Description

2,6-Dichloro-N-trimethylsilylaniline (CAS No. 115910-92-4) is a high-purity organosilicon compound with the molecular formula C₉H₁₃Cl₂NSi. This specialty chemical features a dichlorinated aniline core functionalized with a trimethylsilyl group, making it a valuable intermediate in organic synthesis and pharmaceutical research. The compound exhibits excellent stability under inert conditions and is typically supplied as a clear to pale-yellow liquid or low-melting solid. With a molecular weight of 234.20 g/mol, it is soluble in common organic solvents such as dichloromethane, THF, and toluene. Ideal for nucleophilic substitution reactions, cross-coupling methodologies, and protective group chemistry. Packaged under nitrogen to ensure maximum shelf life and purity (>95% by GC).

Properties

• CAS Number: 115910-92-4
• Complexity: 159
• IUPAC Name: 2,6-dichloro-N-trimethylsilyl-aniline
• InChI: InChI=1S/C9H13Cl2NSi/c1-13(2,3)12-9-7(10)5-4-6-8(9)11/h4-6,12H,1-3H3
• InChI Key: KUGYUMJQEMOJJC-UHFFFAOYSA-N
• Exact Mass: 233.0194313
• Molecular Formula: C9H13Cl2NSi
• Molecular Weight: 234.19
• SMILES: C[Si](C)(C)NC1=C(C=CC=C1Cl)Cl
• Topological: 12
• Monoisotopic Mass: 233.0194313
• Synonyms: 2,6-dichloro-N-trimethylsilylaniline, 115910-92-4, 886-790-5, N-(2,6-Dichlorophenyl)-1,1,1-trimethylsilanamine, N-trimethylsilyl-2,6-dichloroaniline, SCHEMBL8945494, KUGYUMJQEMOJJC-UHFFFAOYSA-N, MFCD32706839, AKOS037621069, G87103

Application

2,6-Dichloro-N-trimethylsilylaniline serves as a key building block in the synthesis of advanced pharmaceutical intermediates, particularly for antimalarial and antiviral agents. Its silyl-protected amine group enables selective functionalization of the aromatic ring in Pd-catalyzed cross-coupling reactions. Researchers utilize this compound as a precursor for modified aniline derivatives in materials science, including liquid crystal and polymer applications. The dichloro substitution pattern allows for sequential Suzuki-Miyaura couplings to create complex biaryl systems.

Safety and Hazards

GHS Hazard Statements

• H301+H311+H331 (100%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
• H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal]
• H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation]
• H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
• H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
• H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (100%)
• Acute Tox. 3 (100%)
• Acute Tox. 3 (100%)
• STOT RE 2 (100%)
• Aquatic Acute 1 (100%)
• Aquatic Chronic 1 (100%)

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