619-05-6

Basic information

• Product Name: 3,4-Diaminobenzoic acid
• Synonyms: 3,4-DIAMINOBENZOIC ACID;4-Carboxy-o-phenylenediamine;3,4-DIAMINOBENZOIC ACID GRAY TO BROWNPOW DER;3,4-diaminebenzoic acid;3,4-Diaminobenzoesure;3,4-DIAMINOBENZOIC ACID 98%;3,4-Diaminobenzoic acid, 97%,;3,4-Diaminobenzoic acid, 95%+
• CAS NO: 619-05-6
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• EINECS: 210-577-2
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 619-05-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 208-210 °C (dec.)(lit.)
• Boiling Point: 274.61°C (rough estimate)
• Flash Point: 202.9 °C
• Appearance: Brown/Powder
• Density: 1.2804 (rough estimate)
• Vapor Pressure: 1.61E-07mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.02±0.10(Predicted)
• Water Solubility: Soluble in water (2.2 mg/ml at 20°C), DMF, and methanol (10 mg/ml).
• BRN: 775892
• CAS DataBase Reference: 3,4-Diaminobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Diaminobenzoic acid(619-05-6)
• EPA Substance Registry System: 3,4-Diaminobenzoic acid(619-05-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• Hazardous Substances Data: 619-05-6(Hazardous Substances Data)

Usage

Chemical Properties

brown powder

Uses

3,4-Diaminobenzoic acid undergoes cyclocondensations to form, for example, quinoxalines1 and benzimidazoles. It acts as a redox label for electrochemical detection of single base mismatches.

Purification Methods

Crystallise it from H2O or toluene. [Beilstein 15 IV 1503.]

InChI:InChI=1/C7H8N2O2/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3H,8-9H2,(H,10,11)/p-1

Synthetic route

3,4-dinitrobenzoic acid (528-45-0) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With sodium tetrahydroborate In water at 40℃; for 2h; chemoselective reaction;	95%
With hydrazine hydrate In ethanol at 20℃; for 0.25h; Sonication;	94%
With hydrazine hydrate In ethanol at 70℃; for 0.166667h;	94%
With hydrazine hydrate In ethanol at 70℃; for 0.266667h;	89%

4-amino-3-nitrobenzoic acid (1588-83-6) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With hydrogenchloride; tin	73.5%
With ethanol; nickel Hydrogenation;
With hydrogenchloride; tin

3-amino-4-nitrobenzoic acid (6968-22-5) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With hydrogenchloride; tin
With hydrogenchloride; tin(ll) chloride

4-amino-3-(4-sulfamoyl-phenylazo)-benzoic acid → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride

furan-2,3,5(4H)-trione pyridine (1:1) + 4-amino-3-nitrobenzoic acid (1588-83-6) + aluminium → 3,4-diaminobenzoic acid (619-05-6)

hydrogenchloride (7647-01-0) + 4-amino-3-nitrobenzoic acid (1588-83-6) + tin → 3,4-diaminobenzoic acid (619-05-6)

hydrogenchloride (7647-01-0) + 3-amino-4-nitrobenzoic acid (6968-22-5) + tin → 3,4-diaminobenzoic acid (619-05-6)

3-nitro-4-acetamidobenzoic acid (1539-06-6) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid 2: tin; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: alcohol; hydrochloric acid 2: aluminium; diluted NaOH-solution View Scheme

4-nitro-3-(N'-nitro-ureido)-benzoic acid (100949-13-1) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: water 2: tin; hydrochloric acid View Scheme

4-chloro-3-nitrobenzoate (96-99-1) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous NH3 / 170 °C 2: Raney nickel; ethanol / Hydrogenation View Scheme

4-methoxy-3-nitrobenzoic acid (89-41-8) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / 140 - 170 °C / im Druckrohr 2: tin; hydrochloric acid View Scheme

3-methoxy-4-hydroxybenzoic acid (121-34-6) → 3,4-diaminobenzoic acid (619-05-6)

Conditions	Yield
With ammonia; metal catalyst

1,2-di(4-methylphenyl)-1,2-ethanedione (3457-48-5) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-bis(4-methylphenyl)-6-quinoxalinecarboxylic acid (90833-49-1)

Conditions	Yield
With sodium acetate; acetic acid at 118℃; for 4h;	100%
In hydrogenchloride for 1h; heating on boiling water bath;	42.3%

1,2-bis(4-fluorophenyl)ethane-1,2-dione (579-39-5) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-bis(4-fluorophenyl)quinoxaline-6-carboxylic acid (355397-64-7)

