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1-Methylindazole-3-carboxylic acid

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Name

1-Methylindazole-3-carboxylic acid

EINECS 626-233-3
CAS No. 50890-83-0 Density 1.35 g/cm3
PSA 55.12000 LogP 1.27150
Solubility Insoluble in water. Soluble in DMSO and Methanol. Melting Point 213 °C
Formula C9H8N2O2 Boiling Point 383.7 °C at 760 mmHg
Molecular Weight 176.175 Flash Point 185.8 °C
Transport Information N/A Appearance White to light yellow needle crystal
Safety 26-36/37/39-22 Risk Codes 22-36-36/37/38
Molecular Structure Molecular Structure of 50890-83-0 (1-Methylindazole-3-carboxylic acid) Hazard Symbols HarmfulXn
Synonyms

1H -Methylindazole-3-carboxylic acid;1-Methylindazole-3-carboxylic acid (Granisetron int.);1-Methyl-1H-indazole-3-carboxylicacid;3-Carboxy-1-methylindazole;

Article Data 10

1-Methylindazole-3-carboxylic acid Synthetic route

109216-60-6

1-Methyl-1H-indazole-3-carboxylic acid methyl ester

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran Ambient temperature;100%
With sodium hydroxide In tetrahydrofuran at 20℃; for 18h;90%
With hydrogenchloride; sodium hydroxide In tetrahydrofuran68%
4498-67-3

1H-Indazole-3-carboxylic acid

77-78-1

dimethyl sulfate

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 1H-Indazole-3-carboxylic acid With calcium oxide In methanol for 2h; Heating / reflux;
Stage #2: dimethyl sulfate In methanol for 4h; Heating / reflux;
85.6%
Stage #1: 1H-Indazole-3-carboxylic acid With magnesium n-propylate In propan-1-ol for 2h; Heating / reflux;
Stage #2: dimethyl sulfate In propan-1-ol at 20℃; for 5h; Heating / reflux;
83.8%
Stage #1: 1H-Indazole-3-carboxylic acid With magnesium ethylate In propan-1-ol for 2h; Heating / reflux;
Stage #2: dimethyl sulfate In propan-1-ol at 20℃; for 2h; Heating / reflux;
79.2%
Stage #1: 1H-Indazole-3-carboxylic acid With barium(II) oxide In propan-1-ol for 2h; Heating / reflux;
Stage #2: dimethyl sulfate In propan-1-ol at 20℃; for 2h; Heating / reflux;
65.4%

methyl 2-(2-iodophenyl)-2-(2-methylhydrazono)acetate

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: methyl 2-(2-iodophenyl)-2-(2-methylhydrazono)acetate With copper(l) iodide; caesium carbonate; L-proline In dimethyl sulfoxide at 95 - 100℃; for 7h;
Stage #2: With hydrogenchloride In water; toluene pH=2 - 2.5;
84%
4498-67-3

1H-Indazole-3-carboxylic acid

74-88-4

methyl iodide

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 1H-Indazole-3-carboxylic acid With calcium oxide In methanol for 2h; Heating / reflux;
Stage #2: methyl iodide In methanol at 20℃; for 26h; Heating / reflux;
83.8%
With hydrogenchloride; sodium chloride; sodium hydrogencarbonate In dimethyl sulfoxide; mineral oil

methyl 2-(2-chlorophenyl)-2-(2-methylhydrazono)acetate

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: methyl 2-(2-chlorophenyl)-2-(2-methylhydrazono)acetate With copper(l) iodide; caesium carbonate; L-proline In dimethyl sulfoxide at 95 - 100℃; for 7h;
Stage #2: With hydrogenchloride In water; toluene pH=2 - 2.5;
83%

Methyl 2-(2-bromophenyl)-2-(2-methylhydrazono)acetate

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: Methyl 2-(2-bromophenyl)-2-(2-methylhydrazono)acetate With copper(l) iodide; caesium carbonate; L-proline In dimethyl sulfoxide at 95 - 100℃; for 7h;
Stage #2: With hydrogenchloride In water; toluene pH=2 - 2.5;
81%
512-56-1

trimethyl phosphite

4498-67-3

1H-Indazole-3-carboxylic acid

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 1H-Indazole-3-carboxylic acid With magnesium ethylate In propan-1-ol for 2h; Heating / reflux;
Stage #2: trimethyl phosphite In propan-1-ol at 20℃; for 7h; Heating / reflux;
78.3%
31748-44-4

1-methyl-1H-indazole-3-carbonitrile

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride
74-88-4

methyl iodide

4498-68-4

ethyl 1H-indazole-3-carboxylate

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
With sodium methylate Der Methylester entsteht beim nachfolgenden Verseifen und Verestern mit Methanol und konz. Schwefelsaeure und dann man verseift ihn waessr-methylalkoh. Kalilauge;
With sodium methylate und verseifen des entstandenen Esters mit waessr.-methylalkoh. Kalilauge;
1-methyl-indazole-carboxylic acid-(3)-methyl ester

1-methyl-indazole-carboxylic acid-(3)-methyl ester

50890-83-0

1-methyl-1H-indazole-3-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide und verseifen des entstandenen Esters mit waessr.-methylalkoh. Kalilauge;

1-Methylindazole-3-carboxylic acid Specification

The IUPAC name of this chemical is 1-methylindazole-3-carboxylic acid. With the CAS registry number 50890-83-0, it is also named as 1H-Indazole-3-carboxylic acid, 1-methyl-. The product's categories are Acids and Derivatives; Heterocycles; Indoles and Derivatives; Pharmacetical; Carboxylic Acids; Benzene Derivates; Organic Acids; Carboxylic Acids; Fused Ring Systems; Building Blocks; Heterocyclic Building Blocks; Indazoles. It is white to light yellow needle crystal which should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.61; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 2.49; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.653; (11)Molar Refractivity: 47.44 cm3; (12)Molar Volume: 129.5 cm3; (13)Polarizability: 18.81×10-24 cm3; (14)Surface Tension: 53.1 dyne/cm; (15)Enthalpy of Vaporization: 66.69 kJ/mol; (16)Vapour Pressure: 1.42E-06 mmHg at 25°C; (17)Rotatable Bond Count: 1; (18)Exact Mass: 176.058578; (19)MonoIsotopic Mass: 176.058578; (20)Topological Polar Surface Area: 55.1; (21)Heavy Atom Count: 13; (22)Complexity: 220.

Preparation of 1-Methylindazole-3-carboxylic acid: It can be obtained by 1-methyl-1H-indazole-3-carboxylic acid methyl ester. This reaction needs reagent 1N NaOH and solvent tetrahydrofuran at ambient temperature. The yield is 100%.

Uses of 1-Methylindazole-3-carboxylic acid: It can be used as the intermediate of drug Granisetron. It also can react with 1-benzyl-4-methyl-[1,4]diazepan-6-ylamine to get 1-methyl-1H-indazole-3-carboxylic acid (1-benzyl-4-methyl-[1,4]diazepan-6-yl)-amide. This reaction needs reagent 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride and solvent CH2Cl2 at ambient temperature. The reaction time is 5 hours. The yield is 46%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe vapour. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)c2nn(c1ccccc12)C
2. InChI:InChI=1/C9H8N2O2/c1-11-7-5-3-2-4-6(7)8(10-11)9(12)13/h2-5H,1H3,(H,12,13)
3. InChIKey:OVVDFORZEGKEJM-UHFFFAOYAK

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