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3600-87-1

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3600-87-1 Usage

Description

2-Amino-1-(2,5-dimethoxyphenyl)ethanol, also known as Midrodine Related Compound A, is an aromatic ether that features a 1,4-dimethoxybenzene molecule substituted at position 2 by a 2-amino-1-hydroxyethyl group. It is the immediate and active metabolite of midrodine, functioning as a direct-acting sympathomimetic with selective alpha-adrenergic agonist activity. 2-Amino-1-(2,5-dimethoxyphenyl)ethanol is presented as a white powder.

Uses

Used in Pharmaceutical Industry:
2-Amino-1-(2,5-dimethoxyphenyl)ethanol is used as an active metabolite for the treatment of hypotensive states. As a direct-acting sympathomimetic with selective alpha-adrenergic agonist activity, it induces alpha-adrenergic receptor stimulation of both arterial and venous systems without direct central nervous system or cardiac effects. This makes it a valuable compound in the development of medications for specific hypotensive conditions.
Used in Metabolite Research:
In the field of metabolite research, 2-Amino-1-(2,5-dimethoxyphenyl)ethanol serves as a key compound for understanding the metabolic pathways and effects of midrodine. This knowledge can be applied to optimize drug formulations, improve pharmacokinetics, and develop new therapeutic strategies for various medical conditions.
Used in Drug Development:
2-Amino-1-(2,5-dimethoxyphenyl)ethanol is used as a starting point for the development of new drugs with improved pharmacological properties. Its unique structure and activity can be leveraged to design novel compounds with enhanced efficacy, selectivity, and safety profiles for the treatment of various diseases and disorders.

Check Digit Verification of cas no

The CAS Registry Mumber 3600-87-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,0 and 0 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 3600-87:
(6*3)+(5*6)+(4*0)+(3*0)+(2*8)+(1*7)=71
71 % 10 = 1
So 3600-87-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H15NO3/c1-13-7-3-4-10(14-2)8(5-7)9(12)6-11/h3-5,9,12H,6,11H2,1-2H3

3600-87-1 Well-known Company Product Price

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  • USP

  • (1443715)  Midodrine Related Compound A  United States Pharmacopeia (USP) Reference Standard

  • 3600-87-1

  • 1443715-40MG

  • 14,309.10CNY

  • Detail

3600-87-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Amino-1-(2,5-dimethoxyphenyl)ethanol

1.2 Other means of identification

Product number -
Other names Midodrine Related Compound A

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:3600-87-1 SDS

3600-87-1Synthetic route

1-(2,5-dimethoxyphenyl)-2-nitroethanol
14438-63-2

1-(2,5-dimethoxyphenyl)-2-nitroethanol

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at -10℃; for 2h; Solvent; Reagent/catalyst;83%
2-(2,5-dimethoxyphenyl)-2-trimethylsilyloxyacetonitrile
141367-35-3

2-(2,5-dimethoxyphenyl)-2-trimethylsilyloxyacetonitrile

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating;54%
1,2-epoxy-1-(2,5-dimethoxyphenyl)ethane
83436-65-1, 141303-39-1

1,2-epoxy-1-(2,5-dimethoxyphenyl)ethane

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
With ammonia In ethanol for 120h; Ambient temperature;
2-amino-1-<2.5-dimethoxy-phenyl>-ethanone-(1)-hydrochloride

2-amino-1-<2.5-dimethoxy-phenyl>-ethanone-(1)-hydrochloride

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
With ethanol; platinum Hydrogenation;
With water; platinum Hydrogenation;
5-<2.5-dimethoxy-phenyl>-oxazolidinone-(2)

5-<2.5-dimethoxy-phenyl>-oxazolidinone-(2)

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
With hydrogenchloride
2-amino-1-(2,5-dimethoxyphenyl)ethanone hydrochloride

2-amino-1-(2,5-dimethoxyphenyl)ethanone hydrochloride

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;
2-bromo-2',5'-dimethoxyacetophenone
1204-21-3

2-bromo-2',5'-dimethoxyacetophenone

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaBH4 / dioxane; H2O / 1 h / Ambient temperature
2: KOH / diethyl ether; H2O / 0.5 h / Heating
3: NH3 / ethanol / 120 h / Ambient temperature
View Scheme
2-Bromo-1-(2,5-dimethoxy-phenyl)-ethanol

