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(2R)-3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide is a complex organic compound with a unique molecular structure. It is characterized by its chiral center at the 2nd carbon (R-configuration), a bromine atom at the 3rd carbon, a hydroxyl group at the 2nd carbon, and a methyl group at the same position. The amide group is connected to a substituted phenyl ring, which includes a nitro group and a trifluoromethyl group. (2R)-3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide serves as a crucial intermediate in the synthesis of pharmaceuticals.

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  • (2R)-3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

    Cas No: 206193-18-2

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  • 206193-18-2 Structure
  • Basic information

    1. Product Name: (2R)-3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
    2. Synonyms: (2R)-3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide;(R)-3-bromo-2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide
    3. CAS NO:206193-18-2
    4. Molecular Formula: C11H10BrF3N2O4
    5. Molecular Weight: 371.108
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 206193-18-2.mol
  • Chemical Properties

    1. Melting Point: 100-101.5 °C
    2. Boiling Point: 491.7 °C at 760 mmHg
    3. Flash Point: 251.2 °C
    4. Appearance: /
    5. Density: 1.753
    6. Refractive Index: N/A
    7. Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
    8. Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
    9. PKA: 11.68±0.29(Predicted)
    10. CAS DataBase Reference: (2R)-3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide(CAS DataBase Reference)
    11. NIST Chemistry Reference: (2R)-3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide(206193-18-2)
    12. EPA Substance Registry System: (2R)-3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide(206193-18-2)
  • 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: 206193-18-2(Hazardous Substances Data)

206193-18-2 Usage

Uses

(2R)-3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide is used as an intermediate in the pharmaceutical industry for the synthesis of 4-Desacetamido-4-fluoro Andarine (D289530), a Selective Androgen Receptor Modulator (SARM). The application reason for this compound is its role in the development of a potential treatment for androgen-related diseases such as muscle wasting and osteoporosis. By modulating the androgen receptor, this SARM can help improve muscle mass and bone density, offering a therapeutic option for patients suffering from these conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 206193-18-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,6,1,9 and 3 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 206193-18:
(8*2)+(7*0)+(6*6)+(5*1)+(4*9)+(3*3)+(2*1)+(1*8)=112
112 % 10 = 2
So 206193-18-2 is a valid CAS Registry Number.

206193-18-2SDS

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 3-Bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]p ropanamide

1.2 Other means of identification

Product number -
Other names (R)-3-bromo-1,2-propanediol

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:206193-18-2 SDS

206193-18-2Downstream Products

206193-18-2Relevant articles and documents

SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF

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Paragraph 00243; 00369-00372, (2021/09/04)

This invention is directed to selective androgen receptor degrader (SARD) compounds including heterocyclic rings and pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, triple negative breast cancer, other cancers expressing the androgen receptor, androgenic alopecia or other hyperandrogenic dermal diseases, Kennedy's disease, amyotrophic lateral sclerosis (ALS), abdominal aortic aneurysm (AAA), and uterine fibroids, and to methods for reducing the levels of androgen receptor-full length (AR-FL) including pathogenic or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.

PYRAZOLYLPROPANAMIDE COMPOUNDS AND USES THEREOF FOR TREATMENT OF PROSTATE CANCER

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Paragraph 00291-00294; 00192, (2021/10/11)

This invention relates to pyrazolylpropanamide compounds and uses thereof for treatment of prostate cancer, advanced prostate cancer, refractory prostate cancer, AR overexpressing prostate cancer, castration-resistant prostate cancer, castration-sensitive

Pyrazol-1-yl-propanamides as SARD and Pan-Antagonists for the Treatment of Enzalutamide-Resistant Prostate Cancer

He, Yali,Hwang, Dong-Jin,Ponnusamy, Suriyan,Thiyagarajan, Thirumagal,Mohler, Michael L.,Narayanan, Ramesh,Miller, Duane D.

, p. 12642 - 12665 (2020/11/13)

We report herein the design, synthesis, and pharmacological characterization of a library of novel aryl pyrazol-1-yl-propanamides as selective androgen receptor degraders (SARDs) and pan-Antagonists that exert broad-scope AR antagonism. Pharmacological ev

Synthetic method of alpha-hydroxypropanamide derivatives with optical activity

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Paragraph 0036; 0037, (2019/06/05)

The invention discloses a synthetic method of alpha-hydroxypropanamide derivatives with optical activity and belongs to the field of organic synthesis. Proline taken as a chiral auxiliary, as well asmethacryloyl chloride, is subjected to acylation, bromination and chiral auxiliary removal, a product and 4-cyano-3-trifluoromethylaniline are subjected to nucleophilic substitution, and 3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-trifluoromethyl)phenyl]propanamide is obtained and subjected to nucleophilic substitution with 4-cyanophenol, and the compound 3-(4-cyanophenoxy)-N-[4-cyano-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. 3-bromo-2-hydroxy-2-methyl propionic acid and 4-nitro-3-trifluoromethylaniline are subjected to aminolysis, a product is subjected to nucleophilic substitution with paracetamol, and the compound 3-(4-acetoxyphenoxy)-N-[4-nitro-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. The efficient synthetic method of the alpha-hydroxypropanamide derivatives with optical activity is provided.

