140-65-8

Basic information

• Product Name: pramocaine
• Synonyms: pramocaine;4-(3-(4-BUTOXYPHENOXY)PROPYL)-MORPHOLINE;4-[3-(4-Butoxyphenoxy)propyl]morphorine;Proxazocain;Tronopthane;Tronothane;Tronotene;Pramoxin
• CAS NO: 140-65-8
• Molecular Formula: C₁₇H₂₇NO₃
• Molecular Weight: 293.404
• EINECS: 205-425-7
• Product Categories: research chemical
• Mol File: 140-65-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: bp6 196°; bp2.8 183-184°
• Flash Point: 123.5°C
• Appearance: /
• Density: 1.0112 (rough estimate)
• Vapor Pressure: 1.7E-07mmHg at 25°C
• Refractive Index: 1.5420 (estimate)
• PKA: 7.18±0.10(Predicted)
• Water Solubility: 3.574mg/L(22.5 oC)
• CAS DataBase Reference: pramocaine(CAS DataBase Reference)
• NIST Chemistry Reference: pramocaine(140-65-8)
• EPA Substance Registry System: pramocaine(140-65-8)

Safety Data

• Hazardous Substances Data: 140-65-8(Hazardous Substances Data)

Usage

Description

Pramocaine, also known as Tronothane, is a member of the morpholine class of compounds. It is characterized by a morpholine molecule substituted at the nitrogen atom by a 3-(4-butoxyphenoxy)propyl group. Pramocaine is a pharmaceutical compound with anesthetic properties, making it a valuable asset in the medical field.

Uses

Used in Medical Applications:
Pramocaine is used as a topical anesthetic for local pain relief during minor medical procedures, such as injections, venipuncture, and wound cleaning. Its anesthetic properties help to numb the area, reducing discomfort and pain experienced by patients.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, pramocaine is used as an active ingredient in various formulations, such as creams and ointments, under the brand names Tronolane (Ross) and Tronothane (Abbott). These products are specifically designed to provide localized pain relief and are widely used in medical practices for their effectiveness and safety.

Originator

Tronothane, Abbott, US ,1954

Manufacturing Process

About 5.6 g of potassium hydroxide is dissolved in about 150 cc of refluxing ethanol, and then about 16.6 g of hydroquinone monobutyl ether is added to the alcoholic solution. When the hydroquinone is dissolved, about 16.3 g of γmorpholinopropyl chloride (dissolved in a small amount of ethanol) is added to the refluxing solution. The solution is refluxed for about 24 hours and then cooled. The product is recovered by filtering the reaction mixture and then removing the solvent by vacuum distillation. The oily residue is acidified and shaken with ether. The acidic phase is made strongly alkaline with 40% sodium hydroxide, and the oil which separates is extracted into ether. The ethereal phase is dried, and the solvent removed by vacuum distillation. The product distills at 183° to 184°C at a pressure of 2.8 mm. The hydrochloride salt of the foregoing base is prepared by dissolving the base in ether and acidifying with hydrochloric acid and is found to have a MP of 181° to 183°C.

Therapeutic Function

Local anesthetic

InChI:InChI=1/C17H27NO3/c1-2-3-12-20-16-5-7-17(8-6-16)21-13-4-9-18-10-14-19-15-11-18/h5-8H,2-4,9-15H2,1H3

Upstream product

• 7357-67-7 4-(3-chloropropyl)morpholine 
• 122-94-1 4-n-butoxyphenol 
• 4441-30-9 3-morpholin-4-ylpropan-1-ol 
• 2372-45-4 sodium butanolate 
• 106-41-2 4-bromo-phenol 
• 39969-57-8 1-bromo-4-butoxybenzene 
• 110-91-8 morpholine 

Relevant articles and documents

Synthetic method 4 - alkoxyphenol compounds

The invention discloses a synthetic method of 4 - alkoxyphenol compounds, and belongs to the field of organic chemical synthesis. The method is as follows: An aryl alkyl ether compound is added to the sealing tube. The catalyst dimerization acetic acid rhodium and the oxidizing agent iodobenzene diethyl ester are added, a solvent trifluoroacetic anhydride is added, and the 4 -alkoxyphenol compound is prepared by heating reaction. To the invention, high regioselectivity direct hydroxylation of the aryl alkyl ether compound is realized, the application range of the substrate is wide, the yield is high, the activity after amplification reaction does not significantly decay, and higher yield is still obtained. The utility model has good practicability and industrial application prospect.

Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound

The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.

Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction

A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.