Safrole

Base Information

• Chemical Name: Safrole
• CAS No.: 94-59-7
• Deprecated CAS: 1406-55-9,8022-92-2,1548770-71-3,8022-92-2
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Hs Code.: 2909309090
• European Community (EC) Number: 202-345-4
• NSC Number: 11831
• UN Number: 3082
• UNII: RSB34337V9
• DSSTox Substance ID: DTXSID0021254
• Nikkaji Number: J3.946B
• Wikipedia: Safrole
• Wikidata: Q412424
• NCI Thesaurus Code: C44443
• RXCUI: 2383532
• Metabolomics Workbench ID: 46121
• ChEMBL ID: CHEMBL242273
• Mol file: 94-59-7.mol

Synonyms:4 Allyl 1,2 methylenedioxybenzene;4-Allyl-1,2-methylenedioxybenzene;4-Allyl-1,2-methylenedioxybenzenes;Safrol;Safrole;Safroles;Safrols;Shikimol;Shikimols

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Safrole

Chemical Property:

• Appearance/Colour: light yellow-green liquid
• Vapor Pressure: 1 mm Hg ( 63.8 °C)
• Melting Point: 11.2 °C(lit.)
• Refractive Index: 1.536 - 1.538
• Boiling Point: 233.087 °C at 760 mmHg
• Flash Point: 97.778 °C
• PSA: 18.46000
• Density: 1.118 g/cm^>3
• LogP: 2.14380
• Water Solubility.: insoluble,
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 167
• Transport DOT Label: Class 9

Purity/Quality:

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-22-68
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C=CCC1=CC2=C(C=C1)OCO2

Technology Process of Safrole

There total 29 articles about Safrole 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: 95.0%

saffrole dibromide (5458-11-7) → 1-allyl-3,4-methylenedioxybenzene (94-59-7)

Guidance literature:

With (2-((dimethylamino)methyl)phenyl)dimethyltin; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo00063a024

Reference yield: 88.0%

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) + allyl bromide (106-95-6) → 1-allyl-3,4-methylenedioxybenzene (94-59-7)

Guidance literature:

1,2-(methylenedioxy)-4-bromobenzene; With iodine; magnesium; In tetrahydrofuran; at 20 ℃;

allyl bromide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jacs.1c01916

Reference yield: 86.0%

3,4-(methylenedioxy)-benzeneboronic acid (94839-07-3) + allyl bromide (106-95-6) → 1-allyl-3,4-methylenedioxybenzene (94-59-7)

Guidance literature:

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate; In acetonitrile; at 65 ℃; for 18h; chemoselective reaction;

DOI:10.1002/anie.201402924

upstream raw materials:

diiodomethane

4-allylpyrocatechol

saffrole dibromide

5-<1-hydroxy-3-(trimethylsilyl)prop-1-yl>-1,3-benzodioxole

Downstream raw materials:

chavibetol

2-ethoxy-5-allyl-phenol

1,2-diethoxy-4-allylbenzene

5-(3-(octylthio)propyl)benzo[d][1,3]dioxole

Refernces

Gold-Catalyzed Ring Expansion of Alkynyl Heterocycles through 1,2-Migration of an Endocyclic Carbon-Heteroatom Bond

10.1002/chem.201504165

The research explores a gold-catalyzed oxidative ring-expansion of alkynyl heterocycles, aiming to develop a mild and efficient method to synthesize valuable six- or seven-membered heterocycles from easily available starting materials. The study employs pyridine-N-oxide as the oxidant and various gold catalysts, such as [PPh3AuNTf2] and [IPrAuNTf2], to facilitate the reaction. The key innovation lies in the regioselective oxidation and chemoselective migration of endocyclic carbon–heteroatom bonds (C–S, C–N, and C–O), with the migratory aptitude order being C–S > C–N > C–O. The reaction demonstrates wide functional group tolerance and high yields, producing polycyclic products in the absence of an oxidant through a ring-expansion/Nazarov cyclization sequence. The findings suggest a new and general protocol for heterocycle synthesis, with potential applications in the construction of complex organic structures.