134-50-9

Basic information

• Product Name: Acridin-9-amine hydrochloride
• Synonyms: TIMTEC-BB SBB003279;MONACRIN;9-AMINOACRIDINE HCL;9-AMINOACRIDINE HYDROCHLORIDE;ACRAMINE YELLOW;AMINACRINE HYDROCHLORIDE;5-aminoacridinehydrochloride;9-acridinamine,monohydrochloride
• CAS NO: 134-50-9
• Molecular Formula: C₁₃H₁₀N₂*ClH
• Molecular Weight: 230.69
• EINECS: 205-145-5
• Mol File: 134-50-9.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 413.5°Cat760mmHg
• Flash Point: 233.2°C
• Appearance: /
• Density: 1.268g/cm³
• Vapor Pressure: 4.76E-07mmHg at 25°C
• CAS DataBase Reference: Acridin-9-amine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Acridin-9-amine hydrochloride(134-50-9)
• EPA Substance Registry System: Acridin-9-amine hydrochloride(134-50-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 134-50-9(Hazardous Substances Data)

Usage

Uses

Anti-infective, topical.

Definition

ChEBI: A hydrochloride salt resulting from the reaction of equimolar amounts of 9-aminoacridine and hydrogen chloride.

Brand name

Monacrin (Sterling Winthrop).

General Description

Pale yellow crystals. One of the most highly fluorescent substances.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Acridin-9-amine hydrochloride forms from treatment of 9-aminoacridine with hydrogen chloride. Is amphoteric (reacts both as a weak acid and as a weak base).

Fire Hazard

Flash point data for Acridin-9-amine hydrochloride is not available, but Acridin-9-amine hydrochloride is probably combustible.

InChI:InChI=1/C13H10N2.ClH.H2O/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13;;/h1-8H,(H2,14,15);1H;1H2

Synthetic route

acridin-9-amine hydrochloride (134-50-9) → aminacrine (110166-26-2)

Conditions	Yield
With sodium hydroxide In water; ethyl acetate for 0.25h; Concentration; Reagent/catalyst; Solvent;	100%

sodium dodecyl-sulfate (151-21-3) + acridin-9-amine hydrochloride (134-50-9) → 9-aminoacridinium dodecyl sulfate

Conditions	Yield
In ethanol; water for 0.25h; Heating;	99%

N-(7-bromoheptyl)phthalimide (52824-42-7) + acridin-9-amine hydrochloride (134-50-9) → 2-[7-(acridin-9-ylamino)-heptyl]-isoindole-1,3-dione

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 12h;	74%

acetic anhydride (108-24-7) + acridin-9-amine hydrochloride (134-50-9) → N-(acridin-9-yl)acetamide (23043-52-9)

Conditions	Yield
In pyridine at 70℃; for 24h;	67.8%

4-bis-(β-chloroethyl)aminophenyl isocyanate (82484-59-1) + acridin-9-amine hydrochloride (134-50-9) → 1-acridin-9-yl-3-{4-[bis(2-chloroethyl)amino]phenyl}urea (1036724-69-2)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;	60%

2-(9-bromononyl)isoindoline-1,3-dione (93667-91-5) + acridin-9-amine hydrochloride (134-50-9) → 2-[9-(acridin-9-ylamino)-nonyl]-isoindole-1,3-dione

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 12h;	55.5%

3-Carboxyphenylboronic acid (25487-66-5) + acridin-9-amine hydrochloride (134-50-9) → C20H15BN2O3 (1428587-11-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In dimethyl sulfoxide at 20 - 40℃; for 49h;	53%
Stage #1: acridin-9-amine hydrochloride With triethylamine In water; dimethyl sulfoxide at 20℃; for 1h; Stage #2: 3-Carboxyphenylboronic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; dimethyl sulfoxide at 40℃; for 48h;	53%

N-8-bromooctylphthalimide (17702-83-9) + acridin-9-amine hydrochloride (134-50-9) → 2-[8-(acridin-9-ylamino)-octyl]-isoindole-1,3-dione

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 12h;	18.5%

acridin-9-amine hydrochloride (134-50-9) → 2-nitro-9-aminoacridine (23045-35-4) + 9-amino-2,7-dinitroacridine (157996-62-8)

Conditions	Yield
With sodium nitrate; sulfuric acid at 0℃; for 0.5h;	A 9.6% B 15%
With sodium nitrate; sulfuric acid at 0℃; for 0.5h;	A 9.6% B 15%

2-(6-bromohexyl)isoindole-1,3-dione (24566-79-8) + acridin-9-amine hydrochloride (134-50-9) → 2-[6-(acridin-9-ylamino)-hexyl]-isoindole-1,3-dione

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 12h;	15%

acridin-9-amine hydrochloride (134-50-9) → 2-bromo-9-aminoacridine + 9-amino-2,7-dibromoacridine (157996-60-6)

Conditions	Yield
With bromine In chloroform for 2h; Ambient temperature;	A 11.1% B 2.4%

