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23828-92-4

Basic Information
CAS No.: 23828-92-4
Name: Ambroxol hydrochloride
Article Data: 10
Molecular Structure:
Molecular Structure of 23828-92-4 (Ambroxol hydrochloride)
Formula: C13H19Br2ClN2O
Molecular Weight: 414.568
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;
EINECS: 245-899-2
Density: 1.612 g/cm3
Melting Point: 233-234.5 °C
Boiling Point: 468.6 °C at 760 mmHg
Flash Point: 237.2 °C
Solubility: Slightly soluble in water (~5 mg/ml) or ethanol (~5 mg/ml).
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
PSA: 58.28000
LogP: 4.96100
Synthetic route
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%
27489-62-9

trans-4-hydroxycyclohexylamine

50910-55-9

3,5-dibromo-2-amino benzaldehyde

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

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

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%
95-53-4

o-toluidine

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
861787-48-6

3,5-dibromo-2-nitro-benzaldehyde

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
552-89-6

2-nitro-benzaldehyde

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
26908-34-9

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

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
48140-35-8

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

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
54840-15-2

4-N-tert-butoxycarbonylaminophenol

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
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Chemistry

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

Uses

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

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.

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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