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636-41-9

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636-41-9 Usage

Uses

2-Methylpyrrole was used as one of the starting materials for synthesizing boron-dipyrromethene dyes for incorporation in synthetic multi-pigment light-harvesting arrays. Acid-promoted condensations of benzaldehyde with methylpyrrole gives dipyrromethens and their borondipyrromethene analogs.

Check Digit Verification of cas no

The CAS Registry Mumber 636-41-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 6 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 636-41:
(5*6)+(4*3)+(3*6)+(2*4)+(1*1)=69
69 % 10 = 9
So 636-41-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H7N/c1-5-3-2-4-6-5/h2-4,6H,1H3

636-41-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methyl-1H-pyrrole

1.2 Other means of identification

Product number -
Other names 1H-Pyrrole, 2-methyl-

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:636-41-9 SDS

636-41-9Synthetic route

2-pyrrole aldehyde
1003-29-8

2-pyrrole aldehyde

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With lithium aluminium tetrahydride87%
Stage #1: 2-pyrrole aldehyde With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;
Stage #2: With water In tetrahydrofuran at 0℃;
77%
With lithium aluminium tetrahydride In tetrahydrofuran75%
ethyl 5-methyl-1H-pyrrole-2-carboxylate
3284-51-3

ethyl 5-methyl-1H-pyrrole-2-carboxylate

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With sodium hydroxide In ethylene glycol at 180 - 185℃; for 6h; Decarboxylation;81%
With phosphoric acid
acetylene
74-86-2

acetylene

acetone oxime
127-06-0

acetone oxime

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

1-vinyl-2-methylpyrrole
57807-64-4

1-vinyl-2-methylpyrrole

C

acetone oxime O-vinyl ether
5883-10-3

acetone oxime O-vinyl ether

Conditions
ConditionsYield
Stage #1: acetone oxime With potassium hydroxide In dimethyl sulfoxide at 110 - 115℃; for 0.0833333h; Metallation;
Stage #2: acetylene In dimethyl sulfoxide at 74℃; for 0.5h; Addition; Cyclisation; Vinylation;
A 8%
B n/a
C 65.9%
With potassium hydroxide In dimethyl sulfoxide at 77℃; for 0.1h; Addition; Cyclisation; Vinylation;A 0.2%
B 12.7%
C 38.2%
(2Z,4Z)-6-Methanesulfonyloxy-3-methyl-hexa-2,4-dienoic acid methyl ester
80288-20-6

(2Z,4Z)-6-Methanesulfonyloxy-3-methyl-hexa-2,4-dienoic acid methyl ester

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide for 20h; Ambient temperature;48%
1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

acetone oxime
127-06-0

acetone oxime

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

1-vinyl-2-methylpyrrole
57807-64-4

1-vinyl-2-methylpyrrole

C

2,9-dimethyl-4,7-dioxa-3,8-diaza-2,8-decadiene
92670-19-4

2,9-dimethyl-4,7-dioxa-3,8-diaza-2,8-decadiene

Conditions
ConditionsYield
In dimethyl sulfoxide at 112 - 125℃; for 3.5h; Product distribution; var. time, var. temperatures;A 30%
B 1%
C 2%
With potassium hydroxide In dimethyl sulfoxide at 115 - 125℃; for 0.5h; Title compound not separated from byproducts;A 24%
B 8%
C 1%
1-(1-Piperidin-1-yl-cyclopropyl)-ethylideneamine
124706-35-0

1-(1-Piperidin-1-yl-cyclopropyl)-ethylideneamine

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With tetrafluoroboric acid dimethyl ether complex In xylene for 0.25h; Heating;10%
acetone
67-64-1

acetone

acetylene
74-86-2

acetylene

acetone oxime
127-06-0

acetone oxime

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

acetone oxime O-vinyl ether
5883-10-3

acetone oxime O-vinyl ether

C

C8H13NO
1169876-90-7

C8H13NO

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 70 - 90℃; Autoclave;A n/a
B n/a
C 7%
propan-2-one oxime; potassium salt
54565-19-4

