1477-55-0

Basic information

• Product Name: 1,3-Bis(aminomethyl)benzene
• Synonyms: LABOTEST-BB LT00053687;1,3-BIS(AMINOMETHYL)BENZENE;1,3-Benzenedimethanamine;ALPHA,ALPHA'-DIAMINO-M-XYLENE;RARECHEM AL BW 0017;OMEGA,OMEGA'-DIAMINO-M-XYLENE;M-XYLENE-ALPHA,ALPHA'-DIAMINE;M-XYLENE-A,A'-DIAMINE
• CAS NO: 1477-55-0
• Molecular Formula: C8H12N2
• Molecular Weight: 136.19
• EINECS: 216-032-5
• Product Categories: Intermediates of Dyes and Pigments;Acetone series;Rubber & Plastic Auxiliary Agent;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Polyamines;Fine Chemical
• Mol File: 1477-55-0.mol
• Article Data: 53

Chemical Properties

• Melting Point: 14°C
• Boiling Point: 265 °C745 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear slightly yellow/Liquid
• Density: 1.032 g/mL at 25 °C(lit.)
• Vapor Pressure: 15 mm Hg ( 145 °C)
• Refractive Index: n20/D 1.571(lit.)
• PKA: 9.37±0.10(Predicted)
• Water Solubility: Miscible
• BRN: 1099911
• CAS DataBase Reference: 1,3-Bis(aminomethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(aminomethyl)benzene(1477-55-0)
• EPA Substance Registry System: 1,3-Bis(aminomethyl)benzene(1477-55-0)

Safety Data

• Hazard Codes: T,C
• Statements: 21/22-23-34-43-52/53-20/22
• Safety Statements: 26-36/37/39-45-61-28A
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 2
• RTECS: PF8970000
• F: 2-9
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1477-55-0(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 1477-55-0 differently. You can refer to the following data:
1. CLEAR SLIGHTLY YELLOW LIQUID
2. m-Xylene-α,α0-diamine is a colorless liquid.

Uses

Different sources of media describe the Uses of 1477-55-0 differently. You can refer to the following data:
1. Manufacture of polyamide fibers and resins, as a curing agent.
2. m-Xylylenediamine can be used:As a monomer for the synthesis of poly(vinylogous urethane) vitrimers.As a starting material for the synthesis of carbamate-protected multisubstituted bis-guanidine.For the synthesis of polyamides by catalytic dehydrogenation with diols.

General Description

Colorless liquid with an amine smell. Mp: 14.1°C; bp: 273°C . Water soluble.

Reactivity Profile

1,3-Bis(aminomethyl)benzene is combustible (Flash point 139°C). Incompatible with acids, acid chlorides, acid anhydrides.

Hazard

Moderately toxic by skin contact and ingestion. Mildly toxic by inhalation. A severe skin, eye, and gastrointestinal irritant.

Safety Profile

Moderately toxic by skin contact and ingestion. Mildly toxic by inhalation. A severe skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx. Used to make polyamide fibers and resins and as a curing agent.

Potential Exposure

m-Xylene-α,α0-diamine is a source of m-xylene di-isocyanate and used as an intermediate in the manufacture of epoxy and polyamide resins.

Shipping

UN 2735A mines, liquid, corrosive, n.o.s, or Polyamines, liquid, corrosive, n.o.s., Hazard class: 8; Labels: 8-Corrosive material, Technical Name Required. UN3267 Corrosive liquid, basic, organic, n.o.s., Hazard class: 8; Labels: 8-Corrosive material, Technical Name Required.

Incompatibilities

Combustible; vapors may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides.

