3-Butyn-1-yl chloroformate

Base Information

• Chemical Name: 3-Butyn-1-yl chloroformate
• CAS No.: 190774-49-3
• Molecular Formula: C5H5 Cl O2
• Molecular Weight: 132.546
• Hs Code.: 2915900090
• European Community (EC) Number: 626-048-8
• DSSTox Substance ID: DTXSID80398957
• Nikkaji Number: J1.464.096G
• Wikidata: Q82201224
• Mol file: 190774-49-3.mol

Synonyms:3-Butyn-1-yl chloroformate;190774-49-3;but-3-ynyl carbonochloridate;3-BUTYN-1-YL CHLOROFORMATE 98;BUT-3-YN-1-YL CARBONOCHLORIDATE;Carbonochloridic acid, 3-butyn-1-yl ester;(BUT-3-YN-1-YLOXY)(CHLORO)METHANONE;SCHEMBL1128347;DTXSID80398957;Chloroformic acid 3-butynyl ester;3-Butyn-1-yl chloroformate, 98%;BUT-3-YN-1-YLCARBONOCHLORIDATE;EN300-200046

Chemical Property of 3-Butyn-1-yl chloroformate

Chemical Property:

• Vapor Pressure: 1.78 psi ( 20 °C)
• Refractive Index: n20/D 1.443(lit.)
• Boiling Point: 149 °C(lit.)
• Flash Point: 135 °F
• PSA: 26.30000
• Density: 1.166 g/mL at 25 °C(lit.)
• LogP: 1.38510
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 131.9978071
• Heavy Atom Count: 8
• Complexity: 122

Purity/Quality:

99%min ^*data from raw suppliers

(but-3-yn-1-yloxy)(chloro)methanone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,C
• Statements: 23/24/25-34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCCOC(=O)Cl

Technology Process of 3-Butyn-1-yl chloroformate

There total 2 articles about 3-Butyn-1-yl chloroformate 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%

bis(trichloromethyl) carbonate (32315-10-9) + 3-Butyn-1-ol (927-74-2) → but-3-ynyl-1-oxycarbonyl chloride (190774-49-3)

Guidance literature:

bis(trichloromethyl) carbonate; 3-Butyn-1-ol; In tetrahydrofuran; at 0 - 20 ℃;

With pyridine; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

DOI:10.1002/anie.201807825

Reference yield:

phosgene (75-44-5) + 3-Butyn-1-ol (927-74-2) → but-3-ynyl-1-oxycarbonyl chloride (190774-49-3)

Guidance literature:

In benzene; Ambient temperature;

DOI:10.1021/jo00043a030

Reference yield: 93.0%

but-3-ynyl-1-oxycarbonyl chloride (190774-49-3) + aniline (62-53-3) → 1-methyl-3-butynyl phenylcarbamate

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane;

DOI:10.1016/j.tet.2007.06.066

upstream raw materials:

phosgene

3-Butyn-1-ol

bis(trichloromethyl) carbonate

Downstream raw materials:

O-but-3-yn-1-yl Se-phenyl selenocarbonate

α-cis-benzylidene-γ-butyrolactone

α-methylene-γ-butyrolactone

(E)-benzylidenedihydro-2(3H)-furanone

Refernces

• 1、 D'Ascenzio, Melissa,Pugh, Kathryn M.,Konietzny, Rebecca,Berridge, Georgina,Tallant, Cynthia,Hashem, Shaima,Monteiro, Octovia,Thomas, Jason R.,Schirle, Markus,Knapp, Stefan,Marsden, Brian,Fedorov, Oleg,Bountra, Chas,Kessler, Benedikt M.,Brennan, Paul E.. "An Activity-Based Probe Targeting Non-Catalytic, Highly Conserved Amino Acid Residues within Bromodomains". . p. 1007 - 1012. Retrieved 2019.
• 2、 Li, Fahui,Dong, Jianshu,Hu, Xiaosong,Gong, Weimin,Li, Jiasong,Shen, Jing,Tian, Huifang,Wang, Jiangyun. "A Covalent Approach for Site-Specific RNA Labeling in Mammalian Cells". supporting information. p. 4597 - 4602. Retrieved 2015/04/14.