4136-86-1

Basic information

• Product Name: 2-Butylsuccinic acid dimethyl ester
• Synonyms: 2-Butylsuccinic acid dimethyl ester;Hexane-1,2-dicarboxylic acid dimethyl ester
• CAS NO: 4136-86-1
• Molecular Formula: C10H18O4
• Molecular Weight: 0
• Mol File: 4136-86-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Butylsuccinic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butylsuccinic acid dimethyl ester(4136-86-1)
• EPA Substance Registry System: 2-Butylsuccinic acid dimethyl ester(4136-86-1)

Safety Data

• Hazardous Substances Data: 4136-86-1(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 1457-39-2 n-butylsuccinic acid 
• 5199-50-8 methyl 2-iodoacetate 
• 106-70-7 methyl hexanoate 
• 1461-25-2 tetra-n-butyltin(IV) 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 201230-82-2 carbon monoxide 
• 693-02-7 hex-1-yne 
• 624-49-7 dimethylfumarate 
• 592-41-6 1-hexene 

Relevant articles and documents

Generation of Functionalized Alkyl Radicals via the Direct Photoexcitation of 2,2′-(Pyridine-2,6-diyl)diphenol-Based Borates

A new type of alkylborate was developed for the purpose of generating radicals via direct photoexcitation. These borates were prepared using 2,2′-(pyridine-2,6-diyl)diphenol as a tridentate ligand together with organoboronic acids or potassium trifluoroborates. The ready availability of organoboron compounds is a significant advantage of this direct photoexcitation protocol. The excited states of these borates can also serve as strong reductants, enabling various transformations.

Synergetic Catalysis for One-pot Bis-alkoxycarbonylation of Terminal Alkynes over Pd/Xantphos?Al(OTf)3 Bi-functional Catalytic System

Tandem bis-alkoxycarbonylation of alkynes allows for the preparation of 2-substituted succinates from alkynes and nucleophile alcohol via two successive alkoxycarbonylation with advantages of 100 % atomic economy and simplified one-pot operation. Herein, the one-pot tandem bis-alkoxycarbonylation of alkynes was accomplished over the bi-functional catalytic system containing Xantphos-modified Pd-complex and Lewis super-acid of Al(OTf)3. It was found that, via the synergetic catalysis, the involved Xantphos-modified Pd-complex was responsible for the activation of CO and the alkynes through coordination to Pd-center while Al(OTf)3 was in charge of the activation of the alcohol to facilitate the formation of [Pd?H]+ active species. The in situ high-pressure FT-IR analysis, coupled with 1H/13C NMR spectral characterizations, confirmed that the introduced Al(OTf)3 with intensive oxophilicity (via acid-base pair interaction) was able to activate nucleophilic MeOH to be a reliable proton-donor (i. e. hydride-source) to warrant the formation and stability of [Pd?H]+ species upon the oxidation of Pd0 by H+ (Pd0+H+→[PdII?H]+). Over the developed bi-functional catalytic system, the yields of the target diesters were obtained in the range of 36～86 % in this sequence with the wide substrate scope.

Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate

The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excitation of a boracene-based alkylborate. This system is based on the photophysical properties of the organoboron molecule. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond formations such as alkyl-aryl cross-coupling or vicinal alkylarylation of alkenes, enabling the introduction of various C(sp3) fragments to organic molecules.

