1,4-Diacetoxy-2-butyne

Base Information

• Chemical Name: 1,4-Diacetoxy-2-butyne
• CAS No.: 1573-17-7
• Molecular Formula: C8H10 O4
• Molecular Weight: 170.165
• Hs Code.: 2915390090
• European Community (EC) Number: 216-394-4
• NSC Number: 76565
• DSSTox Substance ID: DTXSID40883697
• Nikkaji Number: J191.434K
• Wikidata: Q72462500
• Mol file: 1573-17-7.mol

Synonyms:1,4-Diacetoxy-2-butyne;1573-17-7;But-2-yne-1,4-diyl diacetate;2-Butyne-1,4-diol diacetate;Butynediol diacetate;4-acetyloxybut-2-ynyl acetate;2-Butyne-1,4-diol, diacetate;2-Butyne-1,4-diol, 1,4-diacetate;1,4-DIACETYL-2-BUTYNE-1,4-DIOL;NSC 76565;1,4-diacetoxy-but-2-yne;EINECS 216-394-4;4-(acetyloxy)but-2-yn-1-yl acetate;AI3-26931;But-2-yne-1,4-diyldiacetate;MFCD00014982;2-Butyne-1, diacetate;Bis(acetoxymethyl)acetylene;2-Butynediol-1,4-diacetate;ghl.PD_Mitscher_leg0.686;SCHEMBL487316;DTXSID40883697;NSC76565;4-(Acetyloxy)-2-butynyl acetate #;NSC-76565;2-Butyne-1,4-diol diacetate, 95%;AKOS005215912;AS-60941;B2087;FT-0664175;FT-0666329;D88893;J-009562

Chemical Property of 1,4-Diacetoxy-2-butyne

Chemical Property:

• Appearance/Colour: Orange Liquid
• Vapor Pressure: 0.042mmHg at 25°C
• Melting Point: 27-28°C
• Refractive Index: n20/D 1.454(lit.)
• Boiling Point: 122-123 °C10 mm Hg(lit.)
• Flash Point: 114.1°C
• PSA: 52.60000
• Density: 1.127g/cm³
• LogP: 0.11600
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 170.05790880
• Heavy Atom Count: 12
• Complexity: 208

Purity/Quality:

98% ^*data from raw suppliers

1,4-Diacetyl-2-butyne-1,4-diol ^*data from reagent suppliers

Safty Information:

• Statements: 10-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC#CCOC(=O)C
• Uses: 1.125 g/mL at 25 °C(lit. 1.125 g/mL at 25 °C(lit.)

Technology Process of 1,4-Diacetoxy-2-butyne

There total 11 articles about 1,4-Diacetoxy-2-butyne which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,3-dibromo-2(E)-butenylene diacetate (186697-76-7) → 2-butyn-1,4-diol diacetate (1573-17-7)

Guidance literature:

With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; tri-n-butyl-tin hydride; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(97)10203-4

Reference yield: 96.0%

1,4-dihydroxybut-2-yne (110-65-6) + acetic anhydride (108-24-7) → 2-butyn-1,4-diol diacetate (1573-17-7)

Guidance literature:

With lithium bis(perfluorooctylsulfonyl)amide; at 30 ℃; for 42h; Reagent/catalyst; Time; Catalytic behavior;

DOI:10.1080/00397911.2011.589563

Reference yield: 95.0%

1,4-dihydroxybut-2-yne (110-65-6) + acetyl chloride (75-36-5) → 2-butyn-1,4-diol diacetate (1573-17-7)

Guidance literature:

With sodium hydroxide; In dichloromethane; 1.) r.t., overnight. 2.) reflux, 2 h;

DOI:10.1021/jo00109a015

upstream raw materials:

1,4-dihydroxybut-2-yne

acetic acid

acetic anhydride

acetyl chloride

Downstream raw materials:

6-Acetyl-1,2,3,4-tetrahydronaphthalene

2-phenylnaphthalene

1-acetoxybut-3-en-2-one

butane-1,4-diol diacetate

Refernces

• 1、 Muchow, G.,Brunel, J. M.,Maffei, M.,Buono, G.. "Synthesis of 2,3-Bis(acetoxymethyl)bicyclohepta-2,5-diene and its Use in Palladium-Catalyzed Elimination". . p. 852 - 855. Retrieved 1995.
• 2、 Jiang, Bing,Liang, Qiu-Ju,Han, Yu,Zhao, Meng,Xu, Yun-He,Loh, Teck-Peng. "Copper-Catalyzed Dehydrogenative Diels-Alder Reaction". supporting information. p. 3215 - 3219. Retrieved 2018/06/11.
• 3、 Li, Guilong,Zhao, Gang. "Efficient acetylation of alcohols and phenols catalyzed by recyclable lithium bis(perfluoroalkylsulfonyl)imide". . p. 34 - 43,10. Retrieved 2020/08/24.