3-O-Methyldopamine hydrochloride supplier

Name
3-O-Methyldopamine hydrochloride
EINECS 216-035-1
CAS No. 1477-68-5
Article Data8
CAS DataBase
Density
Solubility
Melting Point 213-215 °C(lit.)
Formula C₉H₁₃NO₂.ClH
Boiling Point 304.5 °C at 760 mmHg
Molecular Weight 203.669
Flash Point 138 °C
Transport Information
Appearance light beige crystalline solid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Methoxytyramine hydrochloride;3-Methoxy-4-hydroxyphenethylamine hydrochloride;Guaiacol,4-(2-aminoethyl)-, hydrochloride (6CI);Phenol, 4-(2-aminoethyl)-2-methoxy-,hydrochloride (8CI,9CI);4-Hydroxy-3-methoxyphenethylaminehydrochloride;4-Hydroxy-3-methoxy-b-phenethylamine hydrochloride;4-(2-Aminoethyl)-2-methoxyphenol hydrochloride;
PSA 55.48000
LogP 2.40430

Synthetic route

: 4468-59-1
4-hydroxy-3-methoxyphenylacetonitrile

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 20℃; for 12h;	82%
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol under 7600 - 11400 Torr; for 1.5h;	75%

: 6178-42-3
vanillalnitromethane

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 0℃; under 760 Torr;	81%
With hydrogenchloride; zinc In ethanol; water at 40 - 60℃; for 3h;	67.08%
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / 1,4-dioxane; ethanol / 20 °C 2.1: hydrogenchloride; zinc / ethyl acetate; water / 3 h / 50 - 70 °C 2.2: 2 h / -20 °C View Scheme

: 63909-38-6, 1860-56-6
3-methoxy-4-benzyloxy-ω-nitrostyrolene

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; iron(III) chloride; platinum In water for 4h;	76%

: 528594-30-1
2-methoxy-4-(2-nitroethyl)phenol

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-methoxy-4-(2-nitroethyl)phenol With hydrogenchloride; zinc In water; ethyl acetate at 50 - 70℃; for 3h; Stage #2: With hydrogenchloride In methanol at -20℃; for 2h;	72%
Stage #1: 2-methoxy-4-(2-nitroethyl)phenol With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; Stage #2: With hydrogenchloride In water	31%

: 2426-87-1
3-methoxy-4-(phenylmethoxy)benzaldehyde

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / KOH, tetrabutylammonium bromide / ethanol / 1 h / 0 °C 2: 85 percent / AcONa. Ac2O / 0.08 h / Heating 3: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme
Multi-step reaction with 2 steps 1: 72 percent / KOH / aq. ethanol / 2 h / 0 °C 2: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme

: 60372-07-8
1-(3-methoxy-4-benzyloxyphenyl)-2-nitroethanol

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / AcONa. Ac2O / 0.08 h / Heating 2: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme

: 121-33-5
vanillin

<4-oxy-3-methoxy-phenyl>-bis-<4-dimethylamino-phenyl>-methane: <4-oxy-3-methoxy-phenyl>-bis-<4-dimethylamino-phenyl>-methane

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / K2CO3, tetrabutylammonium bromide / dimethylformamide / 5 h / 18 - 20 °C 2: 71 percent / KOH, tetrabutylammonium bromide / ethanol / 1 h / 0 °C 3: 85 percent / AcONa. Ac2O / 0.08 h / Heating 4: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme
Multi-step reaction with 3 steps 1: 100 percent / K2CO3, tetrabutylammonium bromide / dimethylformamide / 5 h / 18 - 20 °C 2: 72 percent / KOH / aq. ethanol / 2 h / 0 °C 3: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme

: 498-00-0
4-hydroxymethyl-2-methoxyphenol

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / dimethylformamide / 20 h / 130 °C 2: 82 percent / H2; HCl / Pd/C / ethanol / 12 h / 20 °C View Scheme

: 29121-49-1
2-(4-hydroxy-3-methoxyphenyl)acetamide

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-(4-hydroxy-3-methoxyphenyl)acetamide With borane-THF In tetrahydrofuran at 0℃; for 8h; Reflux; Stage #2: With hydrogenchloride In water for 3h; Reflux;	54.2 g

: 121-33-5
vanillin

: 1477-68-5
3-Methoxytyramine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: methanol; methylamine / 2 h / 50 °C 2.1: sodium tetrahydroborate / 1,4-dioxane; ethanol / 20 °C 3.1: hydrogenchloride; zinc / ethyl acetate; water / 3 h / 50 - 70 °C 3.2: 2 h / -20 °C View Scheme
Multi-step reaction with 3 steps 1: ethylenediamine / 4 h / Reflux 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 0 - 20 °C 3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C View Scheme

: 17283-16-8
3,4-dimethylphenylacetic acid

: 1477-68-5
3-Methoxytyramine hydrochloride

: 2-(3,4-dimethylphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	100%

: 1877-73-2
3-nitro-benzeneacetic acid

: 1477-68-5
3-Methoxytyramine hydrochloride

: N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(3-nitrophenyl)acetamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	100%

