1H-Pyrrole-2-carboxaldehyde,5-methyl- supplier

Name
5-METHYL-1H-PYRROLE-2-CARBALDEHYDE
EINECS
CAS No. 1192-79-6
Article Data30
CAS DataBase
Density 1.14 g/cm³
Solubility
Melting Point 68 °C
Formula C₆H₇NO
Boiling Point 226.1 °C at 760 mmHg
Molecular Weight 109.128
Flash Point 95.8 °C
Transport Information
Appearance
Safety 26
Risk Codes 36
Molecular Structure
Hazard Symbols
Synonyms 5-Methyl-2-formylpyrrole;
PSA 32.86000
LogP 1.13560

Synthetic route

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

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
With trichlorophosphate	70%
With trichlorophosphate In 1,2-dichloro-ethane 1) 0 deg C, 1 h, 2) up to r.t., 3) reflux, 30 min;	64.5%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In 1,2-dichloro-ethane at 0 - 20℃; for 0.25h; Stage #2: 2-methyl-1H-pyrrole In 1,2-dichloro-ethane at 0 - 80℃; for 0.5h; Stage #3: With water; sodium acetate In 1,2-dichloro-ethane at 80℃; for 0.333333h;	56%
With trichlorophosphate 1.)from 0 deg C to 20 deg C, 15 min; 2.)ethylene chloride, ethylene dichloride, 15 min, reflux; Yield given. Multistep reaction;
With trichlorophosphate In 1,2-dichloro-ethane

: 124647-46-7
N-(hydroxy-2' ethyl) amino-3 butene-2 oate d'ethyle

A: 1192-79-6
formyl-2 methyl-5 pyrrole

B: 17619-39-5
2-methyl-1H-pyrrole-3-carbaldehyde

C: 124647-59-2
formyl-1 methyl-2 pyrrole

Conditions

Conditions	Yield
In tetrahydrofuran at 400℃; sealed tube;	A 30% B 23% C 9%
In tetrahydrofuran at 400℃; sealed tube;	A n/a B 23% C n/a
In tetrahydrofuran at 400℃; sealed tube;	A n/a B n/a C 9%

...Expand

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

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.333333h; Stage #2: 2-methyl-1H-pyrrole In 1,2-dichloro-ethane for 0.25h; Heating / reflux; Stage #3: With sodium acetate In 1,2-dichloro-ethane at 80℃; for 0.333333h;	18%

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

: 60-29-7
diethyl ether

: 925-90-6
ethylmagnesium bromide

: 109-94-4
formic acid ethyl ester

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield

...Expand

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

: 109-94-4
formic acid ethyl ester

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
With diethyl ether; ethylmagnesium bromide

: 4205-23-6
D-gulose

: 56-40-6
glycine

A: 1192-79-6
formyl-2 methyl-5 pyrrole

B: 1121-78-4
5-Hydroxy-2-methylpyridine

C: 1121-25-1
2-methyl-3-pyridinol

D: 1072-83-9
2-Acetylpyrrole

Conditions

Conditions	Yield
In water at 100℃; for 24h; Product distribution; pH 2.0; other pH; times;

...Expand

: 4134-97-8, 30382-30-0, 50455-94-2, 82399-12-0, 4084-27-9
3-deoxyglucosone

: 56-40-6
glycine

A: 1192-79-6
formyl-2 methyl-5 pyrrole

B: 1121-78-4
5-Hydroxy-2-methylpyridine

C: 1121-25-1
2-methyl-3-pyridinol

Conditions

Conditions	Yield
In water at 100℃; for 24h; Product distribution; pH 3.0;

...Expand

: 4429-05-4
N-(1-deoxy-D-fructos-1-yl)-L-glycine

: 56-40-6
glycine

A: 1192-79-6
formyl-2 methyl-5 pyrrole

B: 1121-78-4
5-Hydroxy-2-methylpyridine

C: 1121-25-1
2-methyl-3-pyridinol

D: 1072-83-9
2-Acetylpyrrole

Conditions

Conditions	Yield
In water at 100℃; for 24h; Product distribution; pH 3.0;

...Expand

: 64435-30-9
N5,N5,N10,N10-tetramethyl-5,10-dihydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-diamine

: 77-78-1
dimethyl sulfate

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 64435-30-9
N5,N5,N10,N10-tetramethyl-5,10-dihydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-diamine

: 74-88-4
methyl iodide

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 6-(diisopropylamino)-2-lithio-1-azafulvene

