Aminomethyl phenols

A tetradentate ligand 2- bis[2-(2-pyridyl)ethyl]aminomethyl phenolate complexes zinc with an N30 donor set including pyridyl and phenolic groups. The X-ray structure reveals that a dimeric... 

Auf diese Weise Iassen sich die folgenden Aminomethyl-phenole herstellen (2-Acetyl-, 2-Alkoxycarbonyl- und 4-Methoxy-phenole gehen die Reaktion nicht ein) ... 

Support-bound C-nucleophiles have also been successfully added to imines. Poly-styrene-bound thiol esters can be converted into ketene acetals by O-silylation, and then alkylated with imines in the presence of Lewis acids. Further examples include Mannich reactions of support-bound alkynes and indoles (Table 10.10). Some Man-nich-type products (e.g. 3-(aminomethyl)indoles, 2-(aminomethyl)phenols, (3-amino ketones) are unstable and can decompose upon treatment with acids. 3-(Amino-... 

In several deamination reactions, formation of the hydroxymethyl derivatives 243 (Fig. 90) is frequently reported instead of the expected unsaturated product. Thus, deamination of para-aminomethyl phenols (242, R = p-hydroxyphenyl) produces an intermediate methylenequinonc, which then evolves to hydroxymethyl phenol by reaction with water, - whereas deamination of aminome-thane sulfonates (242, R = SO Na) proceeds through an Sn2 attack by water on the zwit-terionie form of the Mannich base to yield the hydroxylated derivative. - "... 

With para-aminomethyl phenols, the participation of an intermediate para-methy-... 

Phenolic Mannich bases afford cyclic derivatives as the result of deamination, O-heterocycles being prepared to a larger extent than N-heterocycles, although an interesting example of homocycle synthc.sis (Fig. 135) from para-aminomethylated phenolic Mannich bases is worth mentioning. ... 

The reaction is catalysed by an organic base, usually an amine, which in the past has nearly always been the tertiary amine 2,4,6-tri(dimethyl aminomethyl) phenol. Such LP-modified epoxy resins have been in existence for more than 30 years. Their popularity declined because of the mercaptan odour of the polysulphide polymers in the uncured state and because of the use of a tertiary aromatic amine. 

The classical Mannich reaction converts phenols to aminomethylated phenols. The reaction involves the addition of phenols to C=N bonds of imines or iminium salts formed from formaldehyde and primary or secondary amines, respectively . Recent modifications employ the reaction of an aminal in the presence of SO3, which gives a sulfonate ester, followed by o-aminomethylation (equation Sc(OTf)3 catalyzed... 

As modifiers, low molecular weight rubbers with carboxyl terminal reactive groups are more effective. As hardeners, we recommend phenolic Mannich bases, such as dimethylaminomethyl phenols for hot curing and ethylene di aminomethyl phenols for cold curing. 

CAS 90-72-2 EINECS/ELINCS 202-013-9 Synonyms DMP DMP-30 Mesitol. a,a, a"-tris (dimethylamino)- Phenol, 2,4,6-tris (dimelhylaminomethyl) TDM/tMP 2,4,6-Tii (dimethyl-aminomethyl) phenol Empirical CkHjjNjO Formula [(CH,)2NCHJ,CeH20H... 

Brandao FM, Pinto J (1980) Allergic contact dermatitis to epoxy resin in hemodialysis needles. Contact Dermatitis 6 218-219 Brooke R, Beck MH (1998) Contact allergy to 2,4,6-tris(dimethyl-aminomethyl)phenol. Contact Dermatitis 38 284-285 Bruze M, Almgren G (1989) Occupational dermatoses in workers exposed to epoxy-impregnated fiberglass fabric. Dermatosen 37 171-176... 

Tri(dimethyl-aminomethyl)phenol (DMP-30) Antioxidant, epoxy embedding medium, accelerator 0.1% Pet 90-72-2 C15H27N3O... 

PbO, Sulfur, diphenyl-guanidine, 2,4,6-tris(dimethyl-aminomethyl)phenol Stearic acid, stearates Widely used formulation... 

Dihydropyrano[3,2-c]chromenes have recently attracted much attention as an important class of heterocycles having useful biological and pharmacological properties such pyran-annulated scaffolds are obtained from the reaction of 4-hydroxycoumarin (13) with aldehydes and C-H activated acids (e.g., malononitrile, ethyl 2-cyanoacetate, etc.). Recently, Khoobi et al. [95] developed an efficient protocol for the synthesis of dihydropyrano[3,2-c]chromenes 14 in aqueous medium in the presence of nanocatalyst, (2-aminomethyl)phenol, supported on HAp-encapsulated-Y-Fe203 ([Y-Fe203 Hap-Si(CH2)3-AMP]) under reflux condition (Scheme 7). "Qn-water" syntheses of such scaffolds were also reported earlier by Khurana et al. [81] and Shaabani et al. [86] (Scheme 7). 

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