InChI:InChI=1/C8H12N2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6,9-10H2/p+2

Synthetic route

3-Cyanobenzaldehyde (24964-64-5) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With ammonia; hydrogen In methanol at 100℃; under 37503.8 Torr; for 5h;	100%
With ammonia; hydrogen In methanol at 80℃; under 22502.3 Torr; for 5h;	74%

benzene-1,3-dicarbonitrile (626-17-5) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With ammonia; hydrogen In methanol at 100℃; under 22502.3 Torr; for 2h; Pressure; Reagent/catalyst; Temperature;	99%
With hydrogen; cobalt/diatomaceous earth catalyst "G67", cobalt content=56percent; pretreatment is given in full text In 1,2,4-Trimethylbenzene; ammonia at 100℃; for 50h; Product distribution / selectivity;	96.2%
With hydrogen; Ni(NO3)2, Cu(NO3)2, Cr(NO3)3, Na2CO3; calcined at 380 deg C for 18 h; pretreatment is given in full text In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24h; Product distribution / selectivity;	95.2%

Isophthalaldehyde (626-19-7) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With Co-doped zirconium dioxide; ammonia; hydrogen; N-butylamine In methanol at 99.84℃; for 10h; Autoclave; chemoselective reaction;	97%

benzene-1,3-dicarbonitrile (626-17-5) → 1,3-di(aminomethyl)benzene (1477-55-0) + 3-methyl-benzenemethanamine (100-81-2)

Conditions	Yield
With hydrogen; Ni(NO3)2, Cu(NO3)2, Cr(NO3)3, Na2CO3; calcined at 380 deg C for 18 h; pretreatment is given in full text In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24h; Product distribution / selectivity;	A 96.8% B 0.1%
With hydrogen; Ni(NO3)2, Cu(NO3)2, Cr(NO3)3, Na2CO3; calcined at 380 deg C for 18 h; activated with H2 In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24h; Product distribution / selectivity;	A 92.1% B 0.1%

benzene-1,3-dicarbonitrile (626-17-5) → 1,3-di(aminomethyl)benzene (1477-55-0) + xylylene diamine condensation product

Conditions	Yield
With ammonia; hydrogen; catalyst A In mata-xylene at 80 - 110℃; Conversion of starting material;	A 93.1% B 5.5%

benzene-1,3-dicarbonitrile (626-17-5) → 1,3-di(aminomethyl)benzene (1477-55-0) + 3-(aminomethyl)benzonitrile (10406-24-3)

Conditions	Yield
With hydrogen; nickel catalyst "NDHT"; pretreatment is given in full text In methanol; ammonia at 65℃; for 4h; Product distribution / selectivity;	A 92.8% B 0.2%
With hydrogen; Pd-alumina In ammonia; 1,3,5-trimethyl-benzene at 50℃; under 36753.7 Torr;	A 7.7% B 87.3%
With hydrogen; nickel catalyst "NDHT" In methanol; ammonia at 65℃; for 4h; Product distribution / selectivity; autoclave;	A 84.8% B 0.2%

benzene-1,3-dicarbonitrile (626-17-5) + 3-(aminomethyl)benzonitrile (10406-24-3) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With hydrogen; catalyst A In ammonia; 1,3,5-trimethyl-benzene at 50℃; under 36753.7 Torr;	91.1%
With hydrogen; Ni-diatomaceous earth In ammonia; 1,3,5-trimethyl-benzene at 50℃; under 36753.7 Torr;	89.4%

benzene-1,3-dicarbonitrile (626-17-5) + ammonia (7664-41-7) + m-xylene (108-38-3) → 1,3-di(aminomethyl)benzene (1477-55-0) + 3-(aminomethyl)benzonitrile (10406-24-3)

Conditions	Yield
With hydrogen; Ni-3266E manufactured by Harshaw Co., Ltd.; nickel content: about 50percent at 55℃; under 112511 Torr; Product distribution / selectivity; tube reactor; feed rate = 1.5 t/h; supplying hydrogen rate = 100 Nm3/h;	A 91% B 0.1%
With hydrogen; catalyst A at 55℃; under 52505.3 Torr; Product distribution / selectivity; tube reactor; feed rate = 32 g/h; supplying hydrogen rate = 20 NL/h;	A 90.9% B 0.1%

3-(chloromethyl)benzyl chloride (626-16-4) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
Stage #1: 3-(chloromethyl)benzyl chloride With ammonia In methanol at 50℃; for 6h; Stage #2: With sodium hydroxide In water pH=13; Solvent;	89%

benzene-1,3-dicarbonitrile (626-17-5) + ammoniacal methanol → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
	81.7%
	79.5%