propan-2-one oxime; potassium salt

acetylene
74-86-2

acetylene

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

1-vinyl-2-methylpyrrole
57807-64-4

1-vinyl-2-methylpyrrole

C

1-(2-methyl-5-pyrrolyl)-1-(1-vinyl-2-methyl-5-pyrrolyl)ethane
119830-62-5

1-(2-methyl-5-pyrrolyl)-1-(1-vinyl-2-methyl-5-pyrrolyl)ethane

D

1,1-di(2-methyl-5-pyrrolyl)ethane
73649-00-0

1,1-di(2-methyl-5-pyrrolyl)ethane

Conditions
ConditionsYield
In dimethyl sulfoxide at 95℃; atmospheric pressure;A n/a
B n/a
C 0.08%
D 0.09%
propan-2-one oxime; potassium salt
54565-19-4

propan-2-one oxime; potassium salt

acetylene
74-86-2

acetylene

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

1-vinyl-2-methylpyrrole
57807-64-4

1-vinyl-2-methylpyrrole

C

1,1-di(2-methyl-5-pyrrolyl)ethane
73649-00-0

1,1-di(2-methyl-5-pyrrolyl)ethane

Conditions
ConditionsYield
In dimethyl sulfoxide at 95℃; atmospheric pressure;A n/a
B n/a
C 0.09%
2-methyl-1-pyrrolidine
765-38-8

2-methyl-1-pyrrolidine

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
leiten ueber ein Gemisch von Titan(IV)-oxid und Aluminiumoxid bei 600grad;
2-methylfuran
534-22-5

2-methylfuran

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With aluminium silicate; ammonia at 450℃;
With aluminium trichloride; ammonia at 450℃;
With aluminum oxide; steam; ammonia at 365 - 400℃;
With ammonium hydroxide; copper; copper(II) oxide at 300℃;
N-Methylpyrrole
96-54-8

N-Methylpyrrole

A

pyridine
110-86-1

pyridine

B

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
beim Destillieren durch ein gluehendes Rohr;
beim Destillieren durch ein schwach gluehendes Rohr;
N-Methylpyrrole
96-54-8

N-Methylpyrrole

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
bei der Destillation durch ein schwach gluehendes Rohr;
Leiten ueber schwach rotgluehende Tonscherben;
N-Methylpyrrole
96-54-8

N-Methylpyrrole

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

3-methylpyrrole
616-43-3

3-methylpyrrole

Conditions
ConditionsYield
at 475 - 575℃; Rate constant; Isomerisierung;
at 826.9℃; under 9880 - 10640 Torr; Rate constant; Mechanism; Product distribution; var. temp.;
2,5-dimethoxy-2-methyl-tetrahydro-furan
58518-63-1

2,5-dimethoxy-2-methyl-tetrahydro-furan

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With aluminium trichloride; ammonia at 250℃;
2-methyl-1H-pyrrole-3-carboxylic acid
37102-48-0

2-methyl-1H-pyrrole-3-carboxylic acid

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
beim Erhitzen ueber den Schmelzpunkt;
pyrrole-2-acetic acid
79673-53-3

pyrrole-2-acetic acid

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
under 70 Torr;
Erhitzen unter vermindertem Druck;
methanol
67-56-1

methanol

pyrrole
109-97-7

pyrrole

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With zinc
2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester
936-12-9

2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With sodium hydroxide; hydrazine hydrate; ethylene glycol at 170℃;
pyrrole-2-carbaldehyde semicarbazone
120445-73-0

pyrrole-2-carbaldehyde semicarbazone

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With potassium hydroxide unter Stickstoff;
5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With aluminium trichloride; ammonia at 350℃;
levulinonitrile
927-56-0

levulinonitrile

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

2-methyl-1-pyrrolidine
765-38-8

2-methyl-1-pyrrolidine

Conditions
ConditionsYield
With cobalt catalyst at 100 - 200℃; under 73550.8 - 147102 Torr; Hydrogenation;
With nickel at 90 - 120℃; under 110326 Torr; Hydrogenation;
4-oxopentanal
626-96-0

