2-Cyclopropylphenol

Base Information

• Chemical Name: 2-Cyclopropylphenol
• CAS No.: 10292-60-1
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• Hs Code.: 2907199090
• DSSTox Substance ID: DTXSID00454529
• Nikkaji Number: J570.187B
• Wikidata: Q82276099
• Mol file: 10292-60-1.mol

Synonyms:2-cyclopropylphenol;10292-60-1;Phenol, 2-cyclopropyl-;cyclopropylphenol;cyclopropyl phenol;2-cyclopropyl-phenol;SCHEMBL929830;DTXSID00454529;VKTBILBRBSALKI-UHFFFAOYSA-N;MFCD06802666;AKOS004118732;PS-11816;BB 0223815;CS-0372408;FT-0768430;EN300-190721

Chemical Property of 2-Cyclopropylphenol

Chemical Property:

• Boiling Point: 169.8±9.0 °C(Predicted)
• PKA: 10.31±0.30(Predicted)
• PSA: 20.23000
• Density: 1.158±0.06 g/cm3(Predicted)
• LogP: 2.26960
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 118

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Cyclopropylphenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C2=CC=CC=C2O
• Uses: 2-Cyclopropyl-phenol is a reagent used to prepare imidazolines which display significant adrenergic α2C-Agonism/α2A-Antagonism. It is also an intermediate used in preparation of Cirazoline Hydrochloride (C497400) which is a potent α-1 adrenergic receptor agonist and an even more potent α-2 receptor antagonist.

Technology Process of 2-Cyclopropylphenol

There total 26 articles about 2-Cyclopropylphenol 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: 90.0%

O-allyl-2-bromophenol (60333-75-7) → 2-cyclopropylphenol (10292-60-1)

Guidance literature:

O-allyl-2-bromophenol; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 2h;

With N,N,N,N,-tetramethylethylenediamine; In diethyl ether; pentane; at -78 - 25 ℃;

With water; ammonium chloride; In diethyl ether; pentane;

Reference yield: 61.0%

O-allyl-2-bromophenol (60333-75-7) → 3-methyl-2,3-dihydrobenzofuran (13524-73-7) + 2-cyclopropylphenol (10292-60-1)

Guidance literature:

O-allyl-2-bromophenol; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.5h;

With N,N,N,N,-tetramethylethylenediamine; In diethyl ether; pentane; at -78 ℃; for 0.5h; Further stages.;

DOI:10.1021/ol026078x

Reference yield: 45.0%

O-allyl-2-bromophenol (60333-75-7) → 2-cyclopropylphenol (10292-60-1) + 1-Phenyl-2-propen-1-ol (4393-06-0)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; at -78 - 0 ℃; for 3h;

DOI:10.1021/ol0258029

upstream raw materials:

o-Allylphenol

1-allyloxy-2-iodobenzene

tert.-butyl lithium

2-cyclopropylaniline

Downstream raw materials:

(RS)-6-acetoxy-6-cyclopropylcyclohexa-2,4-dien-1-one

4-bromo-2-cyclopropylphenol

2-(2-cyclopropylphenoxy)propionic acid methyl ester

1,2-bis(3-cyclopropyl-4-(difluoromethoxy)phenyl)ethane-1,2-dione

Refernces

• 1、 Riley,Hanzlik. "Electron transfer in P450 mechanisms. Microsomal metabolism of cyclopropylbenzene and p-cyclopropylanisole". . p. 1 - 16. Retrieved 1994.
• 2、 Capocasa, Giorgio,Olivo, Giorgio,Barbieri, Alessia,Lanzalunga, Osvaldo,Di Stefano, Stefano. "Direct hydroxylation of benzene and aromatics with H2O2 catalyzed by a self-assembled iron complex: Evidence for a metal-based mechanism". . p. 5677 - 5686. Retrieved 2017.
• 3、 Satoh, Tsuyoshi,Kimura, Tsutomu,Sasaki, Yuki,Nagamoto, Shinobu. "Synthesis of spiro[26]nonadienones and spiro[3.6]decadienones by the reaction of cyclopropyl- and cyclobutylmagnesium carbenoids with lithium phenolates and naphtholates". experimental part. p. 2091 - 2101. Retrieved 2012/08/27.
• 4、 Hudlicky, Jason Reed,Hopkins-Hill, John,Hudlicky, Tomas. "Explorations of [4+2] and [5+2] cycloadditions of dienylcyclopropane derived enzymatically from cyclopropylbenzene". supporting information; experimental part. p. 2891 - 2895. Retrieved 2012/01/06.