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762-21-0

762-21-0

Identification

  • Product Name:Diethyl acetylenedicarboxylate

  • CAS Number: 762-21-0

  • EINECS:212-095-8

  • Molecular Weight:170.165

  • Molecular Formula: C8H10O4

  • HS Code:29171990

  • Mol File:762-21-0.mol

Synonyms:2-Butynedioicacid, diethyl ester (9CI);Acetylenedicarboxylic acid, diethyl ester(6CI,7CI,8CI);Bis(carboethoxy)acetylene;Bis(ethoxycarbonyl)acetylene;Diethyl1,2-acetylenedicarboxylate;Diethylacetylenedicarboxylate;Diethyl acetylenedicarboxylic acid;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes:C

  • Signal Word:Danger

  • Hazard Statement:H314 Causes severe skin burns and eye damage

  • 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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  • Manufacture/Brand:TRC
  • Product Description:Diethyl acetylenedicarboxylate
  • Packaging:500mg
  • Price:$ 45
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Diethyl Acetylenedicarboxylate >96.0%(GC)
  • Packaging:250mL
  • Price:$ 527
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Diethyl Acetylenedicarboxylate >96.0%(GC)
  • Packaging:25mL
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Diethyl acetylenedicarboxylate
  • Packaging:25 g
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Diethyl acetylenedicarboxylate
  • Packaging:5 g
  • Price:$ 27
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diethyl acetylenedicarboxylate 95%
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  • Price:$ 23.3
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diethyl acetylenedicarboxylate for synthesis
  • Packaging:10 mL
  • Price:$ 44.58
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diethyl acetylenedicarboxylate for synthesis. CAS 762-21-0, molar mass 170.16 g/mol., for synthesis
  • Packaging:8415140010
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diethyl acetylenedicarboxylate 95%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diethyl acetylenedicarboxylate for synthesis. CAS 762-21-0, molar mass 170.16 g/mol., for synthesis
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Relevant articles and documentsAll total 10 Articles be found

Generating carbyne equivalents with photoredox catalysis

Wang, Zhaofeng,Herraiz, Ana G.,Del Hoyo, Ana M.,Suero, Marcos G.

, p. 86 - 91 (2018/02/09)

Carbon has the unique ability to bind four atoms and form stable tetravalent structures that are prevalent in nature. The lack of one or two valences leads to a set of species - carbocations, carbanions, radicals and carbenes - that is fundamental to our understanding of chemical reactivity. In contrast, the carbyne - a monovalent carbon with three non-bonded electrons - is a relatively unexplored reactive intermediate; the design of reactions involving a carbyne is limited by challenges associated with controlling its extreme reactivity and the lack of efficient sources. Given the innate ability of carbynes to form three new covalent bonds sequentially, we anticipated that a catalytic method of generating carbynes or related stabilized species would allow what we term an € assembly point' disconnection approach for the construction of chiral centres. Here we describe a catalytic strategy that generates diazomethyl radicals as direct equivalents of carbyne species using visible-light photoredox catalysis. The ability of these carbyne equivalents to induce site-selective carbon-hydrogen bond cleavage in aromatic rings enables a useful diazomethylation reaction, which underpins sequencing control for the late-stage assembly-point functionalization of medically relevant agents. Our strategy provides an efficient route to libraries of potentially bioactive molecules through the installation of tailored chiral centres at carbon-hydrogen bonds, while complementing current translational late-stage functionalization processes. Furthermore, we exploit the dual radical and carbene character of the generated carbyne equivalent in the direct transformation of abundant chemical feedstocks into valuable chiral molecules.

A 2- fluoro fumaric acid ester (formula I) and its preparation method and application

-

Paragraph 0045, (2017/01/23)

The invention discloses 2-fuloro fumarate (formula I) and a preparation method thereof. Experiments show that: the kinds of compounds are capable of effectively inhibiting NF-kB transcriptional activity introduced by TNF-alpha, and further are capable of treating diseases introduced by NF-kB, such as psoriasis, multiple sclerosis, arthritis, eye inflammation or allergy, asthma and lupus erythematosus, and can be used as an immunosuppressant for organ transplantation.