4-oxopentanal

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With diethyl ether; ammonia durch trockne Destillation oder Kochen mit verd. Essigsaeure;
pyrrole-1,2-dicarboxylic acid diethyl ester
66202-48-0

pyrrole-1,2-dicarboxylic acid diethyl ester

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With copper oxide-chromium oxide at 200℃; partielle Hydrierung;
bis-(1-pyrrol-2-yl-ethylidene)-hydrazine

bis-(1-pyrrol-2-yl-ethylidene)-hydrazine

sodium methylate
124-41-4

sodium methylate

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
at 200 - 210℃;
2-methylpyrrolidine hydrochloride
54677-53-1

2-methylpyrrolidine hydrochloride

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

Conditions
ConditionsYield
With zinc Erhitzen im Wasserstoffstrom;
Conditions
ConditionsYield
das Ammoniumsalz liefert bei der Destillation;
2-methylfuran
534-22-5

2-methylfuran

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

pyrrole
109-97-7

pyrrole

Conditions
ConditionsYield
With ammonia; zeolite HZSM-5 at 209.9℃; under 760 Torr; for 0.5h; other amines; var. temp. and reaction times;
pyrrole
109-97-7

pyrrole

Methyl fluoride
593-53-3

Methyl fluoride

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

N-Methylpyrrole
96-54-8

N-Methylpyrrole

C

3-methylpyrrole
616-43-3

3-methylpyrrole

Conditions
ConditionsYield
With oxygen; trimethylamine at 37.5℃; Product distribution; Irradiation;A 15 % Chromat.
B 35 % Chromat.
C 50 % Chromat.
pyrrole
109-97-7

pyrrole

dimethylfluoronium ion
64710-12-9

dimethylfluoronium ion

A

2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

B

N-Methylpyrrole
96-54-8

N-Methylpyrrole

C

3-methylpyrrole
616-43-3

3-methylpyrrole

Conditions
ConditionsYield
With oxygen; trimethylamine In gas under 760 Torr; Product distribution; other pressure; gas-phase methylation of pyrrole and N-methylpyrrole, pressure dependence, effect of partial pressure of NMe3, competition experiments in the presence of benzene; methylation by radiolytic CH3ClCH3+ ions; mechanism of methylation;
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

2,3-dihydro-3-methylene-4H-benzopyran-4-one
78115-49-8

2,3-dihydro-3-methylene-4H-benzopyran-4-one

C15H15NO2

C15H15NO2

Conditions
ConditionsYield
With C45H55O4P In chlorobenzene at -15℃; for 12h; Inert atmosphere; enantioselective reaction;99%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

C22H23IN2O2
1227204-45-6

C22H23IN2O2

1-(5-((4-iodophenyl)(5-methyl-1H-pyrrol-2-yl)methyl)-2,4-dimethyl-1H-pyrrol-3-yl)ethanone
1227204-47-8

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

Conditions
ConditionsYield
With acetyl chloride In methanol at -78 - 0℃; Inert atmosphere;98%
With methanol; acetyl chloride at -78 - 0℃; for 1.5h;98%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-hydroxy-1-(thiophen-2-yl)ethyl)phenol

4-(1-hydroxy-1-(thiophen-2-yl)ethyl)phenol

A

(S)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-(thiophen-2-yl)ethyl)phenol

(S)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-(thiophen-2-yl)ethyl)phenol

B

(R)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-(thiophen-2-yl)ethyl)phenol

(R)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-(thiophen-2-yl)ethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve;A 98%
B n/a
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-hydroxy-1-(naphthalen-2-yl)ethyl)phenol

4-(1-hydroxy-1-(naphthalen-2-yl)ethyl)phenol

(R)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-(naphthalen-2-yl)ethyl)phenol

(R)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-(naphthalen-2-yl)ethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;98%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-hydroxy-1-phenylethyl)-2-methylphenol
1190957-91-5

4-(1-hydroxy-1-phenylethyl)-2-methylphenol

(S)-2-methyl-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-phenylethyl)phenol

(S)-2-methyl-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-phenylethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;98%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1-hydroxyethyl)phenol

