Product Name

  • Name

    4,4'-Diaminobenzanilide

  • EINECS 212-321-5
  • CAS No. 785-30-8
  • Article Data15
  • CAS DataBase
  • Density 1.314 g/cm3
  • Solubility Practically insoluble in water
  • Melting Point 205-207 °C(lit.)
  • Formula C13H13N3O
  • Boiling Point 384 °C at 760 mmHg
  • Molecular Weight 227.266
  • Flash Point 186 °C
  • Transport Information
  • Appearance off-white to grey-beige powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 785-30-8 (4,4'-Diaminobenzanilide)
  • Hazard Symbols IrritantXi
  • Synonyms Benzanilide,4,4'-diamino- (6CI,7CI,8CI);4-Amino-N-(4-aminophenyl)benzamide;4-Aminobenzoyl-4'-aminoanilide;N-(4-Aminophenyl)-4-aminobenzamide;NSC 37092;
  • PSA 81.14000
  • LogP 3.33870

Synthetic route

C13H11N5O

C13H11N5O

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20℃; chemoselective reaction;98%
4,4'-dinitrobenzanilide
6333-15-9

4,4'-dinitrobenzanilide

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

Conditions
ConditionsYield
Stage #1: 4,4'-dinitrobenzanilide With palladium on activated charcoal; hydrogen In N,N-dimethyl-formamide at 10℃; under 6000.6 Torr; Autoclave;
Stage #2: In butan-1-ol at 25 - 135℃; for 0.333333h; Autoclave;		96.1%
With hydrogenchloride; iron In water at 95 - 98℃; for 2h;75%
With iron; acetic acid In ethanol; water for 15h; Reflux;27%

1,4-phenylenediamine

1,4-phenylenediamine

Conditions
ConditionsYield
With sodium hydroxide
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

CO

CO

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PCl5 / Ambient temperature
2: 10percent aq. NaOH
View Scheme
4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / chlorobenzene / 4.5 h / 90 - 95 °C
2: hydrogenchloride; iron / water / 2 h / 95 - 98 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / 1,4-dioxane / 1 h / 60 °C
2: iron; acetic acid / water; ethanol / 15 h / Reflux
View Scheme
4-nitro-aniline
100-01-6

4-nitro-aniline

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / chlorobenzene / 4.5 h / 90 - 95 °C
2: hydrogenchloride; iron / water / 2 h / 95 - 98 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / 1,4-dioxane / 1 h / 60 °C
2: iron; acetic acid / water; ethanol / 15 h / Reflux
View Scheme
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride; N,N-dimethyl-formamide / 65 - 70 °C
2: triethylamine / chlorobenzene / 4.5 h / 90 - 95 °C
3: hydrogenchloride; iron / water / 2 h / 95 - 98 °C
View Scheme
4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

4-nitro-aniline
100-01-6

4-nitro-aniline

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 12 h / 20 °C
2: palladium on activated charcoal; hydrogen / ethyl acetate / 16 h / 20 °C
View Scheme
4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

Ethoxycarbonyl isothiocyanate
16182-04-0

Ethoxycarbonyl isothiocyanate

ethyl N-((4-((4-((((ethoxycarbonyl)amino)methanethioyl)amino)phenyl)carbamoyl)phenyl)carbamothioyl)carbamate
1615693-67-8

ethyl N-((4-((4-((((ethoxycarbonyl)amino)methanethioyl)amino)phenyl)carbamoyl)phenyl)carbamothioyl)carbamate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; Inert atmosphere;96%
4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

N-tert-butoxycarbonyl-proline
15761-39-4

N-tert-butoxycarbonyl-proline

2-(4-(4-(pyrrolidine-1'-carboxylic acid tert-butyl ester)-phenylcarbamoyl)phenylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester

2-(4-(4-(pyrrolidine-1'-carboxylic acid tert-butyl ester)-phenylcarbamoyl)phenylcarbamoyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With BC 347 In dichloromethane at 20℃; for 17h;93%
thiophosgene
463-71-8

thiophosgene

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

4-isothiocyanato-N-(4-isothiocyanatophenyl)benzamide
2114-85-4

4-isothiocyanato-N-(4-isothiocyanatophenyl)benzamide

Conditions
ConditionsYield
In diethyl ether; water at 20℃;92%
4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

