4-[3-(Trifluoromethyl)diazirin-3-yl]benzoic Acid N-Hydroxysuccinimide Ester

Base Information

• Chemical Name: 4-[3-(Trifluoromethyl)diazirin-3-yl]benzoic Acid N-Hydroxysuccinimide Ester
• CAS No.: 87736-89-8
• Molecular Formula: C13H8 F3 N3 O4
• Molecular Weight: 327.219
• Mol file: 87736-89-8.mol

Synonyms:2,5-Pyrrolidinedione,1-[[4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzoyl]oxy]- (9CI); 3H-Diazirine,2,5-pyrrolidinedione deriv.

Chemical Property of 4-[3-(Trifluoromethyl)diazirin-3-yl]benzoic Acid N-Hydroxysuccinimide Ester

Chemical Property:

• Melting Point: 92-93°C
• Boiling Point: 402.5±55.0 °C(Predicted)
• PSA: 88.40000
• Density: 1.68±0.1 g/cm3(Predicted)
• LogP: 0.89740
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Ethyl Acetate (Slightly, Heated)

Purity/Quality:

99%min ^*data from raw suppliers

4-[3-(Trifluoromethyl)diazirin-3-yl]benzoicAcidN-HydroxysuccinimideEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A novel compound of aromatic diazirines for Photoaffinity Labeling A novel compound of aromatic diazirines for Photoaffinity Labeling.

Technology Process of 4-[3-(Trifluoromethyl)diazirin-3-yl]benzoic Acid N-Hydroxysuccinimide Ester

There total 23 articles about 4-[3-(Trifluoromethyl)diazirin-3-yl]benzoic Acid N-Hydroxysuccinimide 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: 95.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzoic acid (85559-46-2) → 1-<<4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoyl>oxy>-2,5-pyrrolidinedione (87736-89-8)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; for 2h;

DOI:10.3987/COM-95-7345

Reference yield:

3-phenyl-3-(trifluoromethyl)-3H-diazirine (73899-14-6) → 1-<<4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoyl>oxy>-2,5-pyrrolidinedione (87736-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Tl(CO₂CF₃)3, TFA; 2.) MgO, LiCl; 3.) 1N NaOH / 2.) PdCl₂ / 1.) 75 deg C, 24 h; 2.) r.t., 24 h; 3.) MeOH, r.t., 2 h

2: 95 percent / DCC / CH₂Cl₂ / 2 h

With sodium hydroxide; magnesium oxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium chloride; thallium(III) trifluoroacetate; palladium dichloride; In dichloromethane;

DOI:10.3987/COM-95-7345

Reference yield:

4-bromobenzenemethanol (873-75-6) → 1-<<4-<3-(trifluoromethyl)-3H-diazirin-3-yl>benzoyl>oxy>-2,5-pyrrolidinedione (87736-89-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / imidazole

2: 1) n-BuLi / 1) hexane, ether, -30 to 0 deg C in 2 h, 2) ether, -50 deg C, 3 h

3: 93 percent / NH₃OHCl, NaOH / ethanol / 16 h / Heating

4: 70 percent / pyridine / 3 h / Heating

5: 86 percent / liq. NH₃ / diethyl ether / 12 h / Ambient temperature

6: 91 percent / Ag₂O / diethyl ether / 1 h

7: 92 percent / conc. HCl / methanol

8: 72 percent / 0.2N KOH, KMnO₄ / dioxane / 2 h / Ambient temperature

9: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium hydroxide; potassium permanganate; n-butyllithium; hydroxylamine hydrochloride; ammonia; dicyclohexyl-carbodiimide; silver(l) oxide; In 1,4-dioxane; pyridine; methanol; diethyl ether; ethanol; ethyl acetate;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzoic acid

3-phenyl-3-(trifluoromethyl)-3H-diazirine

2,2,2-trifluoro-1-(p-tolyl)ethanone

Downstream raw materials:

C₁₈H₂₃F₃N₄O₃S₂

N,N',N''-(2,2',2''-(2,2',2''-(2,2',2''-(benzene-1,3,5-triyltris(oxy))tris(ethane-2,1-diyl))tris(oxy)tris(ethane-2,1-diyl))tris(oxy)tris(ethane-2,1-diyl))tris(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamide)

N,N'-([4-(2-{4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamido}ethyl)-1,2-phenylene]bis(oxyethane-2,1-diyloxyethane-2,1-diyl))bis{4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide}

N,N'-(2,2'-(2,2'-(2,2'-(4-(2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamido)ethyl)-1,2-phenylene)bis(oxy)bis(ethane-2,1-diyl))bis(oxy)bis(ethane-2,1-diyl))bis(oxy)bis(ethane-2,1-diyl))bis(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamide)

Refernces

• 1、 Athanassopoulos, Constantinos M.,Avgoustakis, Konstantinos,Kalantzi, Stefania,Karamanos, Nikos,Koutsakis, Christos,Lymberi, Peggy,Papaioannou, Dionissios,Piperigkou, Zoi,Stivarou, Theodora,Vachlioti, Eleanna,Vassileiou, Christos. "New Analogs of Polyamine Toxins from Spiders and Wasps: Liquid Phase Fragment Synthesis and Evaluation of Antiproliferative Activity". supporting information. . Retrieved 2022/01/14.
• 2、 -. "NOVEL CROSSLINKING REAGENTS, MACROMOLECULES, THERAPEUTIC CONJUGATES, AND SYNTHETIC METHODS THEREOF". Paragraph 00354; 00355; 00359. . Retrieved 2013/03/26.