3-Methyl-4-iodopyrazole supplier

Name
3-Methyl-4-iodopyrazole
EINECS
CAS No. 15802-75-2
Article Data10
CAS DataBase
Density 2.094 g/cm³
Solubility
Melting Point 185-187 °C
Formula C₄H₅IN₂
Boiling Point 292.112 °C at 760 mmHg
Molecular Weight 208.002
Flash Point 130.465 °C
Transport Information
Appearance
Safety
Risk Codes 22
Molecular Structure
Hazard Symbols Xi
Synonyms Pyrazole,4-iodo-3-methyl- (8CI);4-Iodo-3-methyl-1H-pyrazole;
PSA 28.68000
LogP 1.32270

Synthetic route

: 1453-58-3
3-Methylpyrazole

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
With sodium hydroxide; Rodapon N 50; iodine In water at 20℃; for 0.25h;	90%
With ammonium cerium(IV) nitrate; iodine In acetonitrile at 20℃; for 3h;	90%
With dihydrogen peroxide; iodine In water	85.6%
With sodium nitrate; sodium hydrogencarbonate; potassium iodide In chloroform; water at 30℃; Electrolysis;	71%
With water; iodine; sodium acetate; potassium iodide

: 2033-45-6
4-iodo-3,5-dimethyl-1H-pyrazole

A: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

B 4-iodo-pyrazole-carboxylic acid-(3): 4-iodo-pyrazole-carboxylic acid-(3)

Conditions

Conditions	Yield
With sodium hydroxide; potassium permanganate

: 2033-45-6
4-iodo-3,5-dimethyl-1H-pyrazole

potassium permanganate: potassium permanganate

alkali: alkali

A: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

B 4-iodo-pyrazole-carboxylic acid-(3): 4-iodo-pyrazole-carboxylic acid-(3)

...Expand

: 1453-58-3
3-Methylpyrazole

A: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

B: 15802-75-2
3-iodo-2-methyl-1H-pyrazole

Conditions

Conditions	Yield
With iodine; iodic acid In tetrachloromethane; water; acetic acid at 50℃; for 1.5h; Title compound not separated from byproducts.;

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 4,5,8-tris(4-iodo-3-methyl-1H-pyrazol-1-yl)-1,3,7-trimethyl-3,4,5,7-tetrahydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 45℃; for 10h; Inert atmosphere; Electrochemical reaction; Green chemistry; diastereoselective reaction;	97%

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 5334-39-4
3-methyl-4-nitro-1H-pyrazole

Conditions

Conditions	Yield
With nitric acid In tetrahydrofuran at 20℃; for 2h;	92%
With nitric acid In tetrahydrofuran; water at 20℃; for 3h;	73%

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 14047-29-1
4-carboxyphenylboronic acid

: 207726-97-4
2-bromo-5-[4-(6-bromopyridin-3-yl)phenyl]pyridine

: C38H28N6O4

Conditions

Conditions	Yield
Stage #1: 4-iodo-3-methyl-1H-pyrazole; 2-bromo-5-[4-(6-bromopyridin-3-yl)phenyl]pyridine With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: 4-carboxyphenylboronic acid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; potassium carbonate In water; toluene at 100℃; for 24h; Inert atmosphere; Schlenk technique;	77%

Yield

Stage #1: 4-iodo-3-methyl-1H-pyrazole; 2-bromo-5-[4-(6-bromopyridin-3-yl)phenyl]pyridine With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;
Stage #2: 4-carboxyphenylboronic acid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; potassium carbonate In water; toluene at 100℃; for 24h; Inert atmosphere; Schlenk technique;

77%

...Expand

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 292638-85-8
acrylic acid methyl ester

: 1175275-82-7
methyl 3-(4-iodo-1H-pyrazol-1-yl)propanoate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 2h;	77%

: benzene-1,3-dicarboxylic-5-boronic triacid

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 3,6-diiodo-1,2,4,5-tetrazine

: C26H18N8O8

Conditions

Conditions	Yield
Stage #1: 4-iodo-3-methyl-1H-pyrazole; 3,6-diiodo-1,2,4,5-tetrazine With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 18h; Inert atmosphere; Schlenk technique; Stage #2: benzene-1,3-dicarboxylic-5-boronic triacid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; caesium carbonate In water; toluene at 100℃; for 48h; Inert atmosphere; Schlenk technique;	76%

