Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 87% |
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 tetrahydrofuran | 75% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethylene glycol at 180 - 185℃; for 6h; Decarboxylation; | 81% |
With phosphoric acid |
acetylene
acetone oxime
A
2-methyl-1H-pyrrole
B
1-vinyl-2-methylpyrrole
C
acetone oxime O-vinyl ether
Conditions | Yield |
---|---|
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
2-methyl-1H-pyrrole
Conditions | Yield |
---|---|
With sodium azide In N,N-dimethyl-formamide for 20h; Ambient temperature; | 48% |
1,2-dichloro-ethane
acetone oxime
A
2-methyl-1H-pyrrole
B
1-vinyl-2-methylpyrrole
C
2,9-dimethyl-4,7-dioxa-3,8-diaza-2,8-decadiene
Conditions | Yield |
---|---|
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
2-methyl-1H-pyrrole
Conditions | Yield |
---|---|
With tetrafluoroboric acid dimethyl ether complex In xylene for 0.25h; Heating; | 10% |
acetone
acetylene
acetone oxime
A
2-methyl-1H-pyrrole
B
acetone oxime O-vinyl ether
C
C8H13NO
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 70 - 90℃; Autoclave; | A n/a B n/a C 7% |
propan-2-one oxime; potassium salt
acetylene
A
2-methyl-1H-pyrrole
B
1-vinyl-2-methylpyrrole
C
1-(2-methyl-5-pyrrolyl)-1-(1-vinyl-2-methyl-5-pyrrolyl)ethane
D
1,1-di(2-methyl-5-pyrrolyl)ethane
Conditions | Yield |
---|---|
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
acetylene
A
2-methyl-1H-pyrrole
B
1-vinyl-2-methylpyrrole
C
1,1-di(2-methyl-5-pyrrolyl)ethane
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 95℃; atmospheric pressure; | A n/a B n/a C 0.09% |
Conditions | Yield |
---|---|
leiten ueber ein Gemisch von Titan(IV)-oxid und Aluminiumoxid bei 600grad; |
Conditions | Yield |
---|---|
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℃; |
Conditions | Yield |
---|---|
beim Destillieren durch ein gluehendes Rohr; | |
beim Destillieren durch ein schwach gluehendes Rohr; |
Conditions | Yield |
---|---|
bei der Destillation durch ein schwach gluehendes Rohr; | |
Leiten ueber schwach rotgluehende Tonscherben; |
Conditions | Yield |
---|---|
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
2-methyl-1H-pyrrole
Conditions | Yield |
---|---|
With aluminium trichloride; ammonia at 250℃; |
2-methyl-1H-pyrrole-3-carboxylic acid
2-methyl-1H-pyrrole
Conditions | Yield |
---|---|
beim Erhitzen ueber den Schmelzpunkt; |
pyrrole-2-acetic acid
2-methyl-1H-pyrrole
Conditions | Yield |
---|---|
under 70 Torr; | |
Erhitzen unter vermindertem Druck; |
Conditions | Yield |
---|---|
With zinc |
Conditions | Yield |
---|---|
With sodium hydroxide; hydrazine hydrate; ethylene glycol at 170℃; |
pyrrole-2-carbaldehyde semicarbazone
2-methyl-1H-pyrrole
Conditions | Yield |
---|---|
With potassium hydroxide unter Stickstoff; |
Conditions | Yield |
---|---|
With aluminium trichloride; ammonia at 350℃; |
Conditions | Yield |
---|---|
With cobalt catalyst at 100 - 200℃; under 73550.8 - 147102 Torr; Hydrogenation; | |
With nickel at 90 - 120℃; under 110326 Torr; Hydrogenation; |
Conditions | Yield |
---|---|
With diethyl ether; ammonia durch trockne Destillation oder Kochen mit verd. Essigsaeure; |
pyrrole-1,2-dicarboxylic acid diethyl ester
2-methyl-1H-pyrrole
Conditions | Yield |
---|---|
With copper oxide-chromium oxide at 200℃; partielle Hydrierung; |
Conditions | Yield |
---|---|
at 200 - 210℃; |