: 1477-68-5
3-Methoxytyramine hydrochloride

: 581-96-4
2-naphthylacetic acid

: N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(naphthalen-2-yl)acetamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	100%

: 17078-28-3
2-[4-(dimethylamino)phenyl]acetic acid

: 1477-68-5
3-Methoxytyramine hydrochloride

: 2-[4-(dimethylamino)phenyl]-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	99%

: 1477-68-5
3-Methoxytyramine hydrochloride

: 79-22-1
methyl chloroformate

: methyl 3-methoxy-4-((methoxycarbonyl)oxy)phenethylcarbamate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;	99%

: 32315-10-9
bis(trichloromethyl) carbonate

: 1477-68-5
3-Methoxytyramine hydrochloride

: 18162-48-6
tert-butyldimethylsilyl chloride

: tert-butyl(4-(2-isocyanatoethyl)-2-methoxyphenoxy)dimethylsilane

Conditions

Conditions	Yield
Stage #1: 3-Methoxytyramine hydrochloride With 1H-imidazole In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; for 3h; Inert atmosphere; Stage #3: bis(trichloromethyl) carbonate In toluene at 20 - 100℃; for 1.5h; Inert atmosphere;	98%

...Expand

: 1477-68-5
3-Methoxytyramine hydrochloride

: 18162-48-6
tert-butyldimethylsilyl chloride

: 2-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethanamine

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 3h; Inert atmosphere;	97%

: 29973-91-9
4-benzyloxy-3-methoxyphenylacetic acid

: 1477-68-5
3-Methoxytyramine hydrochloride

: 60917-45-5
2-[4-(benzyloxy)-3-methoxyphenyl]-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	96%

: 112-80-1
cis-Octadecenoic acid

: 1477-68-5
3-Methoxytyramine hydrochloride

: 3'-O-methyl-N-oleoyl-dopamine

Conditions

Conditions	Yield
With triethanolamine; benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate In tetrahydrofuran at 20℃; for 15.25h;	92%

: 1477-68-5
3-Methoxytyramine hydrochloride

: 108-24-7
acetic anhydride

: 10211-09-3
N-acetyl-3-O-methyldopamine

Conditions

Conditions	Yield
With potassium carbonate; triethylamine In methanol; chloroform	91%
With triethylamine In dichloromethane at 20℃; for 0.5h;	87%

: 93-40-3
(3,4-Dimethoxyphenyl)acetic acid

: 1477-68-5
3-Methoxytyramine hydrochloride

: 1451411-31-6
2-(3,4-dimethoxyphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	91%

: 85589-35-1
o-methylmandelic acid

: 1477-68-5
3-Methoxytyramine hydrochloride

: 2-(2-bromophenyl)-2-hydroxy-N-(4-hydroxy-3-methoxyphenethyl)acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;	82%

: 124-38-9
carbon dioxide

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 1477-68-5
3-Methoxytyramine hydrochloride

: 391609-22-6
C19H33NO4Si

Conditions

Conditions	Yield
Stage #1: carbon dioxide; 3-Methoxytyramine hydrochloride In dichloromethane at -78℃; for 1h; Stage #2: triisopropylsilyl trifluoromethanesulfonate at -78 - 20℃;	78%
With triethylamine In dichloromethane at -78℃;	78%

...Expand

: 1477-68-5
3-Methoxytyramine hydrochloride

: 100-52-7
benzaldehyde

: 72105-97-6
6-methoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-7-ol

Conditions

Conditions	Yield
Stage #1: 3-Methoxytyramine hydrochloride; benzaldehyde With magnesium sulphate; triethylamine In methanol for 3h; Reflux; Stage #2: With trifluoroacetic acid In ethyl acetate for 1h; Reflux; Stage #3: With sodium hydrogencarbonate	74%

: 1477-68-5
3-Methoxytyramine hydrochloride

: 149-73-5
trimethyl orthoformate

: 282721-32-8
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide

Conditions

Conditions	Yield
for 2h; Heating;	71%

: 4476-28-2
(4-isopropylphenyl)acetic acid

: 1477-68-5
3-Methoxytyramine hydrochloride

: N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-[4-(propan-2-yl)phenyl]acetamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	71%

: 50-00-0
formaldehyd

: 1477-68-5
3-Methoxytyramine hydrochloride

: 1078-26-8
1,2,3,4-tetrahydro-6-methoxy-7-isoquinolinol hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride at 70℃; for 1h; Pictet-Spengler isoquinoline synthesis;	70%

