Description

(R)-6,6′-Dimethyl-1,1′-biphenyl-2,2′-diyldiamine (CAS No. 3685-06-1) is a highly specialized chiral diamine compound with the molecular formula C₁₄H₁₆N₂. This optically active biphenyl derivative is characterized by its two amine functional groups positioned at the 2- and 2′-positions of the biphenyl scaffold, each flanked by a methyl group at the 6- and 6′-positions. The (R)-enantiomer exhibits exceptional stereochemical purity, making it a valuable building block for asymmetric synthesis, chiral ligand design, and coordination chemistry. Its rigid biphenyl backbone and electron-donating amine groups render it ideal for constructing metal-organic frameworks (MOFs), chiral catalysts, and advanced materials. Supplied as a high-purity solid, this compound is rigorously tested via HPLC, NMR, and chiral analysis to ensure compliance with research-grade standards. Store under inert conditions to preserve its reactivity and optical integrity.

Properties

• CAS Number: 3685-06-1
• Complexity: 205
• IUPAC Name: 2-(2-amino-6-methyl-phenyl)-3-methyl-aniline
• InChI: InChI=1S/C14H16N2/c1-9-5-3-7-11(15)13(9)14-10(2)6-4-8-12(14)16/h3-8H,15-16H2,1-2H3
• InChI Key: MCUUKQCKNKUMBP-UHFFFAOYSA-N
• Exact Mass: 212.131348519
• Molecular Formula: C14H16N2
• Molecular Weight: 212.29
• SMILES: CC1=C(C(=CC=C1)N)C2=C(C=CC=C2N)C
• Topological: 52
• Monoisotopic Mass: 212.131348519
• Solubility: >31.8 [ug/mL]
• Synonyms: 3685-05-0, 3685-06-1, (S-(-)6,6′-Dimethyl-2,2′-biphenyldiamine, (R)-6,6′-Dimethyl-1,1′-biphenyl-2,2′-diyldiamine, 622-534-9, 635-212-8, 20261-65-8, 6,6′-Dimethyl-[1,1′-biphenyl]-2,2′-diamine, 2-(2-amino-6-methylphenyl)-3-methylaniline, (R)-6,6′-Dimethyl-[1,1′-biphenyl]-2,2′-diamine, (S)-6,6′-Dimethyl-[1,1′-biphenyl]-2,2′-diamine, [1,1′-Biphenyl]-2,2′-diamine, 6,6′-dimethyl-, 2,2′-Diamino-6,6′-dimethylbiphenyl, (S)-2,2mu-Diamino-6,6mu-dimethylbiphenyl, (S)-6,6mu-Dimethyl-2,2mu-diaminobiphenyl, (S)-6,6mu-Dimethyl-1,1mu-biphenyl-2,2mu-diamine, (S)-6,6mu-Dimethyl-1,1mu-biphenyl-2,2mu-diyldiamine, MFCD00114959, NoName_3867, (+/-)-2,2′-Diamino-6,6′-dimethyl-biphenyl, (R)-(+)-6,6′-Dimethyl-2,2′-biphenyldiamine, (S)-(-)-6,6′-Dimethyl-2,2′-biphenyldiamine, Oprea1_421415, Oprea1_742699, MLS000684026, SCHEMBL3462069, 6,6′-Diamino-2,2′-ditolyl, CHEMBL1729081, DTXSID90903238, MCUUKQCKNKUMBP-UHFFFAOYSA-N, HMS1587I15, HMS2740P14, STK964132, 6,6′-dimethylbiphenyl-2,2′-diamine, AKOS002161918, SB79239, SB79278, 2,2′-Diamino-6,6′-dimethyl-biphenyl, SMR000291667, biphenyl, 2,2′-diamino-6,6′-dimethyl-, (R)-2,2′-Diamino-6,6′-dimethylbiphenyl, (R)-6,6′-Dimethyl-2,2′-diaminobiphenyl, (S)-2,2′-Diamino-6,6′-dimethylbiphenyl, (S)-6,6′-Dimethyl-2,2′-diaminobiphenyl, DB-066102, ST50036770, (2′-amino-6,6′-dimethyl-2-biphenylyl)amine, 6,6′-dimethyl-2,2′-diamino-1,1′-biphenyl, Y13606, 2-(2-amino-6-methylphenyl)-3-methylphenylamine, 2′-amino-6,6′-dimethyl[1,1′-biphenyl]-2-ylamine, (R)-(+)-6,6′-Dimethyl-2,2′-biphenyldiamine, >=98%, (S)-(-)-6,6′-Dimethyl-2,2′-biphenyldiamine, >=98%

Application

(R)-6,6′-Dimethyl-1,1′-biphenyl-2,2′-diyldiamine serves as a key chiral auxiliary in asymmetric catalysis, particularly for transition-metal-catalyzed C–C bond-forming reactions. It is widely employed in the synthesis of enantiopure pharmaceuticals and agrochemicals due to its ability to induce high stereoselectivity. Researchers also utilize it to prepare chiral ligands for asymmetric hydrogenation and cross-coupling reactions. Its structural features make it a promising candidate for designing luminescent materials and supramolecular architectures.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

Precautionary Statements

• P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, P391, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)
• Aquatic Acute 1 (100%)

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