2-Bromo-1-(2,5-dimethoxy-phenyl)-ethanol

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOH / diethyl ether; H2O / 0.5 h / Heating
2: NH3 / ethanol / 120 h / Ambient temperature
View Scheme
2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

alkaline permanganate

alkaline permanganate

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / zinc iodide / 1 h / Ambient temperature
2: 54 percent / lithium aluminum hydride / diethyl ether / 1 h / Heating
View Scheme
2-(2,5-dimethoxyphenyl)-2-hydroxyacetonitrile
56979-58-9

2-(2,5-dimethoxyphenyl)-2-hydroxyacetonitrile

desglymidodrine
3600-87-1

desglymidodrine

Conditions
ConditionsYield
With hydrogenchloride; borane In tetrahydrofuran1.5 g (52%)
BOC-glycine
4530-20-5

BOC-glycine

desglymidodrine
3600-87-1

desglymidodrine

midodrine hydrochloride

midodrine hydrochloride

Conditions
ConditionsYield
Stage #1: BOC-glycine With 1,1'-carbonyldiimidazole In ethyl acetate for 1h;
Stage #2: desglymidodrine In ethyl acetate at 20℃; for 1h;
Stage #3: With hydrogenchloride In water; ethyl acetate at 20℃; for 4.25h;
87%
desglymidodrine
3600-87-1

desglymidodrine

2-{[(tert-butoxy)carbonyl]amino}acetate ester

2-{[(tert-butoxy)carbonyl]amino}acetate ester

N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid
176851-43-7

N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid

Conditions
ConditionsYield
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In acetonitrile at 40℃; for 15h; Schlenk technique; Inert atmosphere;75%
N-(tert-butoxycarbonyl)glycine methyl ester
31954-27-5

N-(tert-butoxycarbonyl)glycine methyl ester

desglymidodrine
3600-87-1

desglymidodrine

N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid
176851-43-7

N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid

Conditions
ConditionsYield
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In acetonitrile at 40℃; for 15h; Temperature; Schlenk technique; Inert atmosphere;70%
desglymidodrine
3600-87-1

desglymidodrine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide
60681-99-4

2-chloro-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water for 4h; Ambient temperature;50%
desglymidodrine
3600-87-1

desglymidodrine

phenyl chloroformate
1885-14-9

phenyl chloroformate

5-(2,5-dimethoxyphenyl)oxazolidin-2-one
141367-36-4

5-(2,5-dimethoxyphenyl)oxazolidin-2-one

Conditions
ConditionsYield
With pyridine; sodium hydride 1.) RT, 3 h, 2.) THF, RT, 12 h; Yield given. Multistep reaction;
desglymidodrine
3600-87-1

desglymidodrine

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

A

(R)-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]-2,2,2-trifluoroacetamide

(R)-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]-2,2,2-trifluoroacetamide

B

(S)-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]-2,2,2-trifluoroacetamide

(S)-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.166667h;
desglymidodrine
3600-87-1

desglymidodrine

6-(2,5-Dimethoxy-phenyl)-morpholin-3-one
83436-68-4

6-(2,5-Dimethoxy-phenyl)-morpholin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / NaOH / CH2Cl2; H2O / 4 h / Ambient temperature
2: KOH / ethanol / 24 h / Ambient temperature
View Scheme
desglymidodrine
3600-87-1

desglymidodrine

2-(2,5-dimethoxyphenyl)morpholine
83436-71-9

2-(2,5-dimethoxyphenyl)morpholine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 50 percent / NaOH / CH2Cl2; H2O / 4 h / Ambient temperature
2: KOH / ethanol / 24 h / Ambient temperature
3: 70 percent / LiAlH4 / diethyl ether / 8 h / Heating
View Scheme
desglymidodrine
3600-87-1

desglymidodrine

C12H15(2)H2NO3
83436-76-4

C12H15(2)H2NO3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 50 percent / NaOH / CH2Cl2; H2O / 4 h / Ambient temperature
2: KOH / ethanol / 24 h / Ambient temperature
3: 65 percent / LiAlD4 / diethyl ether / 8 h / Heating
View Scheme
desglymidodrine
3600-87-1

desglymidodrine

5,5'-bis(2,5-dimethoxyphenyl)-3,3'-tetramethylenedi(oxazolidin-2-one)
141367-38-6

