Product Name

  • Name

    Bromhexine hydrochloride

  • EINECS 210-280-8
  • CAS No. 611-75-6
  • Article Data7
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 240-244 °C
  • Formula C14H20Br2N2.HCl
  • Boiling Point 441.5 °C at 760 mmHg
  • Molecular Weight 412.595
  • Flash Point 220.8 °C
  • Transport Information
  • Appearance White Solid
  • Safety 22-24/25-36-26
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 611-75-6 (Bromhexine hydrochloride)
  • Hazard Symbols HarmfulXn
  • Synonyms Benzenemethanamine,2-amino-3,5-dibromo-N-cyclohexyl-N-methyl-, monohydrochloride (9CI);Toluene-a,2-diamine,3,5-dibromo-Na-cyclohexyl-Na-methyl-, monohydrochloride (8CI);2-Amino-3,5-dibromo-N-cyclohexyl-N-methylbenzylamine monohydrochloride;Auxit;Bisolvon;Bisolvon hydrochloride;Bromhexine chloride;Bromhexine monohydrochloride;Cyclohexylmethyl(2-amino-3,5-dibromobenzyl)ammonium chloride;N-Cyclohexyl-N-methyl-(2-amino-3,5-dibromobenzyl)ammonium chloride;N-Cyclohexyl-N-methyl-N-(2-amino-3,5-dibromobenzyl)ammonium chloride;Na-Cyclohexyl-Na-methyl-3,5-dibromotoluene-a,2-diaminehydrochloride;Ophtosol;Quentan;
  • PSA 29.26000
  • LogP 5.94150

Synthetic route

N-methylcyclohexylamine
100-60-7

N-methylcyclohexylamine

(2-amino-3,5-dibromophenyl)methanol
50739-76-9

(2-amino-3,5-dibromophenyl)methanol

bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

Conditions
ConditionsYield
Stage #1: N-methylcyclohexylamine; (2-amino-3,5-dibromophenyl)methanol With bis(trichloromethyl) carbonate; sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethanol		95%
Stage #1: N-methylcyclohexylamine; (2-amino-3,5-dibromophenyl)methanol With acetic acid In toluene at 85℃; for 12h; Industrial scale;
Stage #2: With hydrogenchloride In acetone at 20℃; for 1.33333h; pH=2 - 3; Industrial scale;		80%
Stage #1: N-methylcyclohexylamine; (2-amino-3,5-dibromophenyl)methanol With acetic acid In toluene at 143 - 178℃; for 30h;
Stage #2: With hydrogenchloride In water; ethyl acetate; toluene at 0 - 10℃; Reagent/catalyst; Temperature;
N-methylcyclohexylamine
100-60-7

N-methylcyclohexylamine

2,4-dibromo-6-chloromethylaniline

2,4-dibromo-6-chloromethylaniline

bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

Conditions
ConditionsYield
at 45 - 55℃; for 3h;89.8%
Stage #1: N-methylcyclohexylamine; 2-chloromethyl-4,6-dibromoaniline With pyrographite In ethanol at 20 - 30℃; for 1h; Heating;
Stage #2: With hydrogenchloride In ethanol at 0 - 10℃; for 0.5h; pH=4 - Ca. 5; Temperature; pH-value; Solvent; Heating;		63.25%
Stage #1: N-methylcyclohexylamine; 2-chloromethyl-4,6-dibromoaniline In dichloromethane at 0 - 5℃; for 3h;
Stage #2: With hydrogenchloride In ethanol; dichloromethane at 25 - 30℃;		59.6%
N-methylcyclohexylamine
100-60-7

N-methylcyclohexylamine

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

3,5-dibromo-2-amino benzaldehyde

bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

Conditions
ConditionsYield
Stage #1: N-methylcyclohexylamine; 3,5-dibromo-2-amino benzaldehyde With titanium(IV)isopropoxide In isopropyl alcohol at 20 - 30℃; for 5h;
Stage #2: With sodium tetrahydroborate In isopropyl alcohol at 30℃; for 2h;
Stage #3: With hydrogenchloride In water; isopropyl alcohol at 30℃; for 3h; Solvent; Temperature; Reagent/catalyst;		81%
N-methylcyclohexylamine
100-60-7

