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

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

Uses

Used in Pharmaceutical Industry:
2,2'-Ethylenedianiline is used as a reagent for the synthesis of Oxcarbazepine (O869250), a broad-spectrum, second-generation anticonvulsant drug. This drug is effective in treating partial and complex partial seizures in both children and adults, providing relief and improved quality of life for patients suffering from these conditions.
Additionally, 2,2'-Ethylenedianiline is used as a reagent to prepare a series of triterpenes, such as Lupeol (L474850). These compounds exhibit chemopreventative activity, making them valuable in the development of cancer-fighting drugs and therapies.

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

• 71-41-0 pentan-1-ol 
• 28096-87-9 2,2'-diaminostilbene 
• 21372-42-9 cis-5,6-Dihydrodibenzo<1,2>diazocine 
• 612-23-7 2-nitrobenzyl chloride 
• 88-72-2 1-methyl-2-nitrobenzene 
• 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

• 74808-60-9 5,6-dihydrodibenzo1,2-diazocine N,N'-dioxide 
• 40754-26-5 5,6-dihydrodibenzo-1,2-diazocine N-oxide 
• 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 
• 90018-60-3 2,2'-diamino-4,4'-dinitrobibenzyl 
• 29338-20-3 1,2-bis-(2'-hydroxyphenyl)ethane 
• 21372-42-9 cis-5,6-Dihydrodibenzo<1,2>diazocine 

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