19851-44-6

Basic information

• Product Name: N,N'-(1,3-Xylylene)bis(dimethylamine)
• Synonyms: (1,3-Phenylene)bismethylenebis(dimethylamine);1,3-Bis(dimethylaminomethyl)benzene;N,N'-(1,3-Phenylenebismethylene)bis(dimethylamine);N,N'-(1,3-Xylylene)bis(dimethylamine);N,N,N',N'-Tetramethylbenzene-1,3-bis(methanamine);N,N,N',N'-Tetramethylbenzene-1,3-bismethanamine
• CAS NO: 19851-44-6
• Molecular Formula: C₁₂H₂₀N₂
• Molecular Weight: 192.3006
• Mol File: 19851-44-6.mol

Chemical Properties

• Boiling Point: 233.9±20.0 °C(Predicted)
• Appearance: /
• Density: 0.949±0.06 g/cm3(Predicted)
• Refractive Index: 1.5020 to 1.5060
• PKA: 9.06±0.28(Predicted)
• CAS DataBase Reference: N,N'-(1,3-Xylylene)bis(dimethylamine)(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-(1,3-Xylylene)bis(dimethylamine)(19851-44-6)
• EPA Substance Registry System: N,N'-(1,3-Xylylene)bis(dimethylamine)(19851-44-6)

Safety Data

• RIDADR: UN 2735 8/PG II
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 19851-44-6(Hazardous Substances Data)

Usage

Uses

Used in Epoxy Resin Industry:
N,N'-(1,3-Xylylene)bis(dimethylamine) is used as a curing agent for epoxy resins, which are essential in various applications such as coatings, adhesives, and electrical insulation materials. Its role in curing enhances the mechanical properties and chemical resistance of the final product.
Used in Polyurethane Industry:
In the polyurethane industry, N,N'-(1,3-Xylylene)bis(dimethylamine) serves as a catalyst for the production of polyurethane foams and elastomers. It accelerates the reaction process, leading to improved production efficiency and product quality.
Used in Agrochemical Industry:
N,N'-(1,3-Xylylene)bis(dimethylamine) is also used in the production of herbicides and pesticides, where it contributes to the effectiveness of these products in controlling unwanted plant growth and pests.
Safety Measures:
Due to its harmful nature if swallowed, inhaled, or absorbed through the skin, and its potential to cause irritation to the respiratory system and skin, it is crucial to handle N,N'-(1,3-Xylylene)bis(dimethylamine) with care. Safety precautions include wearing protective clothing and gloves, ensuring adequate ventilation, and avoiding release into the environment to minimize its toxic effects on aquatic life and potential long-term environmental impacts.

Upstream product

• 114762-92-4 Ir{C₆H₃(CH₂N(CH₃)2)2}(C₈H₁₂) 
• 114762-89-9 Ir{C₆H₃(CH₂NMe₂)2-o,o'}(1,5-cyclooctadiene) 
• 115338-69-7 rhodium{C₆H₃(CH₂NMe₂)2-o,o'}(norbornadiene) 
• 115338-66-4 rhodium{C₆H₃(CH₂NMe₂)2-o,o'}(1,5-cyclooctadiene) 
• 75-24-1 trimethylaluminum 
• 64-17-5 ethanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 67-63-0 isopropyl alcohol 
• 141-43-5 ethanolamine 
• 626-18-6 1,3-dimethanol benzene 
• 124-40-3 dimethyl amine 
• 82622-01-3 Li₂{C₆H₃(CH₂NMe₂)2-o,o'}2 
• 112596-46-0 Rh(III)Cl((CH₃CO)2CH)(C₆H₃(CH₂NMe₂)2-o,o')2 
• 112596-40-4 trans-Rh(III)Cl₂(C₆H₃(CH₂NMe₂)2-o,o')(H₂O) 

Downstream Products

• 192123-75-4 (MeReO₃)2(C₆H₄(CH₂NMe₂-1,3)2) 
• 474888-54-5 [Au(C₆H₃(CH₂NMe₂)2-2,6)(triphenylphosphine)] 
• 882031-96-1 BiCl(C₆H₃(CH₂N(CH₃)2)2)2 
• 15827-34-6 2,6-bis-<(dimethyamino)methyl>phenol 
• 66479-06-9 1-bromo-2,6-bis-((dimethylamino)methyl)benzene 
• 94725-71-0 (3-Dimethylaminomethyl-2-methoxy-benzyl)-dimethyl-amine 

Relevant articles and documents

Novel Five-co-ordinate Diorganorhodium Compounds. X-Ray Structure of Bis-ortho-chelated >