3-chloro-3-methylbut-1-yne (1111-97-3) + acridin-9-amine hydrochloride (134-50-9) → 10-(3-Methyl-1,2-butadienyl)-9(10H)-iminoacridin (133286-71-2) + 9-(3-Methyl-1,2-butadienyl)-9-aminoacridin (133286-69-8) + 9-(1,1-Dimethyl-2-propinyl)-9-aminoacridin (133286-70-1) + 10-(1,1-Dimethyl-2-propinyl)-9(10H)-iminoacridin (133286-72-3)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In toluene for 72h; Heating;	A 370 mg B 1.69 g C 40 mg D 490 mg

acridin-9-amine hydrochloride (134-50-9) → 9-acetylamino-2-bromoacridine

Conditions	Yield
Multi-step reaction with 2 steps 1: 67.8 percent / pyridine / 24 h / 70 °C 2: 27.2 percent / Br2 / CHCl3 / 2 h / Ambient temperature View Scheme

1-phenyl-1H-pyrazole-5-carbonyl chloride (423768-37-0) + acridin-9-amine hydrochloride (134-50-9) → C23H16N4O (908562-71-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;

4--phenyl-carbamoylchlorid (806608-18-4) + acridin-9-amine hydrochloride (134-50-9) → 1-acridin-9-yl-3-{4-[bis(2-chloroethyl)amino]phenyl}urea (1036724-69-2)

Conditions	Yield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 16h;

acridin-9-amine hydrochloride (134-50-9) + benzene-1,2-dicarboxylic acid (88-99-3) → 9-aminoacridiniun ortho-phthalate monohydrate (1272425-79-2)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + benzoic acid (65-85-0) → 9-aminoacridiniun benzoate monohydrate (1272425-77-0)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + salicylic acid (69-72-7) → 9-aminoacridiniun salicylate (109653-41-0)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + 3-Carboxyphenol (99-06-9) → 9-aminoacridinium 3-hydroxybenzoate hydrochloride

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + para-chlorobenzoic acid (74-11-3) → 9-aminoacridinium 4-chlorobenzoate (1302149-89-8)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + 3-chlorobenzoate (535-80-8) → 9-aminoacridinium 3-chlorobenzoate (1302149-88-7)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) → (acridin-9-ylamino)acetic acid ethyl ester (934991-54-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water; ethyl acetate / 0.25 h 2: N,N-dimethyl-formamide / 5 h / 80 - 85 °C View Scheme

acridin-9-amine hydrochloride (134-50-9) + bovine serum albumin → 9-aminoacridine hydrochloride binding with bovine serum albumin

Conditions	Yield
In aq. phosphate buffer at 24.84℃; pH=7.4; Thermodynamic data; Temperature;

acridin-9-amine hydrochloride (134-50-9) → aminacrine (110166-26-2)

Conditions	Yield
With sodium hydroxide In water; ethyl acetate for 0.25h; Concentration; Reagent/catalyst; Solvent;	100%

sodium dodecyl-sulfate (151-21-3) + acridin-9-amine hydrochloride (134-50-9) → 9-aminoacridinium dodecyl sulfate

Conditions	Yield
In ethanol; water for 0.25h; Heating;	99%

N-(7-bromoheptyl)phthalimide (52824-42-7) + acridin-9-amine hydrochloride (134-50-9) → 2-[7-(acridin-9-ylamino)-heptyl]-isoindole-1,3-dione

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 12h;	74%

acetic anhydride (108-24-7) + acridin-9-amine hydrochloride (134-50-9) → N-(acridin-9-yl)acetamide (23043-52-9)

Conditions	Yield
In pyridine at 70℃; for 24h;	67.8%

4-bis-(β-chloroethyl)aminophenyl isocyanate (82484-59-1) + acridin-9-amine hydrochloride (134-50-9) → 1-acridin-9-yl-3-{4-[bis(2-chloroethyl)amino]phenyl}urea (1036724-69-2)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;	60%

2-(9-bromononyl)isoindoline-1,3-dione (93667-91-5) + acridin-9-amine hydrochloride (134-50-9) → 2-[9-(acridin-9-ylamino)-nonyl]-isoindole-1,3-dione

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 12h;	55.5%

3-Carboxyphenylboronic acid (25487-66-5) + acridin-9-amine hydrochloride (134-50-9) → C20H15BN2O3 (1428587-11-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In dimethyl sulfoxide at 20 - 40℃; for 49h;	53%
Stage #1: acridin-9-amine hydrochloride With triethylamine In water; dimethyl sulfoxide at 20℃; for 1h; Stage #2: 3-Carboxyphenylboronic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; dimethyl sulfoxide at 40℃; for 48h;	53%

N-8-bromooctylphthalimide (17702-83-9) + acridin-9-amine hydrochloride (134-50-9) → 2-[8-(acridin-9-ylamino)-octyl]-isoindole-1,3-dione

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 12h;	18.5%

acridin-9-amine hydrochloride (134-50-9) → 2-nitro-9-aminoacridine (23045-35-4) + 9-amino-2,7-dinitroacridine (157996-62-8)

