Tris(dimethylaminomethyl)phenol supplier

Name
Tris(dimethylaminomethyl)phenol
EINECS 202-013-9
CAS No. 90-72-2
Article Data10
CAS DataBase
Density 1.03 g/cm³
Solubility Insoluble in water, slightly soluble in water, soluble in alcohol, benzene, acetone
Melting Point 316℃
Formula C₁₅H₂₇N₃O
Boiling Point 320.5 °C at 760 mmHg
Molecular Weight 265.399
Flash Point 116.6 °C
Transport Information UN 2735 8/PG 3
Appearance Colorless or light yellow transparent liquid
Safety 26-28-2
Risk Codes 22-36/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 2,4,6-Tris((N,N-dimethylamino)methyl)phenol;AI3-03346;Actiron NX 3;Ancamine K 54;Anchor K 54;Araldite DY 061;Mesitol, alpha(sup 2),alpha(sup 4),alpha(sup 6)-tris(dimethylamino)- (6CI);Mesitol, alpha2,alpha4,alpha6-tris(dimethylamino)-;alpha,alpha',alpha''-Tris(dimethylamino)mesitol;NSC 3257;Sumicure D;Phenol,2,4,6-tris[(dimethylamino)methyl]-;
PSA 29.95000
LogP 1.57700

Synthetic route

: 1353053-97-0
triethylsiloxymethyl-N,N-dimethylamine

: 15827-34-6
2,6-bis-<(dimethyamino)methyl>phenol

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

Conditions

Conditions	Yield
Sealed tube; Heating;	90%

: 50-00-0
formaldehyd

: 124-40-3
dimethyl amine

: 108-95-2
phenol

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

Conditions

Conditions	Yield
In water for 2.5h;	80%
In water at 25 - 100℃; for 3h; Mannich reaction;	80%
With water
Stage #1: formaldehyd; dimethyl amine In water at 60℃; under 3000.3 Torr; for 5h; Large scale; Stage #2: phenol In water at 90℃; for 3.5h; Temperature; Large scale;

...Expand

: 131253-33-3
3-chloro-2,4,6-tris-dimethylaminomethyl-phenol; trihydrochloride

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

Conditions

Conditions	Yield
With water; platinum Hydrogenation;

: 50-00-0
formaldehyd

: 124-40-3
dimethyl amine

: 99-96-7
4-hydroxy-benzoic acid

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

Conditions

Conditions	Yield
With water

...Expand

: 50-00-0
formaldehyd

: 7732-18-5
water

: 124-40-3
dimethyl amine

: 108-95-2
phenol

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

Conditions

Conditions	Yield
at 90 - 95℃;

...Expand

: 27804-64-4
bis(diethylamino)dihydrosilane

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: bis[2,4,6-tris((dimethylamino)methyl)phenoxy]dihydrosilane

Conditions

Conditions	Yield
In chloroform at 20℃; for 0.25h;	96%

: 55147-59-6, 65455-92-7
lead(II) bis(trimethylsilyl)amide

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: bis[2,4,6-tris(dimethylaminomethyl)phenoxy]-plumbylene

Conditions

Conditions	Yield
In pentane N2 or Ar-atmosphere; stirring (room temp., 2 h); evapn. (reduced pressure), recrystn. (pentane, -30°C); elem. anal.;	96%
In benzene byproducts: HN(SiMe3)2; 2 equiv. ligand;

: 59863-12-6
bis[bis(trimethylsilyl)amino]germanium(II)

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: bis[2,4,6-tris((dimethylamino)methyl)phenoxy]germanium(II)

Conditions

Conditions	Yield
In pentane N2 or Ar-atmosphere; stirring (room temp., 2 h); evapn. (vac.), extg. (pentane), pptn. (-30°C, 48 h), filtering, drying (vac.); elem. anal.;	96%
In benzene byproducts: HN(SiMe3)2; 2 equiv. ligand;
In benzene byproducts: (Me3Si)2NH; N2 or Ar-atmosphere, 20°C;

: 55147-78-9
bis(bis(trimethylsilyl)amido)tin(II)

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 524960-14-3
bis[2,4,6-tris(dimethylaminomethyl)phenoxy]-stannylene