N-methylcyclohexylamine

2-Amino-3,5-dibromo-benzoyl chloride
63498-16-8

2-Amino-3,5-dibromo-benzoyl chloride

bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

Conditions
ConditionsYield
Stage #1: N-methylcyclohexylamine; 2-Amino-3,5-dibromo-benzoyl chloride In ethanol at 20℃;
Stage #2: With hydrogenchloride In water; ethyl acetate at 0 - 5℃; pH=5 - 6;		41%
3,5-dibromo-2-amino benzaldehyde
50910-55-9

3,5-dibromo-2-amino benzaldehyde

bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / ethanol / 10 - 40 °C
2.1: thionyl chloride / 0 - 40 °C
3.1: ethanol / 20 °C
3.2: 0 - 5 °C / pH 5 - 6
View Scheme
2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bromine / dichloromethane; water / 0.17 h / 20 °C / Industrial scale
1.2: 6 h / Industrial scale
2.1: ethanol; potassium borohydride / 0.5 h / 20 - 40 °C / Industrial scale
3.1: acetic acid / toluene / 12 h / 85 °C / Industrial scale
3.2: 1.33 h / 20 °C / pH 2 - 3 / Industrial scale
View Scheme
bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

sodium 2-(4-isobutylphenyl)propionate
31121-93-4

sodium 2-(4-isobutylphenyl)propionate

bromohexinium ibuprofenate
1347703-29-0

bromohexinium ibuprofenate

Conditions
ConditionsYield
In methanol at 20℃;84%
2-(2-methylphenyl)pyridine
10273-89-9

2-(2-methylphenyl)pyridine

bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

C38H40N4

C38H40N4

Conditions
ConditionsYield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 72h; Inert atmosphere; Glovebox;69%
carbon monoxide
201230-82-2

carbon monoxide

bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

phenylboronic acid
98-80-6

phenylboronic acid

A

4-benzoyl-2-bromo-6-{[cyclohexyl(methyl)amino]methyl}aniline
1571070-22-8

4-benzoyl-2-bromo-6-{[cyclohexyl(methyl)amino]methyl}aniline

B

2,4-dibenzoyl-6-{[cyclohexyl(methyl)amino]methyl}aniline
1571070-15-9

2,4-dibenzoyl-6-{[cyclohexyl(methyl)amino]methyl}aniline

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; palladium diacetate; catacxium A In toluene at 100℃; under 7500.75 Torr; for 20h; Reagent/catalyst; Solvent; Suzuki-Miyaura Coupling; Inert atmosphere; Autoclave;A 24%
B 60%
...Expand
bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

N-nitroso-N-methylcyclohexylamine
5432-28-0

N-nitroso-N-methylcyclohexylamine

Conditions
ConditionsYield
With sodium nitrite In water for 6h; Product distribution; time, pH, and concentration dependence of the reaction;
bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

A

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

3,5-dibromo-2-amino benzaldehyde

B

3-Cyclohexyl-6,8-dibromchinazolin

3-Cyclohexyl-6,8-dibromchinazolin

C

3-Cyclohexyl-6,8-dibromchinazolin-4-on
114390-40-8

3-Cyclohexyl-6,8-dibromchinazolin-4-on

Conditions
ConditionsYield
With oxygen
With oxygen In hydrogenchloride for 100h; Mechanism; Heating; other solvents and temperature;
With acid Title compound not separated from byproducts;
With oxygen Title compound not separated from byproducts;
...Expand
bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

A

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

3,5-dibromo-2-amino benzaldehyde

B

3-Cyclohexyl-6,8-dibromchinazolin-4-on
114390-40-8

3-Cyclohexyl-6,8-dibromchinazolin-4-on

Conditions
ConditionsYield
With water Mechanism; Heating;
bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

acetyl chloride
75-36-5

acetyl chloride

SF-150B(1)
114390-43-1

SF-150B(1)

Conditions
ConditionsYield
Ambient temperature;
bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

Methacryloyl chloride
920-46-7

Methacryloyl chloride

C18H24Br2N2O

C18H24Br2N2O

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;
bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

