Dicyclopropylmethanol

Base Information

• Chemical Name: Dicyclopropylmethanol
• CAS No.: 14300-33-5
• Molecular Formula: C7H12O
• Molecular Weight: 112.172
• Hs Code.: 2906199090
• European Community (EC) Number: 238-236-3
• UNII: 3GA978VBJ6
• DSSTox Substance ID: DTXSID10162284
• Nikkaji Number: J81.746E
• Wikidata: Q83030900
• Mol file: 14300-33-5.mol

Synonyms:Dicyclopropylmethanol;14300-33-5;Dicyclopropyl carbinol;dicyclopropylmethan-1-ol;Cyclopropanemethanol, .alpha.-cyclopropyl-;Cyclopropanemethanol, a-cyclopropyl-;3GA978VBJ6;EINECS 238-236-3;dicyclopropylmethyl alcohol;Di(cyclopropyl)methanol;Dicyclopropylmethanol #;Methanol, dicyclopropyl-;UNII-3GA978VBJ6;SCHEMBL2329063;DTXSID10162284;Dicyclopropyl carbinol, AldrichCPR;alpha-cyclopropylcyclopropanemethanol;MFCD00019249;AKOS006229847;CS-0146055;FT-0624748;FT-0624750;.ALPHA.-CYCLOPROPYLCYCLOPROPANEMETHANOL;EN300-322042

Chemical Property of Dicyclopropylmethanol

Chemical Property:

• Vapor Pressure: 0.357mmHg at 25°C
• Refractive Index: n20/D 1.464
• Boiling Point: 175.3 °C at 760 mmHg
• PKA: 15.04±0.20(Predicted)
• Flash Point: 72.8 °C
• PSA: 20.23000
• Density: 1.172 g/cm³
• LogP: 1.16730
• Storage Temp.: 2-8°C
• Water Solubility.: Sparingly soluble in water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 112.088815002
• Heavy Atom Count: 8
• Complexity: 80.6

Purity/Quality:

99% ^*data from raw suppliers

Dicyclopropylmethanol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C(C2CC2)O
• Uses: Dicyclopropylmethanol is used as protecting group reagent for carboxylic acids; the formed esters are very mildly and selectively cleaved.

Technology Process of Dicyclopropylmethanol

There total 5 articles about Dicyclopropylmethanol 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: 89.0%

dicyclopropyl ketone (1121-37-5) → dicyclopropylmethanol (14300-33-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 1h;

DOI:10.1039/b503124a

Reference yield: 60.0%

cyclopropylmagnesium bromide (23719-80-4) + Cyclopropanecarboxaldehyde (1489-69-6) → dicyclopropylmethanol (14300-33-5)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201402524

Reference yield: 39.0%

dicyclopropyl ketone (1121-37-5) → dicyclopropylmethanol (14300-33-5) + 1.2-Methylen-decanon-(3) (618429-00-8) + 1,1-Dicyclopropyl-pentan-1-ol

Guidance literature:

With 18-crown-6 ether; In tetrahydrofuran; -78 deg C, then RT, quenching with water;

DOI:10.1021/ja00308a054

upstream raw materials:

dicyclopropyl ketone

cyclopropylmagnesium bromide

Cyclopropanecarboxaldehyde

Downstream raw materials:

4-bromo-1-cyclopropyl-1-butane

(Dicyclopropylmethyl)-triphenylphosphonium-bromid

bis(cyclopropyl)methylamine hydrochloride

Refernces

• 1、 Jaimes, Maria Camila Blanco,Ahrens, Alexander,Pfl?sterer, Daniel,Rudolph, Matthias,Hashmi, A. Stephen K.. "Synthesis of highly substituted γ-butyrolactones by a gold-catalyzed cascade reaction of benzyl esters". supporting information. p. 427 - 433. Retrieved 2015/02/18.
• 2、 Fifer, Nathan L.,White, Jonathan M.. "Determining the σ-donor ability of the cyclopropane C-C bond". . p. 1776 - 1780. Retrieved 2007/10/03.