2-Methyl-ethinylestradiol

Base Information

• Chemical Name: 2-Methyl-ethinylestradiol
• CAS No.: 3240-39-9
• Molecular Formula: C₂₁H₂₆O₂
• Molecular Weight: 310.436
• UNII: YD0T6YEK7D
• ChEMBL ID: CHEMBL1627958
• DSSTox Substance ID: DTXSID40186115
• Wikidata: Q27294465
• Mol file: 3240-39-9.mol

Synonyms:2-Methyl-ethinylestradiol;3240-39-9;2-Methyl Ethynyl Estradiol;2-Methyl-ethinyl estradiol;Ethinyl Estradiol Impurity M;YD0T6YEK7D;NIOSH/RC8945100;(8R,9S,13S,14S,17R)-17-ethynyl-2,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol;RC89451000;17-alpha-Ethinyl-2-methyl-8-alpha-estradiol;17-alpha-Ethinyl-2-methyl-8-alpha-E(sub 2);17-alpha-Ethinyl-2-methyl-8-alpha-estra-1,3,5(10)-triene-3,17-beta-diol;19-Nor-8-alpha,17-alpha-pregna-1,3,5(10)-trien-20-yne-3,17-diol, 2-methyl-;2-Methyl-19-nor-8-alpha,17-alpha-pregna-1,3,5(10)-trien-20-yne-3,17-diol;UNII-YD0T6YEK7D;2-Methyl Ethinyl Estradiol;Ethinylestradiol impurity M [EP];CHEMBL1627958;DTXSID40186115;2-Methyl-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yne-3,17-diol;19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol, 2-methyl-, (17alpha)-;ETHINYLESTRADIOL IMPURITY M [EP IMPURITY];Q27294465;19-NORPREGNA-1,3,5(10)-TRIEN-20-YNE-3,17-DIOL, 2-METHYL-, (17.ALPHA.)-;2-METHYL-19-NOR-17.ALPHA.-PREGNA-1,3,5(10)-TRIEN-20-YNE-3,17-DIOL

Chemical Property of 2-Methyl-ethinylestradiol

Chemical Property:

• Boiling Point: 463.3±45.0 °C(Predicted)
• PKA: 10.61±0.60(Predicted)
• PSA: 40.46000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 3.92100
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 310.193280068
• Heavy Atom Count: 23
• Complexity: 533

Purity/Quality:

99% ^*data from raw suppliers

2-MethylEthynylEstradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(CCC3C2CCC4(C3CCC4(C#C)O)C)C=C1O
• Isomeric SMILES: CC1=CC2=C(CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)C=C1O
• Uses: 2-Methylethynylestradiol is a 17α-ethynyl steroid. 2-Methylethynylestradiol is an impurity of Ethynylestradiol (E685100). 2-Methylethynylestradiol (Ethinylestradiol EP Impurity M) is a 17α-ethynyl steroid. 2-Methylethynylestradiol is an impurity of Ethynylestradiol (E685100).

Technology Process of 2-Methyl-ethinylestradiol

There total 5 articles about 2-Methyl-ethinylestradiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

8-Epiestradiol (517-04-4) → 17α-ethinyl-2-methyl-8α-estra-1,3,5(10)-triene-3,17β-diol (3240-39-9)

Guidance literature:

Multi-step reaction with 5 steps

1: benzene; ethanol / 18 h / Heating

2: 1) MeI, 2) NaBH₄ / 1) ether, 12 h, r.t., 2) EtOH, reflux, 7 h

3: Pb(OAc)2 / dimethylformamide / 50 °C

4: Jones' reagent / acetone / 0 °C

5: 1.6M BuLi / tetrahydrofuran; hexane / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; jones' reagent; lead acetate; methyl iodide; In tetrahydrofuran; ethanol; hexane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/0039-128X(82)90031-9

Reference yield:

2-methyl-8α-estra-1,3,5(10)-triene-3,17β-diol (85440-31-9) → 17α-ethinyl-2-methyl-8α-estra-1,3,5(10)-triene-3,17β-diol (3240-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Pb(OAc)2 / dimethylformamide / 50 °C

2: Jones' reagent / acetone / 0 °C

3: 1.6M BuLi / tetrahydrofuran; hexane / Ambient temperature

With n-butyllithium; jones' reagent; lead acetate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0039-128X(82)90031-9

Reference yield:

(8S,9S,13S,14S,17S)-2-Dimethylaminomethyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol → 17α-ethinyl-2-methyl-8α-estra-1,3,5(10)-triene-3,17β-diol (3240-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) MeI, 2) NaBH₄ / 1) ether, 12 h, r.t., 2) EtOH, reflux, 7 h

2: Pb(OAc)2 / dimethylformamide / 50 °C

3: Jones' reagent / acetone / 0 °C

4: 1.6M BuLi / tetrahydrofuran; hexane / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; jones' reagent; lead acetate; methyl iodide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0039-128X(82)90031-9

upstream raw materials:

acetylene

8-Epiestradiol

2-methyl-8α-estra-1,3,5(10)-triene-3,17β-diol