Propeller-Shaped D3h-Symmetric Macrocycles with Three 1,8-Diazaanthracene Blades as Building Blocks for Photochemically Induced Growth Reactions

Servalli, Marco,Gyr, Luzia,Sakamoto, Junji,Schlüter, A. Dieter

supporting information, p. 4519 - 4523 (2015/07/27)

The efficient synthesis of new D3h-symmetric propeller-shaped, double-decker compounds with three vertically standing diazaanthracene units arranged so as to allow for photochemically induced intermolecular growth reaction by [4+4] cycloaddition is presented. The propellers bear alkyl chains of four different lengths (ethyl, propyl, hexyl, dodecyl) to have flexibility in creating ordered arrays by packing them into single crystals, onto solid substrates or into mesophases. All propellers are obtained in only six steps and on a 50-200 mg scale. The sequence passes through the ditriflated 1,8-diazaanthracene derivatives 6 which are a very versatile building block for many purposes and were therefore synthesized on a 30 g scale. A new class of propeller-shaped macrocycles is accessible via a six-step procedure with overall yields ranging from 6-16%. These cyclophanes are equipped with 1,8-diazaanthracene units and are designed for photochemical growth reactions in two dimensions.

Molecular structures and preferred conformations of stabilized keto diester phosphonium ylides

Casta?eda, Fernando,Silva, Paul,Teresa Garland,Shirazi, Ata,Bunton, Clifford A.

experimental part, p. 284 - 291 (2011/12/13)

Triphenylphosphonium ylidic keto diesters with a nonylidic ester group, Ph3PC(CO2CH2CH3)COCO 2CH2CH3, 1, and Ph3PC(CO 2CH2CH3)COCH2CO2CH 2CH3, 2, have the keto group syn and the ylidic ester acyl group anti to phosphorus. Conformation of 2 is assigned by X-ray crystallography, while conformations of 1 and 2 are based on 1H and 13C NMR spectroscopy, and comparisons of acyl stretching frequencies with predicted values from HF and DFT methods. Thermolyses of 1 and 2 gave the expected acetylene derivatives in high yield, consistent with the syn keto conformation and in agreement with earlier observations of thermolyses of stabilized phosphonium ylides. Results from the X-ray spectrum of 2 confirm the proposed structure.

N-heterocyclic carbenes of indazole: Ring enlargement reactions by α-halo ketones and dehalogenations of vicinal dihalides

Schmidt, Andreas,Snovydovych, Bohdan,Gjikaj, Mimoza

experimental part, p. 2798 - 2804 (2009/04/05)

On decarboxylation, 1,2-dimethylindazolium-3-carboxylate forms the N-heterocyclic carbene, 1,2-dimethylindazol-3-ylidene, which deprotonates α-halo ketones. The resulting indazolium salt and the corresponding enolate form 1:1 adducts which undergo a ring enlargement to cinnolines. Reaction with 2-bromo-2,3-dihydro-1H-inden-1-one gives a 4- hydroxyspiro[cinnoline-3,2′-inden]-1′-one by ring enlargement reaction (X-ray crystal structure analysis). Vicinal dibromides undergo debromination under these conditions to give alkenes, and substrates with 1,2-dibromoethene partial structure give acetylenes. As 3-bromoindazole is found as the second product of this reaction, an E1cb mechanism, initiated by Br+ abstraction by the N-heterocyclic carbene of indazole, is suggested. Georg Thieme Verlag Stuttgart.