2-methylpyrrolidine hydrochloride
2-methyl-1H-pyrrole
Conditions | Yield |
---|---|
With zinc Erhitzen im Wasserstoffstrom; |
Conditions | Yield |
---|---|
das Ammoniumsalz liefert bei der Destillation; |
Conditions | Yield |
---|---|
With ammonia; zeolite HZSM-5 at 209.9℃; under 760 Torr; for 0.5h; other amines; var. temp. and reaction times; |
pyrrole
Methyl fluoride
A
2-methyl-1H-pyrrole
B
N-Methylpyrrole
C
3-methylpyrrole
Conditions | Yield |
---|---|
With oxygen; trimethylamine at 37.5℃; Product distribution; Irradiation; | A 15 % Chromat. B 35 % Chromat. C 50 % Chromat. |
pyrrole
dimethylfluoronium ion
A
2-methyl-1H-pyrrole
B
N-Methylpyrrole
C
3-methylpyrrole
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With C45H55O4P In chlorobenzene at -15℃; for 12h; Inert atmosphere; enantioselective reaction; | 99% |
2-methyl-1H-pyrrole
C22H23IN2O2
1-(5-((4-iodophenyl)(5-methyl-1H-pyrrol-2-yl)methyl)-2,4-dimethyl-1H-pyrrol-3-yl)ethanone
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
4-(1-hydroxy-1-phenylethyl)-2-methylphenol
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With C45H55O4P In dichloromethane at -65℃; for 12h; Inert atmosphere; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at 20℃; for 0.0333333h; | 98% |
2-methyl-1H-pyrrole
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
(E)-3-(4,4,4-trifluorobut-2-enoyl)oxazolidin-2-one
Conditions | Yield |
---|---|
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
(E)-3-(4,4,4-trifluorobut-2-enoyl)oxazolidin-2-one
C12H13F3N2O3
Conditions | Yield |
---|---|
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
(E)-3-(4,4,4-trifluorobut-2-enoyl)oxazolidin-2-one
A
C12H13F3N2O3
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
4-(1-hydroxy-1-phenylpropyl)phenol
Conditions | Yield |
---|---|
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
4-(1-(4-methoxyphenyl)vinyl)phenol
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
1-(2,4-dimethyl-5-((5-methyl-1H-pyrrol-2-yl)(phenyl)methyl)-1H-pyrrol-3-yl)ethanone
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
1-p-hydroxyphenyl-1-phenyl-1-ethanol
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
1-(2,2,2-trifluoro)-1-(4-bromophenyl)ethylimine
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
The 1H-Pyrrole, 2-methyl-, with the CAS registry number of 636-41-9, is also known as Methyl pyrrole. Its EINECS registry number is 211-255-4. This chemical's molecular formula is C5H7N and molecular weight is 81.12. What's more, its IUPAC name is 2-Methyl-1H-pyrrole.
Physical properties about the 1H-Pyrrole, 2-methyl- are: (1)ACD/LogP: 1.21; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.21; (4)ACD/LogD (pH 7.4): 1.21; (5)ACD/BCF (pH 5.5): 4.89; (6)ACD/BCF (pH 7.4): 4.89; (7)ACD/KOC (pH 5.5): 108.46; (8)ACD/KOC (pH 7.4): 108.46; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 4.93 Å2; (13)Index of Refraction: 1.519; (14)Molar Refractivity: 25.51 cm3; (15)Molar Volume: 84 cm3; (16)Surface Tension: 35 dyne/cm; (17)Density: 0.965 g/cm3; (18)Flash Point: 47.2 °C; (19)Enthalpy of Vaporization: 36.86 kJ/mol; (20)Boiling Point: 147.5 °C at 760 mmHg; (21)Vapour Pressure: 5.6 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
(1) SMILES: c1(cccn1)C
(2) InChI: InChI=1/C5H7N/c1-5-3-2-4-6-5/h2-4,6H,1H3
(3) InChIKey: TVCXVUHHCUYLGX-UHFFFAOYAZ
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