Product Name

  • Name

    Ambroxol hydrochloride

  • EINECS 245-899-2
  • CAS No. 23828-92-4
  • Article Data10
  • CAS DataBase
  • Density 1.612 g/cm3
  • Solubility Slightly soluble in water (~5 mg/ml) or ethanol (~5 mg/ml).
  • Melting Point 233-234.5 °C
  • Formula C13H19Br2ClN2O
  • Boiling Point 468.6 °C at 760 mmHg
  • Molecular Weight 414.568
  • Flash Point 237.2 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety 36
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 23828-92-4 (Ambroxol hydrochloride)
  • Hazard Symbols HarmfulXn
  • Synonyms Hustless (TN);trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride;(2-amino-3,5-dibromo-phenyl)methyl-(4-hydroxycyclohexyl)azanium;18683-91-5;Ambroxol lozenge;Ambroxol Hcl;Altretamine;Mucoangin;Hustless;Mucolear;
  • PSA 58.28000
  • LogP 4.96100

Synthetic route

ambroxol
18683-91-5, 36557-04-7, 107814-37-9

ambroxol

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol for 1h; pH=Ca. 1; Concentration;97%
With hydrogenchloride In water; acetone at 0℃; for 1h; Solvent; Temperature;97%
trans-4-hydroxycyclohexylamine
27489-62-9

trans-4-hydroxycyclohexylamine

3,5-dibromo-2-amino benzaldehyde
50910-55-9

3,5-dibromo-2-amino benzaldehyde

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Stage #1: trans-4-hydroxycyclohexylamine; 3,5-dibromo-2-amino benzaldehyde With lithium perchlorate; sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 1.5h;
Stage #2: With hydrogenchloride In water; acetone at 20℃; for 1h; Solvent;		96.26%
trans-4-[(2-amino-3,5-dibromobenzylidene)amino]cyclohexanol

trans-4-[(2-amino-3,5-dibromobenzylidene)amino]cyclohexanol

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Stage #1: trans-4-[(2-amino-3,5-dibromobenzylidene)amino]cyclohexanol With methanol; formic acid; 5%-palladium/activated carbon at 40℃; for 5h; Inert atmosphere; Green chemistry;
Stage #2: With hydrogenchloride In ethanol; water at 20℃; for 2.5h; Reagent/catalyst; Solvent; Green chemistry;		95%
Stage #1: trans-4-[(2-amino-3,5-dibromobenzylidene)amino]cyclohexanol With sodium tetrahydroborate In ethylene glycol at 20℃; for 7h;
Stage #2: With hydrogenchloride In ethylene glycol; acetone at 20℃; for 2h;
Stage #1: trans-4-[(2-amino-3,5-dibromobenzylidene)amino]cyclohexanol With sodium tetrahydroborate In ethanol at 25℃;
Stage #2: With hydrogenchloride In 1,4-dioxane at 25℃;		n/a
trans-4-[(2-amino-3,5-dibromobenzoyl)amino]cyclohexanol

trans-4-[(2-amino-3,5-dibromobenzoyl)amino]cyclohexanol

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Stage #1: trans-4-[(2-amino-3,5-dibromobenzoyl)amino]cyclohexanol With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran; water at 65℃; for 24h; Inert atmosphere; Cooling with ice;
Stage #2: With hydrogenchloride In water for 2h; Temperature; Solvent; Reflux;		84%
o-toluidine
95-53-4

o-toluidine

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / water / 0.5 h / 0 - 20 °C
1.2: 30 - 90 °C
1.3: pH 7
2.1: sodium carbonate / N,N-dimethyl-formamide / 90 - 110 °C
3.1: hydrogenchloride / methanol / 1 h / pH Ca. 1
View Scheme
3,5-dibromo-2-nitro-benzaldehyde
861787-48-6

