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499-61-6

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499-61-6 Usage

Preparation

Preparation by reaction of 35% aqueous ammonia with 3,4-dihydroxy-a-chloroacetophenone in methanol or in ethanol.

Check Digit Verification of cas no

The CAS Registry Mumber 499-61-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 9 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 499-61:
(5*4)+(4*9)+(3*9)+(2*6)+(1*1)=96
96 % 10 = 6
So 499-61-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO3.ClH/c9-4-8(12)5-1-2-6(10)7(11)3-5;/h1-3,10-11H,4,9H2;1H

499-61-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-amino-1-(3,4-dihydroxyphenyl)ethanone

1.2 Other means of identification

Product number -
Other names EINECS 207-883-3

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:499-61-6 SDS

499-61-6Synthetic route

C14H19N4O3(1+)*Cl(1-)

C14H19N4O3(1+)*Cl(1-)

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
Stage #1: C14H19N4O3(1+)*Cl(1-) With hydrogenchloride In methanol; water at 60 - 65℃; for 3 - 4h;
Stage #2: With hydrogenchloride In isopropyl alcohol
96.3%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

glycine
56-40-6

glycine

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
Stage #1: benzene-1,2-diol With zinc(II) chloride In 1,2-dichloro-ethane at 10 - 15℃; for 0.5h;
Stage #2: glycine In 1,2-dichloro-ethane at 70℃; for 20h; Time;
78.8%
Stage #1: benzene-1,2-diol With zinc(II) chloride In 1,2-dichloro-ethane at 10 - 70℃; for 0.5h;
Stage #2: glycine In 1,2-dichloro-ethane for 20h; Concentration; Reflux;
76.82%
2-chloro-3',4'-dihydroxyacetophenone
99-40-1

2-chloro-3',4'-dihydroxyacetophenone

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With ammonium hydroxide
Multi-step reaction with 2 steps
1: H2O; NaN3
2: palladium; aq.-ethanolic HCl / Hydrogenation
View Scheme
N-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)benzamide
70216-33-0

N-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)benzamide

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With mineral acid
2-dibenzylamino-1-(3,4-dihydroxy-phenyl)-ethanone
13062-58-3

2-dibenzylamino-1-(3,4-dihydroxy-phenyl)-ethanone

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With water; palladium under 7355.08 Torr; Hydrogenation;
2-azido-1-(3,4-dihydroxy-phenyl)-ethanone
165947-83-1

2-azido-1-(3,4-dihydroxy-phenyl)-ethanone

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With hydrogenchloride; palladium Hydrogenation;
2,5-bis-(3,4-dimethoxy-phenyl)-pyrazine
187101-62-8

2,5-bis-(3,4-dimethoxy-phenyl)-pyrazine

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With hydrogen iodide; acetic acid
2-amino-1-(3,4-dimethoxy-phenyl)-ethanone
40869-57-6

2-amino-1-(3,4-dimethoxy-phenyl)-ethanone

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With hydrogenchloride
1-(3,4-dihydroxy-phenyl)-2-nitro-ethanone

1-(3,4-dihydroxy-phenyl)-2-nitro-ethanone

A

Norepinephrine
138-65-8

Norepinephrine

B

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
bei der Reduktion;
1-(3,4-dihydroxy-phenyl)-2-nitro-ethanone

1-(3,4-dihydroxy-phenyl)-2-nitro-ethanone

arterenone
499-61-6

arterenone

N-(3,4-diethoxy-phenacyl)-benzamide

N-(3,4-diethoxy-phenacyl)-benzamide

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With mineral acid
2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin
76734-99-1

2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin

A

dopamine
51-61-6

dopamine

B

arterenone
499-61-6

arterenone

C

2-hydroxy-3′,4′-dihydroxyacetophenone
29477-54-1

2-hydroxy-3′,4′-dihydroxyacetophenone

Conditions
ConditionsYield
With hydrogenchloride at 110℃; for 3h;
hydrogenchloride
7647-01-0

hydrogenchloride

(3,4-Dimethoxyphenyl)-(phthalimidomethyl)-keton
111114-09-1

(3,4-Dimethoxyphenyl)-(phthalimidomethyl)-keton

acetic acid
64-19-7

acetic acid

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
at 150℃;
2,5-bis-(3,4-dimethoxy-phenyl)-pyrazine
187101-62-8