Yield

Stage #1: 4-iodo-3-methyl-1H-pyrazole; 3,6-diiodo-1,2,4,5-tetrazine With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 18h; Inert atmosphere; Schlenk technique;
Stage #2: benzene-1,3-dicarboxylic-5-boronic triacid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; caesium carbonate In water; toluene at 100℃; for 48h; Inert atmosphere; Schlenk technique;

76%

...Expand

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 14047-29-1
4-carboxyphenylboronic acid

: 263012-59-5
4,4'-bis[5-(2-bromopyridyl)]1,1'-biphenyl

: C44H32N6O4

Conditions

Conditions	Yield
Stage #1: 4-iodo-3-methyl-1H-pyrazole; 4,4'-bis[5-(2-bromopyridyl)]1,1'-biphenyl With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 18h; Inert atmosphere; Schlenk technique; Stage #2: 4-carboxyphenylboronic acid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; sodium carbonate In water; toluene at 100℃; for 36h; Inert atmosphere; Schlenk technique;	73%

Yield

Stage #1: 4-iodo-3-methyl-1H-pyrazole; 4,4'-bis[5-(2-bromopyridyl)]1,1'-biphenyl With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 18h; Inert atmosphere; Schlenk technique;
Stage #2: 4-carboxyphenylboronic acid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; sodium carbonate In water; toluene at 100℃; for 36h; Inert atmosphere; Schlenk technique;

73%

...Expand

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 14047-29-1
4-carboxyphenylboronic acid

: C8H4I2N4

: C30H22N8O4

Conditions

Conditions	Yield
Stage #1: 4-iodo-3-methyl-1H-pyrazole; C8H4I2N4 With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: 4-carboxyphenylboronic acid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; sodium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Schlenk technique;	72%

Yield

Stage #1: 4-iodo-3-methyl-1H-pyrazole; C8H4I2N4 With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;
Stage #2: 4-carboxyphenylboronic acid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; sodium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Schlenk technique;

72%

...Expand

: benzene-1,3-dicarboxylic-5-boronic triacid

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 207726-97-4
2-bromo-5-[4-(6-bromopyridin-3-yl)phenyl]pyridine

: C40H28N6O8

Conditions

Conditions	Yield
Stage #1: 4-iodo-3-methyl-1H-pyrazole; 2-bromo-5-[4-(6-bromopyridin-3-yl)phenyl]pyridine With t-BuBrettPhos; potassium tert-butylate; palladium diacetate In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: benzene-1,3-dicarboxylic-5-boronic triacid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; potassium carbonate In 1,4-dioxane at 100℃; for 40h; Inert atmosphere; Schlenk technique;	68%

Yield

Stage #1: 4-iodo-3-methyl-1H-pyrazole; 2-bromo-5-[4-(6-bromopyridin-3-yl)phenyl]pyridine With t-BuBrettPhos; potassium tert-butylate; palladium diacetate In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; Schlenk technique;
Stage #2: benzene-1,3-dicarboxylic-5-boronic triacid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; potassium carbonate In 1,4-dioxane at 100℃; for 40h; Inert atmosphere; Schlenk technique;

68%

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: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 149105-19-1
2-carboxyphenylboronic acid

: 147496-14-8
6,6’-dibromo-3,3’-bipyridine

: C32H24N6O4

Conditions

Conditions	Yield
Stage #1: 4-iodo-3-methyl-1H-pyrazole; 6,6’-dibromo-3,3’-bipyridine With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: 2-carboxyphenylboronic acid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; potassium carbonate In water; toluene at 100℃; for 48h; Inert atmosphere; Schlenk technique;	67%

Yield

Stage #1: 4-iodo-3-methyl-1H-pyrazole; 6,6’-dibromo-3,3’-bipyridine With t-BuBrettPhos; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;
Stage #2: 2-carboxyphenylboronic acid With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; potassium carbonate In water; toluene at 100℃; for 48h; Inert atmosphere; Schlenk technique;

67%

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: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 150-76-5
4-methoxy-phenol

: 2-(4-iodo-3-methyl-1H-pyrazol-1-yl)-4-methoxyphenol

Conditions

Conditions	Yield
With dipotassium peroxodisulfate In acetonitrile at 80℃; for 5h; Inert atmosphere; Schlenk technique;	67%

