34124-14-6

Basic information

• Product Name: 2,2'-ETHYLENEDIANILINE
• Synonyms: 2,2'-(1,2-ETHANEDIYL)BISBENZENAMINE;2,2'-DIAMINOBIBENZYL;2,2'-DIAMINO-1,2-DIPHENYLETHANE;2,2'-ETHYLENEDIANILINE;2,2-ETHYLENEDIANILINE;ALPHA,ALPHA'-BI-O-TOLUIDINE;2,2'-ETHYLENEDIANILINE 97+%;2,2'-Diaminodibenzyl
• CAS NO: 34124-14-6
• Molecular Formula: C₁₄H₁₆N₂
• Molecular Weight: 212.29
• EINECS: 251-837-5
• Mol File: 34124-14-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 72-77 °C
• Boiling Point: 342.14°C (rough estimate)
• Flash Point: 221°C
• Appearance: /
• Density: 1.0799 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.49±0.10(Predicted)
• CAS DataBase Reference: 2,2'-ETHYLENEDIANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-ETHYLENEDIANILINE(34124-14-6)
• EPA Substance Registry System: 2,2'-ETHYLENEDIANILINE(34124-14-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• Hazardous Substances Data: 34124-14-6(Hazardous Substances Data)

Usage

Chemical Properties

BROWN POWDER

Uses

2,2''-Ethylenedianiline is used as a reagent to synthesize Oxcarbazepine (O869250), a broad-specturm, second-generation anticonvulsant drug that is used to treat partial and complex partial seizures in children and adults. 2,2''-Ethylenedianiline is also used as a reagent to prepare a series of triterpines (e.g. Lupeol [L474850]), compounds that have chemopreventative activity.

Synthetic route

2,2'-dinitrobibenzyl (16968-19-7) → 2,2'-ethylenedianiline (34124-14-6)

Conditions	Yield
With hydrazine hydrate; hydrated iron(III) oxide In ethanol; N,N-dimethyl acetamide for 3h; Heating;	95%
With zinc; hydrazinium monoformate In water for 0.0833333h;	90%
With ammonium formate at 20℃; for 1h; Reduction;	85%

2,2'-diaminostilbene (617-20-9) → 2,2'-ethylenedianiline (34124-14-6)

Conditions	Yield
With i-Amyl alcohol; sodium

2-nitrobenzyl 2-nitrophenyl ketone (107127-66-2) → 2-(2-aminophenyl)-1H-indole (32566-01-1) + 2,2'-ethylenedianiline (34124-14-6)

Conditions	Yield
With ethanol; nickel; ethyl acetate Hydrogenation;

(Z)-2,2'-diaminostilbene (116668-54-3) → 2,2'-ethylenedianiline (34124-14-6)

Conditions	Yield
With pentan-1-ol; sodium

cis-5,6-Dihydrodibenzo<1,2>diazocine (21372-42-9) + hydrogenchloride (7647-01-0) + tin dichloride → 2,2'-ethylenedianiline (34124-14-6)

2.2'-azo-dibenzyl → 2,2'-ethylenedianiline (34124-14-6)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

2.2'-dinitro-dibenzyl → 2,2'-ethylenedianiline (34124-14-6)

Conditions	Yield
With hydrogenchloride; tin; ethanol

ethanol (64-17-5) + 2-nitrobenzyl 2-nitrophenyl ketone (107127-66-2) + ethyl acetate (141-78-6) + water containing mixture + Raney nickel → 2-(2-aminophenyl)-1H-indole (32566-01-1) + 2,2'-ethylenedianiline (34124-14-6)

pentan-1-ol (71-41-0) + 2,2'-diaminostilbene (28096-87-9) + sodium → 2,2'-ethylenedianiline (34124-14-6)

1-methyl-2-nitrobenzene (88-72-2) → 2,2'-ethylenedianiline (34124-14-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium amide 2: hydrogen View Scheme

2-nitrobenzyl chloride (612-23-7) → 2,2'-ethylenedianiline (34124-14-6)

Conditions	Yield
With hydrazine hydrate In water at 20℃; for 0.333333h; Reagent/catalyst;	51 %Chromat.