N-benzyl-N-(2,4-dibromo-6-((cyclohexyl(methyl)amino)methyl)phenyl)methacrylamide

N-benzyl-N-(2,4-dibromo-6-((cyclohexyl(methyl)amino)methyl)phenyl)methacrylamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; dmap / dichloromethane / 0 - 20 °C
2.1: sodium hydride / tetrahydrofuran; paraffin oil / 0.5 h / 0 - 20 °C
2.2: 4 h / 0 - 20 °C
View Scheme
bromhexine monohydrochloride
611-75-6

bromhexine monohydrochloride

1-benzyl-6-bromo-8-((cyclohexyl(methyl)amino)methyl)-3-methylquinolin-2(1H)-one

1-benzyl-6-bromo-8-((cyclohexyl(methyl)amino)methyl)-3-methylquinolin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine; dmap / dichloromethane / 0 - 20 °C
2.1: sodium hydride / tetrahydrofuran; paraffin oil / 0.5 h / 0 - 20 °C
2.2: 4 h / 0 - 20 °C
3.1: cesium fluoride; 1,3-bis(4-methoxy-2-methylphenyl)-4,5-dimethyl-1H-imidazol-3-ium chloride / toluene / 40 h / 140 °C / Glovebox; Sealed tube; Inert atmosphere
View Scheme

Bromhexine hydrochloride Specification

The Bromhexine hydrochloride, with the CAS registry number 611-75-6, is also known as N-(2-Amino-3,5-dibromobenzyl)-N-methylcyclohexylamine hydrochloride. It belongs to the product categories of Amines; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 210-280-8. This chemical's molecular formula is C14H21Br2ClN2 and molecular weight is 412.59. What's more, both its IUPAC name and systematic name are the same which is called 2,4-Dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline hydrochloride. This chemical can be prepared by orthotoluidine with acetic anhydride. It is used as expectorant and used to treat acute or chronic bronchitis, asthma, bronchiectasis, emphysema.

Physical properties about Bromhexine hydrochloride are: (1)ACD/LogP: 5.081; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.35; (4)ACD/LogD (pH 7.4): 3.97; (5)ACD/BCF (pH 5.5): 7.90; (6)ACD/BCF (pH 7.4): 333.79; (7)ACD/KOC (pH 5.5): 25.55; (8)ACD/KOC (pH 7.4): 1078.72; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 29.26 Å2; (13)Flash Point: 220.8 °C; (14)Enthalpy of Vaporization: 71.22 kJ/mol; (15)Boiling Point: 441.5 °C at 760 mmHg; (16)Vapour Pressure: 3.37E-08 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system. It may cause damage to health by inhalation, in contacting with skin and if swallowed. Therefore, you should wear suitable protective clothing and avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: Cl.Brc1cc(c(N)c(Br)c1)CN(C)C2CCCCC2
(2) InChI: InChI=1S/C14H20Br2N2.ClH/c1-18(12-5-3-2-4-6-12)9-10-7-11(15)8-13(16)14(10)17;/h7-8,12H,2-6,9,17H2,1H3;1H
(3) InChIKey: UCDKONUHZNTQPY-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 2210mg/kg (2210mg/kg)   Gendai no Rinsho. Vol. 3, Pg. 259, 1969.
mouse LD50 intravenous 44mg/kg (44mg/kg)   Gendai no Rinsho. Vol. 3, Pg. 259, 1969.
mouse LD50 oral 3gm/kg (3000mg/kg)   Zentralblatt fuer Pharmazie, Pharmakotherapie und Laboratoriums-diagnostik. Vol. 109, Pg. 385, 1970.
mouse LD50 subcutaneous > 14gm/kg (14000mg/kg)   Drugs in Japan Vol. 6, Pg. 737, 1982.
rabbit LD50 oral 10gm/kg (10000mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 163, Pg. 284, 1966.
rat LD50 intraperitoneal 1680mg/kg (1680mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA		 Gendai no Rinsho. Vol. 3, Pg. 259, 1969.
rat LD50 oral 6gm/kg (6000mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA		 Gendai no Rinsho. Vol. 3, Pg. 259, 1969.
rat LD50 subcutaneous > 14gm/kg (14000mg/kg)   Yakkyoku. Pharmacy. Vol. 35(1), Pg. -, 1984.

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