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4-Methoxy-1H-indazol-3-amine is an organic compound with the chemical formula C8H10N2O. It is a derivative of indazole, a fused heterocyclic compound consisting of a benzene ring attached to a pyrazole ring. The presence of a methoxy group at the 4-position and an amino group at the 3-position of the indazole core provides unique chemical and biological properties to this molecule.

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  • 886362-07-8 Structure
  • Basic information

    1. Product Name: 4-METHOXY-1H-INDAZOL-3-AMINE
    2. Synonyms: 4-METHOXY-1H-INDAZOL-3-AMINE;1H-Indazol-3-aMine, 4-Methoxy-;4-(Methyloxy)-1H-indazol-3-amine;4-Methoxy-1H-indazol-3-ylamine
    3. CAS NO:886362-07-8
    4. Molecular Formula: C8H9N3O
    5. Molecular Weight: 163.18
    6. EINECS: 200-528-9
    7. Product Categories: Amines;Building Blocks;C8;Chemical Synthesis;Ethers;Nitrogen Compounds;Organic Building Blocks;Oxygen Compounds
    8. Mol File: 886362-07-8.mol
  • Chemical Properties

    1. Melting Point: 85-87°C
    2. Boiling Point: 406.3 °C at 760 mmHg
    3. Flash Point: 199.5 °C
    4. Appearance: /
    5. Density: 1.344
    6. Vapor Pressure: 8.21E-07mmHg at 25°C
    7. Refractive Index: 1.712
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 15.19±0.40(Predicted)
    11. CAS DataBase Reference: 4-METHOXY-1H-INDAZOL-3-AMINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-METHOXY-1H-INDAZOL-3-AMINE(886362-07-8)
    13. EPA Substance Registry System: 4-METHOXY-1H-INDAZOL-3-AMINE(886362-07-8)
  • Safety Data

    1. Hazard Codes: Xi,Xn
    2. Statements: 22
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 886362-07-8(Hazardous Substances Data)

886362-07-8 Usage

Uses

Used in Pharmaceutical Industry:
4-Methoxy-1H-indazol-3-amine is used as a reactant in the preparation and structure-activity relationship of indazole arylsulfonamides. These compounds serve as allosteric CC-chemokine receptor 4 (CCR4) antagonists, which are important in the development of drugs targeting inflammatory and immune-related disorders. By modulating the activity of CCR4, indazole arylsulfonamides can potentially be used to treat various diseases, such as autoimmune diseases, allergies, and certain types of cancer, where the CCR4 receptor plays a significant role in the pathophysiology of the condition.

Synthesis

A mixture of 2-fluoro-6-(methyloxy)benzonitrile (8a) (10 g, 66 mmol) and hydrazine hydrate (9.63 mL, 198 mmol) in n-butanol (100 mL) was heated to reflux under nitrogen for 18 h. The reaction mixture was allowed to cool, water (300 mL) was added and the organic phase was removed. The solid in the aqueous phase was collected by filtration and dried in vacuo at 40 °C to give a white solid (0.6 g). The butanol phase was evaporated in vacuo and the residue and the aqueous mother liquors were combined and extracted using ethyl acetate (2 × 200 mL). The combined ethyl acetate extractions were dried (MgSO4) and evaporated in vacuo. The residue was dissolved in DCM and applied to a 100 g silica cartridge. This was eluted with cyclohexane (500 mL), cyclohexane ethyl acetate (1:1, 500 mL) and ethyl acetate (500 mL). The required fractions were combined and evaporated in vacuo to give 9a (9.92 g, 92%) as an off-white solid. MS ES + ve m/z 164 (M + H)+. 1H NMR δ (DMSO-d6) 11.35 (1H, s), 7.10 (1H, t, J = 8 Hz), 6.76 (1H, d, J = 8 Hz), 6.29 (1H, d, J = 8 Hz), 4.95 (2H, br s), 3.85 (3H, s).

Check Digit Verification of cas no

The CAS Registry Mumber 886362-07-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,8,6,3,6 and 2 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 886362-07:
(8*8)+(7*8)+(6*6)+(5*3)+(4*6)+(3*2)+(2*0)+(1*7)=208
208 % 10 = 8
So 886362-07-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H9N3O/c1-12-6-4-2-3-5-7(6)8(9)11-10-5/h2-4H,1H3,(H3,9,10,11)

886362-07-8 Well-known Company Product Price

  • Brand
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  • Alfa Aesar

  • (H33750)  3-Amino-4-methoxy-1H-indazole, 97%   

  • 886362-07-8

  • 250mg

  • 464.0CNY

  • Detail
  • Alfa Aesar

  • (H33750)  3-Amino-4-methoxy-1H-indazole, 97%   

  • 886362-07-8

  • 1g

  • 1288.0CNY

  • Detail
  • Alfa Aesar

  • (H33750)  3-Amino-4-methoxy-1H-indazole, 97%   

  • 886362-07-8

  • 5g

  • 4298.0CNY

  • Detail

886362-07-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methoxy-1H-indazol-3-amine

1.2 Other means of identification

Product number -
Other names 4-(methyloxy)-1H-indazol-3-amine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:886362-07-8 SDS

886362-07-8Relevant articles and documents

COMPOUND, PREPARATION METHOD THEREFOR, AND USE THEREOF

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Paragraph 0047-0048, (2021/03/19)

The present disclosure provides a compound of formula I or a pharmaceutically acceptable salt, a solvate, or a prodrug thereof, wherein M is a monovalent alkali metal. The present disclosure also provides a method for preparing the compound or its pharmaceutically acceptable salt, solvate, or prodrug, and further provides a pharmaceutical composition containing the compound and its use in the preparation of a medicine, which can be used for the treatment of CCR4-mediated diseases.

