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Tris(dimethylaminomethyl)phenol

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Name

Tris(dimethylaminomethyl)phenol

EINECS 202-013-9
CAS No. 90-72-2 Density 1.03 g/cm3
PSA 29.95000 LogP 1.57700
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 Molecular Structure of 90-72-2 (Tris(dimethylaminomethyl)phenol) Hazard Symbols HarmfulXn,IrritantXi
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]-;

Article Data 10

Tris(dimethylaminomethyl)phenol 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
ConditionsYield
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
ConditionsYield
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;
131253-33-3

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

90-72-2

2,4,6-tris(dimethylaminomethyl)phenol

Conditions
ConditionsYield
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
ConditionsYield
With water
50-00-0

formaldehyd

124-40-3

dimethyl amine

108-95-2

phenol

90-72-2

2,4,6-tris(dimethylaminomethyl)phenol

Conditions
ConditionsYield
at 90 - 95℃;
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In toluene for 2h; Heating;95%

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.

Tris(dimethylaminomethyl)phenol is prepared by reaction of phenol, 40% dimethylamine with formaldehyde.

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.

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