121-72-2

Basic information

• Product Name: N,N-DIMETHYL-M-TOLUIDINE
• Synonyms: N,N-DIMETHYL-3-TOLUIDINE;N,N-DIMETHYL-3-METHYLANILINE;N,N,3-TRIMETHYLBENZENAMINE;N,N-DIMETHYL-M-TOLUIDINE;TIMTEC-BB SBB008276;3,N,N-TRIMETHYLANILINE;N,N-Dimethyl-3-methylaniline~N,N,3-Trimethylaniline;N,N-Dimethyl-m-toliudine
• CAS NO: 121-72-2
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21
• EINECS: 204-495-6
• Product Categories: Amines;C9 to C10;Nitrogen Compounds
• Mol File: 121-72-2.mol
• Article Data: 59

Chemical Properties

• Melting Point: -15 °C
• Boiling Point: 215 °C(lit.)
• Flash Point: 185 °F
• Appearance: Clear yellow/Liquid
• Density: 0.93 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00383mmHg at 25°C
• Refractive Index: n20/D 1.55(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.22±0.10(Predicted)
• BRN: 1422766
• CAS DataBase Reference: N,N-DIMETHYL-M-TOLUIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYL-M-TOLUIDINE(121-72-2)
• EPA Substance Registry System: N,N-DIMETHYL-M-TOLUIDINE(121-72-2)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-33-52/53
• Safety Statements: 28-36/37-45-61
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 2
• RTECS: XU5798000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 121-72-2(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Uses

Different sources of media describe the Uses of 121-72-2 differently. You can refer to the following data:
1. N,N,3-Trimethylaniline, is an building block used for the synthesis of more complex compounds, such as BTK (Bruton''s tyrosine kinase) inhibitor.
2. N,N-Dimethyl-m-toluidine may be used in chemical synthesis studies.

General Description

A clear colorless liquid with an aromatic odor. Density 0.932 g / cm3 (Lancaster) and insoluble in water. Hence floats on water. Toxic by skin absorption and inhalation. Flash point 185°F. May release toxic vapors when burned.

Air & Water Reactions

Tends to darken upon exposure to air. Insoluble in water.

Reactivity Profile

N,N-DIMETHYL-M-TOLUIDINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Purification Methods

Reflux it for 3hours with 2 molar equivalents of Ac2O, then fractionally distil it under reduced pressure. Alternatively, dry over BaO, distil and store it over KOH. The hydrochloride has m 176o (from EtOH) and the picrate has m 131o. Methods described for N,N-dimethylaniline are applicable. [Beilstein 12 H 857, 12 III 1953, 12 IV 1815.]

InChI:InChI=1/C13H21N/c1-4-9-14(10-5-2)13-8-6-7-12(3)11-13/h6-8,11H,4-5,9-10H2,1-3H3

Upstream product

• 141-52-6 sodium ethanolate 
• 22237-91-8 3,N,N,N-tetramethylanilinium 
• 512-56-1 trimethyl phosphite 
• 108-44-1 1-amino-3-methylbenzene 
• 67-56-1 methanol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 12109-10-3 (N,N-dimethylaniline)tricarbonylchromium 
• 67530-30-7 N,N-dimethyl O-(2,4,6-trimethylphenyl-sulfonyl) hydroxylamine 
• 28987-79-3 m-tolylmagnesium bromide 
• 696-44-6 N-methyl-m-toluidine 
• 39970-42-8 N-methyl-N-(3-methylphenyl)carboxamide 
• 615-37-2 ortho-methylphenyl iodide 
• 928-49-4 hex-3-yne 

Downstream Products

• 56860-14-1 4,4'-bis-dimethylamino-2,2'-dimethyl-benzophenone 
• 64969-07-9 2-(4-dimethylamino-2-methyl-benzoyl)-benzoic acid 
• 71050-29-8 bis(2-methyl-4-dimethylaminophenyl)-methane 
• 24619-07-6 tris(2-methyl-4-dimethylaminophenyl)methane 
• 32267-91-7 3,N,N-trimethyl-4-m-tolylazo-aniline 
• 90110-90-0 3,N-dimethyl-2,4,6,N-tetranitro-aniline 
• 59709-69-2 methyl-m-tolyl-carbamonitrile 
• 635683-12-4 N-methyl-N-(3-methylphenyl)aminoacetonitrile 
• 447462-59-1 (R)-2-(4-dimethylamino-2-methylphenyl)-4-oxobutyric acid methyl ester 
• 615-01-0 3-methyl-4-nitroso-phenol 
• 15258-50-1 N-ethyl-N-methyl-3-methylaniline 
• 678986-46-4 5-bromo-2-dimethylamino-4-methyl-benzyl alcohol 
• 95756-59-5 (4-amino-phenyl)-bis-(4-dimethylamino-2-methyl-phenyl)-methane 
• 90887-95-9 Trichlormethyl-(3,5-dinitro-4-dimethylamino-2-methyl-phenyl)-sulfid 

Relevant articles and documents

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CO2-tuned highly selective reduction of formamides to the corresponding methylamines

We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.

Utilization of renewable formic acid from lignocellulosic biomass for the selective hydrogenation and/or N-methylation

Lignocellulosic biomass is one of the most abundant renewable sources in nature. Herein, we have developed the utilization of renewable formic acid from lignocellulosic biomass as a hydrogen source and a carbon source for the selective hydrogenation and further N-methylation of various quinolines and the derivatives, various indoles under mild conditions in high efficiencies. N-methylation of various anilines is also developed. Mechanistic studies indicate that the hydrogenation occurs via a transfer hydrogenation pathway.

Alcohol promoted N -methylation of anilines with CO2/H2over a cobalt catalyst under mild conditions

N-Methylation of amines with CO2/H2 to N-methylamines over non-noble metal catalysts is very interesting but remains challenging. Herein, we present an alcohol (e.g., ethanol) promoted strategy for the N-methylation of anilines with CO2/H2 with high efficiency under mild conditions (e.g., 125 °C), which is achieved over a cobalt catalytic system composed of Co(OAc)2·4H2O, triphos and Sn(OTf)2. This catalytic system has a broad substrate scope and is tolerant toward a wide range of anilines and N-methyl anilines, and a series of N,N-dimethyl anilines were obtained in high yields. Mechanism investigation indicates that the alcohol solvent shifts the equilibrium of CO2 hydrogenation by forming an alkyl formate, which further reacts with the amine to produce N-formamide, and Sn(OTf)2 promotes the deoxygenative hydrogenation of N-formamides to afford N-methylamines. This is the first example of the N-methylation of amines with CO2/H2 over a cobalt catalytic system, which shows comparable performance to the reported Ru catalysts and may have promising applications.