Conditions	Yield
With sodium acetate; acetic acid at 118℃; for 4h;	100%
H6P2W18O62 In acetic acid at 20℃; for 0.0833333h;	97%
In methanol; chloroform at 20℃;	95%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + 3,4-diaminobenzoic acid (619-05-6) → 3-N-[(9H-fluoren-9-yl)methoxycarbonyl]-amino-4-aminobenzoic acid (1071446-05-3)

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 20℃; for 16.0833h;	100%
With sodium hydrogencarbonate In acetonitrile at 20℃; for 16.0833h;	100%
With sodium hydrogencarbonate In acetonitrile for 22h;	94%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + 3,4-diaminobenzoic acid (619-05-6) → 7,8-dihydroxyphenazine-2-carboxylic acid (1055878-48-2)

Conditions	Yield
In water at 95℃; for 15h;	100%
In ethanol for 24h; Reflux;	85%
With acetic acid In ethanol at 20℃; for 5h;	65%

formic acid (64-18-6) + 3,4-diaminobenzoic acid (619-05-6) → 1H-benzimidazole-6-carboxylic acid (15788-16-6)

Conditions	Yield
for 4h; Reflux;	99.06%
at 110℃; for 4h;	89%
With potassium tert-butylate at 110℃; for 4h;	88%
Stage #1: formic acid; 3,4-diaminobenzoic acid With hydrogenchloride In water at 20℃; for 24h; Cooling; Stage #2: With ammonia In water pH=2 - 3;	54%

p-benzyloxybenzaldehyde (4397-53-9) + 3,4-diaminobenzoic acid (619-05-6) → 2-(4-(benzyloxy)phenyl)-1H-benzo[d]imidazole-5-carboxylic acid (174422-18-5)

Conditions	Yield
With sodium metabisulfite In N,N-dimethyl-formamide at 80℃; for 6h;	99%
With hydrogenchloride; sodium sulfide; copper diacetate 1.) MeOH, heating, 2.) EtOH; Yield given. Multistep reaction;

(3Z)-1-ethyl-3-[(ethylcarbamoylamino)-methylsulfanyl-methylene]urea (797047-27-9) + 3,4-diaminobenzoic acid (619-05-6) → C11H12N4O3

Conditions	Yield
With sulfuric acid; sodium acetate In 1,4-dioxane for 1h; pH=3.5; Heating;	99%

trifluoroacetic acid (76-05-1) + 3,4-diaminobenzoic acid (619-05-6) → 2-(trifluoromethyl)-1H-benzo[d]imidazole-5-carboxylic acid (82791-93-3)

Conditions	Yield
at 70℃; for 16h;	99%
With hydrogenchloride In water for 24h; Inert atmosphere; Reflux;	94%
With hydrogenchloride; formic acid In water Reflux;

benzil (134-81-6) + 3,4-diaminobenzoic acid (619-05-6) → 2,3‐diphenylquinoxaline‐6‐carboxylic acid (32387-96-5)

Conditions	Yield
In hydrogenchloride for 1h; heating on boiling water bath;	98.5%
H6P2W18O62 In acetic acid at 20℃; for 0.166667h;	97%
With sodium acetate; acetic acid at 118℃; for 4h;	97%

methanol (67-56-1) + 3,4-diaminobenzoic acid (619-05-6) → Methyl 3,4-diaminobenzoate (36692-49-6)

Conditions	Yield
With sulfuric acid at 90℃; for 12h; Temperature;	98.1%
With thionyl chloride for 4h; Inert atmosphere;	95%
With thionyl chloride for 11h; Reflux;	94%

4,4'-dinitrobenzil (6067-45-4) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-bis(4-nitrophenyl)quinoxaline-6-carboxylic acid (514197-15-0)

Conditions	Yield
With acetic acid for 12h; Heating;	98%
With nitrogen In acetic acid	98%

3,6-dibromo-phenanthrene-9,10-dione (53348-05-3) + 3,4-diaminobenzoic acid (619-05-6) → 2,7-dibromodibenzo[a,c]phenazine-11-carboxylic acid (1616777-39-9)

Conditions	Yield
With acetic acid In ethanol for 2h; Reflux;	98%

hexaketocyclohexane (527-31-1) + 3,4-diaminobenzoic acid (619-05-6) → 5,6,11,12,17,18-hexaazatrinaphthylene-2,8,14-tricarboxylic acid (872140-77-7)

