1,3-Propanediol, 2-(2-iodoethyl)-, diacetate

Base Information

• Chemical Name: 1,3-Propanediol, 2-(2-iodoethyl)-, diacetate
• CAS No.: 127047-77-2
• Molecular Formula: C9H15 I O4
• Molecular Weight: 314.12
• European Community (EC) Number: 411-780-0
• UNII: UGI04T2ZSI
• DSSTox Substance ID: DTXSID70155394
• Nikkaji Number: J639.177J
• Wikidata: Q27291072
• Mol file: 127047-77-2.mol

Synonyms:127047-77-2;1,3-Propanediol, 2-(2-iodoethyl)-, diacetate;[2-(acetyloxymethyl)-4-iodobutyl] acetate;BRL-47539;2-(Acetoxymethyl)-4-iodobutyl acetate;UNII-UGI04T2ZSI;UGI04T2ZSI;2-(2-Iodoethyl-1,3-propanediol diacetate;BRL 47539;2-acetoxymethyl-4-iodobut-1-yl acetate;EC 411-780-0;2-(2-IODOETHYL)-1,3-PROPANEDIOL DIACETATE;1,3-Propanediol, 2-(2-iodoethyl)-, 1,3-diacetate;C9H15IO4;SCHEMBL6916715;DTXSID70155394;C9-H15-I-O4;4-acetoxy-3-(acetoxymethyl)butyl iodide;cis R-138727, (Prasugrel Metabolite);2-(2-Iodoethyl)propane-1,3-diyl=diacetate;FT-0741888;2-ACETOXYMETHYL-4-IODOBUTYL 1-ACETATE;Q27291072

Chemical Property of 1,3-Propanediol, 2-(2-iodoethyl)-, diacetate

Chemical Property:

• Vapor Pressure: 0.000182mmHg at 25°C
• Boiling Point: 329.1°C at 760 mmHg
• Flash Point: 152.8°C
• PSA: 52.60000
• Density: 1.545g/cm³
• LogP: 1.55390
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 314.00151
• Heavy Atom Count: 14
• Complexity: 175

Purity/Quality:

99.9% ^*data from raw suppliers

2-(Acetoxymethyl)-4-iodobutylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 36-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(CCI)COC(=O)C

Technology Process of 1,3-Propanediol, 2-(2-iodoethyl)-, diacetate

There total 8 articles about 1,3-Propanediol, 2-(2-iodoethyl)-, diacetate 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: 58.0%

3-acetoxymethyl tetrahydrofuran (78386-41-1) + acetyl chloride (75-36-5) → 4-acetoxy-3-(acetoxymethyl)-1-iodobutane (127047-77-2)

Guidance literature:

With samarium; iodine; In acetonitrile; at 20 ℃; for 48h;

Reference yield: 55.0%

3-tetrahydrofuranmethanol (124391-75-9,124506-31-6,15833-61-1) + acetyl chloride (75-36-5) → 4-acetoxy-3-(acetoxymethyl)-1-iodobutane (127047-77-2)

Guidance literature:

With samarium; iodine; In acetonitrile; at 20 ℃; for 48h;

Reference yield:

2-(2-(benzyloxy)ethyl)propane-1,3-diol (77661-80-4) → 4-acetoxy-3-(acetoxymethyl)-1-iodobutane (127047-77-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / pyridine, 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 1 h / 0 °C

2: H₂ / 10percent Pd/C / ethanol / 18 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1 h / -5 °C

4: NaI / acetone / 2 h / Heating

With pyridine; dmap; hydrogen; triethylamine; sodium iodide; palladium on activated charcoal; In ethanol; dichloromethane; acetone;

DOI:10.1016/S0040-4020(01)87878-9

upstream raw materials:

Acetic acid 2-acetoxymethyl-4-methanesulfonyloxy-butyl ester

3-acetoxymethyl tetrahydrofuran

acetyl chloride

3-tetrahydrofuranmethanol

Downstream raw materials:

9-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-bromopurine

7-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-bromopurine

9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine

7-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine

Refernces

• 1、 -. "A PROCESS FOR THE PREPARATION OF 2-ACETOXYMETHYL-4 HALO-BUT-1-YL ACETATES". Page 12; 13. . Retrieved 2010/02/06.