2-chloro-6,7-dimethoxyquinazolin-4-amine

• ChemBase ID: 34677
• Molecular Formular: C10H10ClN3O2
• Molecular Mass: 239.6583
• Monoisotopic Mass: 239.04615426
• SMILES: n1c(c2c(nc1Cl)cc(c(c2)OC)OC)N
• Canonical SMILES: COc1cc2nc(Cl)nc(c2cc1OC)N
• InChI: InChI=1S/C10H10ClN3O2/c1-15-7-3-5-6(4-8(7)16-2)13-10(11)14-9(5)12/h3-4H,1-2H3,(H2,12,13,14)
• InChIKey: HWIIAAVGRHKSOJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-6,7-dimethoxyquinazolin-4-amine
• IUPAC Traditional name: 2-chloro-6,7-dimethoxyquinazolin-4-amine
• Synonyms: 2-Chloro-6,7-dimethoxyquinazolin-4-amine; 2-Chloro-6,7-dimethoxyquinazolin-4-amine; 4-Amino-2-chloro-6,7-dimethoxyquinazoline; 2-Chloro-6,7-dimethoxy-4-quinazolinamine; 4-Amino-2-chloro-6,7-dimethoxyquinazoline; 2-Chloro-4-amino-6,7-dimethoxyquinazoline; 2-chloro-6,7-diMethoxy-4-QuinazolinaMine; 2-氯-6,7-二甲氧基-4-喹唑啉胺; 4-氨基-2-氯-6,7-二甲氧基喹唑啉

Database IDs

• CAS Number: 23680-84-4
• EC Number: 245-821-7
• MDL Number: MFCD00051734
• Beilstein Number: 747463
• PubChem SID: 160997984; 24884886; 24874035
• PubChem CID: 90235

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.7826276
• LogD (pH = 7.4): 1.7837871
• Log P: 1.7838019
• Molar Refractivity: 62.2394 cm^3
• Polarizability: 24.22446 Å^3
• Polar Surface Area: 70.26 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: >300°C dec.; 259 - 260°C; 262-268 °C (dec.)(lit.); 262-268°C; ca 280°C dec.
• Hydrophobicity(logP): 0.202

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (HPLC); 95%; 98%; 98+%
• Grade: puriss.
• Empirical Formula (Hill Notation): C10H10ClN3O2

DETAILS

Sigma Aldrich - 518654

Packaging
25 g in glass bottle

Sigma Aldrich - 66715

Other Notes
Building block for preparing terazosine and its analogues, α1-adrenoceptor antagonists, see e.g.1

Toronto Research Chemicals - A603439

Intermediate in the production on Terazosin.

REFERENCES

• Shaw, Y., et al.: J. Med. Chem., 47, 4453 (2004)
• Mendes da Silva, J., et al.: Bioorg. Med. Chem., 16, 7254 (2004)
• Key starting material for synthesis of the ɑ ₁-adrenergic blocker Prazosin. It has also been used in the synthesis of related compounds: J. Med. Chem., 36, 690 (1993).