Conditions	Yield
With acetic acid for 5h; Reflux;	98%

1,2-bis(4-methoxyphenyl)-1,2-ethanedione (1226-42-2) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-bis(4-methoxyphenyl)-quinoxaline-6-carboxylic acid (40622-01-3)

Conditions	Yield
In hydrogenchloride for 1h; heating on boiling water bath;	97.8%
In deoxygenated acetic acid	97%
With acetic acid In sodium hydroxide	44%

dimethylglyoxal (431-03-8) + 3,4-diaminobenzoic acid (619-05-6) → 2,3-dimethyl-6-quinoxalinecarboxylic acid (17635-26-6)

Conditions	Yield
In neat (no solvent) at 24.84℃;	97%
Heating;	87%
In hydrogenchloride for 1h; heating on boiling water bath;	81.6%

5-fluoro-2-hydroxybenzaldehyde (347-54-6) + 3,4-diaminobenzoic acid (619-05-6) → 2‐(5‐fluoro‐2‐hydroxyphenyl)‐1H‐benzo[d]imidazole‐5‐carboxylic acid

Conditions	Yield
With sodium metabisulfite; choline chloride In glycerol at 50℃; for 0.5h;	97%
With sodium metabisulfite In glycerol at 50℃; for 0.5h;	97%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 3,4-diaminobenzoic acid (619-05-6) → 1H-benzimidazole-6-carboxylic acid (15788-16-6)

Conditions	Yield
With carbon dioxide In water at 150℃; under 37503.8 Torr; for 5h;	96.1%

salicylaldehyde (90-02-8) + 3,4-diaminobenzoic acid (619-05-6) → N,N′-bis(salicylidene)-3-carboxyl-o-phenylenediamine (87578-89-0)

Conditions	Yield
In methanol for 3h; Reflux;	96%
In methanol for 3h; Reflux;	96%
In methanol at 20℃; for 6h; Inert atmosphere;	85%

malonic acid (141-82-2) + 3,4-diaminobenzoic acid (619-05-6) → 2-methyl-1H-benzoimidazole-5-carboxylic acid (709-19-3)

Conditions	Yield
With hydrogenchloride for 2.5h; Heating;	95%

benzaldehyde (100-52-7) + 3,4-diaminobenzoic acid (619-05-6) → 2-phenyl-1H-1,3-benzimidazole-5-carboxylic acid (66630-70-4)

Conditions	Yield
With ammonium acetate In ethanol at 75℃; for 5.5h;	95%
With air In ethanol at 20℃; for 2.25h;	94%
With vanadium(IV)-salen complex nanoparticles immobilized onto silica In ethanol at 20℃; for 1h;	94%

di-tert-butyl dicarbonate (24424-99-5) + 3,4-diaminobenzoic acid (619-05-6) → N,N'-di-(tert-butoxycarbonyl)-3,4-diaminobenzoic acid (66636-17-7)

Conditions	Yield
With amberlyst-15 In ethanol at 20℃; for 4.5h; chemoselective reaction;	95%
With guanidine hydrochloride In ethanol at 35 - 40℃; for 1.83333h;	93%
With potassium hydroxide In water; tert-butyl alcohol at 20℃; for 48h;	85%

3,4-diaminobenzoic acid (619-05-6) → benzo[c][1,2,5]selenadiazole-5-carboxylic acid (140669-75-6)

Conditions	Yield
With hydrogenchloride; selenium(IV) oxide In water at 80℃; for 2h;	95%
With hydrogenchloride; selenium(IV) oxide In water for 2h;	95%
With hydrogenchloride; selenium(IV) oxide In water at 20℃; for 2h;	93%

2,7-dibromobenzo[1,2-b:4,3-b’]dithiophene-4,5-dione (1258459-51-6) + 3,4-diaminobenzoic acid (619-05-6) → 2,5-dibromodithieno[2,3-a:3',2'-c]phenazine-9-carboxylic acid (1616777-44-6)

Conditions	Yield
With acetic acid In ethanol for 2h; Reflux;	95%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + 3,4-diaminobenzoic acid (619-05-6) → N,N'-bis(3,5-di-tert-butylsalicylidene)-1-carboxy-3,4-phenylene-diamine

Conditions	Yield
Stage #1: 3,5-di-tert-butyl-2-hydroxybenzaldehyde; 3,4-diaminobenzoic acid In tetrahydrofuran for 0.333333h; Stage #2: With zinc(II) chloride In tetrahydrofuran for 0.75h; Reflux;	95%
With sulfuric acid In ethanol at 78℃; for 24h;	48.2%
With sulfuric acid In ethanol at 78℃; for 24h;	48.2%

