2432-63-5

Basic information

• Product Name: Dipropyl cis-butenedioic acid
• Synonyms: 2-Butenedioicacid (2Z)-, dipropyl ester (9CI);2-Butenedioic acid (Z)-, dipropyl ester;Maleic acid, dipropyl ester (6CI,7CI,8CI);Di-n-propyl maleate;Dipropylmaleate
• CAS NO: 2432-63-5
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.2316
• EINECS: 219-408-7
• Mol File: 2432-63-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 258.4 °C at 760 mmHg
• Flash Point: 119.6 °C
• Appearance: /
• Density: 1.031 g/cm³
• Vapor Pressure: 0.0138mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: Dipropyl cis-butenedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Dipropyl cis-butenedioic acid(2432-63-5)
• EPA Substance Registry System: Dipropyl cis-butenedioic acid(2432-63-5)

Safety Data

• Hazardous Substances Data: 2432-63-5(Hazardous Substances Data)

Usage

General Description

Dipropyl cis-butenedioic acid, also known as citraconic acid, is a chemical compound with the molecular formula C7H10O4. It is a dicarboxylic acid with two carboxylic acid groups, and its structure includes a cis double bond between the central carbon atoms. Dipropyl cis-butenedioic acid is a colorless, crystalline solid that is soluble in water and organic solvents. It is used in various industrial applications, including as a precursor for the synthesis of polymers, resins, and plasticizers. It also has potential medical and pharmaceutical applications, such as in the production of malic acid, which is used as a food additive and in the synthesis of pharmaceuticals. Additionally, citraconic acid is used in the production of flavoring and fragrance compounds.

InChI:InChI=1/C10H16O4/c1-3-7-13-9(11)5-6-10(12)14-8-4-2/h5-6H,3-4,7-8H2,1-2H3/b6-5+

Upstream product

• 108-31-6 maleic anhydride 
• 71-23-8 propan-1-ol 
• 106-94-5 propyl bromide 
• 110-16-7 maleic acid 
• 24761-89-5 ⁿpropyl diazoacetate 

Downstream Products

• 321578-52-3 (+/-)-trans-9,10-dihydro-9,10-ethano-anthracene-dicarboxylic acid-(11.12)-dipropyl ester 
• 608-85-5 dipropyl ester of/the/ racemic 2,3-dibromo-succinic acid 
• 3700-91-2 dimethoxythiophosphorylsulfanyl-succinic acid dipropyl ester 

Relevant articles and documents

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Photoorganocatalytic synthesis of lactones: Via a selective C-H activation-alkylation of alcohols

Selective C-H activation is an area of growing importance in modern organic chemistry. Herein, we report our efforts in combining organocatalysis and photocatalysis for the development of a highly efficient and selective visible-light mediated protocol for the C-H activation and addition of various alcohols to a plethora of Michael acceptors, followed by a cyclization reaction leading to lactones, a repeatedly occurring motif in nature. Utilizing phenylglyoxylic acid as the photocatalyst and common household bulbs as the light source, we describe a versatile α-alkylation/lactonization of alcohols with α,β-unsaturated esters leading to products in excellent yields. The reaction mechanism was extensively studied.

Highly chemo- and stereoselective intermolecular coupling of diazoacetates to give cis-olefins by using Grubbs second-generation catalyst

Highly stereoselective formation of cis-2-ene-1,4-diesters by homo- and heterocoupling of α-diazoacetates in the presence of Grubbs second-generation catalyst is demonstrated. The dual reactivity of the catalyst in alkene metathesis and diazocoupling has been exploited in the synthesis of 12-26-membered macrocyclic dienyl dilactones by one-pot carbene dimerisation/ring-closing metathesis.