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N-methylcyclohexylamine
(2-amino-3,5-dibromophenyl)methanol
bromhexine monohydrochloride
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
3,5-dibromo-2-amino benzaldehyde
bromhexine monohydrochloride
Conditions | Yield |
---|---|
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
2-Amino-3,5-dibromo-benzoyl chloride
bromhexine monohydrochloride
Conditions | Yield |
---|---|
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
bromhexine monohydrochloride
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
sodium 2-(4-isobutylphenyl)propionate
bromohexinium ibuprofenate
Conditions | Yield |
---|---|
In methanol at 20℃; | 84% |
Conditions | Yield |
---|---|
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
bromhexine monohydrochloride
phenylboronic acid
A
4-benzoyl-2-bromo-6-{[cyclohexyl(methyl)amino]methyl}aniline
B
2,4-dibenzoyl-6-{[cyclohexyl(methyl)amino]methyl}aniline
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium nitrite In water for 6h; Product distribution; time, pH, and concentration dependence of the reaction; |
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. |