1,10-phenanthroline-5,6-dione (27318-90-7) + 3,4-diaminobenzoic acid (619-05-6) → 4,5,9,14-tetraaza-benzo[b]triphenylene-11-carboxylic acid (259796-23-1)

Conditions	Yield
In ethanol for 0.166667h; Condensation; Heating;	94%
With sulfated titania (TiO2-SO42-) In ethanol at 20℃; for 0.5h;	92.8%
With toluene-4-sulfonic acid In neat (no solvent) for 2.5h; Milling; Green chemistry;	91%

indan-1,2,3-trione hydrate (485-47-2) + (methyloxycarbonylmethyl)triphenylphosphonium bromide (1779-58-4) + 3,4-diaminobenzoic acid (619-05-6) → methyl (8-carboxylindeno[1,2-b]quinoxalin-11-ylidene)acetate

Conditions	Yield
With sodium acetate In acetonitrile at 110℃; for 1h;	94%

1,1,1-trimethoxybutane (43083-12-1) + 3,4-diaminobenzoic acid (619-05-6) → 2-propyl-1H-benzo[d]imidazole-6-carboxylic acid (141838-50-8)

Conditions	Yield
Stage #1: 1,1,1-trimethoxybutane; 3,4-diaminobenzoic acid With hydrogenchloride In water at 20℃; Stage #2: With sodium hydrogencarbonate In water pH=8;	94%

Cyclohexyl isocyanide (931-53-3) + cyclohexanone (108-94-1) + 3,4-diaminobenzoic acid (619-05-6) → 4a'-(cyclohexylcarbamoyl)-1',2',3',4',4a',5',10',11a'-octahydrospiro[cyclohexane-1,11'-dibenzo[b,e][1,4]diazepine]-7'-carboxylic acid (1039656-72-8)

Conditions	Yield
With wool supported Fe3O4 nanoparticles In methanol at 20℃; for 18h; Reagent/catalyst;	94%
Stage #1: cyclohexanone; 3,4-diaminobenzoic acid With Fe3O4/SiO2 In ethanol at 20℃; for 1h; Stage #2: Cyclohexyl isocyanide In ethanol at 20℃; for 4h; regioselective reaction;	90%

methanol (67-56-1) + 3,4-diaminobenzoic acid (619-05-6) → methyl 3,4-diaminobenzoate dihydrochloride

Conditions	Yield
Stage #1: methanol; 3,4-diaminobenzoic acid With sulfuryl dichloride at 0℃; for 5h; Reflux; Stage #2: With hydrogenchloride In water	94%

Upstream product

• 1588-83-6 4-amino-3-nitrobenzoic acid 
• 7647-01-0 hydrogenchloride 
• 1539-06-6 3-nitro-4-acetamidobenzoic acid 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 89-41-8 4-methoxy-3-nitrobenzoic acid 
• 528-45-0 3,4-dinitrobenzoic acid 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 100949-13-1 4-nitro-3-(N'-nitro-ureido)-benzoic acid 
• 6968-22-5 3-amino-4-nitrobenzoic acid 

Downstream Products

• 90846-59-6 2,3-bis(2-furyl)-6-quinoxalinecarboxylic acid 
• 87578-89-0 3,4-bis(((E)-2-hydroxybenzylidene)amino)benzoic acid 
• 16405-98-4 benzo[c][1,2,5]thiadiazole-5-carboxylic acid 
• 134859-17-9 dibenzo[a,c]phenazine-2-carboxylic acid 
• 174422-18-5 2-(4-(benzyloxy)phenyl)-1H-benzo[d]imidazole-5-carboxylic acid 
• 174422-10-7 2-(furan-2-yl)-1H-benzimidazole -5-carboxylic acid 
• 174422-11-8 2-(thiophen-2-yl)-1H-benzimidazole -5-carboxylic acid 
• 174422-16-3 2-(2-methoxyphenyl)-1H-benzimidazole-5-carboxylic acid 
• 63655-47-0 n-Butyl 3,4-diaminobenzoate 
• 612847-29-7 3-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-2-phenylquinoxaline-6-carboxylic Acid 
• 612847-31-1 2-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-phenylquinoxaline-6-carboxylic acid 
• 1027219-57-3 2-(4-nitro-2-trifluoromethyl-phenyl)-1H-benzoimidazole-5-carboxylic acid 

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