1,3-dimethanol benzene (626-18-6) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-Amyl alcohol at 150℃; for 20h; Inert atmosphere; Cooling;	70%
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-Amyl alcohol at 150℃; under 12001.2 Torr; for 20h; Inert atmosphere; Autoclave; chemoselective reaction;	70 %Chromat.

benzene-1,3-dicarbonitrile (626-17-5) + methylamine (74-89-5) → 1,3-di(aminomethyl)benzene (1477-55-0) + N,N'-(1,3-phenylenedimethylidyne)bis(methanamine) (85067-98-7) + 3-((methylimino)methyl)benzonitrile

Conditions	Yield
With hydrogen; Raney Nickel In tetrahydrofuran at 125℃; under 19393.6 Torr; for 16.6667h;	A 7% B 45.3% C 14.3%

benzene-1,3-dicarbonitrile (626-17-5) + methylamine (74-89-5) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With hydrogen In tetrahydrofuran at 125℃; under 19393.6 Torr; for 16.6667h;	44.9%
With hydrogen; Rh/Al2O3 In tetrahydrofuran at 125℃; under 19393.6 Torr; for 16.6667h;
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran at 125℃; under 19393.6 Torr; for 16.6667h;

benzene-1,3-dicarbonitrile (626-17-5) + methylamine (74-89-5) → 1,3-di(aminomethyl)benzene (1477-55-0) + 3-(methylaminomethyl)benzylamine (1035316-05-2) + N,N′-dimethyl-m-xylylenediamine (23399-62-4) + N,N'-(1,3-phenylenedimethylidyne)bis(methanamine) (85067-98-7)

Conditions	Yield
With hydrogen; Raney Nickel In tetrahydrofuran at 125℃; under 19393.6 Torr; for 19.6667h;	A 9.5% B 41.3% C 14.5% D 9.4%
With hydrogen; Raney nickel In tetrahydrofuran at 125℃; under 19393.6 Torr; for 19.6667h;

xylylene diamine condensation product → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With ammonia; hydrogen; catalyst A In m-xylene at 100 - 120℃; under 90009 Torr; Conversion of starting material;	10.8%

N,N'-(1,3-phenylenebismethylene)bisphthalimide (27199-63-9) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With potassium hydroxide Erhitzen des Reaktionsprodukts mit wss.Salzsaeure;
With hydrazine hydrate In ethanol for 4h; Reflux;
With sodium hydroxide at 80 - 120℃; under 760.051 Torr; for 2h; Dean-Stark;	51.5 g

urea (57-13-6) + 1,3-bis-(bromomethyl)benzene (626-15-3) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
anschliessendes Erwaermen mit wss.NaOH;

hydrogenchloride (7647-01-0) + N,N'-(1,3-phenylenebismethylene)bisphthalimide (27199-63-9) → 1,3-di(aminomethyl)benzene (1477-55-0) + benzene-1,2-dicarboxylic acid (88-99-3)

Conditions	Yield
at 200 - 220℃;

m-xylylene-bis-phthalimide → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With hydrogenchloride at 200 - 220℃;

3-(aminomethyl)benzonitrile (10406-24-3) → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With hydrogen; nickel/diatomaceous earth catalyst (nickel 50wtpercent) reduced with hydrogen at 200C at 100℃; under 30003 Torr; Product distribution / selectivity;

Reaxys ID: 11464042 → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With hydrogen; catalyst A In ammonia; xylene at 75℃; under 112511 Torr; Conversion of starting material; The continuous flow reaction .The concentration of benzamide compound-0.011%, benzoic acid compound-0.001%;	90.9 %Chromat.
With hydrogen; catalyst A In ammonia; xylene at 90℃; under 112511 Torr; for 504h; Conversion of starting material; The continuous flow reaction .The concentration of bezamide compound-0.011%, benzoic acid compound-0.001%;	90.9 %Chromat.

