Description

2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine (CAS No. 63200-54-4) is a high-purity heterocyclic compound with the molecular formula C₆H₃Cl₂N₃. This chlorinated pyrrolopyrimidine derivative is a versatile building block in medicinal chemistry and pharmaceutical research, particularly for the synthesis of nucleoside analogs and kinase inhibitors. Its rigid bicyclic structure and reactive chloro substituents make it an ideal intermediate for cross-coupling reactions, nucleophilic substitutions, and other functionalizations. The compound is supplied as an off-white to light yellow crystalline powder with ≥95% purity (HPLC), ensuring consistency for demanding synthetic applications. Proper storage at 2-8°C under inert atmosphere is recommended to maintain stability.

Properties

• CAS Number: 63200-54-4
• Complexity: 155
• IUPAC Name: 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine
• InChI: InChI=1S/C6H3Cl2N3/c7-5-4-3(1-2-9-4)10-6(8)11-5/h1-2,9H
• InChI Key: MVTLFDKTYGKJEX-UHFFFAOYSA-N
• Exact Mass: 186.9704025
• Molecular Formula: C6H3Cl2N3
• Molecular Weight: 188.01
• SMILES: C1=CNC2=C1N=C(N=C2Cl)Cl
• Topological: 41.6
• Monoisotopic Mass: 186.9704025
• Synonyms: 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, DTXSID20418749, 2,4-dichloro-5H-pyrrolo(3,2-d)pyrimidine, DTXCID30369596, 810-549-5, 63200-54-4, 2,4-Dichloropyrrolo[3,2-d]pyrimidine, 2,4-Dichloro-1H-pyrrolo[3,2-d]pyrimidine, 1310680-17-1, MFCD08059281, 4,2-Dichloro-5H-pyrrolo[3,2-d]pyrimidine, 5H-PYRROLO[3,2-D]PYRIMIDINE, 2,4-DICHLORO-, SCHEMBL1021282, SCHEMBL1674225, CHEMBL3236416, DYXMNZRXOLJCKW-UHFFFAOYSA-N, BCP13922, AKOS006282969, AKOS027441136, AC-2994, CS-W003450, GS-6603, PB34250, BP-11342, SY003513, 2,4-Dichloro-3H-pyrrolo[3,2-d]pyrimidine, CS-0527262, EN300-84002, 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine #, O10588, 2,4-bis(chloranyl)-5H-pyrrolo[3,2-d]pyrimidine, A834265, Z1198175555, 2 pound not4-dichloro-5H-pyrrolo[3 pound not2-d]pyrimidine

Application

2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine serves as a key precursor in the synthesis of adenosine receptor antagonists and anticancer agents targeting purine-binding enzymes. Researchers utilize this scaffold to develop novel kinase inhibitors for tyrosine and serine/threonine kinases through selective substitution at the 2- and 4-positions. In drug discovery programs, it enables rapid generation of compound libraries via Suzuki-Miyaura and Buchwald-Hartwig coupling reactions. The dichloro functionality allows sequential functionalization, making it valuable for structure-activity relationship studies in lead optimization.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)

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