Propargyl bromide

Base Information

• Chemical Name: Propargyl bromide
• CAS No.: 106-96-7
• Deprecated CAS: 1009031-47-3,1187488-61-4,1802649-19-9
• Molecular Formula: C3H3Br
• Molecular Weight: 118.961
• Hs Code.: 29033990
• European Community (EC) Number: 203-447-1
• NSC Number: 8801
• UN Number: 2345
• UNII: F3H7ZXK9ZU
• DSSTox Substance ID: DTXSID3042340
• Nikkaji Number: J5.054G
• Wikipedia: Propargyl_bromide
• Wikidata: Q7250094
• Mol file: 106-96-7.mol

Synonyms:3-bromopropyne;propargyl bromide

Chemical Property of Propargyl bromide

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 64.6mmHg at 25°C
• Melting Point: -61°C
• Refractive Index: 1.4940
• Boiling Point: 90 °C at 760 mmHg
• Flash Point: 17.1 °C
• PSA: 0.00000
• Density: 1.586 g/cm³
• LogP: 1.01450
• Storage Temp.: Refrigerator
• Sensitive.: Light Sensitive
• Water Solubility.: Miscible with ethanol, ether, benzene, carbon tetrachloride and chloroform. Immiscible with water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 117.94181
• Heavy Atom Count: 4
• Complexity: 38.5
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

PropargylBromide(StablizedwithMgO) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T,C
• Statements: 60-61-20/21-25-63-36/37/38-11-67-65-48/20
• Safety Statements: 53-16-36/37/39-45-37/39-28A-26-62-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Fumigants
• Canonical SMILES: C#CCBr
• Uses: Propargyl Bromide is used in the synthesis of betulonic acid-peptide conjugates with anti-inflammatory activity. Also used in the synthesis of PEG and peptide-grafted polyesters. Used to make propargylic amines employed in enyne metathesis.1Employed in the propargylation of spiro ketones,2 allylic alcohols,3 and enone complexes.4 Propargyl bromide, 80% in toluene is used to prepare betulonic acid-peptide conjugates with anti-inflammatory activity and propargylic amines employed in enyne metathesis. It finds application in the propargylation of spiro ketones, allylic alcohols and enone complexes. In Barbier-type reaction, it reacts with aldehydes to give alkyne alcohols. It is actively involved in the synthesis of polyethylene glycol (PEG) and peptide-grafted polyesters. Used to make propargylic amines employed in enyne metathesis.Employed in the propargylation of spiro ketones, allylic alcohols, and enone complexes.
• Description: Propargyl bromide is a Shock sensitive liquid, lachrymator. Supplied as an 80% solution in toluene stabilized with magnesium oxide. Alternative formulations are currently under development.

Technology Process of Propargyl bromide

There total 37 articles about Propargyl bromide 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: 88.0%

propargyl alcohol (107-19-7) → propargyl bromide (106-96-7)

Guidance literature:

With carbon tetrabromide; sodium bromide; In N,N-dimethyl-formamide; for 3h; Catalytic behavior; Irradiation;

DOI:10.1039/c5cc03067f

Reference yield: 78.81%

propargyl alcohol (107-19-7) → bromoallene (10024-18-7) + propargyl bromide (106-96-7) + 1,3-dibromopropene (627-15-6) + 2-bromoallyl bromide (513-31-5)

Guidance literature:

With phosphorus tribromide; In toluene; at 0 - 50 ℃; for 3.25h; Product distribution / selectivity;

Reference yield: 64.37%

propargyl alcohol (107-19-7) → propargyl bromide (106-96-7) + 1,3-dibromopropene (627-15-6) + 2-bromoallyl bromide (513-31-5)

Guidance literature:

With phosphorus tribromide; In isopar C; at 6 - 50 ℃; for 3.71667h; Product distribution / selectivity;

upstream raw materials:

bromocyane

N-methyl-N-propargylaniline

propargyl p-toluenesulfonate

propargyl alcohol

Downstream raw materials:

1-(prop-2-yn-1-yl)piperidine

N-propargylmorpholine

3-(prop-2-yn-1-yl)quinazolin-4(3H)-one

N-Propargyl-2-benzothiazolon

Refernces

• 1、 Seyferth, Dietmar,Jula, Theodore F.. "Trimethylhalosilane elimination from trimethylsilylsubstituted gem-dihalocyclopropanes". . p. 109 - 114. Retrieved 1968.
• 2、 Zhang, Qian,Chen, Ying,Xia, Peng,Xia, Yi,Yang, Zheng-Yu,Yu, Donglei,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung. "Anti-AIDS agents. Part 62: Anti-HIV activity of 2′-substituted 4-methyl-3′,4′-di-O-(-)-camphanoyl-(+)-cis-khellactone (4-methyl DCK) analogs". . p. 5855 - 5857. Retrieved 2004.
• 3、 Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.. "Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method". supporting information. p. 4176 - 4182. Retrieved 2021/02/01.
• 4、 Ogiwara, Yohei,Sato, Kazuya,Sakai, Norio. "Palladium-catalyzed cyclization of alkynoic acids to form vinyl dioxanones bearing a quaternary allylic carbon". supporting information. p. 5296 - 5299. Retrieved 2017/11/06.