3,5-dibromo-2-nitro-benzaldehyde

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene / 3 h / Reflux
2: palladium on activated charcoal; hydrogen / methanol / 10 h / 70 °C / Autoclave
3: hydrogenchloride / acetone; water / 1 h / 0 °C
View Scheme
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: bromine / methanol / 3 h / 50 °C
2: toluene / 3 h / Reflux
3: palladium on activated charcoal; hydrogen / methanol / 10 h / 70 °C / Autoclave
4: hydrogenchloride / acetone; water / 1 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: toluene-4-sulfonic acid / toluene / 1.5 h / Reflux
2.1: hydrazine hydrate / tetrahydrofuran / 1.5 h / 50 - 55 °C / Inert atmosphere
3.1: bromine; dihydrogen peroxide / dichloromethane; water
4.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
5.1: lithium perchlorate; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1.5 h / 20 °C
5.2: 1 h / 20 °C
View Scheme
N-(2-(1,3-dioxolan-2-yl))phenylamine
26908-34-9

N-(2-(1,3-dioxolan-2-yl))phenylamine

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bromine; dihydrogen peroxide / dichloromethane; water
2.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
3.1: lithium perchlorate; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1.5 h / 20 °C
3.2: 1 h / 20 °C
View Scheme
2-(2-nitrophenyl)-1,3-dioxolane
48140-35-8

2-(2-nitrophenyl)-1,3-dioxolane

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrazine hydrate / tetrahydrofuran / 1.5 h / 50 - 55 °C / Inert atmosphere
2.1: bromine; dihydrogen peroxide / dichloromethane; water
3.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C
4.1: lithium perchlorate; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1.5 h / 20 °C
4.2: 1 h / 20 °C
View Scheme
4-N-tert-butoxycarbonylaminophenol
54840-15-2

4-N-tert-butoxycarbonylaminophenol

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen; [Rh(cod)(CI)(CAACCy)] / n-heptane / 48 h / 40 °C
2.1: ethanol / 90 °C
3.1: sodium tetrahydroborate / ethanol / 25 °C
3.2: 25 °C
View Scheme
trans-tert-butyl 4-hydroxycyclohexylcarbamate
111300-06-2

trans-tert-butyl 4-hydroxycyclohexylcarbamate

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: ethanol / 90 °C
2.1: sodium tetrahydroborate / ethanol / 25 °C
2.2: 25 °C
View Scheme
4-amino-phenol
123-30-8

4-amino-phenol

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen; 5% palladium on Al2O3; potassium carbonate / isopropyl alcohol / 48 h / 80 °C
2.1: ethanol / 90 °C
3.1: sodium tetrahydroborate / ethanol / 25 °C
3.2: 25 °C
View Scheme
4-nitro-phenol
100-02-7

4-nitro-phenol

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen; 5% palladium on Al2O3; potassium carbonate / isopropyl alcohol / 48 h / 80 °C
2.1: ethanol / 90 °C
3.1: sodium tetrahydroborate / ethanol / 25 °C
3.2: 25 °C
View Scheme
trans-4-hydroxycyclohexylamine
27489-62-9

trans-4-hydroxycyclohexylamine

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water / 2.5 h / 10 - 40 °C
2.1: acetic acid; bromine / water / 5 - 15 °C
3.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / water; tetrahydrofuran / 24 h / 65 °C / Inert atmosphere; Cooling with ice
3.2: 2 h / Reflux
View Scheme
isatoic anhydride
118-48-9

isatoic anhydride

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water / 2.5 h / 10 - 40 °C
2.1: acetic acid; bromine / water / 5 - 15 °C
3.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / water; tetrahydrofuran / 24 h / 65 °C / Inert atmosphere; Cooling with ice
3.2: 2 h / Reflux
View Scheme
formaldehyd
50-00-0

formaldehyd

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

4-(6,8-dibromo-1,4-dihydroquinazolin-3(2H)-yl)-cyclohexanol hydrochloride

4-(6,8-dibromo-1,4-dihydroquinazolin-3(2H)-yl)-cyclohexanol hydrochloride

Conditions
ConditionsYield
In methanol; water at 25℃; for 10h;93%
formaldehyd
50-00-0

formaldehyd

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

6,8-dibromo-3-(trans-4-hydroxycyclohexyl)-1,2,3,4-tetrahydroquinazoline

6,8-dibromo-3-(trans-4-hydroxycyclohexyl)-1,2,3,4-tetrahydroquinazoline

Conditions
ConditionsYield
In methanol; water at 25℃; for 6h;81%
N-maleimido butane-4-carboxaldehyde