4-(1-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1-hydroxyethyl)phenol

(R)-4-(1-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

(R)-4-(1-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;98%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

5-methoxy-2-methylene-2,3-dihydro-1H-inden-1-one
474090-21-6

5-methoxy-2-methylene-2,3-dihydro-1H-inden-1-one

C16H17NO2

C16H17NO2

Conditions
ConditionsYield
With C45H55O4P In dichloromethane at -65℃; for 12h; Inert atmosphere; enantioselective reaction;98%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

C20H15F3O3

C20H15F3O3

C25H20F3NO2

C25H20F3NO2

Conditions
ConditionsYield
With (Ra)-4-hydroxy-2,6-bis(2,4,6-tricyclohexylphenyl)dinaphtho-[1,3,2]dioxaphosphepine 4-oxide In 1,2-dichloro-ethane at 20℃; for 48h; enantioselective reaction;98%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

2,6-dimethyl-4-(2,2,2-trifluoro-1-phenylethylidene)cyclohexa-2,5-dienone

2,6-dimethyl-4-(2,2,2-trifluoro-1-phenylethylidene)cyclohexa-2,5-dienone

2,6-dimethyl-4-(2,2,2-trifluoro-1-(5-methyl-1H-pyrrol-2-yl)-1-phenylethyl)phenol

2,6-dimethyl-4-(2,2,2-trifluoro-1-(5-methyl-1H-pyrrol-2-yl)-1-phenylethyl)phenol

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at 20℃; for 0.0333333h;98%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-(4-fluorophenyl)-1-hydroxyethyl)phenol

4-(1-(4-fluorophenyl)-1-hydroxyethyl)phenol

(R)-4-(1-(4-fluorophenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

(R)-4-(1-(4-fluorophenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;97%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

1-(4-Chlorphenyl)-1-(4'-hydroxyphenyl)ethanol

1-(4-Chlorphenyl)-1-(4'-hydroxyphenyl)ethanol

(R)-4-(1-(4-chlorophenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

(R)-4-(1-(4-chlorophenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;97%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(hydroxy-(2-methoxyphenyl)(phenyl)methyl)phenol

4-(hydroxy-(2-methoxyphenyl)(phenyl)methyl)phenol

(R)-4-((2-methoxyphenyl)(5-methyl-1H-pyrrol-2-yl)(phenyl)methyl)phenol

(R)-4-((2-methoxyphenyl)(5-methyl-1H-pyrrol-2-yl)(phenyl)methyl)phenol

Conditions
ConditionsYield
With (Ra)-4-hydroxy-2,6-bis(2,4,6-tricyclohexylphenyl)dinaphtho-[1,3,2]dioxaphosphepine 4-oxide In 1,2-dichloro-ethane at 0℃; for 48h; Green chemistry;97%
With (Ra)-4-hydroxy-2,6-bis(2,4,6-tricyclohexylphenyl)dinaphtho-[1,3,2]dioxaphosphepine 4-oxide In 1,2-dichloro-ethane for 48h; Reagent/catalyst; Solvent; enantioselective reaction;97%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

(E)-3-(4,4,4-trifluorobut-2-enoyl)oxazolidin-2-one
243121-09-7

(E)-3-(4,4,4-trifluorobut-2-enoyl)oxazolidin-2-one

3-[4,4,4-trifluoro-3-(5-methyl-1H-pyrrol-2-yl)butyryl]oxazolidin-2-one

3-[4,4,4-trifluoro-3-(5-methyl-1H-pyrrol-2-yl)butyryl]oxazolidin-2-one

Conditions
ConditionsYield
With bis((1,1,1-trifluoro-N-(trifluoromethyl)sulfonyl)methylsulfonamido)zinc; Ph-dbfox In dichloromethane at -75℃; for 24h; Friedel Crafts alkylation; Inert atmosphere; Molecular sieve; optical yield given as %ee; enantioselective reaction;96%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

