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Cas Database

4136-86-1

4136-86-1

Identification

  • Product Name:Butanedioic acid, butyl-, dimethyl ester

  • CAS Number: 4136-86-1

  • EINECS:

  • Molecular Weight:202.24800

  • Molecular Formula: C10H18O4

  • HS Code:2917190090

  • Mol File:4136-86-1.mol

Synonyms:

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 8 Articles be found

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

Miyamoto, Yusuke,Sumida, Yuto,Ohmiya, Hirohisa

supporting information, p. 5865 - 5870 (2021/07/31)

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.

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

Hashizume, Daisuke,Hosoya, Takamitsu,Nakamura, Kei,Ohmiya, Hirohisa,Sato, Yukiya,Sumida, Yuto

supporting information, p. 9938 - 9943 (2020/06/27)

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.

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

Guo, Wen-Di,Liu, Lei,Yang, Shu-Qing,Chen, Xiao-Chao,Lu, Yong,VO-Thanh, Giang,Liu, Ye

, p. 1376 - 1384 (2020/01/24)

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.

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

Yang, Da,Liu, Huan,Wang, Dong-Liang,Luo, Zhoujie,Lu, Yong,Xia, Fei,Liu, Ye

, p. 2588 - 2595 (2018/06/11)

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

Fagnoni, Maurizio,Mella, Mariella,Albini, Angelo

, p. 4026 - 4033 (2007/10/03)

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.

Process route upstream and downstream products

Process route

C<sub>22</sub>H<sub>20</sub>BO<sub>2</sub><sup>(1-)</sup>*Li<sup>(1+)</sup>

C22H20BO2(1-)*Li(1+)

dimethylfumarate
624-49-7

dimethylfumarate

dimethyl 2-butylsuccinate
4136-86-1

dimethyl 2-butylsuccinate

8,9-dioxa-8a-borabenzo[fg]tetracene

8,9-dioxa-8a-borabenzo[fg]tetracene

Conditions
Conditions Yield
In methanol; acetonitrile; at 20 ℃; for 14h; Inert atmosphere; Irradiation; Sealed tube; Glovebox;
31%
57%
tetra-n-butyltin(IV)
1461-25-2

tetra-n-butyltin(IV)

dimethyl cis-but-2-ene-1,4-dioate
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

dimethyl 2-butylsuccinate
4136-86-1

dimethyl 2-butylsuccinate

Conditions
Conditions Yield
With 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; In acetonitrile; Product distribution; Quantum yield; Irradiation; other alkylating agents, sensitizer; electron-transfer-photosensitized conjugate alkylation of alkenes and alkynes; competition experiments, relative efficiency of alkylation; quenching rate constants of different photosensitizers; mechanism;
80%
With TMPM; In acetonitrile; for 15h; Irradiation;
80%
With tetramethyl 1,2,4,5-benzenetetracarboxylate; In acetonitrile; for 15h; Irradiation;
76%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

hex-1-yne
693-02-7

hex-1-yne

dimethyl 2-butylsuccinate
4136-86-1

dimethyl 2-butylsuccinate

Conditions
Conditions Yield
With dichloro bis(acetonitrile) palladium(II); 4,5-bis(diphenylphosphanyl)-9,9-dimethyl-9H-xanthene-2,7-disulfonic acid; at 100 ℃; for 20h; under 7500.75 Torr; Sealed tube; Autoclave;
35 %Chromat.
With dichloro bis(acetonitrile) palladium(II); aluminium(III) triflate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; at 120 ℃; for 20h; under 7500.75 Torr; Autoclave;
36 %Chromat.
C<sub>21</sub>H<sub>20</sub>BNO<sub>2</sub>

C21H20BNO2

dimethylfumarate
624-49-7

dimethylfumarate

dimethyl 2-butylsuccinate
4136-86-1

dimethyl 2-butylsuccinate

Conditions
Conditions Yield
In methanol; acetonitrile; for 14h; Sealed tube; Inert atmosphere; Irradiation;
91%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

dimethyl 2-butylsuccinate
4136-86-1

dimethyl 2-butylsuccinate

Conditions
Conditions Yield
With sodium butyrate; copper dichloride; palladium dichloride;
methyl 2-iodoacetate
5199-50-8

methyl 2-iodoacetate

methyl hexanoate
106-70-7

methyl hexanoate

dimethyl 2-butylsuccinate
4136-86-1

dimethyl 2-butylsuccinate

Conditions
Conditions Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; Yield given. Multistep reaction; THF, hexane, -78 deg C;
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

hex-1-yne
693-02-7

hex-1-yne

dimethyl 2-butylsuccinate
4136-86-1

dimethyl 2-butylsuccinate

dimethyl 2-butylmaleate
36122-38-0

dimethyl 2-butylmaleate

3-n-butyl-2(5H)-furanone
71725-42-3

3-n-butyl-2(5H)-furanone

(E)-2-Butyl-but-2-enedioic acid dimethyl ester
89590-27-2

(E)-2-Butyl-but-2-enedioic acid dimethyl ester

Conditions
Conditions Yield
With I; at 20 ℃; for 8h; Yield given. Further byproducts given. Yields of byproduct given;
methanol
67-56-1

methanol

n-butylsuccinic acid
1457-39-2

n-butylsuccinic acid

dimethyl 2-butylsuccinate
4136-86-1

dimethyl 2-butylsuccinate

Conditions
Conditions Yield
With sulfuric acid;
dimethyl 2-butylsuccinate
4136-86-1

dimethyl 2-butylsuccinate

Conditions
Conditions Yield

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  • SAGECHEM LIMITED
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-571-86818502
  • Emails:will@sagechem.com
  • Main Products:28
  • Country:China (Mainland)
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