Compounds of the type > have been synthesized by (i) oxidative addition of MeI (80percent yield) or EtI (minor product) to (cod)> (cod=cyclo-octa-1,5-diene); (ii) reaction of > (acac=acetylacetonate) with either AlMe3, AlEt3, or LiMe-LiI; (iii) metathesis of > (R=Me or Et, X=Cl or I) with Ag(O2CMe) or Ag(O3SCF3).The solid-state structure of > was determined by an X-ray diffraction study.Crystals are orthorhombic, space group Pbca, with lattice parameters a=14.899(3), b=15.744(3), c=13.191(2) Angstroem, U=3094(2) Angstroem3, Z=8, Dc=1.87 g cm-3, R=0.055.The structure has a square-pyramidal five-co-ordinate rhodium centre.One C and two N atoms of the chelating aryl moiety together with the I atom define the basal plane, and the methyl group lies at the apex . 103Rh N.m.r.studies of the novel five-co-ordinate diorganorhodium(III) compounds have been carried out.

Aerobic oxidation-functionalization of the aryl moiety in van Koten's pincer complex (NCN)Ni(ii)Br: Relevance to carbon-heteroatom coupling reactions promoted by high-valent nickel species

The growing popularity of metal-promoted C-H functionalization methodologies has led to increased efforts aimed at improving our understanding of the mechanistic underpinnings of C-C and C-heteroatom bond forming steps. One approach to such mechanistic studies involves probing the reactivities of model complexes featuring chelate-stabilized M-hydrocarbyl moieties. The present study uses van Koten's (NCN)Ni(ii)Br compound as a model for probing C-heteroatom coupling with protic substrates HX (X = NHR, OR). Our results establish the crucial importance of aerobic (oxidative) conditions for promoting reactivities that give the functionalized ligands NC(X)N. The importance of oxidation for the C-heteroatom bond formation is further deduced from the reaction of the structurally authenticated complex (NCN)Ni(OSiMe3) with CuBr2 to give the C-O functionalization product NC(OSiMe3)N. This journal is

Selective Synthesis of Bisdimethylamine Derivatives from Diols and an Aqueous Solution of Dimethylamine through Iridium-Catalyzed Borrowing Hydrogen Pathway

Bisdimethylamine derivatives are an important class of compounds in the polymer and pharmaceutical industries. However, existing methods for the synthesis of these compounds have several drawbacks such as low selectivity, use of toxic reagents, and generation of waste. In this study, a new system was developed for the selective synthesis of bisdimethylamine derivatives using a diol and dimethylamine as starting materials and an iridium complex bearing an N-heterocyclic carbene ligand as catalyst. The starting materials were easily available, less toxic, inexpensive, and easy to handle. The reaction proceeded efficiently through a borrowing hydrogen pathway under aqueous conditions, without any additional organic solvent, to afford various bisdimethylamine derivatives in good to excellent yields.

Functionalization of the Aryl Moiety in the Pincer Complex (NCN)NiIIIBr2: Insights on NiIII-Promoted Carbon-Heteroatom Coupling

This report describes the C-O, C-N, and C-halogen functionalization of the NiIII-Ar moiety stabilized within a pincer framework that serves as a model system for studying C-heteroatom coupling reactions promoted by high-valent Ni compounds. Treating van Koten's pincer complex (NCN)NiIIIBr2 under a nitrogen atmosphere with water, 1° or 2° alcohols, 1° amines, HCl, or HBr results in heterofunctionalization at the ipso-C of the pincer ligand's aryl moiety. The yields of these heterofunctionalizations are generally a comproportionation reaction between the trivalent precursor and a NiI species arising from the reductive elimination step in the functionalization process. Other side-reactions include a C-OH coupling with residual water and C-H coupling (net protonation) that is prevalent with mineral acids, some alcohols, and aqueous NH3. Kinetic measurements have established that the reaction with MeOH is first-order with respect to [(NCN)NiIIIBr2], and a kinetic isotope effect of 0.47 has been obtained for functionalization with CH3OH/CD3OD. These and other observations have allowed us to propose two different mechanistic postulates for the involvement of trivalent intermediates in the functionalization reactions under discussion. Tetravalent species such as [(NCN)NiIVBr2]+ can be generated in situ under strongly oxidative conditions and they do promote C-Br coupling, but such species play no role in the C-heteroatom coupling reactions under nonoxidative conditions.

Curare-like camphor derivatives and their biological activity

The synthesis of symmetric dimeric camphor derivatives containing two quaternary nitrogen atoms was performed and their myorelaxant activity in mice was evaluated. For the comparison, some salts derived from meta-and para-xylylene dibromides were synthesi

Ortho-chelated arylrhodium(I) complexes. X-ray structure of RhI[C6H3(CH2NMe2) 2-o,o′-C,N ](COD)