N-maleimido butane-4-carboxaldehyde

ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

trans-4-[(2-amino-3,5-dibromophenyl)methyl-4-maleimidobutylamino]cyclohexanol

trans-4-[(2-amino-3,5-dibromophenyl)methyl-4-maleimidobutylamino]cyclohexanol

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol Inert atmosphere;11%
ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

ambroxol
18683-91-5, 36557-04-7, 107814-37-9

ambroxol

Conditions
ConditionsYield
With sodium hydroxide In water pH=9;
ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

alpha cyclodextrin
10016-20-3

alpha cyclodextrin

C36H60O30*C13H18Br2N2O

C36H60O30*C13H18Br2N2O

Conditions
ConditionsYield
In water at 49.99℃;
ambroxol hydrochloride
23828-92-4

ambroxol hydrochloride

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C42H70O35*C13H18Br2N2O

C42H70O35*C13H18Br2N2O

Conditions
ConditionsYield
In water at 49.99℃;

Ambroxol hydrochloride Chemical Properties

Molecular Structure:

Molecular Formula: C13H19Br2ClN2O
Molecular Weight: 414.5638
IUPAC Name: 4-[(2-Amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol hydrochloride
Synonyms of Ambroxol hydrochloride (CAS NO.23828-92-4): Ambroxol lozenge ; CCRIS 8686 ; EINECS 245-899-2 ; Mucoangin ; Mucolear ; Mucosolvan ; NA 872 hydrochloride ; UNII-CC995ZMV90 ; trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride  ; Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, monohydrochloride, trans- (9CI) ; Cyclohexanol, 4-((2-amino-3,5-dibromobenzyl)amino)-, hydrochloride, trans- (8CI) ; Cyclohexanol, 4-(N-(2-amino-3,5-dibromobenzyl)amino)-, hydrochloride (E)-
CAS NO: 23828-92-4
Classification Code: Drug / Therapeutic Agent ; Reproductive Effect
Melting Point: 233-234.5°C 
H bond acceptors: 3
H bond donors: 4
Freely Rotating Bonds: 5
Polar Surface Area: 58.28 Å2
Flash Point: 251.7 °C
Enthalpy of Vaporization: 79.99 kJ/mol
Boiling Point: 492.6 °C at 760 mmHg
Vapour Pressure: 1.61E-10 mmHg at 25°C

Ambroxol hydrochloride Uses

 Ambroxol hydrochloride (CAS NO.23828-92-4) is used as antitussive and expectorant agent.

Ambroxol hydrochloride Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intraperitoneal 125mg/kg (125mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978.
dog LD50 oral 500mg/kg (500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978.
guinea pig LD50 intraperitoneal 280mg/kg (280mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978.
guinea pig LD50 oral 1180mg/kg (1180mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978.
mouse LD50 intraperitoneal 268mg/kg (268mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978.
mouse LD50 intravenous 138mg/kg (138mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978.
mouse LD50 oral 2380mg/kg (2380mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981.
mouse LD50 subcutaneous 1060mg/kg (1060mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 263, 1981.
rabbit LD50 intravenous 64mg/kg (64mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ATAXIA		 Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981.
rabbit LD50 oral 2597mg/kg (2597mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM DUODENUM		 Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981.
rabbit LDLo intraperitoneal 400mg/kg (400mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978.
rat LD50 intraperitoneal 262mg/kg (262mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: PERITONITIS		 Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981.
rat LD50 intravenous 100mg/kg (100mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981.
rat LD50 oral 4203mg/kg (4203mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 263, 1981.
rat LD50 subcutaneous 1489mg/kg (1489mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 263, 1981.

Ambroxol hydrochloride Safety Profile

Safety Information of Ambroxol hydrochloride (CAS NO.23828-92-4):
Hazard Codes:Xn 
Risk Statements:22
22:Harmful if swallowed 
Safety Statements:36
36:Wear suitable protective clothing 
WGK Germany:3
RTECS:GV8423000
Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits very toxic fumes of Br−, NOx, and HCl.

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