Conditions

Conditions	Yield
In pentane N2 or Ar-atmosphere; stirring (room temp., 2 h); concg. (vac.), filtering, drying (vac.); elem. anal.;	96%
In benzene byproducts: HN(SiMe3)2; 2 equiv. ligand;
In benzene byproducts: (Me3Si)2NH; N2 or Ar-atmosphere, 20°C;

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: bis(dimethylamino)bis(trimethylsilyl)silane

: 394739-08-3
bis[2,4,6-tris((dimethylamino)methyl)phenoxy]bis(trimethylsilyl)silane

Conditions

Conditions	Yield
In toluene for 2h; Heating;	95%

: 2083-91-2
N,N-Dimethyltrimethylsilylamine

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 161787-77-5
[2,4,6-tris((dimethylamino)methyl)phenoxy]trimethylsilane

Conditions

Conditions	Yield
In pentane	94%

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: [2,4,6-tris(((dimethylamino)methyl)phenoxy)phenyl]silane

: bis[(2,4,6-tris((dimethylamino)methyl)phenoxy)phenyl]silane

Conditions

Conditions	Yield
In pentane at 20℃; for 3h;	94%

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: bis[(2,4,6-tris((dimethylamino)methyl)phenoxy)phenyl]silane

: C51H83N9O3Si

Conditions

Conditions	Yield
In pentane at 20℃;	94%

: 15112-89-7
tri(dimethylamino)silane

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: tris[2,4,6-tris((dimethylamino)methyl)phenoxy]hydrosilane

Conditions

Conditions	Yield
With ammonium sulfate at 110℃; for 48h;	92%

: 4669-59-4
bis(diethylamino)dimethylsilane

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 394739-06-1
bis[2,4,6-tris((dimethylamino)methyl)phenoxy]dimethylsilane

Conditions

Conditions	Yield
In pentane for 2h; Heating;	91%

: 55147-78-9
bis(bis(trimethylsilyl)amido)tin(II)

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 211423-73-3, 175855-63-7
[bis(trimethylsilyl)amino][2,4,6-tris(dimethylaminomethyl)phenoxy]tin(II)

Conditions

Conditions	Yield
In pentane inert atmosphere; dropwise addn. of ligand to equimolar amt. of Sn-compd., stirring (room temp., 2 h); solvent removal (vac.), dissoln. in pentane, crystn. (-30°C); elem. anal.;	91%

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: lithium 2,4,6-tris((dimethylamino)methyl)phenoxide

Conditions

Conditions	Yield
With n-butyllithium In diethyl ether at 20℃; for 2h;	90%

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: bis[2,4,6-tris((dimethylamino)methyl)phenoxy]dihydrosilane

: tris[2,4,6-tris((dimethylamino)methyl)phenoxy]hydrosilane

Conditions

Conditions	Yield
In chloroform at 20℃; for 24h;	90%

: 59863-12-6
bis[bis(trimethylsilyl)amino]germanium(II)

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 211423-72-2
[bis(trimethylsilyl)amino][2,4,6-tris(dimethylaminomethyl)phenoxy]germanium(II)

Conditions

Conditions	Yield
In pentane inert atmosphere; dropwise addn. of ligand to equimolar amt. of Ge-compd., stirring (room temp., 2 h); solvent removal (vac.), dissoln. in pentane, crystn. (-30°C);	89%

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: (dimethylamino)tris(trimethylsilyl)silane

: [2,4,6-tris((dimethylamino)methyl)phenoxy]tris(trimethylsilyl)silane

Conditions

Conditions	Yield
In pentane for 2h; Heating;	83%

: 55147-59-6, 65455-92-7
lead(II) bis(trimethylsilyl)amide

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 211423-74-4
[bis(trimethylsilyl)amino][2,4,6-tris(dimethylaminomethyl)phenoxy]lead(II)

Conditions

Conditions	Yield
In pentane inert atmosphere; dropwise addn. of ligand to Pb-compd., stirring (room temp., 2 h); solvent removal (vac.), dissoln. in pentane, crystn. (-30°C); elem. anal.;	82%

: germanium(II) chloride dioxane

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 202127-98-8
tris(dimesitylgermylenecarbodiimide)

