(R)-(2-Methyloxiran-2-yl)methyl 4-nitrobenzoate

Base Information

• Chemical Name: (R)-(2-Methyloxiran-2-yl)methyl 4-nitrobenzoate
• CAS No.: 106268-96-6
• Molecular Formula: C11H11 N O5
• Molecular Weight: 237.212
• Hs Code.: 2916399090
• European Community (EC) Number: 624-050-3
• Nikkaji Number: J471.955G
• Mol file: 106268-96-6.mol

Synonyms:106268-96-6;(2R)-(-)-2-Methylglycidyl 4-nitrobenzoate;(R)-(2-Methyloxiran-2-yl)methyl 4-nitrobenzoate;[(2R)-2-methyloxiran-2-yl]methyl 4-nitrobenzoate;SCHEMBL3903585;PUBTVFBOTFDPTA-NSHDSACASA-N;MFCD00012315;AKOS027320363;CS-W009304;AS-81133;(R)-(-)-2-Methylglycidyl 4-Nitrobenzoate;(R)-2-methyloxiran-2-ylmethyl 4-nitrobenzoate;(R)-(2-Methyloxiran-2-yl)methyl4-nitrobenzoate;(2R)-(-)-2-METHYLGLYCIDYL4-NITROBENZOATE;(2R)-(-)-2-Methylglycidyl 4-nitrobenzoate, 98%;J-001560

Chemical Property of (R)-(2-Methyloxiran-2-yl)methyl 4-nitrobenzoate

Chemical Property:

• Vapor Pressure: 4.69E-06mmHg at 25°C
• Melting Point: 87-89 °C(lit.)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 382.6°C at 760 mmHg
• Flash Point: 178.3°C
• PSA: 84.65000
• Density: 1.321g/cm³
• LogP: 2.06370
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 237.06372245
• Heavy Atom Count: 17
• Complexity: 318

Purity/Quality:

98%min ^*data from raw suppliers

(R)-(-)-2-Methylglycidyl4-Nitrobenzoate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CO1)COC(=O)C2=CC=C(C=C2)[N+](=O)[O-]
• Isomeric SMILES: C[C@@]1(CO1)COC(=O)C2=CC=C(C=C2)[N+](=O)[O-]
• Uses: (R)-(-)-2-Methylglycidyl 4-Nitrobenzoate is an intermediate in the synthesis of Delamanid (D230660), a novel anti-tuberculosis medication that inhibits mycolic acid synthesis and shows potent in-vitro and in-vivo activity against drug-resistant strains of Mycobacterium tuberculosis.

Technology Process of (R)-(2-Methyloxiran-2-yl)methyl 4-nitrobenzoate

There total 3 articles about (R)-(2-Methyloxiran-2-yl)methyl 4-nitrobenzoate 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: 82.0%

2-methylglycidol (872-30-0) + 4-nitro-benzoyl chloride (122-04-3) → (2R)-methyl-3-[4-nitrobenzoyl(oxy)]-1,2-epoxy-propane (106268-96-6)

Guidance literature:

With triethylamine; In diethyl ether; for 1h;

DOI:10.1021/jo00126a018

Reference yield: 52.0%

4-nitro-benzoyl chloride (122-04-3) + 3-hydroxy-2-methyl-1-propene (513-42-8) → (2S)-methyl-3-[4-nitrobenzoyl(oxy)]-1,2-epoxy-propane (118200-96-7) + (2R)-methyl-3-[4-nitrobenzoyl(oxy)]-1,2-epoxy-propane (106268-96-6)

Guidance literature:

3-hydroxy-2-methyl-1-propene; With L-(+)-diisopropyl tartrate; Cumene hydroperoxide; In dichloromethane; at -20 ℃; for 16h;

4-nitro-benzoyl chloride; With triethylamine; phosphorous acid trimethyl ester; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(00)00309-4

Reference yield: 29.0%

(R)-2-methylglycidol (86884-89-1) + 4-nitro-benzoyl chloride (122-04-3) → (2R)-methyl-3-[4-nitrobenzoyl(oxy)]-1,2-epoxy-propane (106268-96-6)

Guidance literature:

With dmap; triethylamine; at 20 ℃; for 2h;

upstream raw materials:

4-nitro-benzoyl chloride

3-hydroxy-2-methyl-1-propene

2-methylglycidol

(R)-2-methylglycidol

Downstream raw materials:

(S)-(+)-2-methyl-1-(phenylthio)-2,3-propanediol

(S)-2-methyl-3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)propane-1,2-diol

(R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-nitrobenzoyloxy)]-propyl-4-nitroimidazole

(S)-2-methylglycidol

Refernces

• 1、 Carter, Rich,Hodgetts, Kevin,McKenna, Jeff,Magnus, Philip,Wren, Stephen. "Studies on the stereoselective synthesis of the marine antitumor agent eleutherobin". . p. 4367 - 4382. Retrieved 2007/10/03.
• 2、 Gao, Yun,Hanson, Robert M.,Klunder, Janice M.,Ko, Soo Y.,Masamune, Hiroko,Sharpless, K. Barry. "Catalytic Asymmetric Epoxidation and Kinetic Resolution: Modified Procedures Including in Situ Derivatization". . p. 5765 - 5780. Retrieved 2007/10/02.