Conditions	Yield
With sodium nitrate; sulfuric acid at 0℃; for 0.5h;	A 9.6% B 15%
With sodium nitrate; sulfuric acid at 0℃; for 0.5h;	A 9.6% B 15%

2-(6-bromohexyl)isoindole-1,3-dione (24566-79-8) + acridin-9-amine hydrochloride (134-50-9) → 2-[6-(acridin-9-ylamino)-hexyl]-isoindole-1,3-dione

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 12h;	15%

acridin-9-amine hydrochloride (134-50-9) → 2-bromo-9-aminoacridine + 9-amino-2,7-dibromoacridine (157996-60-6)

Conditions	Yield
With bromine In chloroform for 2h; Ambient temperature;	A 11.1% B 2.4%

3-chloro-3-methylbut-1-yne (1111-97-3) + acridin-9-amine hydrochloride (134-50-9) → 10-(3-Methyl-1,2-butadienyl)-9(10H)-iminoacridin (133286-71-2) + 9-(3-Methyl-1,2-butadienyl)-9-aminoacridin (133286-69-8) + 9-(1,1-Dimethyl-2-propinyl)-9-aminoacridin (133286-70-1) + 10-(1,1-Dimethyl-2-propinyl)-9(10H)-iminoacridin (133286-72-3)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In toluene for 72h; Heating;	A 370 mg B 1.69 g C 40 mg D 490 mg

acridin-9-amine hydrochloride (134-50-9) → 9-acetylamino-2-bromoacridine

Conditions	Yield
Multi-step reaction with 2 steps 1: 67.8 percent / pyridine / 24 h / 70 °C 2: 27.2 percent / Br2 / CHCl3 / 2 h / Ambient temperature View Scheme

1-phenyl-1H-pyrazole-5-carbonyl chloride (423768-37-0) + acridin-9-amine hydrochloride (134-50-9) → C23H16N4O (908562-71-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;

4--phenyl-carbamoylchlorid (806608-18-4) + acridin-9-amine hydrochloride (134-50-9) → 1-acridin-9-yl-3-{4-[bis(2-chloroethyl)amino]phenyl}urea (1036724-69-2)

Conditions	Yield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 16h;

acridin-9-amine hydrochloride (134-50-9) + benzene-1,2-dicarboxylic acid (88-99-3) → 9-aminoacridiniun ortho-phthalate monohydrate (1272425-79-2)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + benzoic acid (65-85-0) → 9-aminoacridiniun benzoate monohydrate (1272425-77-0)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + salicylic acid (69-72-7) → 9-aminoacridiniun salicylate (109653-41-0)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + 3-Carboxyphenol (99-06-9) → 9-aminoacridinium 3-hydroxybenzoate hydrochloride

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + para-chlorobenzoic acid (74-11-3) → 9-aminoacridinium 4-chlorobenzoate (1302149-89-8)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) + 3-chlorobenzoate (535-80-8) → 9-aminoacridinium 3-chlorobenzoate (1302149-88-7)

Conditions	Yield
In ethanol; water for 0.0166667h; Reflux;

acridin-9-amine hydrochloride (134-50-9) → (acridin-9-ylamino)acetic acid ethyl ester (934991-54-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water; ethyl acetate / 0.25 h 2: N,N-dimethyl-formamide / 5 h / 80 - 85 °C View Scheme

acridin-9-amine hydrochloride (134-50-9) + bovine serum albumin → 9-aminoacridine hydrochloride binding with bovine serum albumin

Conditions	Yield
In aq. phosphate buffer at 24.84℃; pH=7.4; Thermodynamic data; Temperature;

acridin-9-amine hydrochloride (134-50-9) + human serum albumin → 9-aminoacridine hydrochloride binding with human serum albumin

Conditions	Yield
In aq. phosphate buffer at 24.84℃; pH=7.4; Thermodynamic data; Temperature;

Downstream Products

• 110166-26-2 aminacrine 
• 109653-41-0 9-aminoacridiniun salicylate 
• 1272425-77-0 9-aminoacridiniun benzoate monohydrate 
• 1272425-79-2 9-aminoacridiniun ortho-phthalate monohydrate 
• 1036724-69-2 1-acridin-9-yl-3-{4-[bis(2-chloroethyl)amino]phenyl}urea 
• 908562-71-0 C₂₃H₁₆N₄O 
• 157996-59-3 9-amino-2-bromoacridine 
• 157996-60-6 9-amino-2,7-dibromoacridine 
• 23045-35-4 2-nitro-9-aminoacridine 
• 157996-62-8 9-amino-2,7-dinitroacridine 
• 23043-52-9 N-(acridin-9-yl)acetamide 
• 1428587-11-4 C₂₀H₁₅BN₂O₃ 
• 1302149-88-7 9-aminoacridinium 3-chlorobenzoate 
• 1302149-89-8 9-aminoacridinium 4-chlorobenzoate