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: LiCl; N2-atmosphere; stirring (room temp.); C6H6 addn., filtering, evapn.;	78%

: 603-35-0
triphenylphosphine

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 20667-12-3
silver(l) oxide

: 616880-27-4
[2,4,6-tris(dimethylaminomethyl)phenolato]bis(triphenylphosphine)silver(I)

Conditions

Conditions	Yield
In toluene Ag2O, PPh3, and 2,4,6-tris(dimethylaminomethyl)phenol in toluene were stirred overnight at room temp.; react. mixt. was filtered, filtrate was left to stand at room temp., ppt. was filtered, washed with toluene and dried in vacuo; elem. anal.;	66%

...Expand

: 51762-67-5
3-nitrobenzene-1,2-dicarbonitrile

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 3-[2,4,6-tris-(N,N-dimethylaminomethyl)phenoxy]phthalonitrile

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 0 - 60℃; Inert atmosphere;	64%
With potassium carbonate In dimethyl sulfoxide at 20 - 60℃; Inert atmosphere;	64%
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 24h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 24h; Inert atmosphere;

: 75-24-1
trimethylaluminum

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: [Me2AlOC6H2(CH2NMe2)3-2,4,6](AlMe3)2

Conditions

Conditions	Yield
In toluene byproducts: CH4; all manipulations under dry O2-free N2 atm.; soln. of org. compd. added dropwise to cooled (-10°C) soln. of Me3Al with vigorous stirring,react. mixt. stirred for 12 h at room temp.; solvent removed in vac., residue recrystd. from hexane/toluene (1/3); elem. anal.;	62%

: 127808-36-0
phenylsilanyl trifluoromethanesulfonate

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

A: [2,4,6-tris(((dimethylamino)methyl)phenoxy)phenyl]silane

B: bis[(2,4,6-tris((dimethylamino)methyl)phenoxy)phenyl]silane

Conditions

Conditions	Yield
With triethylamine In toluene at 20℃; for 3h;	A 60% B n/a

...Expand

: cadmium bis(trimethylsilyl)amide

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 847906-04-1
[Cd(μ-2,4,6-tris(dimethylamino-methylphenolate)(bis(trimethylsilyl)amide)]2

Conditions

Conditions	Yield
In toluene under inert atm. alcohol was slowly added to Cd complex in toluene, stirred for 12 h, pyridine was added, mixt. was warmed until clear; elem. anal.;	59.4%

: tris(bis(trimethylsilyl)amido)praseodymium(III)

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

A: Pr(3+)*3((CH3)2NCH2)3C6H2O(1-)=[Pr(((CH3)2NCH2)3C6H2O)3]

: Pr(((CH3)2NCH2)3C6H2O)3(H2O)2

Conditions

Conditions	Yield
In hexane 25°C; filtn., crystn. of second product after solvent redn.; elem. anal.;	A 59% B 23%

...Expand

: 75-24-1
trimethylaluminum

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: Me2AlOC6H2(CH2NMe2)3-2,4,6

Conditions

Conditions	Yield
In toluene byproducts: CH4; all manipulations under dry O2-free N2 atm.; soln. of org. compd. added dropwise to cooled (-10°C) soln. of Me3Al with vigorous stirring,react. mixt. stirred for 12 h at room temp.; solvent removed in vac., residue washed with hexane, sublimed in vac.; elem. anal.;	55%

: 31643-49-9
4-Nitrophthalonitrile

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 4-(2,4,6-tris((dimethylamino)methyl)phenoxy)phthalonitrile

Conditions

Conditions	Yield
Stage #1: 2,4,6-tris(dimethylaminomethyl)phenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-Nitrophthalonitrile In N,N-dimethyl-formamide at 20℃; for 10.25h;	50.8%
With potassium carbonate In N,N-dimethyl-formamide

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: 19333-10-9
phthalocyanine silicon(IV) dichloride

: 1415224-02-0
bis(2,4,6-tris(N,N-dimethylaminomethyl)phenoxy)[phtalocyaninato]silicon

Conditions

Conditions	Yield
With sodium hydride In toluene for 6h; Inert atmosphere; Reflux;	35.6%

