2-Methoxy-4-[3-(trifluoromethyl)-3H-diazirin-3-YL]benzoic acid, methyl ester

Base Information

• Chemical Name: 2-Methoxy-4-[3-(trifluoromethyl)-3H-diazirin-3-YL]benzoic acid, methyl ester
• CAS No.: 154187-50-5
• Molecular Formula: C11H9 F3 N2 O3
• Molecular Weight: 274.2
• DSSTox Substance ID: DTXSID90434618
• Mol file: 154187-50-5.mol

Synonyms:154187-50-5;2-METHOXY-4-[3-(TRIFLUOROMETHYL)-3H-DIAZIRIN-3-YL]BENZOIC ACID, METHYL ESTER;Methyl 2-methoxy-4-[3-(trifluoromethyl)diazirin-3-yl]benzoate;methyl 2-methoxy-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzoate;DTXSID90434618;IPQMAVSSCOHEMO-UHFFFAOYSA-N;FT-0671381;EN300-18666322;J-009078;Methyl 2-methoxy-4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoate

Chemical Property of 2-Methoxy-4-[3-(trifluoromethyl)-3H-diazirin-3-YL]benzoic acid, methyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.524
• Boiling Point: 319.677°C at 760 mmHg
• Flash Point: 147.135°C
• PSA: 60.25000
• Density: 1.442g/cm³
• LogP: 1.53390
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 274.05652664
• Heavy Atom Count: 19
• Complexity: 391

Purity/Quality:

97% ^*data from raw suppliers

2-Methoxy-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2(N=N2)C(F)(F)F)C(=O)OC
• Uses: A photoaffinity reagent A photoaffinity reagent.

Technology Process of 2-Methoxy-4-[3-(trifluoromethyl)-3H-diazirin-3-YL]benzoic acid, methyl ester

There total 6 articles about 2-Methoxy-4-[3-(trifluoromethyl)-3H-diazirin-3-YL]benzoic acid, methyl ester 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:

3-methoxyphenyl bromide (2398-37-0) → 2-Methoxy-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoic acid methyl ester (154187-50-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Mg / 1.) THF, 2.) THF, r.t., 2 h

2: 96 percent / hydroxylamine hydrochloride, pyridine / ethanol / 12 h / 60 °C

3: Et₃N, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 0.75 h / Ambient temperature

4: liq. NH₃ / CH₂Cl₂ / 18 h / Ambient temperature

5: 77 percent / tert-butyl hypochlorite, Et₃N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature

6: 1.) thallium(III) trifluoroacetate, 2.) PdCl₂, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h

With pyridine; dmap; tert-butylhypochlorite; hydroxylamine hydrochloride; ammonia; magnesium oxide; magnesium; triethylamine; lithium chloride; palladium dichloride; thallium(III) trifluoroacetate; In ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo00081a017

Reference yield:

2,2,2-trifluoro-1-(3-methoxyphenyl)ethanone (30724-22-2) → 2-Methoxy-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoic acid methyl ester (154187-50-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / hydroxylamine hydrochloride, pyridine / ethanol / 12 h / 60 °C

2: Et₃N, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 0.75 h / Ambient temperature

3: liq. NH₃ / CH₂Cl₂ / 18 h / Ambient temperature

4: 77 percent / tert-butyl hypochlorite, Et₃N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature

5: 1.) thallium(III) trifluoroacetate, 2.) PdCl₂, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h

With pyridine; dmap; tert-butylhypochlorite; hydroxylamine hydrochloride; ammonia; magnesium oxide; triethylamine; lithium chloride; palladium dichloride; thallium(III) trifluoroacetate; In ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo00081a017

Reference yield:

2,2,2-Trifluoro-1-(3-methoxyphenyl)ethanone oxime (140854-00-8) → 2-Methoxy-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoic acid methyl ester (154187-50-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 0.75 h / Ambient temperature

2: liq. NH₃ / CH₂Cl₂ / 18 h / Ambient temperature

3: 77 percent / tert-butyl hypochlorite, Et₃N / ethanol; 2-methyl-propan-2-ol / 2 h / Ambient temperature

4: 1.) thallium(III) trifluoroacetate, 2.) PdCl₂, LiCl, MgO / 1.) TFA, r.t., 24 h, 2.) r.t., 43 h

With dmap; tert-butylhypochlorite; ammonia; magnesium oxide; triethylamine; lithium chloride; palladium dichloride; thallium(III) trifluoroacetate; In ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo00081a017

upstream raw materials:

methanol

carbon monoxide

3-(3-methoxyphenyl)-3-(trifluoromethyl)-3H-diazirine

3-methoxyphenyl bromide

Downstream raw materials:

2-Hydroxy-4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoic acid methyl ester

Refernces