(E)-3-(4,4,4-trifluorobut-2-enoyl)oxazolidin-2-one
243121-09-7

(E)-3-(4,4,4-trifluorobut-2-enoyl)oxazolidin-2-one

C12H13F3N2O3
1350661-54-9

C12H13F3N2O3

Conditions
ConditionsYield
With bis((1,1,1-trifluoro-N-(trifluoromethyl)sulfonyl)methylsulfonamido)zinc; (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) In dichloromethane at -75℃; for 24h; Friedel Crafts alkylation; Inert atmosphere; Molecular sieve; optical yield given as %ee; enantioselective reaction;96%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

(E)-3-(4,4,4-trifluorobut-2-enoyl)oxazolidin-2-one
243121-09-7

(E)-3-(4,4,4-trifluorobut-2-enoyl)oxazolidin-2-one

A

C12H13F3N2O3
1350661-54-9

C12H13F3N2O3

B

C12H13F3N2O3

C12H13F3N2O3

Conditions
ConditionsYield
With bis((1,1,1-trifluoro-N-(trifluoromethyl)sulfonyl)methylsulfonamido)zinc; (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) In dichloromethane at -60℃; for 24h; Friedel Crafts alkylation; Inert atmosphere; Molecular sieve; optical yield given as %ee; enantioselective reaction;A 96%
B n/a
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

1-phenyl-2,3-dihydro-1H-indene-1,5-diol

1-phenyl-2,3-dihydro-1H-indene-1,5-diol

A

(S)-1-(5-methyl-1H-pyrrol-2-yl)-1-phenyl-2,3-dihydro-1H-inden-5-ol

(S)-1-(5-methyl-1H-pyrrol-2-yl)-1-phenyl-2,3-dihydro-1H-inden-5-ol

B

(R)-1-(5-methyl-1H-pyrrol-2-yl)-1-phenyl-2,3-dihydro-1H-inden-5-ol

(R)-1-(5-methyl-1H-pyrrol-2-yl)-1-phenyl-2,3-dihydro-1H-inden-5-ol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve;A 96%
B n/a
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-hydroxy-1-phenylpropyl)phenol
80396-08-3

4-(1-hydroxy-1-phenylpropyl)phenol

(S)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-phenylpropyl)phenol

(S)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-phenylpropyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;96%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-(4-methoxyphenyl)vinyl)phenol
92549-05-8

4-(1-(4-methoxyphenyl)vinyl)phenol

(R)-4-(1-(4-methoxyphenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

(R)-4-(1-(4-methoxyphenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;96%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-hydroxy-1-(4-vinylphenyl)ethyl)phenol

4-(1-hydroxy-1-(4-vinylphenyl)ethyl)phenol

(S)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-(4-vinylphenyl)ethyl)phenol

(S)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-(4-vinylphenyl)ethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;96%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

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

1-(2,4-dimethyl-5-((5-methyl-1H-pyrrol-2-yl)(phenyl)methyl)-1H-pyrrol-3-yl)ethanone
1227204-46-7

1-(2,4-dimethyl-5-((5-methyl-1H-pyrrol-2-yl)(phenyl)methyl)-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 1h;95%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

2-(tert-butyl)-4-(1-hydroxy-1-phenylethyl)phenol

2-(tert-butyl)-4-(1-hydroxy-1-phenylethyl)phenol

(S)-2-(tert-butyl)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-phenylethyl)phenol

(S)-2-(tert-butyl)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-phenylethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;95%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(2-hydroxy-4-phenylbut-3-yn-2-yl)phenol

4-(2-hydroxy-4-phenylbut-3-yn-2-yl)phenol

A

(R)-4-(2-(5-methyl-1H-pyrrol-2-yl)-4-phenylbut-3-yn-2-yl)phenol

(R)-4-(2-(5-methyl-1H-pyrrol-2-yl)-4-phenylbut-3-yn-2-yl)phenol

B

(S)-4-(2-(5-methyl-1H-pyrrol-2-yl)-4-phenylbut-3-yn-2-yl)phenol

(S)-4-(2-(5-methyl-1H-pyrrol-2-yl)-4-phenylbut-3-yn-2-yl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve;A 94%
B n/a
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

