15827-34-6

Basic information

• Product Name: alpha,alpha'-bis(dimethylamino)-2,6-xylenol
• Synonyms: alpha,alpha'-bis(dimethylamino)-2,6-xylenol;2,6-bis [(Dimethylamino) methyl] phenol
• CAS NO: 15827-34-6
• Molecular Formula: C₁₂H₂₀N₂O
• Molecular Weight: 208.3
• EINECS: 239-930-9
• Mol File: 15827-34-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 269.9°Cat760mmHg
• Flash Point: 97°C
• Appearance: /
• Density: 1.036g/cm³
• PKA: 7.25±0.50(Predicted)
• CAS DataBase Reference: alpha,alpha'-bis(dimethylamino)-2,6-xylenol(CAS DataBase Reference)
• NIST Chemistry Reference: alpha,alpha'-bis(dimethylamino)-2,6-xylenol(15827-34-6)
• EPA Substance Registry System: alpha,alpha'-bis(dimethylamino)-2,6-xylenol(15827-34-6)

Safety Data

• Hazardous Substances Data: 15827-34-6(Hazardous Substances Data)

Usage

General Description

Alpha,alpha'-bis(dimethylamino)-2,6-xylenol is a chemical compound commonly used as a stabilizer and inhibitor in the production of polymers, such as polyurethane foam and epoxy resins. It is also utilized as a corrosion inhibitor in metalworking fluids and as a component in some adhesives and sealants. alpha,alpha'-bis(dimethylamino)-2,6-xylenol is known for its high thermal stability and excellent resistance to oxidation and hydrolysis, making it a valuable additive in a wide range of industrial applications. It is often used in combination with other antioxidants and stabilizers to enhance its effectiveness in protecting materials from degradation caused by heat, light, and other environmental factors. Additionally, it has been found to be an effective inhibitor of microbial growth, further contributing to its utility in various industrial processes.

Upstream product

• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 108-95-2 phenol 
• 51-80-9 bis-(dimethylamino)methane 
• 109-55-7 1-amino-3-(dimethylamino)propane 
• 90-72-2 2,4,6-tris(dimethylaminomethyl)phenol 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 106-48-9 4-chloro-phenol 
• 19851-44-6 1,3-bis[(dimethylamino)methyl]benzene 
• 67-63-0 isopropyl alcohol 
• 67-56-1 methanol 
• 75-31-0 isopropylamine 
• 120-65-0 ortho-dimethylaminomethylphenol 

Downstream Products

• 120103-43-7 2,6-phenol 
• 576-26-1 2.6-dimethylphenol 
• 90-72-2 2,4,6-tris(dimethylaminomethyl)phenol 

Relevant articles and documents

Functionalization of the Aryl Moiety in the Pincer Complex (NCN)NiIIIBr2: Insights on NiIII-Promoted Carbon-Heteroatom Coupling

This report describes the C-O, C-N, and C-halogen functionalization of the NiIII-Ar moiety stabilized within a pincer framework that serves as a model system for studying C-heteroatom coupling reactions promoted by high-valent Ni compounds. Treating van Koten's pincer complex (NCN)NiIIIBr2 under a nitrogen atmosphere with water, 1° or 2° alcohols, 1° amines, HCl, or HBr results in heterofunctionalization at the ipso-C of the pincer ligand's aryl moiety. The yields of these heterofunctionalizations are generally a comproportionation reaction between the trivalent precursor and a NiI species arising from the reductive elimination step in the functionalization process. Other side-reactions include a C-OH coupling with residual water and C-H coupling (net protonation) that is prevalent with mineral acids, some alcohols, and aqueous NH3. Kinetic measurements have established that the reaction with MeOH is first-order with respect to [(NCN)NiIIIBr2], and a kinetic isotope effect of 0.47 has been obtained for functionalization with CH3OH/CD3OD. These and other observations have allowed us to propose two different mechanistic postulates for the involvement of trivalent intermediates in the functionalization reactions under discussion. Tetravalent species such as [(NCN)NiIVBr2]+ can be generated in situ under strongly oxidative conditions and they do promote C-Br coupling, but such species play no role in the C-heteroatom coupling reactions under nonoxidative conditions.

Triethylsiloxymethyl-N,N-dimethylamine, Et3SiOCH2NMe2: A Dimethylaminomethylation (Mannich) Reagent for O–H, S–H, P–H and Aromatic C–H Systems

Triethylsiloxymethylamine, Et3SiOCH2NMe2, readily synthesized in high yield by the hydrosilylation reaction between Et3SiH and DMF, is an excellent (N,N-dimethylamino)methyl transfer agent to a representative range of aliphatic alcohols, thiols, and Ph2PH (E–H) materials. The reactions are almost instantaneous at room temperature in inert solvents and require no activating agents to produce E–CH2NMe2 products in high yields and illustrate the title compound as an excellent addition to the family of organic reagents. For aromatic alcohols, electrophilic substitution of the aromatic ring occurs in high yield. Crystal structures of new materials such as the cholestero–CH2NMe2 derivative, 2–4-[bis(N,N-dimethylamino)methyl]-1-naphthol, and the phosphine oxide derived from Ph2PCH2NMe2 are reported.

TRANSFORMATIONS OF PHENOLIC MANNICH BASES

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