5,5'-bis(2,5-dimethoxyphenyl)-3,3'-tetramethylenedi(oxazolidin-2-one)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) pyridine, 2.) sodium hydride / 1.) RT, 3 h, 2.) THF, RT, 12 h
2: 77 percent / butyl lithium / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / Heating
View Scheme
desglymidodrine
3600-87-1

desglymidodrine

5,5'-bis(2,5-dimethoxyphenyl)-3,3'-hexamethylenedi(oxazolidin-2-one)
141367-37-5

5,5'-bis(2,5-dimethoxyphenyl)-3,3'-hexamethylenedi(oxazolidin-2-one)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) pyridine, 2.) sodium hydride / 1.) RT, 3 h, 2.) THF, RT, 12 h
2: 80 percent / butyl lithium / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / Heating
View Scheme
desglymidodrine
3600-87-1

desglymidodrine

N,N'-bis<2-hydroxy-2-(2,5-dimethoxyphenyl)ethyl>-tetramethylenediamine
141367-31-9

N,N'-bis<2-hydroxy-2-(2,5-dimethoxyphenyl)ethyl>-tetramethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) pyridine, 2.) sodium hydride / 1.) RT, 3 h, 2.) THF, RT, 12 h
2: 77 percent / butyl lithium / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / Heating
3: 85percent potassium hydroxide, H2O / ethanol / 12 h / Heating
View Scheme
desglymidodrine
3600-87-1

desglymidodrine

N,N'-bis<2-hydroxy-2-(2,5-dimethoxyphenyl)ethyl>-hexamethylenediamine
141381-40-0

N,N'-bis<2-hydroxy-2-(2,5-dimethoxyphenyl)ethyl>-hexamethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) pyridine, 2.) sodium hydride / 1.) RT, 3 h, 2.) THF, RT, 12 h
2: 80 percent / butyl lithium / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 3 h / Heating
3: 85percent potassium hydroxide, H2O / ethanol / 12 h / Heating
View Scheme
desglymidodrine
3600-87-1

desglymidodrine

1-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indazole
85302-16-5

1-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indazole

1-(2,5-dimethoxyphenyl)-2-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ylamino)ethanol

1-(2,5-dimethoxyphenyl)-2-(1-methyl-4,5,6,7-tetrahydro-1H-indazol-4-ylamino)ethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: titanium(IV) isopropylate; N-trimethylsilyl-pyrrolidin-2-one / 6 h / 70 °C / Sealed tube
2: N-trimethylsilyl-pyrrolidin-2-one; sodium tetrahydroborate / ethanol / 20 °C
View Scheme
desglymidodrine
3600-87-1

desglymidodrine

1-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indazole
85302-16-5

1-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indazole

C18H23N3O3

C18H23N3O3

Conditions
ConditionsYield
With titanium(IV) isopropylate; N-trimethylsilyl-pyrrolidin-2-one at 70℃; for 6h; Sealed tube;

3600-87-1Relevant articles and documents

Preparation method of 1-(2,5-dimethoxy phenyl)-2-aminoethanol

-

Paragraph 0032; 0035; 0036, (2017/03/08)

The invention provides a preparation method of hydrochloric acid midodrine intermediate 1-(2,5-dimethoxy phenyl)-2-aminoethanol, comprising the steps of adopting 2,5-dimethoxy benzaldehyde as the raw material to condense with nitromethane under the effect of alkali to obtain 1-(2,5-dimethoxy phenyl)-2-nitroethanol, reducing 1-(2,5-dimethoxy phenyl)-2-nitroethanol with a boron reductant to obtain 1-(2,5-dimethoxy phenyl)-2-aminoethanol. The preparation method of 1-(2,5-dimethoxy phenyl)-2-aminoethanol has the advantages of being mild in reaction conditions, simple in the operation process, high in yield, environment-friendly and low in production cost, and is applicable to industrial production.

Synthesis of midodrine HCI from a novel intermediate 1-(2′,5′-dimethoxyphenyl)-2-azidoethanone

-

, (2008/06/13)

Midodrine hydrochloride, ±1-(2′,5′-dimethoxyphenyl)-2-glycineamido-ethanol-(1)-HCl, is prepared from a novel intermediate, 1-(2′,5′-dimethoxyphenyl)-2-azidoethanone.

Synthesis and adrenergic properties of new duplicated analogs of methoxamine

Perez,Rosell,Mauleon,Carganico

, p. 1155 - 1166 (2007/10/02)

New duplicated analogs of the α1-selective agonist methoxamine and of its cyclic derivative 5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthylamine have been synthesized and tested for their adrenergic properties. All the compounds prepared, presenting a polymethylene spacer of varying length between two units of the active structure, turned out to be completely devoid of any α-stimulating activity. Surprisingly, some of them showed a marked β-adrenergic agonistic effect, being the most interesting compound active at nanomolar concentration.

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