91-67-8

Basic information

• Product Name: N,N-Diethyl-m-toluidine
• Synonyms: 3-Methyl-N,N-diethylaniline;3-Methyl-N,N-diethylbenzenamine;dlethyl-toluidine;meta-methyl(diethylamino)benzene;m-Methyl(diethylamino)benzene;m-Methyl-N,N-diethylaniline;m-Toluidine, N,N-diethyl-;N,N-Diethyl-3-methylaniline
• CAS NO: 91-67-8
• Molecular Formula: C₁₁H₁₇N
• Molecular Weight: 163.26
• EINECS: 202-089-3
• Product Categories: Intermediates of Dyes and Pigments;organic chemical;Indazoles
• Mol File: 91-67-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: 46.25°C (estimate)
• Boiling Point: 97 °C (17 mmHg)
• Flash Point: 101 °C
• Appearance: clear pale yellow to orange-brown liquid
• Density: 0.92
• Vapor Pressure: 0.0317mmHg at 25°C
• Refractive Index: 1.535-1.537
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 6.84±0.30(Predicted)
• CAS DataBase Reference: N,N-Diethyl-m-toluidine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Diethyl-m-toluidine(91-67-8)
• EPA Substance Registry System: N,N-Diethyl-m-toluidine(91-67-8)

Safety Data

• Hazard Codes: Xn,N,T
• Statements: 36/37/38-20/21/22-51/53-26-24/25-20
• Safety Statements: 24/25-61-45-36/37-28
• RIDADR: UN 1708 6.1/PG 2
• RTECS: CX9869375
• Hazardous Substances Data: 91-67-8(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR PALE YELLOW TO ORANGE-BROWN LIQUID

InChI:InChI=1/C11H17N/c1-4-12(5-2)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3

Upstream product

• 64-17-5 ethanol 
• 638-03-9 m-toluidine hydrochloride 
• 64-67-5 diethyl sulfate 
• 108-44-1 1-amino-3-methylbenzene 
• 591-17-3 meta-bromotoluene 
• 109-89-7 diethylamine 
• 106-38-7 para-bromotoluene 
• 95-46-5 2-methylphenyl bromide 
• 1066-87-1 (N,N-diethylamino)tributyltin 
• 352-70-5 m-Fluorotoluene 
• 75-36-5 acetyl chloride 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 108-88-3 toluene 
• 4913-13-7 3,5,N,N-tetramethylaniline 

Downstream Products

• 3474-87-1 2-methylisoindoline 
• 78818-96-9 4,4'-methylenebis(N,N-diethyl-3-methylaniline) 
• 60813-13-0 (4-diethylamino-2-methyl-phenyl)-bis-(4-diethylamino-phenyl)-methane 
• 73664-10-5 N,N-diethyl-N-methyl-m-toluidinium; iodide 
• 6442-10-0 3-methyl-4-nitroso-N,N-diethylaniline 
• 31538-83-7 Diethyl-(3-methyl-4-p-tolylazo-phenyl)-amine 
• 70895-80-6 bis<4-(N,N-diethylamino)-2-methylphenyl>(4-methylphenyl)methane 
• 69432-33-3 C₃₄H₄₀N₈ 
• 102128-66-5 C₂₆H₃₂N₂O₂ 
• 116884-79-8 3-Bromo-2-(4-diethylamino-2-methyl-phenyl)-1,1-dioxo-1H-1λ⁶-thiochromen-4-one 
• 4913-13-7 3,5,N,N-tetramethylaniline 
• 2217-07-4 N,N-dipropylaniline 
• 5022-99-1 7-(4-Diaethylamino-2-methyl-phenyl)-1,3,5-cycloheptatrien 
• 70837-23-9 C₂₈H₃₈N₄ 

Relevant articles and documents

Hydrogenation and: N-Alkylation of anilines and imines via transfer hydrogenation with homogeneous nickel compounds

The nickel-catalyzed N-Alkylation of a variety of arylamines via transfer hydrogenation in the absence of pressurized hydrogen and basic or acidic additives was achieved in a tandem reaction. This process was further extended to the CN bond reduction and N-Alkylation of a variety of imines with ethanol, the latter acting as a hydrogen and acetaldehyde source, which allowed for the reduction and subsequent condensation to yield the corresponding N-Alkylated products.

Homogeneous catalytic hydrogenation of amides to amines

Hydrogenation of amides in the presence of [Ru(acac)3] (acacH=2,4-pentanedione), triphos [1,1,1-tris- (diphenylphosphinomethyl)ethane] and methanesulfonic acid (MSA) produces secondary and tertiary amines with selectivities as high as 93 % provided that there is at least one aromatic ring on N. The system is also active for the synthesis of primary amines. In an attempt to probe the role of MSA and the mechanism of the reaction, a range of methanesulfonato complexes has been prepared from prepared from [Ru(acac) 3], triphos and MSA, or from reactions of [RuX-(OAc)(triphos)] (X=H or OAc) or [RuH2(CO)(triphos)] with MSA. Crys-tallographically characterised complexes include: [Ru(OAc-κ1O) 2(H2O)-(triphos)], [Ru(OAc-κ2O,O') (CH3SO3-κ1O)(triphos)], [Ru(CH 3SO3-κ1O)2-(H 2O)(triphos)] and [Ru2(μ-CH3SO 3)3-(triphos)2][CH3SO3], whereas other complexes, such as [Ru(OAc-κ1O)(OAc- κ2O,O')(triphos)],[Ru(CH3SO3- κ1O)(CH3SO3-κ2O,O')- (triphos)], H[Ru(CH3SO3-κ1O) 3-(triphos)], [RuH(CH3SO3-κ1O) (CO)-(triphos)] and [RuH(CH3SO3-k2O,O')- (triphos)] have been characterised spectroscopically. The interactions between these various complexes and their relevance to the catalytic reactions are discussed.

One-pot photo-reductive N-alkylation of aniline and nitroarene derivatives with primary alcohols over Au-TiO2

We report the photo-catalytic N-alkylation of aniline by Au-TiO 2. We successfully alkylate aniline with several primary alcohols. The combined selectivities of mono- and di-alkylated products were always in excess of 70% and dependent on the alkylating alcohol used. A one-pot reaction from nitrobenzene was found to be possible with several substrates. Preliminary experiments showed that this approach could be adopted for the production of lactams using terminal amino-alcohols. The Royal Society of Chemistry 2013.