5-Propylbenzene-1,3-diol

Base Information

• Chemical Name: 5-Propylbenzene-1,3-diol
• CAS No.: 500-49-2
• Molecular Formula: C9H12O2
• Molecular Weight: 152.193
• Hs Code.: 2907299090
• European Community (EC) Number: 817-016-6
• UNII: V6Z4S3VKS6
• DSSTox Substance ID: DTXSID40198172
• Nikkaji Number: J11.678E
• Wikidata: Q83070958
• Mol file: 500-49-2.mol

Synonyms:5-propylbenzene-1,3-diol;500-49-2;Divarin;Divarinol;1,3-Benzenediol, 5-propyl-;5-propyl-1,3-benzenediol;5-PROPYLRESORCINOL;MFCD10686919;5-propyl resorcinol;5-N-PROPYLRESORCINOL;V6Z4S3VKS6;SCHEMBL67909;1,3-dihydroxy-5-propylbenzene;DTXSID40198172;CHEBI:144241;AKOS022634802;5-N-PROPYL-1,3-DIHYDROXYBENZENE;SY042170;WS-00349;CS-0168735;EN300-36597;W19028;A902049;A1-02506;Z367653796

Chemical Property of 5-Propylbenzene-1,3-diol

Chemical Property:

• Vapor Pressure: 0.0017mmHg at 25°C
• Melting Point: 82.8°C
• Refractive Index: 1.4024 (estimate)
• Boiling Point: 284.8°C at 760 mmHg
• PKA: 9.56±0.10(Predicted)
• Flash Point: 137.9°C
• PSA: 40.46000
• Density: 1.122g/cm³
• LogP: 2.05030
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 104

Purity/Quality:

98%, ^*data from raw suppliers

5-Propylbenzene-1,3-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1=CC(=CC(=C1)O)O
• Description: A White to Brown crystalline solid.
• Uses: 5-Propylbenzene-1,3-diol is an intermediate used to prepare Cannabigerovarin (C175140) which stimulates thermosensitive transient receptor potential (TRP) channels of vanilloid type-4 (TRPV4)-mediated [Ca2+]i with moderate-high efficacy (30-60% of the effect of ionomycin) and potency (EC50 0.9-6.4 μM),

Technology Process of 5-Propylbenzene-1,3-diol

There total 42 articles about 5-Propylbenzene-1,3-diol 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: 96.3%

(E)-(((5-(prop-1-en-1-yl)-1,3-phenylene)bis(oxy))bis(methylene))dibenzene → 5-propyl-1,3-benzenediol (500-49-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; ethyl acetate;

Reference yield:

methyl 6-n-propyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate (27871-91-6) → 5-propyl-1,3-benzenediol (500-49-2)

Guidance literature:

With bromine; In N,N-dimethyl-formamide; at 80 - 160 ℃; Cooling with ice;

Reference yield:

3,5-dimethoxybenzoic acid (1132-21-4) → 5-propyl-1,3-benzenediol (500-49-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / (COCl)2 / benzene / 2 h, room t., 1 h, reflux

2: 70 percent / NaOAc, H₂ / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight

3: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux

4: hydrogen, conc. H₂SO₄ / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature

5: NaI, ClSiMe₃ / acetonitrile / 36 h / Heating

With chloro-trimethyl-silane; oxalyl dichloride; sulfuric acid; hydrogen; sodium acetate; magnesium; sodium iodide; methyl iodide; palladium on activated charcoal; In diethyl ether; ethyl acetate; acetonitrile; benzene;

DOI:10.1016/S0031-9422(00)80159-4

upstream raw materials:

1,3-dimethoxy-5-propylbenzene

2-hydroxy-4-methoxy-6-propylbenzoic acid

divaricatic acid

2,4-dihydroxy-6-propylbenzoic acid

Downstream raw materials:

2,4-dihydroxy-6-propylbenzaldehyde

(6aS,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol

3-norpentyl-3-propyl-Δ⁸-tetrahydrocannabinol

cannabidivarin

Refernces

• 1、 Golliher, Alexandra E.,Tenorio, Antonio J.,Dimauro, Nina O.,Mairata, Nicolas R.,Holguin, F. Omar,Maio, William. "Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV". . . Retrieved 2021/02/20.
• 2、 Bloemendal, Victor R. L. J.,Sondag, Daan,Elferink, Hidde,Boltje, Thomas J.,van Hest, Jan. C. M.,Rutjes, Floris P. J. T.. "A Revised Modular Approach to (–)-trans-Δ8-THC and Derivatives Through Late-Stage Suzuki–Miyaura Cross-Coupling Reactions". . p. 2289 - 2296. Retrieved 2019/04/03.