Triethyl phosphonoacetate-13C2

Base Information

• Chemical Name: Triethyl phosphonoacetate-13C2
• CAS No.: 100940-60-1
• Molecular Formula: C8H17 O5 P
• Molecular Weight: 226.21
• European Community (EC) Number: 621-452-0
• DSSTox Substance ID: DTXSID50448099
• Nikkaji Number: J1.163.910K
• Wikidata: Q82267042
• Mol file: 100940-60-1.mol

Synonyms:Triethyl phosphonoacetate-13C2;100940-60-1;Carbethoxymethyldiethyl phosphonate-C13;Acetic-13C2 acid, 2-(diethoxyphosphinyl)-, ethyl ester;HY-Y0677S;DTXSID50448099;13C Labeled triethyl phosphonoacetate;AKOS015915629;CS-0103248;Triethyl phosphonoacetate-13c2,99 atom % 13c;Triethyl phosphonoacetate-13C2, 99 atom % 13C;J-000285

Chemical Property of Triethyl phosphonoacetate-13C2

Chemical Property:

• Refractive Index: n20/D 1.431(lit.)
• Boiling Point: 142-145 °C9 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 71.64000
• Density: 1.13 g/mL at 25 °C(lit.)
• LogP: 1.81560
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 226.08807031
• Heavy Atom Count: 14
• Complexity: 206

Purity/Quality:

98%min ^*data from raw suppliers

Triethyl Phosphonoacetate-13C2 ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CP(=O)(OCC)OCC
• Isomeric SMILES: CCO[13C](=O)[13CH2]P(=O)(OCC)OCC
• Uses: Triethyl Phosphonoacetate-13C2 is the isotope labelled analog of Triethyl Phosphonoacetate (T777000). Triethyl Phosphonoacetate is a reagent used for Horner-Emmons modification.

Technology Process of Triethyl phosphonoacetate-13C2

There total 1 articles about Triethyl phosphonoacetate-13C2 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: 100.0%

ethyl bromoacetate-(13)C2 (61898-49-5) + triethyl phosphite (122-52-1) → [13C2]-triethyl phosphonoacetate (100940-60-1)

Guidance literature:

at 180 ℃; for 0.5h;

DOI:10.1002/recl.19921110307

Reference yield: 99.0%

(E)-β-ionone (79-77-6,14901-07-6) + [13C2]-triethyl phosphonoacetate (100940-60-1) → [10,11-13C2]-(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate (347367-53-7)

Guidance literature:

With sodium hydride; In diethyl ether;

DOI:10.1002/jlcr.464

Reference yield: 90.0%

(2E,4E)‐3‐methyl‐5‐(2,6,6‐tri(methyl‐13C)cyclohex‐1‐en‐1‐yl)penta‐2,4‐dienal‐1,2‐13C2 + [13C2]-triethyl phosphonoacetate (100940-60-1) → ethyl (2E,4E,6E)‐5‐methyl‐7‐(2,6,6‐tri(methyl‐13C)cyclohex‐1‐en‐1‐yl)hepta‐2,4,6‐trienoate‐1,2,3,4‐13C4

Guidance literature:

[¹³C₂]-triethyl phosphonoacetate; With sodium hydride; In diethyl ether; mineral oil; at 0 - 20 ℃; for 1h; Inert atmosphere;

(2E,4E)‐3‐methyl‐5‐(2,6,6‐tri(methyl‐¹³C)cyclohex‐1‐en‐1‐yl)penta‐2,4‐dienal‐1,2‐¹³C₂; In diethyl ether; mineral oil; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1002/jlcr.3576

upstream raw materials:

ethyl bromoacetate-⁽¹³⁾C₂

triethyl phosphite

Downstream raw materials:

ethyl 5-methyl-7-(2,6,6-trimethyl-1-cyclohexenyl)heptatrienoate

(2E,4R)-<1,2-¹³C>ethyl 4-benzyloxy-2-octadecenoate

[10,11-13C₂]-(2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate

14,15-¹³C₂-retinoic acid ethyl ester

Refernces

• 1、 Shrestha-Dawadi, Prativa Bade,Lugtenburg, Johan. "Preparation of [1,2,3,4,5-13C 5]-5-Amino-4-oxopentanoic Acid (ALA) - Design of a Synthetic Scheme to Prepare Any 13C- and 15N-Isotopomer with High Isotopic Enrichment". . p. 4654 - 4663. Retrieved 2003.
• 2、 Leeder, Alexander J.,Brown, Lynda J.,Becker-Baldus, Johanna,Mehler, Michaela,Glaubitz, Clemens,Brown, Richard C.D.. "Synthesis of isotopically labeled all-trans retinals for DNP-enhanced solid-state NMR studies of retinylidene proteins". . . Retrieved 2018/02/06.