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249289-07-4

Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate, commonly known as Octodrine, is a chemical compound belonging to the acylphenethylamines class. It is recognized for its stimulant and thermogenic properties, which are utilized in dietary supplements and weight loss products to enhance energy levels, mental alertness, and focus. Structurally, Octodrine shares similarities with other stimulants like ephedrine and amphetamine. Despite its benefits, its use has been a subject of controversy due to potential side effects and regulatory issues in some regions. It is crucial to use Octodrine cautiously and under medical supervision, considering the potential risks and the absence of extensive safety data.

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  • 249289-07-4 Structure

  • Basic information

    1. Product Name: Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate
    2. Synonyms:
    3. CAS NO:249289-07-4
    4. Molecular Formula: C25H37NO6
    5. Molecular Weight: 447.572
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 249289-07-4.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate(CAS DataBase Reference)
    10. NIST Chemistry Reference: Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate(249289-07-4)
    11. EPA Substance Registry System: Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate(249289-07-4)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 249289-07-4(Hazardous Substances Data)

249289-07-4 Usage

Uses

Used in Dietary Supplements:
Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate is used as a stimulant and thermogenic agent in dietary supplements for its ability to increase energy levels, mental alertness, and focus, aiding in weight management and performance enhancement.
Used in Weight Loss Products:
In the weight loss industry, Diethyl 2-(4-octanoylphenethyl)-2-acetamidomalonate is utilized as a key ingredient to boost metabolism and stimulate fat oxidation, contributing to the reduction of body weight and improved body composition.

Check Digit Verification of cas no

The CAS Registry Mumber 249289-07-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,9,2,8 and 9 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 249289-07:
(8*2)+(7*4)+(6*9)+(5*2)+(4*8)+(3*9)+(2*0)+(1*7)=174
174 % 10 = 4
So 249289-07-4 is a valid CAS Registry Number.

249289-07-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

1.2 Other means of identification

Product number -
Other names -

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:249289-07-4 SDS

249289-07-4Synthetic route

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

2-acetamido-1,3-diacetoxy-2-(2-phenylethyl)propane
162359-95-7

2-acetamido-1,3-diacetoxy-2-(2-phenylethyl)propane

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

Conditions
ConditionsYield
With aluminum (III) chloride; 1,2-dichloro-ethane at 0 - 20℃; for 18.5h; Friedel-Crafts Acylation;81%
With aluminium trichloride In 1,2-dichloro-ethane at 20℃; for 12h; Friedel-Crafts acylation;64%
Stage #1: n-octanoic acid chloride With aluminum (III) chloride In 1,2-dichloro-ethane at -15 - -10℃; for 1.5h; Inert atmosphere;
Stage #2: 2-acetamido-1,3-diacetoxy-2-(2-phenylethyl)propane In 1,2-dichloro-ethane at -15 - 20℃; for 19h; Inert atmosphere;
2-acetylamino-2-phenylethylmalonic acid diethyl ester
5463-92-3

2-acetylamino-2-phenylethylmalonic acid diethyl ester

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C
2: pyridine / 16 h / 20 °C
3: 64 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol / 18 h / 0 - 20 °C
2: pyridine / 15 h / 20 °C
3: aluminum (III) chloride; 1,2-dichloro-ethane / 18.5 h / 0 - 20 °C
View Scheme
1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C
1.2: ethanol / 3 h / 65 °C
2.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C
3.1: pyridine / 16 h / 20 °C
4.1: 64 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: caesium carbonate / dimethyl sulfoxide / 6 h / 65 °C
2: sodium tetrahydroborate / methanol / 18 h / 0 - 20 °C
3: pyridine / 15 h / 20 °C
4: aluminum (III) chloride; 1,2-dichloro-ethane / 18.5 h / 0 - 20 °C
View Scheme
2-acetylaminomalonic acid diethyl ester
1068-90-2

2-acetylaminomalonic acid diethyl ester

(+-)-<2-bromo-ethyl>-phenyl-phosphinic acid ethyl ester

(+-)-<2-bromo-ethyl>-phenyl-phosphinic acid ethyl ester

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C
1.2: ethanol / 3 h / 65 °C
2.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C
3.1: pyridine / 16 h / 20 °C
4.1: 64 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / 20 °C
View Scheme
N-(1-hydroxy-2-(hydroxymethyl)-4-phenylbut-2-yl)acetamide

N-(1-hydroxy-2-(hydroxymethyl)-4-phenylbut-2-yl)acetamide

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 16 h / 20 °C
2: 64 percent / AlCl3 / 1,2-dichloro-ethane / 12 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: pyridine / 15 h / 20 °C
2: aluminum (III) chloride; 1,2-dichloro-ethane / 18.5 h / 0 - 20 °C
View Scheme
2-acetylaminomalonic acid diethyl ester
1068-90-2

