3-Bromopropyne

3-Bromopropyne Basic information
Uses
Product Name:3-Bromopropyne
Synonyms:G-BROMOALLYLENE;3-BROMO-1-PROPYNE;3-BROMOPROPYNE;1-Brom-2-propin;1-Bromo-2-propyne;2-Propynyl bromide;3-bromo-1-propyn;3-bromo-propyn
CAS:106-96-7
MF:C3H3Br
MW:118.96
EINECS:203-447-1
Product Categories:Alkynes;Building Blocks;Acetylenes;Functionalized Acetylenes;Chemical Synthesis;Organic Building Blocks;ALKYL BROMIDE;Terminal;Electronic Chemicals;Materials Science;Micro/NanoElectronics;Others;pharmaceutical;106-96-7;bc0001
Mol File:106-96-7.mol
3-Bromopropyne Structure
3-Bromopropyne Chemical Properties
Melting point -61°C
Boiling point 97 °C
density 1.38 g/mL at 20 °C
refractive index n20/D 1.494
Fp 65 °F
storage temp. 2-8°C
solubility Chloroform, Methanol (Slightly)
form Liquid
color Colorless - Yellow
Water Solubility Miscible with ethanol, ether, benzene, carbon tetrachloride and chloroform. Immiscible with water.
Sensitive Light Sensitive
BRN 605309
Exposure limitsACGIH: TWA 20 ppm
OSHA: Ceiling 300 ppm; TWA 200 ppm
NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3)
InChIKeyYORCIIVHUBAYBQ-UHFFFAOYSA-N
CAS DataBase Reference106-96-7(CAS DataBase Reference)
NIST Chemistry Reference1-Propyne, 3-bromo-(106-96-7)
EPA Substance Registry SystemPropargyl bromide (106-96-7)
Safety Information
Hazard Codes F,T,C
Risk 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
RIDADR UN 2345 3/PG 2
WGK Germany 3
RTECS UK4375000
8
Hazard Note Highly Flammable/Toxic/Corrosive
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29033990
Hazardous Substances Data106-96-7(Hazardous Substances Data)
MSDS Information
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3-Bromopropyne English
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3-Bromopropyne Usage And Synthesis
UsesPropargyl 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.
DescriptionPropargyl bromide is a Shock sensitive liquid, lachrymator. Supplied as an 80% solution in toluene stabilized with magnesium oxide. Alternative formulations are currently under development.
Chemical Propertiesyellow solution
UsesUsed to make propargylic amines employed in enyne metathesis.1Employed in the propargylation of spiro ketones,2 allylic alcohols,3 and enone complexes.4
UsesPropargyl 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.
UsesUsed to make propargylic amines employed in enyne metathesis.
Employed in the propargylation of spiro ketones, allylic alcohols, and enone complexes.
PreparationAdd hydrogen bromide and solvent into the reaction flask, in the presence of CuBr and Cu catalyst, add propargyl alcohol dropwise with stirring, after the drop is completed, the temperature is slightly raised to react, and then post-processing, rectification to obtain bromopropane. alkyne. Reaction equation: CH≡C-CH2OH+HBr→CH≡C-CH2Br+H2O or the product can also be obtained by reacting propargyl alcohol with (PhO)3PBr2 in the presence of pyridine.
It is derived from the reaction of propargyl alcohol with phosphorus bromide. The propargyl alcohol was added to pyridine under cooling, and phosphorus tribromide was slowly added dropwise with stirring at -5°C, and the reaction temperature was maintained below 0°C. After the addition was completed, stirring was continued for 15 min. Then, vacuum distillation is performed to collect all the distillate, and fractional distillation is carried out again under normal pressure to obtain the finished product. Or add a small amount of pyridine to dry propargyl alcohol, add phosphorus tribromide and a small amount of pyridine solution dropwise at 0 °C under stirring, stir for 20 min after dropping, and distill under reduced pressure to obtain the product. Reaction equation: CH≡C-CH2OH+PBr3→CH≡C-CH2Br
Synthesis Reference(s)Tetrahedron Letters, 4, p. 483, 1963 DOI: 10.1039/jr9630005127
General DescriptionA colorless to light yellow liquid substance with a sharp odor. Flash point 65°F. Denser than water and insoluble in water. Vapors are heavier than air. May be irritating to skin and eyes. Used to make other chemicals. 3-Bromopropyne may decompose explosively with mild shock.
Air & Water ReactionsHighly flammable. Insoluble in water.
Reactivity Profile3-Bromopropyne is soluble in alcohol, ether, chloroform, carbon tetrachloride and carbon disulfide. 3-Bromopropyne is highly flammable and a dangerous fire risk, sensitive to shock. 3-Bromopropyne is used in organic syntheses, preparation of resins and perfume intermediates [Hawley]. There is a high danger of formation of explosive metal acetylides, when 3-Bromopropyne comes in contact with copper, high-copper alloys, mercury, or silver.
HazardFlammable, dangerous fire and explosion risk. Irritant.
Health Hazard3-Bromopropyne is very toxic via the oral route. If inhaled, may be harmful; contact may cause burns to skin and eyes.
Fire Hazard3-Bromopropyne detonates at 428F or more; ignites by impact. Emits highly toxic fumes of bromides when heated to decomposition. Reacts vigorously with oxidizing materials. Becomes shock-sensitive when mixed with chloropicrin. Unstable, avoid heat, flame, shock, and other chemicals
PharmacologyMode of action is considered to be reaction with nucleophiles in living organisms.
Safety ProfileA poison by ingestion. A dangerous fire hazard when exposed to heat or flame. The aerated liquid may be ignited by pressure. A dangerous, extremely shock-sensitive explosive. It can detonate when heated to 22O°C, by impact (especially when mixed with chloropicrin), or when heated whde confined. May explode on contact with copper, high copper alloys, mercury, or silver. Mixtures with trichloronitromethane are shockand heat- sensitive explosives. Can react vigorously with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits highly toxic fumes of Br-. See also ACETYLENE COMPOUNDS and BROMIDES.
MetabolismReacts slowly with water to yield propargyl alcohol and bromide ion. It is expected to move as a typical fumigant through the soil. Probably not an ozone-depleting substance due to decomposition on absorption of ultraviolet light.
rich-d-t-Prallethrin Propionyl bromide 3-Bromo-1-propanol Rocuronium bromide Propyne 3-Bromopropyne Vecuronium bromide Propargyl alcohol Sodium bromate :(S)-2-Methyl-3-(2-propynyl)-4-oxocyclopent-2-enyl-(lR)-cis,trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate 3-Bromopropionic acid 3-BROMOPROPIONITRILE Ethidium bromide Allyl bromide Propiolic Acid Profenofos PROPARGYLAMINE Methyl bromide

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