Reaxys ID: 11464043 → 1,3-di(aminomethyl)benzene (1477-55-0) + 3-(aminomethyl)benzonitrile (10406-24-3)

Conditions	Yield
With hydrogen; catalyst A In methanol; ammonia at 80℃; under 150015 Torr; Conversion of starting material; batch-wise method ; concentration benzamide-0.043w.%, benzoic acid-0.004w.%;	A 75.7 %Chromat. B 0.3 %Chromat.

Reaxys ID: 11464046 → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With hydrogen; catalyst A In ammonia; xylene at 75℃; under 112511 Torr; Conversion of starting material; The continuous flow reaction . The concentration of benzamide compound-0.063%, benzoic acid compound-0.001%;	89.4 %Chromat.
With hydrogen; catalyst A In ammonia; xylene at 90℃; under 112511 Torr; for 432h; Conversion of starting material; The continuous flow reaction .The concentration of benzamide compound-0.063%, benzoic acid compound-0.001%;	89.4 %Chromat.

Reaxys ID: 11464047 → 1,3-di(aminomethyl)benzene (1477-55-0) + 3-(aminomethyl)benzonitrile (10406-24-3)

Conditions	Yield
With hydrogen; catalyst A In methanol; ammonia at 80℃; under 150015 Torr; Conversion of starting material; The butch-wize method.The concentration of bezamide-0.30%, benoic acid-0.004%;	A 74.8 %Chromat. B 0.3 %Chromat.

Reaxys ID: 11464048 → 1,3-di(aminomethyl)benzene (1477-55-0) + 3-(aminomethyl)benzonitrile (10406-24-3)

Conditions	Yield
With hydrogen; catalyst A In methanol; ammonia at 80℃; under 150015 Torr; Conversion of starting material; The batch-wize method;	A 70.2 %Chromat. B 0.5 %Chromat.

Reaxys ID: 11464050 → 1,3-di(aminomethyl)benzene (1477-55-0) + 3-(aminomethyl)benzonitrile (10406-24-3)

Conditions	Yield
With hydrogen; catalyst A In methanol; ammonia at 80℃; under 150015 Torr; Conversion of starting material; The batch-wise method;	A 69.9 %Chromat. B 0.9 %Chromat.

Reaxys ID: 11464054 → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With hydrogen; catalyst A In ammonia; xylene at 75℃; under 112511 Torr; Conversion of starting material; The continuous flow reaction .The concentration of benzamide compound-0.114%, benzoic acid compound-0.002%;	87.8 %Chromat.
With hydrogen; catalyst A In ammonia; xylene at 90℃; under 112511 Torr; for 288h; Conversion of starting material; The continuous flow reaction .The concentration of benzamide compound-0.114%, benzoic acid compound-0.002%;	87.8 %Chromat.

Reaxys ID: 11464115 → 1,3-di(aminomethyl)benzene (1477-55-0)

Conditions	Yield
With hydrogen; catalyst A In ammonia; xylene at 75℃; under 112511 Torr; Conversion of starting material; The continuous flow reaction .The concentration of benzamide compound-0.012%, bezoic acid compound-0.012%;	88.8 %Chromat.
With hydrogen; catalyst A In ammonia; xylene at 90℃; under 112511 Torr; for 408h; Conversion of starting material; The continuous flow reaction .The concentration of benzamide compound-0.012%, benzoic acid compound-0.012%;	88.8 %Chromat.

Reaxys ID: 11464115 → 1,3-di(aminomethyl)benzene (1477-55-0) + 3-(aminomethyl)benzonitrile (10406-24-3)

Conditions	Yield
With hydrogen; catalyst A In methanol; ammonia at 80℃; under 150015 Torr; Conversion of starting material; The batch-wise method .The concentration of benzamide0.043%, benzoic acid-0.043%;	A 74.1 %Chromat. B 0.2 %Chromat.
With hydrogen; sodium hydroxide; PDC-3000 In ammonia at 50℃; under 150015 Torr; for 0.5h; Product distribution / selectivity; The batch-wise method . The concentration of benzamide compound-0.043%, benzoic acid compound-0.043%;	A 8.4 %Chromat. B 76 %Chromat.

