Methyl 2-(hex-1-yn-1-yl)benzoate

Base Information

• Chemical Name: Methyl 2-(hex-1-yn-1-yl)benzoate
• CAS No.: 462637-40-7
• Molecular Formula: C14H16O2
• Molecular Weight: 216.28
• Hs Code.: 29163990
• Mol file: 462637-40-7.mol

Synonyms:N-formylanthranilic acid methyl ester;Methyl N-formylanthranilate;Methyl-N-formyl-anthranilat;2-formylamino-benzoic acid methyl ester;methyl 2-hex-1-ynyl benzoate;N-Formyl-anthranilsaeure-methylester;methyl 2-hex-1-yn-1-ylbenzoate;

Chemical Property of Methyl 2-(hex-1-yn-1-yl)benzoate

Chemical Property:

• Boiling Point: 328.7±25.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 3.01490

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-(1-Hexyn-1-yl)benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 2-(1-Hexyn-1-yl)benzoate is an intermediate in synthesizing Apigenin 5-O-β-D-Glucuronide (A426510), a metabolite of Apigenin (A726500), Induces the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentration (12.5 uM) by inhibiting MAP kinase activity. Also inhibits the proliferation of malignant tumor cells by G2/M arrest and induces morphological differentiation. Apigenin has also been reported to enhance the gap junction intracellular communication in liver cells.

Technology Process of Methyl 2-(hex-1-yn-1-yl)benzoate

There total 4 articles about Methyl 2-(hex-1-yn-1-yl)benzoate 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: 99.0%

o-iodo-methyl-benzoic acid (610-97-9) + hex-1-yne (693-02-7) → 2-(1-hexynyl)benzoic acid methyl ester (462637-40-7)

Guidance literature:

o-iodo-methyl-benzoic acid; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine; triphenylphosphine; at 20 ℃; for 1h; Inert atmosphere;

hex-1-yne; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.200902548

Reference yield:

2-(methylthio)iodobenzene (33775-94-9) + hex-1-yne (693-02-7) → 2-(1-hexynyl)benzoic acid methyl ester (462637-40-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 0 - 25 ℃; for 18h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.0c01096

Reference yield:

2-Iodobenzoic acid (88-67-5) → 2-(1-hexynyl)benzoic acid methyl ester (462637-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / H₂SO₄ / 2.5 h / Heating

2: 96 percent / Pd(PPh₃)2Cl₂; CuI; (i-Pr)2NEt / dimethylformamide / 18 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sulfuric acid; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; 1: Fischer esterification;

DOI:10.1016/S0040-4020(03)01019-6

upstream raw materials:

2-bromobenzoic acid methyl ester

hex-1-yne

o-iodo-methyl-benzoic acid

2-Iodobenzoic acid

Downstream raw materials:

(E)-3-(1,1-diphenylhexan-2-ylidene)isobenzofuran-1(3H)-one

3-n-butyl-4-(phenylselenyl)-1H-isochromen-1-one

trans-methyl-2-(hex-1-en-1-yl)benzoate