Description

1,5-Dibromo-2,4-dimethoxybenzene (CAS No. 24988-36-1) is a high-purity aromatic compound with the molecular formula C₈H₈Br₂O₂. This dibrominated dimethoxybenzene derivative is a valuable intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and advanced materials. Its unique structure, featuring two bromine atoms and two methoxy groups in a 1,5-arrangement on the benzene ring, makes it an excellent electrophile for cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. The compound is supplied as a white to off-white crystalline powder with ≥95% purity (GC), ensuring consistent performance in demanding applications. Proper storage at 2-8°C in a tightly sealed container under inert atmosphere is recommended to maintain stability.

Properties

• CAS Number: 24988-36-1
• Complexity: 129
• IUPAC Name: 1,5-dibromo-2,4-dimethoxy-benzene
• InChI: InChI=1S/C8H8Br2O2/c1-11-7-4-8(12-2)6(10)3-5(7)9/h3-4H,1-2H3
• InChI Key: SVPXSTJZZSDWIA-UHFFFAOYSA-N
• Exact Mass: 295.88706
• Molecular Formula: C8H8Br2O2
• Molecular Weight: 295.96
• SMILES: COC1=CC(=C(C=C1Br)Br)OC
• Topological: 18.5
• Monoisotopic Mass: 293.88910
• Synonyms: 1,5-dibromo-2,4-dimethoxybenzene, 24988-36-1, DTXSID80369602, DTXCID40320638, 1,3-Dibromo-4,6-dimethoxybenzene, Benzene, 1,5-dibromo-2,4-dimethoxy-, 4,6-dibromo-1,3-dimethoxybenzene, MFCD00061097, 1,5-Dibromo-2,4-dimethoxy benzene, 2,4-dibromo-1,5-dimethoxybenzene, Maybridge3_005611, SCHEMBL1104878, SCHEMBL3395666, SVPXSTJZZSDWIA-UHFFFAOYSA-N, 4,6-Dibrom-resorcin-dimethylather, HMS1446P01, BBL101938, STL555735, AKOS004903445, AB89981, CCG-245352, DS-4844, IDI1_016998, SY104324, DB-067291, CS-0150486, AE-641/00573016, 1,5-dibromo-2,4-dimethoxybenzene (en)benzene, 1,5-dibromo-2,4-dimethoxy- (en)

Application

1,5-Dibromo-2,4-dimethoxybenzene serves as a versatile building block in medicinal chemistry for the synthesis of biologically active compounds. It is particularly useful in the development of kinase inhibitors and other small molecule therapeutics. In material science, this compound finds application as a precursor for conjugated polymers and organic electronic materials. The bromine substituents allow for further functionalization through various transition metal-catalyzed coupling reactions.

Safety and Hazards

GHS Hazard Statements

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

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