2,2'-ethylenedianiline (34124-14-6) + 3,5-dichlorosalicyclaldehyde (90-60-8) → N,N′-bis(3,5-dichlorosalicylidene)-2,2′-ethylenedianiline

Conditions	Yield
In ethanol at 20℃; Temperature;	100%
In ethanol at 20℃;

2-Picolinic acid (98-98-6) + 2,2'-ethylenedianiline (34124-14-6) → N,N'-(ethane-1,2-diyldi-o-phenylene)-bis(pyridine-2-carboxamide)

Conditions	Yield
Stage #1: 2-Picolinic acid; 2,2'-ethylenedianiline With pyridine at 40℃; for 0.166667h; Stage #2: With triphenyl phosphite at 100℃; for 4h;	95%

2,2'-ethylenedianiline (34124-14-6) + Ethyl oxalyl chloride (4755-77-5) → C22H24N2O6

Conditions	Yield
With triethylamine In tetrahydrofuran at 10 - 65℃;	91%

2,2'-ethylenedianiline (34124-14-6) + salicylaldehyde (90-02-8) → N,N′-bis(salicylidene)-2,2′-ethylenedianiline (129450-69-7)

Conditions	Yield
In toluene for 2h; Reflux;	90%
In toluene for 2h; Reflux;	90%
In ethanol

3-tert-butyl-5-methylsalicylaldehyde (41715-31-5) + 2,2'-ethylenedianiline (34124-14-6) → C38H44N2O2

Conditions	Yield
In ethanol for 18h; Heating;	86%

2,2'-ethylenedianiline (34124-14-6) + chloroacetyl chloride (79-04-9) → N,N'-(ethane-1,2-diylbis(2,1-phenylene))bis(2-chloroacetamide)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 15h;	86%

2-ethoxybenzoyl chloride (42926-52-3) + 2,2'-ethylenedianiline (34124-14-6) → C32H32N2O4

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In 1,2-dichloro-ethane for 4h;	85%

2,2'-ethylenedianiline (34124-14-6) → cis-5,6-Dihydrodibenzo<1,2>diazocine (21372-42-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetic acid for 13h; Concentration; Reagent/catalyst; Solvent;	85%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 2,2'-ethylenedianiline (34124-14-6) → C44H56N2O2

Conditions	Yield
With formic acid In methanol Heating;	82%
In ethanol

2,2'-ethylenedianiline (34124-14-6) + 5-tert-butyl-2-hydroxybenzene-1,3-dioic acid (157436-33-4) → C52H52N4O2 (1085572-85-5)

Conditions	Yield
In toluene for 24h; Reflux;	82%

2,2'-ethylenedianiline (34124-14-6) + 2-Methoxybenzoyl chloride (21615-34-9) → C30H28N2O4

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In 1,2-dichloro-ethane for 4h;	80%

formic acid (64-18-6) + 2,2'-ethylenedianiline (34124-14-6) → N,N'-(ethane-1,2-diylbis(2,1-phenylene))diformamide

Conditions	Yield
In toluene Reflux;	79.2%

2,2'-ethylenedianiline (34124-14-6) → 2,2'-diamino-4,4'-dinitrobibenzyl (90018-60-3)

Conditions	Yield
With sulfuric acid; nitric acid at 10℃; for 2h;	73%
With sulfuric acid Nitrieren;

2-pyrrole aldehyde (1003-29-8) + 2,2'-ethylenedianiline (34124-14-6) → C24H22N4

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 5h;	64%

2,2'-ethylenedianiline (34124-14-6) → cis-5,6-Dihydrodibenzo<1,2>diazocine (21372-42-9) + 5,6-dihydrodibenzo-1,2-diazocine N-oxide (40754-26-5)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetic acid for 13h;	A 17% B 64%

2,6-Diacetylpyridine (1129-30-2) + 2,2'-ethylenedianiline (34124-14-6) → C46H42N6

Conditions	Yield
With acetic acid for 36h; Reflux; Inert atmosphere; Schlenk technique;	52%

phthalic anhydride (85-44-9) + 2,2'-ethylenedianiline (34124-14-6) → C22H18N2O2

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide In toluene at 100℃; for 6.5h;	52%

2,6-Diacetylpyridine (1129-30-2) + 2,2'-ethylenedianiline (34124-14-6) → 1-[6-(1-{(E)-2-[2-(2-Amino-phenyl)-ethyl]-phenylimino}-ethyl)-pyridin-2-yl]-ethanone

Conditions	Yield
With acetic acid In ethanol for 6h; Heating;	51%

2,2'-ethylenedianiline (34124-14-6) → 11,12-dihydrodibenzo[c,g][1,2]diazocine (1194317-15-1, 7092-98-0)

Conditions	Yield
With pyridine; oxygen; copper; ammonium bromide In toluene at 100℃; under 760.051 Torr;	50%

2,2'-ethylenedianiline (34124-14-6) + isobutyraldehyde (78-84-2) → 2-(2-aminophenethyl)-N-isobutylaniline

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In methanol; dichloromethane at 20℃;	46%