1-p-hydroxyphenyl-1-phenyl-1-ethanol
126597-34-0

1-p-hydroxyphenyl-1-phenyl-1-ethanol

(S)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-phenylethyl)phenol

(S)-4-(1-(5-methyl-1H-pyrrol-2-yl)-1-phenylethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;94%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-hydroxy-1-(3-methoxyphenyl)ethyl)phenol

4-(1-hydroxy-1-(3-methoxyphenyl)ethyl)phenol

(R)-4-(1-(3-methoxyphenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

(R)-4-(1-(3-methoxyphenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;93%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-(1-(3,5-dimethylphenyl)-1-hydroxyethyl)phenol

4-(1-(3,5-dimethylphenyl)-1-hydroxyethyl)phenol

(R)-4-(1-(3,5-dimethylphenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

(R)-4-(1-(3,5-dimethylphenyl)-1-(5-methyl-1H-pyrrol-2-yl)ethyl)phenol

Conditions
ConditionsYield
With (11aS)-3,7-di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide diindeno[7,1de:10,70-fg][1,3,2] dioxaphosphocin In chloroform at 0 - 20℃; for 48h; Molecular sieve; enantioselective reaction;93%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

(R)-2,2’-dimethoxy-[1,1’-binaphthalene]-3,3’-dicarbaldehyde

(R)-2,2’-dimethoxy-[1,1’-binaphthalene]-3,3’-dicarbaldehyde

C44H38N4O2

C44H38N4O2

Conditions
ConditionsYield
Stage #1: 2-methyl-1H-pyrrole; (1R)-2,2'-dimethoxy[1,1'-binaphthalene]-3,3'-dicarboxaldehyde With trifluoroacetic acid In dichloromethane at 20℃; Darkness;
Stage #2: With chloranil In dichloromethane for 2h;
93%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

1-(2,2,2-trifluoro)-1-(4-bromophenyl)ethylimine
842169-80-6

1-(2,2,2-trifluoro)-1-(4-bromophenyl)ethylimine

(+)-1,1,1-trifluoro-2-{(5-methyl)-2-pyrrolyl}-2-(4-bromophenyl)ethan-2-amine

(+)-1,1,1-trifluoro-2-{(5-methyl)-2-pyrrolyl}-2-(4-bromophenyl)ethan-2-amine

Conditions
ConditionsYield
With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid In toluene at -78℃; for 24h; Friedel-Crafts Alkylation; Inert atmosphere; Molecular sieve; enantioselective reaction;93%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

4-((2-fluoro-4-methoxyphenyl)(hydroxy)(phenyl)methyl)phenol

4-((2-fluoro-4-methoxyphenyl)(hydroxy)(phenyl)methyl)phenol

(R)-4-((2-fluoro-4-methoxyphenyl)-(5-methyl-1H-pyrrol-2-yl)(phenyl)methyl)phenol

(R)-4-((2-fluoro-4-methoxyphenyl)-(5-methyl-1H-pyrrol-2-yl)(phenyl)methyl)phenol

Conditions
ConditionsYield
With (Ra)-4-hydroxy-2,6-bis(2,4,6-tricyclohexylphenyl)dinaphtho-[1,3,2]dioxaphosphepine 4-oxide In 1,2-dichloro-ethane at 20℃; for 48h; Green chemistry;93%
With (Ra)-4-hydroxy-2,6-bis(2,4,6-tricyclohexylphenyl)dinaphtho-[1,3,2]dioxaphosphepine 4-oxide In 1,2-dichloro-ethane for 48h; enantioselective reaction;93%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

C20H17FO3

C20H17FO3

(S)-4-((4-fluorophenyl)-(2-methoxyphenyl)-(5-methyl-1H-pyrrol-2-yl)methyl)phenol

(S)-4-((4-fluorophenyl)-(2-methoxyphenyl)-(5-methyl-1H-pyrrol-2-yl)methyl)phenol

Conditions
ConditionsYield
With (Ra)-4-hydroxy-2,6-bis(2,4,6-tricyclohexylphenyl)dinaphtho-[1,3,2]dioxaphosphepine 4-oxide In 1,2-dichloro-ethane at 0℃; for 48h; Green chemistry;93%
2-methyl-1H-pyrrole
636-41-9