The reaction of Lin[C6H3(CH2NMe 2)-o-R-o′]n with [RhCl(diene)]2 yields the ortho-chelated arylrhodium(I) complexes Rh[C6H3(CH2NMe 2)-o-R-o′](diene) (R = CH2NMe2, diene = COD (1a) or NBD (1b); diene = COD, R = Me (2) or H (3)). The solid-state structure of 1a was determined by a single-crystal X-ray diffraction study. C20H31N2Rh: triclinic, space group P1, with lattice parameters a = 10.169 (1) ?, b = 13.036 (1) ?, c = 14.688 (2) ?, α = 79.54 (1)°, β = 77.04 (1)°, γ = 79.53°; V = 1845.6 (4) ?3, Z = 4; D(calcd) = 1.448 g cm-3. Refinement with 4696 observed reflections converged at R = 0.0395. The structure of 1a consists of a rhodium(I) center that has a square-planar coordination comprising the two double bonds of COD and a C atom and one of the N atoms of the monoanionic aryl ligand. In solution compounds 1 and 2 exhibit dynamic behavior which involves a reversible dissociation of the Rh-N bond and rotation of the aryl moiety around Rh-C. This process, which generates a highly unsaturated T-shaped 14 electron species, is accompanied by the relief of steric repulsions within the complex. Complex 1 reacts with a range of electrophilic reagents leading to Rh-C bond breakage (HX, X = acac, Cl, Br, OAc, OH, OMe, L-alanyl; MXnLm, SnMe2Br2, NiBr2(PBu3)2, ZrCl4, PdCl2(NCPh)2, HgCl2, PtBr2(COD), and [IrCl(COD)]2). A redox reaction of 1 with AgX (X = OAc, NO3) leads to the formation of RhIIIX2[C6H3(CH2NMe 2)2-o,o′](H2O).

Ortho metalation of m-(Me2NCH2)2C6H4: Crystal structure and chemistry of trans-RhIIICl2[C6H3(CH 2NMe2)2-o,o′](H2O)

From the reaction of m-(Me2NCH2)2C6H4 with aqueous rhodium trichloride in ethanol the ortho-metalated product trans-RhIIICl2(N-C-N)(H2O) could be isolated in 45% yield (N-C-N = C6H3(CH2NMe2) 2-o,o′). Its solid-state structure was determined by an X-ray diffraction study. Crystals are monoclinic, space group P21/n, with lattice parameters a = 9.070 (1) ?, b = 17.277 (3) ?, c = 9.855 (1) ?, β = 91.34 (1)°, V = 1543.9 (4) ?3, Z = 4, and D(calcd) = 1.648 g cm-3. Refinement with 3710 observed reflections converged at R = 0.042. The structure of trans-RhIIICl2(N-C-N)(H2O) consists of a rhodium(III) center that is octahedrally coordinated. A mer arrangement of the C and two N atoms of the monoanionic N-C-N ligand (Rh-C(aryl) = 1.913 (3) ?) and a coordinated water molecule trans to C(aryl) form a planar arrangement. The two mutually trans Cl atoms sited above and below this plane complete the coordination sphere. In the solid state the molecules form infinite chains via intermolecular O-H?Cl hydrogen bonds. Metathesis of this new compound with either a large excess of alkali-metal salt or a slight excess of silver salt led to the formation of a range of new arylrhodium(III) compounds, trans-RhX2(N-C-N)(H2O) (X = Br, O2CH, O2CMe, NO3, and CN). Halogen-bridged bi- and trinuclear complexes RhCl(N-C-N)(μ-Cl)2M(COD) (M = Rh1, Ir1; COD = 1,5-cyclooctadiene) and [RhCl(N-C-N)(μ-Cl)2]2M (M = PdII, CuII) were synthesized by mixing trans-RhCl2(N-C-N)(H2O) with the appropriate metal salt: [MCl(COD)]2, CuCl2, and PdCl2(COD) or Li2PdCl4, respectively. The same reaction with Li(acac) as the metal salt led to the formation of RhCl(acac)(N-C-N).

Formation of octahedral iridium(III) dihydrides from the reaction of ortho-chelated aryliridium(I) compounds with dihydrogen

The reaction of IrI[C6H2(CH2NMe 2)-2-R1-4-R2-6](COD) (COD = cycloocta-1,5-diene) with dihydrogen in CD2Cl2 was monitored by 1H NMR. At -20°C quan

Inclusion Compounds of Organic Onium Salts, IV. Organyl Ammonium Hosts as Versatile Clathrate Formers

The organyl-oligo-ammonium compounds 1 - 25 and their clathrates with a variety of low molecular weight neutral compounds, especially solvent molecules, are prepared.The inclusion capacity of the new clathrands can be explained by interstices in the host lattice.The conformational flexibility of the voluminous onium branches is responsible for the great number of clathrates; their stability depends on the ion lattice.The X-ray analysis of the ethanol clathrate of the onium host 8 shows that one ethanol molecule is surrounded by the host molecules in a cage-type manner.The great variety of the inclusions obtained up to now demonstrates that the oligo onium host compounds have to be considered as the most universal clathrands of organic chemistry.Hints are given for the syntheses of new onium clathrates.