2,5-bis-(3,4-dimethoxy-phenyl)-pyrazine

hydrogen iodide
10034-85-2

hydrogen iodide

acetic acid
64-19-7

acetic acid

arterenone
499-61-6

arterenone

2-chloro-3',4'-dihydroxyacetophenone
99-40-1

2-chloro-3',4'-dihydroxyacetophenone

ammonium hydroxide

ammonium hydroxide

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
bei laengerem Schuetteln mit der Ammoniakloesung;
N-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)benzamide
70216-33-0

N-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)benzamide

diluted mineral acid

diluted mineral acid

arterenone
499-61-6

arterenone

ω-phthalimido-3.4-dimethoxy-acetophenone

ω-phthalimido-3.4-dimethoxy-acetophenone

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With hydrogenchloride; acetic acid at 150℃; im Rohr;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

ω-iodo-3.4-diacetoxy-acetophenone

ω-iodo-3.4-diacetoxy-acetophenone

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
Einw. von alkoh. Salzsaeure auf das Additionsprodukt bei 20grad;
2-chloro-1-<3-hydroxy-3(or 4)-benzoyloxy-phenyl>-ethanone-(1)

2-chloro-1-<3-hydroxy-3(or 4)-benzoyloxy-phenyl>-ethanone-(1)

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With ammonium hydroxide
2-chloro-1-<4-hydroxy-3(or 4)-benzoyloxy-phenyl>-ethanone-(1)

2-chloro-1-<4-hydroxy-3(or 4)-benzoyloxy-phenyl>-ethanone-(1)

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With ammonium hydroxide
N-acetyldopamine
2494-12-4

N-acetyldopamine

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Locusta migratoria, Na2EDTA, O2 / Ambient temperature; 0.2M Na-acetate buffer, pH 5.5, overnight incubation
2: 6M HCl / 3 h / 110 °C
View Scheme
2-chloro-3′,4′-dihydroxyacetophenone
56961-48-9

2-chloro-3′,4′-dihydroxyacetophenone

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol
2: palladium; water / 7355.08 Torr / Hydrogenation
View Scheme
norepinephrine
51-41-2

norepinephrine

arterenone
499-61-6

arterenone

Conditions
ConditionsYield
With (R)-epinephrine dehydrogenase; NADH In aq. phosphate buffer at 45℃; pH=6; Enzymatic reaction;
isopropyl chloride
75-29-6

isopropyl chloride

arterenone
499-61-6

arterenone

Isoproterenone hydrochloride
16899-81-3

Isoproterenone hydrochloride

Conditions
ConditionsYield
Stage #1: isopropyl chloride With triethylamine In ethanol at 10 - 15℃;
Stage #2: arterenone In ethanol at 40℃; for 10h; Concentration;
84.3%
With triethylamine In ethanol at 10 - 40℃; for 10h; Temperature;84.3%
arterenone
499-61-6

arterenone

norepinephrine
51-41-2

norepinephrine

Conditions
ConditionsYield
Stage #1: arterenone With (-)-diisopinocampheylboron chloride In tert-butyl methyl ether at -25 - -20℃; for 3h; Inert atmosphere;
Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 25℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;
70.3%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

arterenone
499-61-6

arterenone

α-(t-butyloxycarbonyl)amino-3,4-dihydroxyacetophenone
165947-25-1

α-(t-butyloxycarbonyl)amino-3,4-dihydroxyacetophenone

Conditions
ConditionsYield
dmap In N-methyl-acetamide; ethyl acetate28%
arterenone
499-61-6

arterenone

Norepinephrine
138-65-8

Norepinephrine

Conditions
ConditionsYield
With sodium amalgam
With alkaline water; nickel Hydrogenation;
arterenone
499-61-6