Synthesis and structure-activity relationships of indazole arylsulfonamides as allosteric CC-chemokine receptor 4 (CCR4) antagonists

Procopiou, Panayiotis A.,Barrett, John W.,Barton, Nicholas P.,Begg, Malcolm,Clapham, David,Copley, Royston C. B.,Ford, Alison J.,Graves, Rebecca H.,Hall, David A.,Hancock, Ashley P.,Hill, Alan P.,Hobbs, Heather,Hodgson, Simon T.,Jumeaux, Coline,Lacroix, Yannick M. L.,Miah, Afjal H.,Morriss, Karen M. L.,Needham, Deborah,Sheriff, Emma B.,Slack, Robert J.,Smith, Claire E.,Sollis, Steven L.,Staton, Hugo

, p. 1946 - 1960 (2013/05/09)

A series of indazole arylsulfonamides were synthesized and examined as human CCR4 antagonists. Methoxy- or hydroxyl- containing groups were the more potent indazole C4 substituents. Only small groups were tolerated at C5, C6, or C7, with the C6 analogues being preferred. The most potent N3-substituent was 5-chlorothiophene-2-sulfonamide. N1 meta-substituted benzyl groups possessing an α-amino-3-[(methylamino)acyl]- group were the most potent N1-substituents. Strongly basic amino groups had low oral absorption in vivo. Less basic analogues, such as morpholines, had good oral absorption; however, they also had high clearance. The most potent compound with high absorption in two species was analogue 6 (GSK2239633A), which was selected for further development. Aryl sulfonamide antagonists bind to CCR4 at an intracellular allosteric site denoted site II. X-ray diffraction studies on two indazole sulfonamide fragments suggested the presence of an important intramolecular interaction in the active conformation.

INDAZOLE COMPOUNDS

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Page/Page column 31, (2012/03/26)

Indazole compounds, processes for their preparation, pharmaceutical compositions containing such compounds and their use in therapy.

CC.CHEMOKINE RECEPTOR 4 ANTAGONISTS

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Page/Page column 32-33, (2012/03/26)

Indazole compounds, processes for their preparation, pharmaceutical compositions containina such compounds and their use in the treatment of a disease or condition for which a CCR4 receptor antagonist is indicated.

Lead optimisation of the N1 substituent of a novel series of indazole arylsulfonamides as CCR4 antagonists and identification of a candidate for clinical investigation

Procopiou, Panayiotis A.,Ford, Alison J.,Graves, Rebecca H.,Hall, David A.,Hodgson, Simon T.,Lacroix, Yannick M.L.,Needham, Deborah,Slack, Robert J.

scheme or table, p. 2730 - 2733 (2012/05/31)

Synthesis and preliminary SAR of the N1 substituent of a novel series of indazole sulfonamide chemokine receptor 4 (CCR4) antagonist is reported. Compound 7r was identified for further development.

3-[(Imidazolidin-2-yl)imino]indazole ligands with selectivity for the α2-adrenoceptor compared to the imidazoline I1 receptor

Sczewski, Franciszek,Kornicka, Anita,Hudson, Alan L.,Laird, Shayna,Scheinin, Mika,Laurila, Jonne M.,Rybczyńska, Apolonia,Boblewski, Konrad,Lehmann, Artur,Gdaniec, Maria

experimental part, p. 321 - 329 (2011/02/26)

A series of 3-[(4,5-dihydroimidazolidin-2-yl)imino]indazoles has been synthesized as positional analogues of marsanidine, a highly selective α2-adrenoceptor ligand. Parent compound 4a and its 4-chloro (4c) and 4-methyl (4d) derivatives display α2-adrenoceptor affinity at nanomolar concentrations (Ki = 39.4, 15.9 and 22.6 nM, respectively) and relatively high α2/I1 selectivity ratios of 82, 115 and 690, respectively. Evidence was obtained that these compounds act as partial agonists at α2A-adrenoceptors. Compound 4d with intrinsic activity comparable with that of marsanidine, but lower than that of clonidine, elicited pronounced cardiovascular effects in anesthetized rats at doses as low as 0.01 mg/kg iv.

INDAZOLYL-PYRIMIDINES AS KINASE INHIBITORS

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Page/Page column 64, (2011/10/13)

Disclosed are compounds having the formula: or a salt thereof, wherein A, n, R1, R1A, and R2 are as defined herein, and methods of making and using the same.

NOVEL COMPOUNDS

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Page/Page column 13, (2010/09/05)

Indazole compounds, processes for their preparation, intermediates usable in these processes, pharmaceutical compositions containing such compounds and their use in therapy.

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