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4-Methylpyrazole

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Name

4-Methylpyrazole

EINECS 231-445-0
CAS No. 7554-65-6 Density 1.062 g/cm3
PSA 28.68000 LogP 0.71810
Solubility soluble Melting Point 13°C
Formula C4H6N2 Boiling Point 243.6 °C at 760 mmHg
Molecular Weight 82.105 Flash Point 96.1 °C
Transport Information UN 2810 Appearance clear colourless to yellowish liquid after melting
Safety 26-36-24/25 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 7554-65-6 (4-Methylpyrazole) Hazard Symbols HarmfulXn
Synonyms

Pyrazole,4-methyl- (6CI,7CI,8CI);4-Methyl-1H-pyrazole;Antizol;Fomepizole;Fomepizolum;

Article Data 19

4-Methylpyrazole Synthetic route

10602-37-6

1,1,3,3-tetraethoxy-2-methyl-propane

7554-65-6

4-methyl-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 1,1,3,3-tetraethoxy-2-methyl-propane With hydrazinium sulfate In water at 80℃; for 3h;
Stage #2: With sodium hydroxide In water at 3 - 30℃; pH=4 - 6;
Stage #3: With sodium hydrogencarbonate In water at 27 - 30℃; pH=7;
84%
Stage #1: 1,1,3,3-tetraethoxy-2-methyl-propane With hydrazinium sulfate In water at 80℃; for 3h;
Stage #2: With sodium hydroxide In water at 3 - 30℃; pH=4 - 6;
Stage #3: With sodium hydrogencarbonate In water at 27℃; pH=7;
84%

4-Methyl-5-trimethylsilanyl-1H-pyrazole

7554-65-6

4-methyl-1H-pyrazole

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Heating;68%
99968-85-1

4-methyl-1H-pyrazole-3,5-dicarboxylic acid

7554-65-6

4-methyl-1H-pyrazole

Conditions
ConditionsYield
bei der trocknen Destillation des Silbersalzes;
82231-51-4

4-methyl-1H-pyrazole-3-carboxylic acid

7554-65-6

4-methyl-1H-pyrazole

Conditions
ConditionsYield
With soda lime Beim Destillieren;

C6H10N2O2

A

7554-65-6

4-methyl-1H-pyrazole

B

820-71-3

methallyl acetate

Conditions
ConditionsYield
With calcium carbonate In 1,4-dioxane at 85 - 110℃; Yield given;
With calcium carbonate In 1,4-dioxane at 85 - 110℃; Yields of byproduct given;

C12H14N2O2

A

7554-65-6

4-methyl-1H-pyrazole

B

128863-93-4

2-methyl-2-propen-1-yl phenylacetate

Conditions
ConditionsYield
With calcium carbonate In 1,4-dioxane at 85 - 110℃; Yield given. Yields of byproduct given;
(+-)-α,β-dibromo-isobutyraldehyde

(+-)-α,β-dibromo-isobutyraldehyde

7554-65-6

4-methyl-1H-pyrazole

Conditions
ConditionsYield
With ethanol; hydrazine hydrate
82231-51-4

4-methyl-1H-pyrazole-3-carboxylic acid

soda lime

soda lime

7554-65-6

4-methyl-1H-pyrazole

30989-81-2

3-amino-2-methyl acrolein

7554-65-6

4-methyl-1H-pyrazole

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride In water at 20 - 80℃; for 4h; Reagent/catalyst; Temperature;82 g
7554-65-6

4-methyl-1H-pyrazole

1072-68-0

1,4-dimethyl-1H-pyrazole

Conditions
ConditionsYield
100%
92.1%
phosphoric acid68%
With sodium hydroxide; dimethyl sulfate
With sulfuric acid In methanol

4-Methylpyrazole Specification

The CAS registry number of 4-Methylpyrazole is 7554-65-6. Its EINECS registry number is 231-445-0. The IUPAC name is 4-methyl-1H-pyrazole. In addition, the molecular formula is C4H6N2 and the molecular weight is 82.10. It is also called pyrazole, 4-methyl-. What's more, it is a kind of clear colourless to yellowish liquid after melting and belongs to the classes of Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines. And it should be stored in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 0.78; (2)ACD/LogD (pH 5.5): 0.77; (3)ACD/LogD (pH 7.4): 0.78; (4)ACD/BCF (pH 5.5): 2.27; (5)ACD/BCF (pH 7.4): 2.29; (6)ACD/KOC (pH 5.5): 62.29; (7)ACD/KOC (pH 7.4): 63.07; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Polar Surface Area: 17.82 Å2; (11)Index of Refraction: 1.523; (12)Molar Refractivity: 23.6 cm3; (13)Molar Volume: 77.2 cm3; (14)Polarizability: 9.35 ×10-24cm3; (15)Surface Tension: 43.7 dyne/cm; (16)Density: 1.062 g/cm3; (17)Flash Point: 96.1 °C; (18)Enthalpy of Vaporization: 46.11 kJ/mol; (19)Boiling Point: 243.6 °C at 760 mmHg; (20)Vapour Pressure: 0.0497 mmHg at 25°C.

Preparation of 4-Methylpyrazole: it can be prepared by 4-methyl-5-trimethylsilanyl-1H-pyrazole. This reaction will need reagent aq. KOH and solvent ethanol. The reaction time is 1 hour by heating. The yield is about 68%.

4-Methylpyrazole can be prepared by 4-methyl-5-trimethylsilanyl-1H-pyrazole.

Uses of 4-Methylpyrazole: it can be used as an antidote in confirmed or suspected methanol or ethylene glycol. It may be used alone or in combination with hemodialysis. In addition, it can react with trichloromethane to get tris(4-methylpyrazol-1-yl)methane. This reaction will need reagents K2CO3 and tetrabutylammonium bromide. The reaction time is 10 hours by heating. The yield is about 40%.

4-Methylpyrazole can react with trichloromethane to get tris(4-methylpyrazol-1-yl)methane

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: n1cc(cn1)C
(2)InChI: InChI=1/C4H6N2/c1-4-2-5-6-3-4/h2-3H,1H3,(H,5,6)
(3)InChIKey: RIKMMFOAQPJVMX-UHFFFAOYAT

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 310mg/kg (310mg/kg)   Experientia. Vol. 28, Pg. 1198, 1972.
mouse LD50 oral 640mg/kg (640mg/kg)   Experientia. Vol. 28, Pg. 1198, 1972.
rat LD50 intravenous 310mg/kg (310mg/kg)   Experientia. Vol. 28, Pg. 1198, 1972.
rat LD50 oral 534mg/kg (534mg/kg)   Experientia. Vol. 28, Pg. 1198, 1972.

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