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Ambroxol

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Identification
Molecular formula
C13H18Br2N2O
CAS number
18683-91-5
IUPAC name
4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol
State
State

At room temperature, Ambroxol is in a solid state, usually available in the form of tablets or capsules when used pharmaceutically.

Melting point (Celsius)
233.00
Melting point (Kelvin)
506.15
Boiling point (Celsius)
440.00
Boiling point (Kelvin)
713.15
General information
Molecular weight
375.10g/mol
Molar mass
375.4750g/mol
Density
1.6430g/cm3
Appearence

Ambroxol is typically a white or slightly yellow crystalline powder. It is odorless or nearly odorless, and it may have a slightly bitter taste.

Comment on solubility

Solubility of 4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol (C13H18Br2N2O)

The solubility of 4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol is influenced by multiple factors, primarily its chemical structure and polarity.

Factors Affecting Solubility

  • Polarity: The presence of hydroxyl (-OH) and amino (-NH2) functional groups enhances the compound's ability to interact with polar solvents like water.
  • Hydrogen Bonding: The ability of 4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol to form hydrogen bonds can contribute to its solubility in certain solvents.
  • Br-Substituents: The presence of bromine atoms may add complexity to solubility behavior by influencing both hydrophobic and hydrophilic interactions.

Based on these factors, one can predict that:

  • 4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol is likely to have moderate solubility in polar solvents.
  • Its solubility may decrease in nonpolar solvents due to the increase in hydrophobic character imparted by the bromine substituents.

In summary, the solubility of this compound demonstrates a balance between its functional groups, molecular interactions, and the nature of the solvent, making it essential to consider these aspects during practical applications and experiments.

Interesting facts

Interesting Facts about 4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol

This compound is a unique member of the family of substituted cyclohexanols, notable for its complex structure that integrates both amino and bromo substituents. Here are some interesting aspects:

  • Multifunctional Applications: The presence of both amino and bromo groups highlights this compound’s potential in medicinal chemistry. Such compounds often exhibit biological activity and could serve as lead compounds for drug development.
  • Structure-Activity Relationship: The intricate design of this molecule allows for the exploration of structure-activity relationships. Modifications to the bromo and amino groups can lead to significant variations in biological activity—an important area of research in pharmaceuticals.
  • Potential Antimicrobial Properties: Compounds with bromine substituents often show antimicrobial activity. Research in this field could explore the compound's effectiveness against various pathogens.
  • Chiral Centers: The presence of cyclohexanol introduces chiral centers into the molecule, leading to the possibility of enantiomeric forms. Different enantiomers can exhibit different biological activities and properties.
  • Research Interest: With the increasing interest in developing compounds for targeted therapies, this molecule could attract the attention of researchers focused on creating more selective agents for treating diseases ranging from bacterial infections to cancer.

Overall, 4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol is a fascinating compound with a diverse range of potential applications, making it a valuable subject for further scientific study.