1,3-di(aminomethyl)benzene (1477-55-0) + (2S,3S,11S,12S)-1,4,7,10,13,16-Hexaoxa-cyclooctadecane-2,3,11,12-tetracarbonyl tetrachloride (61696-55-7, 73891-16-4, 119067-16-2) → C32H40N4O10 (129166-26-3)

Conditions	Yield
In toluene	100%

1,3-di(aminomethyl)benzene (1477-55-0) + 7,11,15,28-tetrakis(bromomethyl)-1,21,23,25-tetramethyl-2,20:3,19-dimetheno-1H,21H,23H,25H-bis<1,3>dioxocino<5,4-i:5',4'-i'>benzo<1,2-d:5,4-d'>bis<1,3>benzodioxocin (887129-89-7) → tetrakis[({[3-(aminomethyl)phenyl]methyl}amino)methyl]-tetramethyl cavitand

Conditions	Yield
at 100℃;	100%

1,3-di(aminomethyl)benzene (1477-55-0) + Diethyl vinylphosphonate (682-30-4) → 1,3-bis{(N,N-bis[(diethoxyphosphoryl)ethyl])aminomethyl}benzene (1073193-35-7)

Conditions	Yield
In water at 20℃; Michael condensation;	100%
In water at 20℃; for 120h; Aza-Michael reaction;	83%

1,3-di(aminomethyl)benzene (1477-55-0) + 4-[(trimethylsilyl)ethynyl]bezaldehyde (77123-57-0) → C32H36N2Si2 (1219537-39-9)

Conditions	Yield
With magnesium sulfate In diethyl ether at 20℃; for 3h;	100%

(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-carboxy-5-methylpyrrolidine-3,4-diol (869857-96-5) + 1,3-di(aminomethyl)benzene (1477-55-0) → C42H50N4O10

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	100%

1,3-di(aminomethyl)benzene (1477-55-0) + 1,2,3,4-butanetetracarboxylic acid (4534-68-3) → 1,3-benzenedimethanammonium dihydrogen 1,2,3,4-butanetetracarboxylate

Conditions	Yield
In water	100%

1,3-di(aminomethyl)benzene (1477-55-0) + tetrahydrofuran-2,3,4,5-tetracarboxylic acid (26106-63-8) → 1,3-benzenedimethanammonium dihydrogen tetrahydrofuran-2,3,4,5-tetracarboxylate

Conditions	Yield
In water	100%

1,3-di(aminomethyl)benzene (1477-55-0) + dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid (2421-28-5) → 1,3-benzenedimethaneammonium dihydrogen 3,3',4,4'-benzophenonetetracarboxylate

Conditions	Yield
In water for 0.5h;	100%

1,3-di(aminomethyl)benzene (1477-55-0) → 1,3-phenylenedimethanamine dihydrochloride

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; methanol for 0.166667h;	100%

phosgene (75-44-5) + 1,3-di(aminomethyl)benzene (1477-55-0) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
Stage #1: 1,3-di(aminomethyl)benzene With hydrogenchloride In water; 1,2-dichloro-benzene at 20℃; Autoclave; Large scale; Stage #2: phosgene In water; 1,2-dichloro-benzene at 145℃; for 2h; Autoclave; Large scale;	99.9%
With picoline In dichloromethane at -5 - 140℃; for 4h; Reagent/catalyst; Temperature;	98.3%
Stage #1: 1,3-di(aminomethyl)benzene With hydrogenchloride In chlorobenzene at 10℃; under 750.075 Torr; for 1.5h; Flow reactor; Large scale; Stage #2: phosgene In chlorobenzene at 131℃; under 750.075 Torr; for 3h; Temperature; Pressure; Solvent; Flow reactor; Large scale;	98.5%

1,3-di(aminomethyl)benzene (1477-55-0) + di-o-tolyl carbonate (617-09-4) → 1,3-bis-[(methoxycarbonylamino)-methyl]-benzene (54772-36-0)

Conditions	Yield
With hydrogenchloride In methanol	99.7%

1,3-di(aminomethyl)benzene (1477-55-0) + bis(2,2,3,3-tetrafluoropropyl) carbonate (1422-70-4) → m-xylylene bis(2,2,3,3-tetrafluoropropylcarbamate) (1338600-43-3)