Process route upstream and downstream products

Process route

diethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate
29393-95-1

diethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
Conditions Yield
at 500 ℃; under 0.01 Torr;
63%
at 500 ℃; for 1h; under 0.001 - 0.1 Torr;
63 % Spectr.
ethanol
64-17-5

ethanol

Acetylenedicarboxylic acid
142-45-0

Acetylenedicarboxylic acid

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Conditions
Conditions Yield
With toluene-4-sulfonic acid; In 1,2-dichloro-ethane; toluene; for 20h; Reflux;
91%
With toluene-4-sulfonic acid; In benzene; for 16h; Inert atmosphere; Schlenk technique; Reflux; Dean-Stark;
77%
With sulfuric acid;
With hydrogenchloride;
With sulfuric acid;
With sulfuric acid; durch azeotrope Destillation mit Toluol;
diethyl 2,3-dibromomaleate
13677-32-2,608-83-3

diethyl 2,3-dibromomaleate

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Conditions
Conditions Yield
With 1,2-dimethyl-1H-indazol-2-ium-3-carboxylate; In acetonitrile; for 0.75h; Reflux; Inert atmosphere;
99%
With zinc; benzene;
diethyl 2,3-dibromo-fumarate
13677-32-2

diethyl 2,3-dibromo-fumarate

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Conditions
Conditions Yield
With 1,2-dimethyl-1H-indazol-2-ium-3-carboxylate; In acetonitrile; Reflux; Inert atmosphere;
99%
With diethyl ether; zinc; at 70 ℃;
ethanol
64-17-5

ethanol

acetylene dicarboxylic acid mono potassium salt
928-04-1

acetylene dicarboxylic acid mono potassium salt

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Conditions
Conditions Yield
With sulfuric acid; In benzene; for 24h; Heating;
95%
diethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate
29393-95-1

diethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Conditions
Conditions Yield
at 150 - 200 ℃;
(2,2'-bipyridine)(diethyl acetylenedicarboxylate)copper(I) hexafluorophosphate
137436-73-8

(2,2'-bipyridine)(diethyl acetylenedicarboxylate)copper(I) hexafluorophosphate

(diethyl acetylenedicarboxylate)bis{(2,2'-bipyridine)copper(I)} hexafluorophosphate
137436-80-7

(diethyl acetylenedicarboxylate)bis{(2,2'-bipyridine)copper(I)} hexafluorophosphate

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Conditions
Conditions Yield
In acetone; dissolving of (Cu(bpy)(DEAD))PF6 in acetone; addn. of hexane, pptn., filtration, two addnl. repptn., washing (hexane, 3 times), drying (vac., overnight); elem. anal.;
80%
(4,4'-dimethyl-2,2'-bipyridine)(diethyl acetylenedicarboxylate)copper(I) hexafluoroantimonate
137436-75-0

(4,4'-dimethyl-2,2'-bipyridine)(diethyl acetylenedicarboxylate)copper(I) hexafluoroantimonate

(diethyl acetylenedicarboxylate)bis{(4,4'-dimethyl-2,2'-bipyridine)copper(I)} hexafluoroantimonate
137436-82-9

(diethyl acetylenedicarboxylate)bis{(4,4'-dimethyl-2,2'-bipyridine)copper(I)} hexafluoroantimonate

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Conditions
Conditions Yield
In acetone; dissolving of (Cu(Me2bpy)(DEAD))SbF6 in acetone; addn. of hexane, pptn., filtration, two addnl. repptn., washing (hexane, 3 times), drying (vac., overnight); elem. anal.;
81%
(1-diazo-2-ethoxy-2-oxoethyl)(2-(2-ethoxy-2-oxoethoxy)carbonylphenyl)iodonium trifluoromethanesulfonate

(1-diazo-2-ethoxy-2-oxoethyl)(2-(2-ethoxy-2-oxoethoxy)carbonylphenyl)iodonium trifluoromethanesulfonate

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Conditions
Conditions Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; bis((1,1,1-trifluoro-N-(trifluoromethyl)sulfonyl)methylsulfonamido)zinc; at 25 ℃; for 2h; Irradiation;
1-(1-diazo-2-ethoxy-2-oxoethyl)-1,2-benziodoxol-3(1H)-one

1-(1-diazo-2-ethoxy-2-oxoethyl)-1,2-benziodoxol-3(1H)-one

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

Conditions
Conditions Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; bis((1,1,1-trifluoro-N-(trifluoromethyl)sulfonyl)methylsulfonamido)zinc; at 25 ℃; for 2h; Irradiation;

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