: 74-88-4
methyl iodide

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
With sodium acetate 1) from -78 deg C to RT; 2) water, 15 h, reflux; Yield given. Multistep reaction;

: 2280-44-6
D-Glucose

A: 98-00-0
(2-furyl)methyl alcohol

B: 1192-79-6
formyl-2 methyl-5 pyrrole

C: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

D: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

E: 1072-83-9
2-Acetylpyrrole

Conditions

Conditions	Yield
With L-Lysine hydrochloride; sodium hydrogencarbonate In water at 75℃; for 24h; Product distribution; pH 6.5; other times;

...Expand

: 121643-36-5
2-Bromo-6-diisopropylamino-1-azafulvene

: 74-88-4
methyl iodide

A: 1192-79-6
formyl-2 methyl-5 pyrrole

B: 1-(5-Bromo-1H-pyrrol-2-yl)-2,2-dimethyl-propan-1-ol

Conditions

Conditions	Yield
With tert.-butyl lithium; sodium acetate Yield given. Multistep reaction;

...Expand

2-methyl-5-formyl-pyrrole-carboxylic acid-(3): 2-methyl-5-formyl-pyrrole-carboxylic acid-(3)

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
at 220℃; unter vermindertem Druck;

: methyl-(5-formyl-1H-pyrrole-2-yl)-4-benzyloxybutyrate

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal

: 1003-29-8
2-pyrrole aldehyde

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / LiAlH4 / tetrahydrofuran 2: 70 percent / POCl3 View Scheme
Multi-step reaction with 2 steps 1: 74 percent / LiAlH4 / tetrahydrofuran / 36 h / Heating 2: 64.5 percent / POCl3 / 1,2-dichloro-ethane / 1) 0 deg C, 1 h, 2) up to r.t., 3) reflux, 30 min View Scheme
Multi-step reaction with 2 steps 1: 68 percent / H2O / 3 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 68 percent / H2O / 3 h / Ambient temperature View Scheme

: 67350-50-9
5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 34 percent / N,N'-carbonyldiimidazole; NaH / dimethylformamide / 40 °C 2: H2 / Pd/C View Scheme

: 121643-34-3
N,N-Diisopropylpyrrole-2-formiminium chloride

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / acetonitrile 2: 1) NBS; 2) 0.5 N HCl, NaOH / 1) THF, -78 deg C; 2) MeOH, 20 min 3: -78 °C 4: 2) NaOAc / 1) from -78 deg C to RT; 2) water, 15 h, reflux View Scheme
Multi-step reaction with 4 steps 1: 74 percent / acetonitrile 2: 1) NBS; 2) 0.5 N HCl, NaOH / 1) THF, -78 deg C; 2) MeOH, 20 min 3: t-BuLi / -78 °C 4: 2) NaOAc / 1) from -78 deg C to RT; 2) water, 15 h, reflux View Scheme

: 2-bromo-6-(diisopropylamino)-1-azafulvene

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: -78 °C 2: 2) NaOAc / 1) from -78 deg C to RT; 2) water, 15 h, reflux View Scheme
Multi-step reaction with 2 steps 1: t-BuLi / -78 °C 2: 2) NaOAc / 1) from -78 deg C to RT; 2) water, 15 h, reflux View Scheme

: Diisopropylamino-(2H-pyrrol-2-yl)-acetonitrile

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) NBS; 2) 0.5 N HCl, NaOH / 1) THF, -78 deg C; 2) MeOH, 20 min 2: -78 °C 3: 2) NaOAc / 1) from -78 deg C to RT; 2) water, 15 h, reflux View Scheme
Multi-step reaction with 3 steps 1: 1) NBS; 2) 0.5 N HCl, NaOH / 1) THF, -78 deg C; 2) MeOH, 20 min 2: t-BuLi / -78 °C 3: 2) NaOAc / 1) from -78 deg C to RT; 2) water, 15 h, reflux View Scheme

: C16H24N4

: 1192-79-6
formyl-2 methyl-5 pyrrole

Conditions

Conditions	Yield
With water; sodium hydrogencarbonate In tetrahydrofuran; pentane at 80℃; for 15h;	156 mg

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 69778-83-2
4-methoxy-3-pyrrolin-2-one

: 4-methoxy-5-(5-methyl-1H-pyrrol-2-ylmethylidene)-1,5-dihydropyrrol-2-one

Conditions

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 60℃; for 20h;	97%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 24424-99-5
di-tert-butyl dicarbonate

