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611-75-6

Basic Information
CAS No.: 611-75-6
Name: Bromhexine hydrochloride
Article Data: 7
Molecular Structure:
Molecular Structure of 611-75-6 (Bromhexine hydrochloride)
Formula: C14H20Br2N2.HCl
Molecular Weight: 412.595
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;
EINECS: 210-280-8
Melting Point: 240-244 °C
Boiling Point: 441.5 °C at 760 mmHg
Flash Point: 220.8 °C
Appearance: White Solid
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37/38
Safety: 22-24/25-36-26
PSA: 29.26000
LogP: 5.94150
Synthetic route
100-60-7

N-methylcyclohexylamine

50739-76-9

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

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;
100-60-7

N-methylcyclohexylamine

2,4-dibromo-6-chloromethylaniline

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%
100-60-7

N-methylcyclohexylamine

50910-55-9

3,5-dibromo-2-amino benzaldehyde

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%
100-60-7

N-methylcyclohexylamine

63498-16-8

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

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%
50910-55-9

3,5-dibromo-2-amino benzaldehyde

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
134-20-3

2-carbomethoxyaniline

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
611-75-6

bromhexine monohydrochloride

31121-93-4

sodium 2-(4-isobutylphenyl)propionate

1347703-29-0

bromohexinium ibuprofenate

Conditions
ConditionsYield
In methanol at 20℃;84%
10273-89-9

2-(2-methylphenyl)pyridine

611-75-6

bromhexine monohydrochloride

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%
201230-82-2

carbon monoxide

611-75-6

bromhexine monohydrochloride

98-80-6

phenylboronic acid

A

1571070-22-8

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

B

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%
611-75-6

bromhexine monohydrochloride

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;
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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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