pyrrole ; 2,4-Dimethyl-3-ethylpyrrole  
Product Categories:  Pharmaceutial intermediates

2,4-Dimethyl-3-ethylpyrrole Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 77mg/kg (77mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Journal of Medicinal Chemistry. Vol. 11, Pg. 1251, 1968.

2,4-Dimethyl-3-ethylpyrrole Safety Profile

Hazard Codes:IrritantXi
Risk Statements:36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:26-36-37/39
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany:3
RTECS:UX9629500

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