: 276239-45-3
5-methyl-2-formyl-N-(tert-butoxycarbonyl)pyrrole

Conditions

Conditions	Yield
Stage #1: formyl-2 methyl-5 pyrrole With sodium hydride In tetrahydrofuran at 20℃; for 1h; Metallation; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 1h; Addition; Further stages.;	95%
dmap In acetonitrile at 0 - 25℃;	94%
With dmap In tetrahydrofuran at 0 - 23℃; Inert atmosphere;	91%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 2-(2-ethoxycarbonylvinyl)-5-methylpyrrole

Conditions

Conditions	Yield
In xylene for 12h; Heating;	93%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 19472-74-3
2-(2-bromophenyl)acetonitrile

: 1-methylpyrrolo[1,2-a]quinoline-5-carbonitrile

Conditions

Conditions	Yield
With potassium phosphate In dimethyl sulfoxide at 130℃; for 24h; Inert atmosphere;	93%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 74-88-4
methyl iodide

: 1193-59-5
1,5-dimethyl-1H-pyrrole-2-carbaldehyde

Conditions

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 25℃;	90%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 2856-63-5
2-Chlorophenylacetonitrile

: 1-methylpyrrolo[1,2-a]quinoline-5-carbonitrile

Conditions

Conditions	Yield
With potassium phosphate In dimethyl sulfoxide at 130℃; for 24h; Inert atmosphere;	81%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 38622-91-2, 36635-61-7
[(p-methylphenyl)sulfonylmethyl]isonitrile

: 179928-16-6
7-methyl-3-tosylpyrrolo[1,2-c]pyrimidine

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 2h; Ambient temperature;	76%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 5697-44-9
p-tolylsulfonylmethyl isocyanide

: 179928-16-6
7-methyl-3-tosylpyrrolo[1,2-c]pyrimidine

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 12h; Cycloaddition;	76%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 108-24-7
acetic anhydride

: 5971-77-7
4-acetyl-5-methyl-1H-pyrrole-2-carbaldehyde

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane for 8h; Ambient temperature;	72%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 40400-15-5
2-(2-iodophenyl)acetonitrile

: 1-methylpyrrolo[1,2-a]quinoline-5-carbonitrile

Conditions

Conditions	Yield
With potassium phosphate In dimethyl sulfoxide at 130℃; for 24h; Inert atmosphere;	72%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 310430-92-3
1-amino-5-methyl-1H-pyrrole-2-carbonitrile

Conditions

Conditions	Yield
Stage #1: formyl-2 methyl-5 pyrrole With mesitylenesulfonylhydroxylamine In N,N-dimethyl-formamide Stage #2: With sodium hydride In dichloromethane	65%
Stage #1: formyl-2 methyl-5 pyrrole With mesitylenesulfonylhydroxylamine In dichloromethane for 0.5h; Stage #2: With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 1.5h;	65%
With potassium hydroxide; hydroxylamine-O-sulfonic acid In water at 0 - 20℃; for 5.5h;	14%

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

: 1192-79-6
formyl-2 methyl-5 pyrrole

: dipyrrylmethene hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether for 0.0833333h;	62%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 292638-84-7
styrene

: 609-36-9
rac-Pro-OH

: 3-methyl-12-phenyl-7,8-dihydro-5H,6H,10H-5a,10-ethanodipyrrolo[1,2-a:1',2'-d]pyrazin-5-one

Conditions

Conditions	Yield
With acetic acid at 110℃; for 6h; Inert atmosphere; Sealed tube; Green chemistry;	57%

...Expand

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 3949-36-8
3-acetylcoumarin

: 1217814-66-8
3-(3-(5-methyl-1H-pyrrol-2-yl)acryloyl)-2H-chromen-2-one

Conditions

Conditions	Yield
With piperidine at 140℃; for 0.0416667h; Microwave irradiation;	50.1%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: o-xylenebis(triphenylphosphonium bromide)

A: 5,5'-dimethyl-2,2'-(o-phenylenedivinylene)dipyrrole

B: trans-5-methyl-2-(2-methylstyryl)pyrrole

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 20℃; for 144h;	A n/a B 50%

...Expand

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 336-64-1
bis(heptafluorobutyryl) peroxide

: 123825-55-8
3-heptafluoro-5-methylpyrrole-2-carbaldehyde

Conditions

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane Ambient temperature; further temperature, further solvent;	48%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 1194-02-1
4-fluorobenzonitrile

: 4-(2-formyl-5-methyl-1H-pyrrol-1-yl)benzonitrile

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃;	45%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 754-34-7
1,1,1,2,2,3,3-heptafluoro-3-iodo-propane