2-acetylaminomalonic acid diethyl ester

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: caesium carbonate / dimethyl sulfoxide / 6 h / 65 °C
2: sodium tetrahydroborate / methanol / 18 h / 0 - 20 °C
3: pyridine / 15 h / 20 °C
4: aluminum (III) chloride; 1,2-dichloro-ethane / 18.5 h / 0 - 20 °C
View Scheme
2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate
162358-09-0

2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 2h;95%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃;6.3 g
2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

1-[4-(3-amino-4-hydroxy-3-hydroxymethyl-butyl)-phenyl]-octan-1-one
249289-08-5

1-[4-(3-amino-4-hydroxy-3-hydroxymethyl-butyl)-phenyl]-octan-1-one

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; methanol for 3h; Hydrolysis; Heating;51%
2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

2-amino-2-{2-[4-(1-hydroxy-octyl)-phenyl]-ethyl}-propane-1,3-diol

2-amino-2-{2-[4-(1-hydroxy-octyl)-phenyl]-ethyl}-propane-1,3-diol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / 2 N aq. LiOH / methanol; tetrahydrofuran / 3 h / Heating
2: 66 percent / NaBH4 / ethanol / 3 h / 20 °C
View Scheme
2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate
249289-07-4

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate

2-amino-2-[2-[4-(1-hydroxyiminooctyl)phenyl]ethyl]propane-1,3-diol

2-amino-2-[2-[4-(1-hydroxyiminooctyl)phenyl]ethyl]propane-1,3-diol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / 2 N aq. LiOH / methanol; tetrahydrofuran / 3 h / Heating
2: 25 percent / H2NOH*HCl / ethanol; CHCl3 / 1.5 h / Heating
View Scheme

249289-07-4Relevant articles and documents

PROCESS FOR PREPARATION OF HIGHLY PURE FINGOLIMOD HYDROCHLORIDE

-

Page/Page column 15, (2020/08/28)

The present invention provides process for preparation of highly pure Fingolimod hydrochloride (I) having purity of greater than 99.8% (by HPLC),(I) without involving the use of column chromatographic purification in the entire process. Fingolimod hydrochloride (I) obtained by the process of present invention may be useful as active pharmaceutical ingredient in pharmaceutical compositions for the treatment of autoimmune related disorder including multiple sclerosis.

Practical synthesis of fingolimod from diethyl acetamidomalonate

Kandagatla, Bhaskar,Prasada Raju, Vetukuri Venkata Naga Kali Vara,Kumar, Narayana Sravan,Reddy, Ganta Madhusudhan,Srinivas, Katkam,Iqbal, Javed,Bandichhor, Rakeshwar,Oruganti, Srinivas

, p. 9687 - 9689 (2013/09/02)

A facile six-step synthesis of fingolimod, starting from readily available and inexpensive starting material diethyl acetamidomalonate, in very good yield is demonstrated.

Synthesis and immunosuppressive activity of 2-substituted 2- aminopropane-1,3-diols and 2-aminoethanols

Kiuchi, Masatoshi,Adachi, Kunitomo,Kohara, Toshiyuki,Minoguchi, Masanori,Hanano, Tokushi,Aoki, Yoshiyuki,Mishina, Tadashi,Arita, Masafumi,Nakao, Noriyoshi,Ohtsuki, Makio,Hoshino, Yukio,Teshima, Koji,Chiba, Kenji,Sasaki, Shigeo,Fujita, Tetsuro

, p. 2946 - 2961 (2007/10/03)

A series of 2-substituted 2-aminopropane-1,3-diols was synthesized and evaluated for their lymphocyte-decreasing effect and immunosuppressive effect on rat skin allograft. A phenyl ring was introduced into the alkyl chain of the lead compound 3, which is an immunosuppressive agent structurally simplified from myriocin (1, ISP-I) via compound 2. The potency of the various compounds was dependent upon the position of the phenyl ring within the alkyl side chain. The most suitable length between the quaternary carbon atom and the phenyl ring was two carbon atoms. 2-Substituted 2-aminoethanols were successively synthesized and evaluated for their T-cell-decreasing effect and immunosuppressive effect using a popliteal lymph node gain assay in rats. The absolute configuration at the quaternary carbon affected the activity, and the (pro-S)-hydroxymethyl group of compound 6 was essential for potent immunosuppressive activity. Favorable substituents for the (pro-R)- hydroxymethyl group of 6 were hydroxyalkyl (hydroxyethyl and hydroxypropyl) or lower alkyl (methyl and ethyl) groups. 2-Amino-2-[2-(4- octylphenyl)ethyl]propane-1,3-diol hydrochloride (6, FTY720) was found to possess considerable activity and is expected to be useful as an immunosuppressive drug for organ transplantation.

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