Conditions	Yield
at 50℃; for 1h;	99.4%

1,3-di(aminomethyl)benzene (1477-55-0) + 4-(4'-tert-butyloxycarbonylphenylethynyl)benzoic acid (652149-71-8) → C40H28N2O6

Conditions	Yield
Stage #1: 4-(4'-tert-butyloxycarbonylphenylethynyl)benzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide Stage #2: 1,3-di(aminomethyl)benzene With triethylamine In dichloromethane Stage #3: With trifluoroacetic acid In dichloromethane	99%

1,3-di(aminomethyl)benzene (1477-55-0) + epichlorohydrin (106-89-8) → N,N,N',N'-tetraglycidyl-m-xylylenediamine (63738-22-7)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 90℃; for 1h; Product distribution / selectivity; Inert atmosphere;	98.4%

1,3-di(aminomethyl)benzene (1477-55-0) + Methyl formate (107-31-3) + carbonic acid dimethyl ester (616-38-6) → 1,3-bis-[(methoxycarbonylamino)-methyl]-benzene (54772-36-0)

Conditions	Yield
With sodium methylate In methanol at 70℃; for 3h;	98.4%

1,3-di(aminomethyl)benzene (1477-55-0) + carbonic acid dimethyl ester (616-38-6) → 1,3-bis-[(methoxycarbonylamino)-methyl]-benzene (54772-36-0)

Conditions	Yield
lipase from Candida antarctica In toluene at 70℃; for 60h; Product distribution / selectivity;	98%
With lead(II) acetate trihydrate; zinc(II) acetate dihydrate In water at 180℃; under 2250.23 Torr; for 6h; Reagent/catalyst; Inert atmosphere;	98.2%
With water; sodium methylate In methanol at 50℃; for 3.5h;	97%
	79.3%

1,3-di(aminomethyl)benzene (1477-55-0) + C64H40N8O4Zn2 → C80H56N12Zn2

Conditions	Yield
With trifluoroacetic acid In chloroform at 20℃; for 24h; Inert atmosphere;	98%

1,3-di(aminomethyl)benzene (1477-55-0) + 4-(trifluoromethoxy)-2-formylphenylboronic acid → C24H24B2F6N2O6

Conditions	Yield
Stage #1: 1,3-di(aminomethyl)benzene; 4-(trifluoromethoxy)-2-formylphenylboronic acid In toluene at 50℃; for 12h; Stage #2: With sodium tetrahydroborate In toluene at 25℃; for 4h; Cooling with ice;	98%

1,3-di(aminomethyl)benzene (1477-55-0) + citraconic acid anhydride (616-02-4) → 1,3-bis(citraconimidomethyl)benzol (119462-56-5)

Conditions	Yield
With acetic acid In toluene at 110℃; for 5h; Temperature; Reagent/catalyst; Solvent;	97.5%
With acetic acid at 110℃; for 4h; Temperature; Time;	92%

1,3-di(aminomethyl)benzene (1477-55-0) + benzoyl chloride (98-88-4) → N,N'-(1,3-phenylenebis(methylene))dibenzamide (33891-00-8)

Conditions	Yield
With sodium hydroxide at 0℃; for 3h;	97%
With (+/-)-propylene oxide In tetrahydrofuran at 20℃;	67%
With pyridine

1,3-di(aminomethyl)benzene (1477-55-0) + 4-oxo-2-(N-phenyl)amino-4H-chromene-3-carbaldehyde (213273-03-1) → C40H30N4O4

Conditions	Yield
In acetonitrile	97%

1,3-di(aminomethyl)benzene (1477-55-0) + 3-benzoylquinoxalin-2(1H)-one (49568-76-5) → 1,3-bis(3-phenyl-4(5H)-oxoimidazo[1,5-a]quinoxalin-5-ylmethyl)benzene

Conditions	Yield
In dimethyl sulfoxide at 150℃; for 72h;	97%

1,3-di(aminomethyl)benzene (1477-55-0) + phthalic anhydride (85-44-9) → N,N'-(1,3-phenylenebismethylene)bisphthalimide (27199-63-9)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one; xylene at 120℃; Product distribution / selectivity;	97%
With acetic acid Heating;	91%