Synonyms
ambroxol
18683-91-5
107814-37-9
rac-cis-Ambroxol
36557-04-7
4-((2-amino-3,5-dibromobenzyl)amino)cyclohexan-1-ol
rac-cis-Ambroxol-d5
Bisolvon metabolite VIII
4-[(2-Amino-3,5-dibromobenzyl)amino]cyclohexanol
Bromhexine-metabolite VIII
NA-872
Tabcin
trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol
4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol
Ambroxol, cis-
cis-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol
Ambroxol [INN]
Cyclohexanol, 4-[[(2-amino-3,5-dibromophenyl)methyl]amino]-, trans-
1217679-83-8
trans-4-((2-Amino-3,5-dibromobencil)amino)ciclohexanol
trans-4-((2-Amino-3,5-dibromobenzyl)amine)cyclohexanol
QH6ZT6J071
Cyclohexanol, 4-((2-amino-3,5-dibromobenzyl)amino)- (E)-
N-(2-Amino-3,4-dibromocyclohexyl)-trans-4-aminocyclohexanol
4-Hydroxydemethylbromhexine, cis-
N-(trans-4-Hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)-amine
N-(trans-p-Hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)amine
Ambroxol Base
Ambroxol (INN)
Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, trans-
200168S0CL
trans-4-[(2-amino-3,5-dibromobenzyl)amino]cyclohexanol
N-(2-Amino-3,4-dibromociclohexil)-trans-4-aminociclohexanol
N-(trans-4-Hidroxiciclohexil)-(2-amino-3,5-dibromobencil)amina
Ambroxol EP Impurity D
Ambroxolum
Ambroxol [INN:BAN]
cis-4-(((2-Amino-3,5-dibromophenyl)methyl)amino)cyclohexanol
cis-4-[[(2-Amino-3,5-dibromophenyl)methyl]amino]cyclohexanol
Ambroxolum [INN-Latin]
Ambroxol EP Impurity D (cis-Ambroxol HCl/ Acebrophylline Impurity D)
Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, cis-
Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, trans- (9CI)
Bromhexine Metabolite VIII
NCGC00016781-04
EINECS 242-500-3
CAS-23828-92-4
Amboxol
cis-Ambroxol
SR-05000001463
UNII-200168S0CL
Cyclohexanol, 4-[[(2-amino-3,5-dibromophenyl)methyl]amino]-, cis-; cis-4-[[(2-Amino-3,5-dibromophenyl)methyl]amino]cyclohexanol; cis-Ambroxol; cis-4-[(2-Amino-3,5-dibromobenzyl)amino]cyclohexanol
Ambroxol impurity D
Ambroxol (Standard)
MFCD00242702
Tabcin (TN)
Spectrum_001346
AMBRO?
AMBROXOL [MI]
Prestwick0_000366
Prestwick1_000366
Prestwick2_000366
Prestwick3_000366
Spectrum2_001518
Spectrum3_000955
Spectrum4_001068
Spectrum5_001021
trans-4-((2-Amino-3,5-dibromobencil)amino)ciclohexanol [Spanish]
N-(2-Amino-3,4-dibromociclohexil)-trans-4-aminociclohexanol [Spanish]
AMBROXOL [WHO-DD]
EC 242-500-3
N-(trans-4-Hidroxiciclohexil)-(2-amino-3,5-dibromobencil)amina [Spanish]
UNII-QH6ZT6J071
Oprea1_766685
SCHEMBL18702
BSPBio_000491
KBioGR_001396
KBioSS_001826
MLS001306470
DivK1c_000027
SCHEMBL423712
SPBio_001595
SPBio_002412
BPBio1_000541
CHEMBL153479
SCHEMBL7855003
4-[(2-amino-3,5-dibromo-phenyl)methylamino]cyclohexanol
CHEMBL1477775
DTXSID8022583
SCHEMBL21765132
BCBcMAP01_000092
CHEBI:92994
GTPL10692
HY-B1039R
KBio1_000027
KBio2_001826
KBio2_004394
KBio2_006962
KBio3_002050
DTXSID60860228
CHEBI:135590
NINDS_000027
4-{[(2-amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol
Cyclohexanol, 4-[[(2-amino-3,5-dibromophenyl)methyl]amino]-
HMS2089D06
HMS2231B19
HMS3373J22
HMS3886M18
ALBB-022461
BCP04489
HY-B1039
SYB67983
BBL009896
BDBM50395322
MFCD28143339
s5710
STK711075
AKOS005530704
AKOS015889660
AKOS027338704
AC-8362
Ambroxol hydrochloride impurity D [EP]
BCP9000283
CCG-207907
CS-4558
DB06742
SB17463
SB82866
IDI1_000027
SMP1_000014
NCGC00016781-01
NCGC00016781-02
NCGC00016781-08
NCGC00159399-02
NCGC00371077-02
AS-56023
IA156916
SMR000718792
VS-02240
4-HYDROXYDEMETHYLBROMHEXINE, TRANS-
BCP0726000066
SBI-0051766.P002
AB00514663
CS-0323348
NS00005443
NS00073281
D07442
H33594
AB00053639_13
AB01275465-01
EN300-18524079
Q221637
SR-05000001463-1
AMBROXOL HYDROCHLORIDE IMPURITY D [EP IMPURITY]
BRD-K11223672-003-03-7
BRD-K11223672-003-04-5
BRD-K11223672-003-05-2
BRD-K56558538-003-02-8
BRD-K56558538-003-11-9
BRD-K56558538-003-12-7
4-[(2-amino-3,5-dibromophenyl)methylamino-]cyclohexanol
4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexanol
(1s,4s)-4-((2-amino-3,5-dibromobenzyl)amino)cyclohexanol
4-[(2-Amino-3,5-dibromobenzyl)amino]cyclohexanol, trans-
trans-4-{[(2-amino-3,5-dibromophenyl)methyl]amino}cyclohexanol
(1r,4r)-4-{[(2-Amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol
Cyclohexanol, 4-[[(2-amino-3,5-dibromo-phenyl)methyl]amino]-, trans