: 694-53-1
phenylsilane

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: C51H83N9O3Si

Conditions

Conditions	Yield
	31%

: 90-72-2
2,4,6-tris(dimethylaminomethyl)phenol

: bis[2,4,6-tris((dimethylamino)methyl)phenoxy]dichlorosilane

Conditions

Conditions	Yield
With bis(N,N-dimethylamino)dichlorosilane In toluene at 110℃; for 6h; slow distillation;	23%
Multi-step reaction with 2 steps 1: 91 percent / pentane / 2 h / Heating 2: 80 percent / SiCl4 / 80 °C View Scheme
Multi-step reaction with 3 steps 1: 90 percent / nBuLi / diethyl ether / 2 h / 20 °C 2: 28 percent / diethyl ether / 48 h / 20 °C 3: 80 percent / SiCl4 / 80 °C View Scheme
Multi-step reaction with 2 steps 1: 90 percent / nBuLi / diethyl ether / 2 h / 20 °C 2: 23 percent / SiCl4 / diethyl ether / 48 h / 20 °C View Scheme

Tris(dimethylaminomethyl)phenol Consensus Reports

Reported in EPA TSCA Inventory.

Tris(dimethylaminomethyl)phenol Specification

1. Introduction of Tris(dimethylaminomethyl)phenol
The Tris(dimethylaminomethyl)phenol with CAS registry number of 90-72-2 is also known as Phenol,2,4,6-tris[(dimethylamino)methyl]-. The IUPAC name and product name are the same. It belongs to product categories of Phenyls & Phenyl-Het; Phenyls & Phenyl-Het. In addition, the formula is C₁₅H₂₇N₃O and the molecular weight is 265.39. This chemical is a colorless or light yellow transparent liquid and should be sealed in cool, ventilated and dry place. What's more, it can be used as curing agent, adhesive, catalyst, antioxidant, and also used for preparation of the dye.

2. Properties of Tris(dimethylaminomethyl)phenol
(1)ACD/LogP: 0.76; (2)ACD/LogD (pH 5.5): -4.26; (3)ACD/LogD (pH 7.4): -2.88; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 7; (11)Polar Surface Area: 18.95Å²; (12)Index of Refraction: 1.548; (13)Molar Refractivity: 81.84 cm³; (14)Molar Volume: 257.5 cm³; (15)Polarizability: 32.44×10^-24cm³; (16)Surface Tension: 40.1 dyne/cm; (17)Density: 1.03 g/cm³; (18)Flash Point: 116.6 °C; (19)Enthalpy of Vaporization: 58.45 kJ/mol; (20)Boiling Point: 320.5 °C at 760 mmHg; (21)Vapour Pressure: 0.000169 mmHg at 25 °C.

3. Structure Descriptors of Tris(dimethylaminomethyl)phenol
1. Canonical SMILES: CN(C)CC1=CC(=C(C(=C1)CN(C)C)O)CN(C)C
2. InChI: InChI=1S/C15H27N3O/c1-16(2)9-12-7-13(10-17(3)4)15(19)14(8-12)11-18(5)6/h7-8,19H,9-11H2,1-6H3
3. InChIKey: AHDSRXYHVZECER-UHFFFAOYSA-N

4. Toxicity of Tris(dimethylaminomethyl)phenol

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	1200mg/kg (1200mg/kg)	PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Russian Pharmacology and Toxicology Vol. 37, Pg. 130, 1974.
rat	LD50	skin	1280mg/kg (1280mg/kg)		Rohm and Haas Company Data Sheets.

5. Preparation of Tris(dimethylaminomethyl)phenol
Tris(dimethylaminomethyl)phenol is prepared by reaction of phenol, 40% dimethylamine with formaldehyde. The reaction occurs by refluxing at the temperature of 25-30 °C for 2 hours. After reaction, product is obtained by stratification, vacuum dehydration and filtration.

6. Other details of Tris(dimethylaminomethyl)phenol
When you are using Tris(dimethylaminomethyl)phenol, please be cautious about it. As a chemical, it is irritating to eyes and skin. After contact with skin, wash immediately. As it is harmful if swallowed, keep out of the reach of children. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Product Name

Tris(dimethylaminomethyl)phenol

Synthetic route

Tris(dimethylaminomethyl)phenol Consensus Reports

Tris(dimethylaminomethyl)phenol Specification

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