1,3-di(aminomethyl)benzene (1477-55-0) + 2,3-dimethoxybenzoic acid (1521-38-6) → N,N'-[1,3-phenylenebis(methylene)]bis-(2,3-dimethoxybenzamide) (188746-15-8)

Conditions	Yield
Stage #1: 2,3-dimethoxybenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Stage #2: 1,3-di(aminomethyl)benzene With triethylamine In dichloromethane for 18h; Further stages.;	97%

1,3-di(aminomethyl)benzene (1477-55-0) + 3-((trimethylsilyl)ethynyl)benzaldehyde (77123-55-8) → C32H36N2Si2 (1219537-45-7)

Conditions	Yield
With magnesium sulfate In diethyl ether at 20℃; for 3h;	97%

1,3-di(aminomethyl)benzene (1477-55-0) + N-(6-(bromomethyl)-2-pyridyl)pivalamide (111477-43-1) → C52H68N10O4 (1258528-12-9)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	97%

1,3-di(aminomethyl)benzene (1477-55-0) + salicylaldehyde (90-02-8) → 2,2'-(1,3-phenylenebis(methylene))bis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)diphenol (51540-97-7)

Conditions	Yield
In ethanol at 20℃; for 0.166667h; Temperature; Microwave irradiation; Green chemistry;	97%
In methanol for 3h; Schiff reaction; Heating;	90%
With formic acid In ethanol for 10h; Reflux;	75.2%
In methanol for 4h; Reflux;	74%
In methanol for 2h; Reflux;

1,3-di(aminomethyl)benzene (1477-55-0) + p-trifluoromethyl-phenylisocyanate (1548-13-6) → 1,1'-(1,3-phenylenebis(methylene))bis(3-(4-(trifluoromethyl)phenyl)urea)

Conditions	Yield
In dichloromethane Inert atmosphere; Reflux;	97%

Upstream product

• 57-13-6 urea 
• 626-15-3 1,3-bis-(bromomethyl)benzene 
• 626-17-5 benzene-1,3-dicarbonitrile 
• 626-19-7 Isophthalaldehyde 
• 24964-64-5 3-Cyanobenzaldehyde 
• 626-16-4 3-(chloromethyl)benzyl chloride 
• 626-18-6 1,3-dimethanol benzene 
• 74-89-5 methylamine 
• 623-26-7 terephthalonitrile 
• 10406-24-3 3-(aminomethyl)benzonitrile 
• 7664-41-7 ammonia 
• 108-38-3 m-xylene 

Downstream Products

• 3634-83-1 m-xylylene diisocyanate 
• 53040-60-1 N,N'-dibenzylidene-m-xylylenediamine 
• 37042-63-0 α,α'-bis(N'-phenylthioureylene)-m-xylene 
• 66128-35-6 1,3-bis(N,N-bis(2-cyanoethyl)aminomethyl)benzene 
• 2842-63-9 m-xylylene bis-acrylamide 
• 54731-28-1 Trimethylsilanyl-{3-[(trimethylsilanyl-amino)-methyl]-benzyl}-amine 
• 16578-48-6 3-[3-(3,3-Dimethyl-ureidomethyl)-benzyl]-1,1-dimethyl-urea 
• 87338-18-9 1,3-bis<<(p-tolylsulfonyl)amino>methyl>benzene 
• 2579-20-6 cis, trans-1,3-dimethylaminocyclohexane 
• 192518-52-8 C₃₆H₃₀N₄O₆ 
• 243982-37-8 N-(3-aminomethyl-benzyl)-N',N'-dibenzyl-N''-butyl-[1,3,5]triazine-2,4,6-triamine 
• 263854-40-6 3-ethoxycarbonylaminomethylbenzylamine 

Relevant articles and documents

Isophthalonitrile (IPN) hydrogenation over K modified Ni-Co supported catalysts: Catalyst characterization and performance evaluation