: 1477-68-5
3-Methoxytyramine hydrochloride

: S-(2-naphthylmethyl)thioacetimidate hydrobromide

: N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamidine

Conditions

Conditions	Yield
With triethylamine In ethanol at 20℃; for 3h;	70%

: 1477-68-5
3-Methoxytyramine hydrochloride

: 62-31-7
dopamine hydrochloride

Conditions

Conditions	Yield
Stage #1: 3-Methoxytyramine hydrochloride With hydrogen bromide for 6h; Reflux; Stage #2: With hydrogenchloride In water	69.81%

: 1477-68-5
3-Methoxytyramine hydrochloride

: 2-(3-(dimethylamino)phenyl)acetic acid

: N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]acetamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	69%

: 64-18-6
formic acid

: 1477-68-5
3-Methoxytyramine hydrochloride

: 282721-32-8
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide

Conditions

Conditions	Yield
Stage #1: formic acid With acetic anhydride at 55℃; for 2h; Stage #2: 3-Methoxytyramine hydrochloride In tetrahydrofuran at 75℃; for 16h; Further stages.;	66%
Stage #1: formic acid With acetic anhydride at 0 - 55℃; for 2h; Stage #2: 3-Methoxytyramine hydrochloride In tetrahydrofuran at 0 - 75℃; for 18h;

: 24424-99-5
di-tert-butyl dicarbonate

: 1477-68-5
3-Methoxytyramine hydrochloride

: 23699-77-6
tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate

Conditions

Conditions	Yield
With triethylamine In chloroform at 20℃; for 24h;	59%
With sodium hydrogencarbonate; triethylamine; citric acid In water; ethyl acetate
With triethylamine In dichloromethane at 20℃; for 18h;	4.59 g

: 1477-68-5
3-Methoxytyramine hydrochloride

: 75-07-0
acetaldehyde

: 4593-97-9
N-Nor-1-methylcorypalline

Conditions

Conditions	Yield
Stage #1: 3-Methoxytyramine hydrochloride; acetaldehyde With hydrogenchloride In water at 100℃; for 24h; Pressure tube; Stage #2: With sodium hydrogencarbonate In water	55%

: 1477-68-5
3-Methoxytyramine hydrochloride

: 75-07-0
acetaldehyde

: 98321-33-6
Isosalsoline hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water at 100℃; for 24h; Sealed tube;	55%

: 1477-68-5
3-Methoxytyramine hydrochloride

: 104943-23-9
nonanoic acid N-hydroxysuccinimide ester

: N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]nonanamide

Conditions

Conditions	Yield
With triethylamine In ethyl acetate for 12h;	46%

: 50-00-0
formaldehyd

: 24424-99-5
di-tert-butyl dicarbonate

: 1477-68-5
3-Methoxytyramine hydrochloride

: tert-butyl 7-hydroxy-6-methoxy-3,4-dihydroisoquinoline-2(1H)- carboxylate

Conditions

Conditions	Yield
Stage #1: formaldehyd; 3-Methoxytyramine hydrochloride With hydrogenchloride In water at 50℃; for 6h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 17h;	41.6%

...Expand

3-O-Methyldopamine hydrochloride Specification

This chemical is called 5-(2-Aminoethyl)guaiacol hydrochloride, and its systematic name is 2-(4-hydroxy-3-methoxyphenyl)ethanaminium chloride. With the molecular formula of C₉H₁₃NO₂.ClH, its CAS registry number of this chemical is 1477-68-5. It's often used as intermediate for dopamine. Additionally, this chemcial should be stored at the temperature of -20 °C.

Other characteristics of the 5-(2-Aminoethyl)guaiacol hydrochloride can be summarised as followings: (1)ACD/LogP: 0.43; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 3; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 18.46 Å²; (7)Flash Point: 138 °C; (8)Enthalpy of Vaporization: 56.66 kJ/mol; (9)Boiling Point: 304.5 °C at 760 mmHg; (10)Vapour Pressure: 0.000484 mmHg at 25°C.

Production method of this chemical: The 5-(2-Aminoethyl)guaiacol hydrochloride could be obtained by the reactant of 4-benzyloxy-3-methoxy-b-nitro-styrene. This reaction needs the reagents of conc. aq. HCl, FeCl₃, H₂, and the catalyst of Pt black. The yield is 76 %. In addition, this reaction should be taken for 4 hours.

Uses of this chemical: The 5-(2-Aminoethyl)guaiacol hydrochloride could react with nonanoic acid 2,5-dioxo-pyrrolidin-1-yl ester, and obtain the N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]nonanamide. This reaction needs the reagent of Et₃N, and the solvent of ethyl acetate. The yield is 46 %. In addition, this reaction should be taken for 12 hours.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: [Cl-].Oc1ccc(cc1OC)CC[NH3+]
2.InChI: InChI=1/C9H13NO2.ClH/c1-12-9-6-7(4-5-10)2-3-8(9)11;/h2-3,6,11H,4-5,10H2,1H3;1H
3.InChIKey: AWRIOTVUTPLWLF-UHFFFAOYAN

Product Name

3-O-Methyldopamine hydrochloride

Synthetic route

3-O-Methyldopamine hydrochloride Specification

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