14300-33-5

Basic information

• Product Name: DICYCLOPROPYLMETHANOL
• Synonyms: Cyclopropanemethanol, alpha-cyclopropyl-;DCPM-OH;DICYCLOPROPYL CARBINOL;DICYCLOPROPYLMETHANOL;Biscyclopropylmethanol;Dicyclopropylmethyl alcohol;Einecs 238-236-3;Dicyclopropyl carbinol 97%
• CAS NO: 14300-33-5
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• EINECS: 238-236-3
• Mol File: 14300-33-5.mol

Chemical Properties

• Boiling Point: 69 °C13 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: /
• Density: 0.951 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.357mmHg at 25°C
• Refractive Index: n20/D 1.464
• Storage Temp.: 2-8°C
• PKA: 15.04±0.20(Predicted)
• Water Solubility: Sparingly soluble in water.
• BRN: 2203215
• CAS DataBase Reference: DICYCLOPROPYLMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: DICYCLOPROPYLMETHANOL(14300-33-5)
• EPA Substance Registry System: DICYCLOPROPYLMETHANOL(14300-33-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 14300-33-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Dicyclopropylmethanol is used as a protecting group reagent for carboxylic acids. The formed esters provide a means to temporarily shield the carboxylic acid functionality during chemical reactions, preventing unwanted side reactions. This selective protection is particularly useful in multi-step synthesis processes, where the integrity of the carboxylic acid group must be maintained until a specific reaction step.
The mild and selective cleavage of the esters formed with dicyclopropylmethanol allows for the controlled deprotection of the carboxylic acid, ensuring minimal disruption to the rest of the molecule and facilitating the completion of the desired synthesis. This application is crucial in the development of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.

InChI:InChI=1/C7H12O/c8-7(5-1-2-5)6-3-4-6/h5-8H,1-4H2

Upstream product

• 1121-37-5 dicyclopropyl ketone 
• 23719-80-4 cyclopropylmagnesium bromide 
• 1489-69-6 Cyclopropanecarboxaldehyde 

Downstream Products

• 34188-88-0 (Dicyclopropylmethyl)-triphenylphosphonium-bromid 
• 51043-72-2 bis(cyclopropyl)methylamine hydrochloride 
• 802911-34-8 (2S,3S)-2-((2S,3R)-2-Amino-3-phenyl-butyrylamino)-3-methyl-pentanoic acid dicyclopropylmethyl ester 
• 802911-33-7 (2S,3S)-2-((2S,3R)-2-Benzyloxycarbonylamino-3-phenyl-butyrylamino)-3-methyl-pentanoic acid dicyclopropylmethyl ester 
• 1154472-19-1 4-benzyl-8-(1-dicyclopropylmethoxy)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine 
• 118285-30-6 (dicyclopropylmethoxy)acetic acid ethyl ester 

Relevant articles and documents

Synthesis of highly substituted γ-butyrolactones by a gold-catalyzed cascade reaction of benzyl esters

Easily accessible benzylic esters of 3-butynoic acids in a gold-catalyzed cyclization/rearrangement cascade reaction provided 3-propargyl γ-butyrolactones with the alkene and the carbonyl group not being conjugated. Crossover experiments showed that the formation of the new C-C bond is an intermolecular process. Initially propargylic-benzylic esters were used, but alkyl-substituted benzylic esters worked equally well. In the case of the propargylic- benzylic products, a simple treatment of the products with aluminum oxide initiated a twofold tautomerization to the allenyl-substituted g-butyrolactones with conjugation of the carbonyl group, the olefin, and the allene. The synthetic sequence can be conducted stepwise or as a one-pot cascade reaction with similar yields. Even in the presence of the gold catalyst the new allene remains intact.

CaSR ANTAGONIST

The present invention provides a compound having a calcium-sensitive receptor antagonistic action, a pharmaceutical composition containing the compound, particularly a calcium receptor antagonist and a therapeutic drug for osteoporosis. A compound represented by the following formula (1), a pharmaceutically acceptable salt thereof or an optically active form thereof: wherein each symbol is as defined in the description.

Determining the σ-donor ability of the cyclopropane C-C bond

The low temperature crystal structures of ester and ether derivatives of varying electron demand, derived from cyclopropylmethanol 8 and dicyclopropylmethanol 9, have been determined. These structures show a very strong response of the C-OR bond distance to the electron demand of the OR substituent, demonstrating the strong σ-donor ability of the strained C-C bonds in the cyclopropane ring. The Royal Society of Chemistry 2005.

Dimerization of Cyclopropanecarboxylic Acid Dianion and Thermal Decarboxylative Rearrangement of the Dimer to 2-Cyclopropyl-4,5-dihydrofuran

The dianion of cyclopropanecarboxylic acid (2) reacted with alkyl halides and deuterated water at temperatures below 0 deg C; however, self-condensation to the β-keto acid 3 was the only observed product at elevated temperatures.This observation contrasts the self-condensation of the ethyl ester where a trimeric diester alcohol is the product.Attempted mixed condensations of the dianion 2 and carboxylic acids without acidic α-protons did not proceed as well, 3 being the major product.Thermal decarboxylation of 3 did not yield the expected dicyclopropyl ketone; rather , a facile rearrangement in a sealed tube at 120 deg C occured, giving rise to 2-cyclopropyl-4,5-dihydrofuran.This "vinyl-cyclopropyl" type rearrangement does not occur through dicyclopropyl ketone or its enolate.