METHODS OF TREATING UROLOGICAL DISORDERS USING SARMs

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Paragraph 0422-0423, (2016/05/10)

The present invention is directed to methods of treating, preventing, suppressing and/or inhibiting urological disorders such as urinary incontinence including stress urinary incontinence and pelvic-floor disorders by administering a SARM compound of the invention.

Facile radiosynthesis of new carbon-11-labeled propanamide derivatives as selective androgen receptor modulator (SARM) radioligands for prostate cancer imaging

Gao, Mingzhang,Wang, Min,Miller, Kathy D.,Zheng, Qi-Huang

experimental part, p. 1505 - 1512 (2011/11/06)

The androgen receptor (AR) is an attractive target for the treatment and molecular imaging of prostate cancer. New carbon-11-labeled propanamide derivatives were first designed and synthesized as selective androgen receptor modulator (SARM) radioligands for prostate cancer imaging using the biomedical imaging technique positron emission tomography (PET). The target tracers, (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(2-[11C] methoxyphenoxy)-2-methylpropanamide ([11C]8a), (S)-2-hydroxy-3-(2- [11C]methoxyphenoxy)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl) propanamide ([11C]8e), (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2- hydroxy-3-(4-[11C]methoxyphenoxy)-2-methylpropanamide ([ 11C]8c) and (S)-2-hydroxy-3-(4-[11C]methoxyphenoxy)-2- methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide ([11C]8g), were prepared by O-[11C]methylation of their corresponding precursors, (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(2- hydroxyphenoxy)-2-methylpropanamide (9a), (S)-2-hydroxy-3-(2-hydroxyphenoxy)-2- methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide (9b), (S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-3-(4-hydroxyphenoxy) -2-methylpropanamide (9c) and (S)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methyl-N-(4- nitro-3-(trifluoromethyl)phenyl)propanamide (9d), with [11C]CH 3OTf under basic conditions and isolated by a simplified C-18 solid-phase extraction (SPE) method in 55 ± 5% (n = 5) radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 277.5 ± 92.5 GBq/μmol (n = 5).

Compositions comprising 5-alpha reductase inhibitors, and SARMs and methods of use thereof

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Page/Page column 23, (2010/11/24)

This invention provides a composition comprising a 5-alpha reductase inhibitor and a class of androgen receptor targeting agents (ARTA), which are selective androgen receptor modulators (SARM). The compositions of this invention are useful for, inter-alia, a) male contraception; b) treatment of a variety of hormone-related conditions, for example conditions associated with Androgen Decline in Aging Male (ADAM), such as fatigue, depression, decreased libido, sexual dysfunction, erectile dysfunction, hypogonadism, osteoporosis, hair loss, anemia, obesity, sarcopenia, osteopenia, osteoporosis, benign prostate hyperplasia, alterations in mood and cognition and prostate cancer; c) treatment of conditions associated with Androgen Decline in Female (ADIF), such as sexual dysfunction, decreased sexual libido, hypogonadism, sarcopenia, osteopenia, osteoporosis, alterations in cognition and mood, depression, anemia, hair loss, obesity, endometriosis, breast cancer, uterine cancer and ovarian cancer; d) treatment of polycystic ovarian disease; e) treatment and/or prevention of acute and/or chronic muscular wasting conditions; f) preventing and/or treating dry eye conditions; g) oral androgen replacement therapy; h) decreasing the incidence of, halting or causing a regression of prostate cancer; and/or i) inducing apoptosis in a cancer cell.

PRODRUGS OF SELECTIVE ANDROGEN RECEPTOR MODULATORS AND METHODS OF USE THEREOF

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Page/Page column 52-53, (2008/06/13)

The present invention provides prodrugs of selective androgen receptor modulators (SARMs), and their use in treating or reducing the incidence of osteoporosis, a variety of hormone-related conditions, conditions associated with Androgen Decline in Aging Male (ADAM); conditions associated with Androgen Decline in Female (ADIF), and muscular wasting conditions, obesity, dry eye conditions, and prostate cancer. The prodrugs are also useful in oral androgen replacement therapy and male contraception.

Haloacetamide and azide substituted compounds and methods of use thereof

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Page 24-25; 27, (2010/02/11)

The present invention relates to a novel class of anti-cancer compounds, which contain a haloacetamide or azide moiety and are, in one embodiment, alkylating agents. These agents, either alone or in a composition, are useful for treating cancer, preventin

HALOACETAMIDE AND AZIDE SUBSTITUTED COMPOUNDS AND METHODS OF USE THEREOF

-

Page/Page column 121-122; 129-130, (2008/06/13)

The present invention relates to a novel class of anti-cancer compounds, which contain a haloacetamide or azide moiety and are, in one embodiment, alkylating agents. These agents, either alone or in a composition, are useful for treating cancer, preventin

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