propargyl bromide Chemical Properties

Melting point:

-61°C

Boiling point:

97 °C

Density 

1.38 g/mL at 20 °C

refractive index 

n20/D 1.494

Flash point:

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 limits

ACGIH: 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)

InChIKey

YORCIIVHUBAYBQ-UHFFFAOYSA-N

CAS DataBase Reference

106-96-7(CAS DataBase Reference)

NIST Chemistry Reference

1-Propyne, 3-bromo-(106-96-7)

EPA Substance Registry System

Propargyl 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

F 

8

Hazard Note 

Highly Flammable/Toxic/Corrosive

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29033990

Hazardous Substances Data

106-96-7(Hazardous Substances Data)

MSDS

• Language:English Provider:3-Bromopropyne
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

propargyl bromide Usage And Synthesis

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.

Chemical Properties

yellow solution

Uses

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.

Uses

Propargyl Bromide is used in the synthesis of betulonic acid-peptide conjugates with anti-inflammatory activity. It is also used in the synthesis of PEG and peptide-grafted polyesters and make propargylic amines employed in enyne metathesis. Additionally, It is Employed in the propargylation of spiro ketones, allylic alcohols, and enone complexes.

Preparation

Add 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 Description

A 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 Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

3-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.

Hazard

Flammable, dangerous fire and explosion risk. Irritant.

Health Hazard

3-Bromopropyne is very toxic via the oral route. If inhaled, may be harmful; contact may cause burns to skin and eyes.

Fire Hazard

3-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

Pharmacology

Mode of action is considered to be reaction with nucleophiles in living organisms.

Safety Profile

A 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.

Metabolism

Reacts 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.

propargyl bromide(106-96-7)Related Product Information

• 3-Bromo-1-propanol
• Profenofos
• Sodium bromate
• Rocuronium bromide
• Propiolic Acid
• :(S)-2-Methyl-3-(2-propynyl)-4-oxocyclopent-2-enyl-(lR)-cis,trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
• Propyne
• PROPARGYLAMINE
• Propionyl bromide
• 3-Bromopropionic acid
• Ethidium bromide
• 3-BROMOPROPIONITRILE
• Dimidium bromide
• Allyl bromide
• Vecuronium bromide
• Propargyl alcohol
• Methyl bromide
• 1-BROMO-2-BUTYNE