5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)-2-pentanone (10487-10-2) + 2,2'-ethylenedianiline (34124-14-6) → 4,4'-(2,2'-(ethane-1,2-diyl)bis(2,1-phenylene))bis(azan-1-yl-1-ylidene)bis(1,1,1-trifluoro-2-(trifluoromethyl)pentan-2-ol)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 100h; Heating;	39%
toluene-4-sulfonic acid In toluene for 100h; Heating / reflux;	39%

2,2'-ethylenedianiline (34124-14-6) → 2,2'-(ethane-1,2-diyl)bis(4-bromoaniline)

Conditions	Yield
With N-Bromosuccinimide In dimethyl sulfoxide	22%

2,2'-ethylenedianiline (34124-14-6) → (E)-11,12-dihydrodibenzo[c,g][1,2]diazocine-5,6-dioxide (74808-60-9)

Conditions	Yield
With sodium tungstate (VI) dihydrate; dihydrogen peroxide In ethanol; water for 24h; Darkness; Cooling;	19%

2,2'-ethylenedianiline (34124-14-6) → 5,6-dihydrodibenzo1,2-diazocine N,N'-dioxide (74808-60-9)

Conditions	Yield
With sodium tungstate; dihydrogen peroxide In ethanol; water for 24h;	18.5%
Multi-step reaction with 3 steps 1: m-chloroperbenzoic acid / CH2Cl2 / 0 - 5 °C 2: 8 percent / trifluoroacetic anhydride, 90percent H2O2 / CH2Cl2 / 24 h / 0 °C 3: 1.) NH4Cl, zinc; 2.) sodium dichromate, conc.H2SO4 / 1.) EtOH, water, 40 deg C, 30 min; 2.) H2O, 0 deg C, 3 min View Scheme
Multi-step reaction with 2 steps 1: m-chloroperbenzoic acid / CH2Cl2 / 0 - 5 °C 2: 53 percent / trifluoroacetic anhydride, 90percent H2O2 / CH2Cl2 / 24 h / 0 °C View Scheme

2,2'-ethylenedianiline (34124-14-6) → 2,2'-(ethane-1,2-diyl)bis(4-iodoaniline)

Conditions	Yield
With N-iodo-succinimide In dimethyl sulfoxide	14%

2,2'-ethylenedianiline (34124-14-6) + 4,7,7-trimethyl-3-oxo-norbornane-2-carbaldehyde (6812-07-3, 16661-95-3, 16662-10-5, 30543-79-4, 87479-91-2) → optically inactive 2.2'-bis-(3-oxo-4.7.7-trimethyl-norbornyl-(2)-methylenamino)-bibenzyl

Conditions	Yield
With ethanol; acetic acid

2,2'-ethylenedianiline (34124-14-6) → tetradecahydro-dibenz[b,f]azepine (854398-56-4)

Conditions	Yield
With 1,4-dioxane; nickel at 220℃; under 147102 - 183877 Torr; Hydrogenation;

Upstream product

• 21372-42-9 cis-5,6-Dihydrodibenzo<1,2>diazocine 
• 612-23-7 2-nitrobenzyl chloride 
• 88-72-2 1-methyl-2-nitrobenzene 
• 71-41-0 pentan-1-ol 
• 28096-87-9 2,2'-diaminostilbene 
• 64-17-5 ethanol 
• 107127-66-2 2-nitrobenzyl 2-nitrophenyl ketone 
• 141-78-6 ethyl acetate 
• 7647-01-0 hydrogenchloride 
• 116668-54-3 (Z)-2,2'-diaminostilbene 
• 617-20-9 2,2'-diaminostilbene 
• 16968-19-7 2,2'-dinitrobibenzyl 

Downstream Products

• 298-46-4 carbamazepin 
• 1250431-00-5 (5H-dibenzo[b,f]azepin-5-yl)(4-phenylpiperazin-1-yl)methanone 
• 256-96-2 dibenzoazepine 
• 494-19-9 9,10-dihydrodibenzazepine 
• 33948-22-0 5H-dibenz[b,f]azepine-5-carbonylchloride 
• 153896-00-5 C₅₀H₄₂N₂P₂ 
• 153896-07-2 C₁₆H₁₂N₂S₂ 
• 82230-83-9 1,2-Bis(2-azidophenyl)ethane 
• 129450-69-7 N,N'-disalicylidene-2,2'-diaminobibenzyl 
• 40754-26-5 5,6-dihydrodibenzo-1,2-diazocine N-oxide 
• 74808-60-9 5,6-dihydrodibenzo1,2-diazocine N,N'-dioxide 
• 28228-84-4 N,N'-bibenzyl-2,2'-diyl-bis-acetamide 

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