4-Azido-N-(4-azido-phenyl)-benzamide
156351-29-0

4-Azido-N-(4-azido-phenyl)-benzamide

Conditions
ConditionsYield
Stage #1: 4,4'-diaminobenzanilide With hydrogenchloride; sodium nitrite at 0 - 5℃; for 0.5h;
Stage #2: With sodium azide at 0 - 5℃;		90%
With sodium azide; sodium nitrite
3,5-di-tert-butyl-2-hydroxybenzaldehyde
37942-07-7

3,5-di-tert-butyl-2-hydroxybenzaldehyde

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

bis[(N-3,5-di-tert-butylsalicylidene)-4-aminophenyl]amide
1422976-23-5

bis[(N-3,5-di-tert-butylsalicylidene)-4-aminophenyl]amide

Conditions
ConditionsYield
With formic acid In ethanol Schiff Reaction; Reflux;87%
5,7-diimino-2,5,6,7-tetrahydro-1H-cyclopenta[cd]phenalene

5,7-diimino-2,5,6,7-tetrahydro-1H-cyclopenta[cd]phenalene

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

4-[(7-amino-1,2-dihydro-5H-cyclopenta[cd]phenalen-5-ylidene)amino]-N1-4-[(7-amino-1,2-dihydro-5H-cyclopenta[cd]phenalen-5-ylidene)amino]phenylbenzamide

4-[(7-amino-1,2-dihydro-5H-cyclopenta[cd]phenalen-5-ylidene)amino]-N1-4-[(7-amino-1,2-dihydro-5H-cyclopenta[cd]phenalen-5-ylidene)amino]phenylbenzamide

Conditions
ConditionsYield
In methanol Heating;83%
3-tert-butyl-2-hydroxybenzaldehyde
24623-65-2

3-tert-butyl-2-hydroxybenzaldehyde

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

bis[(N-3-tert-butylsalicylidene)-4-aminophenyl]amide
1422976-22-4

bis[(N-3-tert-butylsalicylidene)-4-aminophenyl]amide

Conditions
ConditionsYield
With formic acid In ethanol Schiff Reaction; Reflux;82%
2-(1-amino-8-hydroxy-3,6-disulfo-naphthalen-2-ylazo)-5-nitro-benzoic acid

2-(1-amino-8-hydroxy-3,6-disulfo-naphthalen-2-ylazo)-5-nitro-benzoic acid

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

sodium salicylate
54-21-7

sodium salicylate

5-[2-(4-{[4-(2-{8-amino-7-[2-(2-carboxy-4-nitrophenyl)diazen-1-yl]-1-hydroxy-3,6-disulfonaphthalen-2-yl}diazen-1-yl)phenyl]-carbamoyl}phenyl)-diazen-1-yl]-2-hydroxybenzoic acid

5-[2-(4-{[4-(2-{8-amino-7-[2-(2-carboxy-4-nitrophenyl)diazen-1-yl]-1-hydroxy-3,6-disulfonaphthalen-2-yl}diazen-1-yl)phenyl]-carbamoyl}phenyl)-diazen-1-yl]-2-hydroxybenzoic acid

Conditions
ConditionsYield
Stage #1: 4,4'-diaminobenzanilide With hydrogenchloride; sodium nitrite at 0℃;
Stage #2: sodium salicylate With sodium hydroxide; sodium carbonate pH=7.5 - 8; cooling;
Stage #3: 2-(1-amino-8-hydroxy-3,6-disulfo-naphthalen-2-ylazo)-5-nitro-benzoic acid With dispersil VS; sodium carbonate at 10℃; for 3h; pH=9.5 - 10;		78%
...Expand
2-(2-amino-5-hydroxy-7-sulfo-naphthalen-1-ylazo)-5-nitro-benzoic acid

2-(2-amino-5-hydroxy-7-sulfo-naphthalen-1-ylazo)-5-nitro-benzoic acid

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

sodium salicylate
54-21-7

sodium salicylate

C37H25N9O12S

C37H25N9O12S

Conditions
ConditionsYield
Stage #1: 4,4'-diaminobenzanilide With hydrogenchloride; sodium nitrite at 0℃;
Stage #2: sodium salicylate With sodium hydroxide; sodium carbonate pH=7.5 - 8; cooling;
Stage #3: 2-(2-amino-5-hydroxy-7-sulfo-naphthalen-1-ylazo)-5-nitro-benzoic acid With dispersil VS; sodium carbonate at 10℃; for 2h; pH=9.5 - 10;		75%
...Expand
2-phenyl-4-oxo-3,1-benzoxazine-6-sulphonic acid
1221348-26-0