: 123825-55-8
3-heptafluoro-5-methylpyrrole-2-carbaldehyde

Conditions

Conditions	Yield
With dihydrogen peroxide; iron(II) sulfate In dimethyl sulfoxide for 0.5h; Ambient temperature;	36%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 1313014-23-1
(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine

: 1313014-09-3
N-(5-methyl-1H-pyrrol-2-ylmethylene)-N-(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 3h;	33%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran]

: 1-((5-methyl-1H-pyrrol-2-yl)methyl)-6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran] hydrochloride

Conditions

Conditions	Yield
Stage #1: formyl-2 methyl-5 pyrrole; 6',7'-dihydrospiro[piperidine-4,4'-thieno[3,2-c]pyran] at 20℃; Stage #2: Stage #3: With hydrogenchloride In diethyl ether; dichloromethane at 20℃; for 0.333333h;	33%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 108-24-7
acetic anhydride

: 144147-06-8
1-acetyl-5-methylpyrrole-2-carbaldehyde

Conditions

Conditions	Yield
With sodium acetate for 2h; Heating;	31%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 2627-86-3
(S)-1-phenyl-ethylamine

: 2-methyl-5-((L-(-)-α-methylbenzyl)aldimino)pyrrole

Conditions

Conditions	Yield
With magnesium sulfate In toluene at 20℃; Inert atmosphere;	25%

: 1192-79-6
formyl-2 methyl-5 pyrrole

: 77-78-1
dimethyl sulfate

: 1193-59-5
1,5-dimethyl-1H-pyrrole-2-carbaldehyde

Conditions

Conditions	Yield
With ethanol; sodium 1.) toluene, heating, 2.) toluene, reflux, 3 h; Multistep reaction;

1H-Pyrrole-2-carboxaldehyde,5-methyl- Specification

The 1H-Pyrrole-2-carboxaldehyde,5-methyl-, with the CAS registry number 1192-79-6, is also known as 5-Methyl-2-formylpyrrole. This chemical's molecular formula is C₆H₇NO and molecular weight is 109.1259. What's more, its systematic name is called 5-Methyl-1H-pyrrole-2-carbaldehyde.

Physical properties about this chemical are: (1)ACD/LogP: 1.10; (2)#of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.1; (4)ACD/LogD (pH 7.4): 1.1; (5)ACD/BCF (pH 5.5): 4.05; (6)ACD/BCF (pH 7.4): 4.05; (7)ACD/KOC (pH 5.5): 94.7; (8)ACD/KOC (pH 7.4): 94.7; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 22 Å²; (13)Index of Refraction: 1.589; (14)Molar Refractivity: 32.26 cm³; (15)Molar Volume: 95.6 cm³; (16)Polarizability: 12.79×10^-24 cm³; (17)Surface Tension: 46.2 dyne/cm; (18)Density: 1.14 g/cm³; (19)Flash Point: 95.8 °C; (20)Enthalpy of Vaporization: 46.26 kJ/mol; (21)Boiling Point: 226.1 °C at 760 mmHg; (22)Vapour Pressure: 0.0835 mmHg at 25 °C.

Preparation of 1H-Pyrrole-2-carboxaldehyde,5-methyl-: this chemical can be prepared by 2-Methyl-pyrrole and N,N-Dimethyl-formamide.

1H-Pyrrole-2-carboxaldehyde,5-methyl- can be prepared by 2-Methyl-pyrrole and N,N-Dimethyl-formamide.

This reaction needs reagent POCl₃ and solvent 1,2-Dichloro-ethane at temperature of 0 °C. The reaction time is 1 hour. The yield is 64.5%.

Uses of 1H-Pyrrole-2-carboxaldehyde,5-methyl-: it is used to produce other chemicals. For example, it is used to produce 1-Acetyl-5-methylpyrrole-2-carbaldehyde.

1H-Pyrrole-2-carboxaldehyde,5-methyl- is used to produce 1-Acetyl-5-methylpyrrole-2-carbaldehyde

The reaction occurs with reagent Sodium acetate and other condition of heating for 2 hours. The yield is 31%.

You can still convert the following datas into molecular structure:
(1) SMILES: O=Cc1ccc(n1)C
(2) InChI: InChI=1/C6H7NO/c1-5-2-3-6(4-8)7-5/h2-4,7H,1H3
(3) InChIKey: LFWLUDLUCDRDAF-UHFFFAOYAU

Product Name

5-METHYL-1H-PYRROLE-2-CARBALDEHYDE

Synthetic route

1H-Pyrrole-2-carboxaldehyde,5-methyl- Specification

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