arterenone

3,6-bis-(3,4-dihydroxy-phenyl)-2,5-dihydro-pyrazine

3,6-bis-(3,4-dihydroxy-phenyl)-2,5-dihydro-pyrazine

Conditions
ConditionsYield
With ammonium hydroxide
arterenone
499-61-6

arterenone

2-amino-1-(3,4-dihydroxy-phenyl)-ethanone-phenylhydrazone

2-amino-1-(3,4-dihydroxy-phenyl)-ethanone-phenylhydrazone

arterenone
499-61-6

arterenone

acetic anhydride
108-24-7

acetic anhydride

2-oxo-N-acetyldopamine
14522-07-7

2-oxo-N-acetyldopamine

arterenone
499-61-6

arterenone

sodium amalgam

sodium amalgam

Norepinephrine
138-65-8

Norepinephrine

arterenone
499-61-6

arterenone

hydroxylamine
7803-49-8

hydroxylamine

acetic acid
64-19-7

acetic acid

3.4-dioxy-phenylglyoxime

3.4-dioxy-phenylglyoxime

499-61-6Relevant articles and documents

Hydrochloric acid isopropyl adrenergic preparation method

-

Paragraph 0014-0016; 0021-0023; 0028-0030, (2019/03/31)

The invention discloses a hydrochloric acid isopropyl adrenergic preparation method, comprises the following steps: through the catechol with glycine in the role of the catalyst [...] reaction to obtain 2 - amino - 1 - (3, 4 - dihydroxy-phenyl) - ethyl ketone; through the 2 - amino - 1 - (3, 4 - dihydroxy-phenyl) - ethanone with 2 - chloro propane reaction preparation isopropyl adrenergic ketone bodies hydrochloride; through the isopropyl adrenergic ketone bodies hydrochloride in the catalytic reduction of the palladium-carbon under the action of hydrochloric acid isopropyl adrenergic. Selects the glycin, zinc chloride the reaction system, which not only reduces the costs of environmental protection, also improves the reaction yield, is favorable for industrial production; mild reaction conditions, less catalyst levels, the process is simple; it has obvious economic and environmental benefits.

Purification and characterization of a novel carbonyl reductase involved in oxidoreduction of aromatic β-amino ketones/alcohols

He, Shengbin,Wang, Zhenshou,Zou, Yang,Chen, Shaofang,Xu, Xiaoping

, p. 1107 - 1112 (2014/06/10)

Aromatic β-amino ketones/alcohols such as adrenalone play an important role in some stereoselective synthesis of pharmaceuticals. Unfortunately, the transformation of aromatic β-amino ketones to their chiral alcohols has been carried out chemically as no corresponding biocatalyst has been available. Here, a novel carbonyl reductase responsible for the reduction of adrenalone to (R)-(-)-epinephrine was identified and characterized from Kocuria rhizophila. This enzyme was purified to homogeneity by ammonium sulfate precipitation followed by ion-exchange column chromatography, hydrophobic chromatography and gel chromatography. The purified enzyme yielded pure (R)-enantiomer product with high activity and utilized NADH as the cofactor. The enzyme had special significance by showing selectivity for many aromatic β-amino ketones/alcohols such as 2-amino-acetophenone, 2-amino-4′- hydroxyacetophenone, isoproterenol and ephedrine. The maximum reaction rate (Vmax) and apparent Michaelis-Menten constant (Km) for adrenalone and NADH were 14.62 μmol/(min mg) protein and 0.189 mM, 11.66 μmol/(min mg) protein and 0.204 mM respectively. These properties ensure the enzyme a promising future for industrial application as a replacement of chemical synthesis of aromatic β-amino chiral alcohols.

Studies of the sclerotization of insect cuticle. The structure of a dimeric product formed by incubation of N-acetyldopamine with locust cuticle

Andersen,Jacobsen,Roepstorff

, p. 3249 - 3252 (2007/10/02)

-

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