2-phenyl-4-oxo-3,1-benzoxazine-6-sulphonic acid

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

2-phenyl-3-(4'-[N-(4''-aminophenyl)carbamoyl]-phenyl)-quinazoline-4(3H)-one-6-sulphonic acid
1303968-87-7

2-phenyl-3-(4'-[N-(4''-aminophenyl)carbamoyl]-phenyl)-quinazoline-4(3H)-one-6-sulphonic acid

Conditions
ConditionsYield
Stage #1: 2-phenyl-4-oxo-3,1-benzoxazine-6-sulphonic acid; 4,4'-diaminobenzanilide With pyridine for 6h; Reflux;
Stage #2: With hydrogenchloride In water at 20℃;		75%
4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

4,4'-di(phenylthiocarbamoylamino)benzanilide

4,4'-di(phenylthiocarbamoylamino)benzanilide

Conditions
ConditionsYield
In acetone72.3%
2-Thiophenecarbonyl chloride
5271-67-0

2-Thiophenecarbonyl chloride

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

C23H17N3O3S2

C23H17N3O3S2

Conditions
ConditionsYield
In dichloromethane at 20 - 70℃; for 5h; Alkaline conditions;72%
In dichloromethane at 40 - 60℃; for 3h;72%
2-furancarbonyl chloride
527-69-5

2-furancarbonyl chloride

4,4'-diaminobenzanilide
785-30-8

4,4'-diaminobenzanilide

C23H17N3O5

C23H17N3O5

Conditions
ConditionsYield
In dichloromethane at 20 - 70℃; for 5h; Alkaline conditions;68%
In dichloromethane at 40 - 60℃; for 2h;68%

4,4'-Diaminobenzanilide Specification

The IUPAC name of Benzamide,4-amino-N-(4-aminophenyl)- is 4-amino-N-(4-aminophenyl)benzamide . With the CAS registry number 785-30-8, it is also named as 4,4'-Diaminobenzanilide ; 4-Aminobenzoyl-4'-aminoanilide ; CCRIS 8916 ; NSC 37092 ; p,p'-Diaminobenzanilide ; 4,4'-Diaminobenzanilide ; Benzanilide, 4,4'-diamino- (8CI) . The product's categories are intermediates of dyes and pigments, anilines, aromatic amines and nitro compounds, amine monomers, monomers and primary amines.

The Benzamide,4-amino-N-(4-aminophenyl)- is off-white to grey-beige powder which is used to produce direct, blended dyes and plastics stabilizer. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.18 ; (2)# of Rule of 5 Violations: 1 ; (3)ACD/LogD (pH 5.5): 0.11 ; (4)ACD/LogD (pH 7.4): 0.18 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 25.35 ; (8)ACD/KOC (pH 7.4): 29.78 ; (9)#H bond acceptors: 4 ; (10)#H bond donors: 5 ; (11)#Freely Rotating Bonds: 4 ; (12)Index of Refraction: 1.734 ; (13)Molar Refractivity: 69.3 cm3 ; (14)Molar Volume: 172.8 cm3 ; (15)Polarizability: 27.47×10-24 cm3 ; (16)Surface Tension: 69.1 dyne/cm ; (17)Enthalpy of Vaporization: 63.26 kJ/mol ; (18)Vapour Pressure: 4.22E-06 mmHg at 25°C ; (19)Rotatable Bond Count: 2 ; (20)Tautomer Count: 5 ; (21)Exact Mass: 227.105862 ; (22)MonoIsotopic Mass: 227.105862 ; (23)Topological Polar Surface Area: 81.1 ; (24)Heavy Atom Count: 17.

People can use the following data to convert to the molecule structure. SMILES: O=C(Nc1ccc(cc1)N)c2ccc(N)cc2; InChI: InChI=1/C13H13N3O/c14-10-3-1-9(2-4-10)13(17)16-12-7-5-11(15)6-8-12/h1-8H,14-15H2,(H,16,17). Benzamide,4-amino-N-(4-aminophenyl)- has many suppliers, such as Changzhou Sunlight Pharmaceutical Co., Ltd.. The price of this product changes with the market.

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