Methyl 3-bromopropiolate

Base Information

• Chemical Name: Methyl 3-bromopropiolate
• CAS No.: 23680-40-2
• Molecular Formula: C4H3 Br O2
• Molecular Weight: 162.971
• Hs Code.: 2916190090
• European Community (EC) Number: 868-303-8
• NSC Number: 163453
• DSSTox Substance ID: DTXSID90303911
• Nikkaji Number: J450.273F
• Wikidata: Q82049415
• Mol file: 23680-40-2.mol

Synonyms:methyl 3-bromopropiolate;23680-40-2;methyl 3-bromoprop-2-ynoate;Methyl 3-bromo-2-propynoate;methyl 3-bromopropynoate;2-Propynoic acid, 3-bromo-, methyl ester;methyl bromopropiolate;3-bromo-2-propynoic acid methyl ester;MFCD22989330;Methyl-3-bromopropiolate;Methyl bromopropylate;methyl bromopropynoate;methyl3-bromopropiolate;3-Bromo methyl propiolate;SCHEMBL5226186;bromo-propynoic acid methyl ester;DTXSID90303911;PITMUHRRCBFULF-UHFFFAOYSA-N;NSC163453;AKOS004910484;DS-6734;NSC-163453;3-bromo-prop-2-ynoic acid methyl ester;SY039726;A4940;CS-0043861;FT-0760793;EN300-90648;O11909

Chemical Property of Methyl 3-bromopropiolate

Chemical Property:

• Vapor Pressure: 3.89mmHg at 25°C
• Melting Point: 20oC
• Boiling Point: 150.2°Cat760mmHg
• Flash Point: 44.6°C
• PSA: 26.30000
• Density: 1.723g/cm³
• LogP: 0.51520
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 161.93164
• Heavy Atom Count: 7
• Complexity: 127

Purity/Quality:

99% ^*data from raw suppliers

Methyl3-bromopropiolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C#CBr

Technology Process of Methyl 3-bromopropiolate

There total 3 articles about Methyl 3-bromopropiolate 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: 98.0%

propynoic acid methyl ester (922-67-8) → methyl 3-bromopropiolate (23680-40-2)

Guidance literature:

With N-Bromosuccinimide; silver nitrate; In acetone; at 20 - 32 ℃;

Reference yield: 88.0%

N-Bromosuccinimide (128-08-5) + propynoic acid methyl ester (922-67-8) → methyl 3-bromopropiolate (23680-40-2)

Guidance literature:

With silver nitrate; In acetone; at 20 ℃; for 6h;

Reference yield: 75.0%

methanol (67-56-1) + 3-bromopropiolic acid (16900-53-1) → methyl 3-bromopropiolate (23680-40-2)

Guidance literature:

With sulfuric acid;

DOI:10.1016/0040-4020(80)87021-9

upstream raw materials:

methanol

3-bromopropiolic acid

propynoic acid methyl ester

N-Bromosuccinimide

Downstream raw materials:

methyl-5 heptene-4 yne-2 oate de methyle (Z)

(Z)-3-Chloro-4,5-dimethyl-hexa-2,5-dienoic acid methyl ester

2-Chloro-3,4,4-trimethyl-cyclobut-1-enecarboxylic acid methyl ester

5-Dimethylaminomethyl-2-[1-methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-oxazolidin-3-ium; bromide

Refernces

• 1、 Shinohara, Hiroyuki,Sonoda, Motohiro,Hayagane, Naoya,Kita, Shota,Tanimori, Shinji,Ogawa, Akiya. "Silica gel-promoted convenient synthesis of 2-bromo-3-hydroxybenzoate derivatives". . p. 5302 - 5305. Retrieved 2014.
• 2、 Bernardes, Gon?alo J. L.,Corzana, Francisco,Gil de Montes, Enrique,Hoyt, Emily A.,Istrate, Alena,Jiménez-Moreno, Ester,Jiménez-Osés, Gonzalo,Moreno-Vargas, Antonio J.,Navo, Claudio D.,Robina, Inmaculada. "Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation". supporting information. p. 6196 - 6200. Retrieved 2020/02/25.
• 3、 -. "5-HYDROXY-7-OXABICYCLO[2.2.1]HEPTANE-2-CARBOXAMIDE DERIVATIVES FOR INDUCING CHONDROGENESIS FOR TREATING JOINT DAMAGE". Page/Page column 26. . Retrieved 2020/07/05.