: 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 8-(4-iodo-3-methyl-1H-pyrazol-1-yl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In dimethyl sulfoxide; acetonitrile at 45℃; for 3h; Inert atmosphere; Electrochemical reaction; Green chemistry;	50%

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 84476-99-3
2,5-difluoropyridine

: C9H7FIN3

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 25 - 90℃; for 6h;	42.89%

: 110-87-2
3,4-dihydro-2H-pyran

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

A: 1072709-33-1
4-iodo-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

B: C9H13IN2O

Conditions

Conditions	Yield
Stage #1: 3,4-dihydro-2H-pyran; 4-iodo-3-methyl-1H-pyrazole With trifluoroacetic acid In tetrahydrofuran at 60℃; for 4h; Stage #2: With water; sodium carbonate In tetrahydrofuran; tert-butyl methyl ether

...Expand

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 253680-54-5
methanesulfonic acid cyclopent-3-enyl ester

A: 1350323-30-6
1-(Cyclopent-3-en-1-yl)-4-iodo-5-methyl-1H-pyrazole

B: 1350323-31-7
1-(Cyclopent-3-en-1-yl)-4-iodo-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
Stage #1: 4-iodo-3-methyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: methanesulfonic acid cyclopent-3-enyl ester In N,N-dimethyl-formamide at 60℃;

...Expand

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 93164-43-3
ethyl (1s,4s)-4-(p-tolylsulfonyloxy)cyclohexanecarboxylate

A: 1350322-91-6
ethyl trans-4-(4-iodo-3-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylate

B: 1350322-93-8
ethyl trans-4-(4-iodo-5-methyl-1H-pyrazol-1-yl)cyclohexanecarboxylate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 80℃; Product distribution / selectivity;

...Expand

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 54314-84-0
1-[(3-bromopropoxy)methyl]-benzene

A: 1380306-11-5
1-[3-(benzyloxy)propyl]-4-iodo-3-methyl-1H-pyrazole

B: 1380306-13-7
1-[3-(benzyloxy)propyl]-4-iodo-5-methyl-1H-pyrazole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;

...Expand

: 872-55-9
2-ethylthiophene

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

A: C10H11IN2S

B: C10H11IN2S

Conditions

Conditions	Yield
With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 12h; Overall yield = 62 %;

...Expand

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: 3993-78-0
2-amino-4-chloropyrimidine

: 4-(4-iodo-3-methyl-1H-pyrazol-1-yl)pyrimidin-2-amine

Conditions

Conditions	Yield
Stage #1: 4-iodo-3-methyl-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: 2-amino-4-chloropyrimidine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;

: 15802-75-2
4-iodo-3-methyl-1H-pyrazole

: (rac)-1-(2,4-bis(trifluoromethyl)phenyl)ethanol

: 1-(1-(2,4-bis(trifluoromethyl)phenyl)ethyl)-4-iodo-3-methyl-1H-pyrazole

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h;	50 mg

3-Methyl-4-iodopyrazole Chemical Properties

Molecular Structure:

Molecular Formula: C₄H₅IN₂
Molecular Weight: 208.0004
IUPAC Name: 4-Iodo-5-methyl-1H-pyrazole
Synonyms of 3-Methyl-4-iodopyrazole (CAS NO.15802-75-2): 4-Iodo-3-methyl-1H-pyrazole ; 4-Lodo-3-methyl pyrazole
CAS NO: 15802-75-2
Index of Refraction: 1.656
Molar Refractivity: 36.509 cm³
Molar Volume: 99.328 cm³
Surface Tension: 58.143 dyne/cm
Density: 2.094 g/cm³
Flash Point: 130.465 °C
Enthalpy of Vaporization: 51.029 kJ/mol
Boiling Point: 292.112 °C at 760 mmHg
Vapour Pressure: 0.003 mmHg at 25°C

3-Methyl-4-iodopyrazole Safety Profile

Hazard Codes of 3-Methyl-4-iodopyrazole (CAS NO.15802-75-2): Irritant Xi

Product Name

3-Methyl-4-iodopyrazole

Synthetic route

3-Methyl-4-iodopyrazole Chemical Properties

3-Methyl-4-iodopyrazole Safety Profile

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