2-methyl-1H-pyrrole

C23H24O3

C23H24O3

C28H29NO2

C28H29NO2

Conditions
ConditionsYield
With (Ra)-4-hydroxy-2,6-bis(2,4,6-tricyclohexylphenyl)dinaphtho-[1,3,2]dioxaphosphepine 4-oxide In 1,2-dichloro-ethane at 0℃; for 48h; enantioselective reaction;93%

636-41-9Relevant articles and documents

-

Patterson,Drenchko

, p. 1650 (1962)

-

Mechanisms of the Au- and Pt-catalyzed intramolecular acetylenic schmidt reactions: A DFT study

Xia, Yuanzhi,Huang, Genping

, p. 7842 - 7854 (2010)

The reaction mechanisms of the PtCl4- and Au(I)-catalyzed intramolecular acetylenic Schmidt reactions were analyzed by means of hybrid density functional calculations at the B3LYP/6-31G*(LANL2DZ) level of theory for better understanding of the

Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols

Antil, Neha,Kumar, Ajay,Akhtar, Naved,Newar, Rajashree,Begum, Wahida,Manna, Kuntal

supporting information, p. 9029 - 9039 (2021/06/28)

Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal-organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2. The single-site cobalt catalyst (DUT-5-CoH) was easily prepared by postsynthetic metalation of the secondary building units (SBUs) of DUT-5 with CoCl2 followed by the reaction of NaEt3BH. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of CoII and AlIII centers in DUT-5-CoH and DUT-5-Co after catalysis. The coordination environment of the cobalt center of DUT-5-Co before and after catalysis was established by extended X-ray fine structure spectroscopy (EXAFS) and density functional theory. The kinetic and computational data suggest reversible carbonyl coordination to cobalt preceding the turnover-limiting step, which involves 1,2-insertion of the coordinated carbonyl into the cobalt-hydride bond. The unique coordination environment of the cobalt ion ligated by oxo-nodes within the porous framework and the rate independency on the pressure of H2 allow the deoxygenation reactions chemoselectively under ambient hydrogen pressure.

Thermal Behavior Analysis of Two Synthesized Flavor Precursors of N-alkylpyrrole Derivatives

Ai, Lvye,Liu, Mengzhen,Ji, Xiaoming,Lai, Miao,Zhao, Mingqin,Ren, Tianbao

, p. 2389 - 2397 (2019/08/01)

To expand the library of pyrrole-containing flavor precursors, two new flavor precursors—methyl N-benzyl-2-methyl-5-formylpyrrole-3-carboxylate (NBMF) and methyl N-butyl-2-methyl-5-formylpyrrole-3-carboxylate (NUMF)—were synthesized by cyclization, oxidation, and alkylation reactions. Thermogravimetry (TG), differential scanning calorimeter, and pyrolysis–gas chromatography/mass spectrometry were utilized to analyze the thermal degradation behavior and thermal degradation products of NBMF and NUMF. The TG-DTG curve indicated that the maximum mass loss rates of NBMF and NUMF appear at 310 and 268°C, respectively. The largest peaks of NBMF and NUMF showed by the differential scanning calorimeter curve were 315 and 274°C, respectively. Pyrolysis–gas chromatography/mass spectrometry detected small molecule fragrance compounds appeared during thermal degradation, such as 2-methylpyrrole, 1-methylpyrrole-2-carboxylic acid methyl ester, limonene, and methyl formate. Finally, the thermal degradation mechanism of NBMF and NUMF was discussed, which provided a theoretical basis for their application in tobacco flavoring additives.

BACKGROUND-FREE FLUORESCENT PROBES FOR LIVE CELL IMAGING

-

Page/Page column 25, (2017/06/24)

BODIPY (boron-dipyrromethene) containing fluorescent compounds for use in live cell intracellular imaging are described. Methods of producing the compounds, methods of labeling tagged organelles, and methods of live cell intracellular imaging using the compounds/probes are described herein.

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