The hydrogenation of isophthalonitrile (IPN) to meta-xylylenediamine (m-XDA) is usually catalyzed by the Raney or supported Ni based catalysts in the presence of basic additive. Although the supported catalysts are safer than the Raney Ni catalysts, they have lower selectivity to m-XDA. This work revealed that the acid sites of NiCo/Al2O3 were responsible for the condensation reactions between amines and imines, which were the dominant side reactions. Besides the original acid sites on γ-Al2O3, the loading of Ni-Co introduced new acid sites, which had a greater contribution to the condensation reactions. The K modification significantly enhanced the selectivity to m-XDA by reducing the two kinds of acid sites. Due to the formation mechanism of new acid sites and the K modification mechanism on these sites, both the K loading and K impregnation sequence affected the catalytic performance. When 3.0 wt% K was introduced to NiCo/Al2O3 by co-impregnation (3KNiCo/Al2O3), the catalyst acidity decreased by 82%, and the selectivity to m-XDA increased from 45.5% to 99.9%. The superiority of the optimized catalyst 3KNiCo/Al2O3 was also confirmed when no basic additive was used.

Role of acid sites and surface hydroxyl groups in isophthalonitrile hydrogenation catalyzed by supported Ni-Co catalysts

meta-Xylylenediamine (m-XDA) is industrially produced by the hydrogenation of isophthalonitrile (IPN) using Raney Ni/Co and basic additives. Compared with Raney Ni/Co, the supported Ni/Co catalysts are safer and have better mechanical strength. This work aimed at studying the catalytic performance of the supported Ni-Co catalysts in hydrogenation of IPN to m-XDA. The active sites for the condensation side reactions were studied using Ni-Co catalysts supported on different oxides and with different loadings. It was found that the acid sites catalyzed the condensation reactions between intermediate imines and amines. Two types of acid sites existed on the supported Ni-Co catalysts, namely, the original acid sites of the support and new acid sites formed by Ni/Co aluminates. In addition to acid sites, the surface hydroxyl groups on the oxide supports also catalyzed the condensation reactions, but were not active for the hydrogenation reaction. By increasing the Ni-Co loading, the selectivity to m-XDA was significantly enhanced, which was attributed to the suppression of both acid sites and hydroxyl groups. Compared to the low-loading catalysts (5Ni-1.25Co/Al2O3 and 5Ni-1.25Co/SiO2), the high-loading catalysts (20Ni-5Co/Al2O3 and 20Ni-5Co/SiO2) increased the m-XDA selectivity from ～45.5 to 99.9%.

METHOD FOR PRODUCING m-XYLYLENE DIAMINE

PROBLEM TO BE SOLVED: To provide a method for producing m-xylylene diamine that makes it possible to efficiently produce m-xylylene diamine by reducing the formation of by-products even when a reaction temperature is lowered in a hydrogenation reaction step. SOLUTION: In the presence of a catalyst with palladium carried on carbon and in the absence of ammonia and an amine compound (excluding a reaction product), 1,3-dicyanobenzene and hydrogen are reacted at 0°C or higher and 50°C or lower, and hydrogen is added to the 1,3-dicyanobenzene, producing m-xylylene diamine. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Cobalt pincer complexes for catalytic reduction of nitriles to primary amines

Various cobalt pincer type complexes 1-6 were applied for the catalytic hydrogenation of nitriles to amines. Among these, catalyst 4 is the most efficient, allowing the reduction of aromatic as well as aliphatic nitriles in moderate to excellent yields.

Facile synthesis of supported Ru-Triphos catalysts for continuous flow application in selective nitrile reduction

The selective catalytic hydrogenation of nitriles represents an important but challenging transformation for many homogeneous and heterogeneous catalysts. Herein, we report the efficient and modular solid-phase synthesis of immobilized Triphos-type ligands in very high yields, involving only minimal work-up procedures. The corresponding supported ruthenium-Triphos catalysts are tested in the hydrogenation of various nitriles. Under mild conditions and without the requirement of additives, the tunable supported catalyst library provides selective access to both primary amines and secondary imines. Moreover, the first application of a Triphos-type catalyst in a continuous flow process is presented demonstrating high catalyst life-time over at least 195 hours without significant activity loss.