(S)-(+)-1-Phenylethyl 3,5-dinitrobenzoate

Base Information

• Chemical Name: (S)-(+)-1-Phenylethyl 3,5-dinitrobenzoate
• CAS No.: 3205-18-3
• Molecular Formula: C15H12 N2 O6
• Molecular Weight: 316.27
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID80433190
• Nikkaji Number: J56.788D
• Wikidata: Q82247319
• Mol file: 3205-18-3.mol

Synonyms:(S)-(+)-1-Phenylethyl 3,5-dinitrobenzoate;3205-18-3;[(1S)-1-phenylethyl] 3,5-dinitrobenzoate;DTXSID80433190;(S)-(+)-1-Phenylethyl 3,5-dinitrobenzoate, 98%;(S)-(+)-1-PHENYLETHYL3,5-DINITROBENZOATE;J-018616;(+)-3,5-Dinitrobenzoic acid (S)-alpha-methylbenzyl ester

Chemical Property of (S)-(+)-1-Phenylethyl 3,5-dinitrobenzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 122-125 °C(lit.)
• Refractive Index: 1.618
• Boiling Point: 461.213°C at 760 mmHg
• Flash Point: 196.635°C
• PSA: 117.94000
• Density: 1.381g/cm³
• LogP: 4.46740
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 316.06953611
• Heavy Atom Count: 23
• Complexity: 430

Purity/Quality:

99%min ^*data from raw suppliers

(S)-(+)-1-Phenylethyl 3,5-dinitrobenzoate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)OC(=O)C2=CC(=CC(=C2)[N+](=O)[O-])[N+](=O)[O-]
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)OC(=O)C2=CC(=CC(=C2)[N+](=O)[O-])[N+](=O)[O-]

Technology Process of (S)-(+)-1-Phenylethyl 3,5-dinitrobenzoate

There total 9 articles about (S)-(+)-1-Phenylethyl 3,5-dinitrobenzoate 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: 53.4%

1-Phenylethanol (98-85-1,13323-81-4) + 3,5-dinitrobenoyl chloride (99-33-2) → (+/-)-sec-Phenethyl alcohol 3,5-dinitrobenzoate (3205-18-3,3205-33-2,21286-22-6,82222-60-4)

Guidance literature:

With pyridine; at 0 - 25 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.202106603

Reference yield:

(1-diazoethyl)benzene (22293-10-3) + 3,5-dinitrobenzoic acid (99-34-3) → (+/-)-sec-Phenethyl alcohol 3,5-dinitrobenzoate (3205-18-3,3205-33-2,21286-22-6,82222-60-4) + acetophenonazine (729-43-1)

Guidance literature:

In tetrahydrofuran; Yield given. Yields of byproduct given;

DOI:10.1055/s-1982-29821

Reference yield:

1-Phenylethanol (98-85-1,13323-81-4) + 3,5-dinitrobenoyl chloride (99-33-2) → (R)-sec-phenethyl-3,5-dinitrobenzoate (3205-33-2) + (S)-sec-phenethyl-3,5-dinitrobenzoate (3205-18-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 12 h / 0 - 25 °C / Inert atmosphere

2: poly(4-vinyl pyridine) complex with (S)-4-((1-phenylethyl)carbamoyl)benzenesulfonic acid / N,N-dimethyl-formamide; toluene / 0.5 h / 25 °C / Resolution of racemate

With pyridine; In N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.202106603

upstream raw materials:

(1-diazoethyl)benzene

3,5-dinitrobenzoic acid

1-Phenylethanol

3,5-dinitrobenoyl chloride

Downstream raw materials:

(R)-sec-phenethyl-3,5-dinitrobenzoate

2-(1-phenylethyl)phenol

(+)-α-phenethyl alcohol

Refernces

• 1、 Hirose, Daisuke,Taniguchi, Tsuyoshi,Ishibashi, Hiroyuki. "Recyclable mitsunobu reagents: Catalytic mitsunobu reactions with an iron catalyst and atmospheric oxygen". supporting information. p. 4613 - 4617. Retrieved 2013/06/04.
• 2、 Shimon, L. J. W.,Zbaida, D.,Addadi, L.,Leiserowitz, L.,Lahav, M.. "DESIGN OF STEREOSPECIFIC INHIBITORS FOR CRYSTAL DISSOLUTION". . p. 199 - 222. Retrieved 2007/10/02.