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517-22-6 Usage

Chemical Properties

clear yellow to red-brown liquid

Uses

Different sources of media describe the Uses of 517-22-6 differently. You can refer to the following data:
1. 3-Ethyl-2,4-dimethyl-1H-pyrrole is a important diagnostic compound for pyrrole disorder or pyroluria, an abnormality in biochemistry resulting in overproduction of pyrrole molecules and resulting in i mproper hemoglobin synthesis.
2. 3-Ethyl-2,4-dimethyl-1H-pyrrole is a important diagnostic compound for pyrrole disorder or pyroluria, an abnormality in biochemistry resulting in overproduction of pyrrole molecules and resulting in improper hemoglobin synthesis.
3. 3-Ethyl-2,4-dimethylpyrrole can be used as a substrate for the synthesis of: Boradiazaindacene (BODIPY dyes) units as a building block for the fabrication of energy transfer cassettes.Meso-benzyl and meso-alkyl dipyrrins salts by treating with corresponding acid chloride.2,5-Bis[3,5-dimethyl-4-ethylpyrrol-2-yl]cyclohexadiene-1,4-dione by reacting with 1,4-benzoquinone.

Check Digit Verification of cas no

The CAS Registry Mumber 517-22-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 7 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 517-22:
(5*5)+(4*1)+(3*7)+(2*2)+(1*2)=56
56 % 10 = 6
So 517-22-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H13N/c1-4-8-6(2)5-9-7(8)3/h5,9H,4H2,1-3H3

517-22-6 Well-known Company Product Price

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  • Aldrich

  • (D158402)  3-Ethyl-2,4-dimethylpyrrole  97%

  • 517-22-6

  • D158402-5G

  • 1,619.28CNY

  • Detail
  • Aldrich

  • (D158402)  3-Ethyl-2,4-dimethylpyrrole  97%

  • 517-22-6

  • D158402-25G

  • 5,937.75CNY

  • Detail

517-22-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names 1H-Pyrrole, 3-ethyl-2,4-dimethyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:517-22-6 SDS

517-22-6Synthetic 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%

517-22-6Relevant articles and documents

Rational design of fluorescent probes for targeted: In vivo nitroreductase visualization

Chen, Ji-An,Gao, Jie,Gu, Xianfeng,Li, Mimi,Tan, Jiahui,Yin, Xiaofan,Zhao, Zhen

, p. 4744 - 4747 (2020/07/13)

Nitroreductase (NTR) has been recognized as a biomarker for identifying the hypoxic status of cancers. Therefore, it is of high scientific interest to design effective fluorescent probes for tracking NTR activity. However, studies on elucidation of the structure-performance relationship of fluorescent probes and those providing valuable insight into optimized probe design have rarely been reported. Three BODIPY based fluorescent probes were made by conjugation of para-, ortho-, and meta-nitrobenzene to the BODIPY core via a thiolether bond, respectively. Our study revealed that the linkage and nitro substituent position significantly influence the capability of nitroreductase detection.

REACTIVE LABELLING COMPOUNDS AND USES THEREOF

-

, (2015/11/16)

Provided are azido-BODIPY compounds of formula (I), cyclooctyne-based fluorogenic probes of formula (IV), and activity-based probes of formula (VI). These compounds undergo azide alkyne cycloadditions (AAC) with to form triazolyl products. The provided compounds are useful for detection and imaging of alkyne-, or azide-containing molecules. Methods for detection and imaging biomolecules using compounds of the present disclosure are disclosed.

Synthesis and spectral properties of new 3,3'-bis(dipyrrolylmethene) with acetylene spacer

Antina,Guseva,Loginova,Semeikin,V'Yugin

, p. 2374 - 2381 (2011/04/14)

Bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide (H2L·2HBr), new bis(dipyrrolylmethene), in whose molecule dipyrrolylmethene domains were connected through 3,3'-carbon atoms of internal pyrrole nuclei by acetylene spacer, were synthesized by original procedure. The compound was characterized by element analysis, IR, 1H NMR, and electronic spectroscopy. The comparative analysis of spectral properties shows the reduction of the basicity of H2L ligand in comparison with the structural analogs, which contain internal methylene spacer. The quantum-chemical simulation showed that the rigid acetylene spacer gives linear structure to the H2L molecule in contrast to the spiral-shaped geometry of structural analogs with-CH2-spacer. Pleiades Publishing, Ltd., 2010.

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