Co-catalysis over a bi-functional ligand-based Pd-catalyst for tandem bis-alkoxycarbonylation of terminal alkynes

A bi-functional ligand (L1) containing a diphosphino fragment and sulfonic acid group (-SO3H) enabled PdCl2(MeCN)2 to efficiently catalyze the tandem bis-alkoxycarbonylation of terminal alkynes to produce aryl-/alkyl-substituted succinate (α,ω-diesters). It was found that the -SO3H incorporated in L1 indispensably assisted the Pd-catalyst in accomplishing this tandem reaction via intramolecular synergic effects. Co-catalysis over the L1-based Pd-catalyst was not due to the physical mixture of Xantphos and MeSO3H. In situ FTIR analysis verified that the formation and stability of Pd-H active species were facilitated by the presence of L1. The formation of stabilized diacylpalladium intermediate (F) was the critical driving force for the second-step methoxycarbonylation. DFT calculation was carried out to optimize the geometric structure of F, which indicated that the developed intramolecular O?H hydrogen bonds were an important structural feature to stabilize F. In addition, the L1-based Pd-catalyst could be recycled successfully for at least 3 runs in the ionic liquid [Bmim]NTf2 without obvious activity loss and detectable metal leaching.

Electron-Transfer-Photosensitized Conjugate Alkylation

Photoinduced electron transfer (PET) from an aliphatic donor to a sensitizer and fragmentation of the radical cation leads to alkyl radicals. Radical alkylation of electron-withdrawing substituted alkenes and alkynes has been obtained in this way, and its scope has been explored. Effective sensitizers are tetramethyl pyromellitate (TMPM), 1,4-dicyanonaphthalene (in combination with biphenyl, DCN/BP), and 1,2,4,5-tetracyanobenzene. Radical precursors are tetraalkylstannanes, 2,2-dialkyldioxolanes, and, less efficiently, carboxylic acids. Steady-state and flash photolysis experiments show that escape out of cage of radical ions is the main factor determining the yield of radical formation. This is efficient with triplet sensitizers such as TMPM, while with singlet sensitizers, the use of a "cosensitizer" is required, as in the DCN/BP system. Radical cations containing primary alkyl radicals escape and fragment more efficiently than those containing tertiary radicals. The thus-formed radicals are trapped by electron-withdrawing substituted alkenes, and the relative efficiency is determined by the rate of radical addition, in accord with the proposed mechanism. Among the alkynes tested, only dimethyl acetylenedicarboxylate reacts, and the order of radical reactivity is different. It is suggested that a different mechanism operates in this case and involves assistance by the alkyne to the radical cation fragmentation.

Combined oxidative and reductive carbonylation of terminal alkynes with palladium iodide-thiourea catalysts

Oxidative carbonylation of alkynes can be carried out catalytically in the absence of added oxidants if it is coupled with a reductive carbonylation process at the expense of the same alkyne involved in the oxidative process.Maleic esters (from oxidative carbonylation) and unsaturated lactones (from reductive carbonylation) are the main products formed under the catalytic action of palladium iodide complexes with thiourea (tu).A complex, formally corresponding to the ionic formula I, allows the reaction of alkylacetylenes at room temperature and atmospheric pressure.With activated alkynes such as phenylacetylene, or with alkynes containing coordinating groups, other palladium complexes with two or four molecules of thiourea are also active, although to a lesser extent.Identification of the organic by-products gives a hint of the mechanism by which coupling of oxidative and reductive carbonylation occurs.Keywords: Palladium; Alkynes; Oxidative carbonylation; Reductive carbonylation; Catalysis, Thiourea

Radical addition to alkenes via electron transfer photosensitization

A method for radical addition to alkenes is reported which is based on the photosensitized oxidation of a tetraalkylstannane by an excited acceptor (A*), fragmentation of the radical cation, and addition of the thus formed radical to an electron-withdrawing substituted alkene (acrylonitrile and dimethyl maleate). Aromatic nitriles and esters can be used as the electron acceptors, and they are chosen in such a way that their radical anion (A?-) reduces the adduct (and not the educt) radical. In this way the adduct radical is reduced and protonated to yield the end product, and the acceptor functions as a nonconsumed electron transfer sensitizer. In several cases the alkylation occurs more efficiently in the presence of a secondary donor (phenanthrene or biphenyl). However, when the acceptor is too easily reduced in the ground state (as with 1,2,4,5-benzenetetracarbonitrile), coupling of the adduct radical with A?- competes with its reduction.