Conditions | Yield |
---|---|
With carbon tetrabromide; sodium bromide In N,N-dimethyl-formamide for 3h; Catalytic behavior; Irradiation; | 88% |
With tetradecafluorohexane; phosphorus tribromide In diethyl ether at 20℃; for 12h; | 80% |
With phosphorus tribromide 1.) 50 deg C - 60 deg C, 2.) reflux, 1 h; | 59% |
propargyl alcohol
A
bromoallene
B
propargyl bromide
C
1,3-dibromopropene
D
2-bromoallyl bromide
Conditions | Yield |
---|---|
With phosphorus tribromide In toluene at 0 - 50℃; for 3.25h; Product distribution / selectivity; | A 1.38% B 78.81% C 3.17% D 14.78% |
With phosphorus tribromide In isopar C at 6 - 50℃; for 3.71667 - 33.5833h; Product distribution / selectivity; | A 1.22% B 62.1% C 2.88% D 10.14% |
Conditions | Yield |
---|---|
at 400℃; flash vacuum pyrolysis; | A 65% B 15% |
propargyl alcohol
A
propargyl bromide
B
1,3-dibromopropene
C
2-bromoallyl bromide
Conditions | Yield |
---|---|
With phosphorus tribromide In isopar C at 6 - 50℃; for 3.71667h; Product distribution / selectivity; | A 64.37% B 2.54% C 10.26% |
diethoxyphosphoryl-acetic acid ethyl ester
A
ethyl 2-(diethoxyphosphoryl)-2-(2-propynyl)pent-4-ynoate
B
propargyl bromide
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide at 60℃; for 120h; Yields of byproduct given; | A 58% B n/a |
Conditions | Yield |
---|---|
With water; potassium bromide |
3-bromo-2-chloroprop-1-ene
A
bromoallene
B
chloroallene
C
2-propynyl chloride
D
propargyl bromide
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; phenol Yield given; |
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; phenol at 120 - 122℃; Yield given; | |
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; phenol Product distribution; various concentrations of phenol; |
2-bromo-3-chloro-propene
A
bromoallene
B
chloroallene
C
2-propynyl chloride
D
propargyl bromide
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; phenol Yield given; |
2-bromo-3-chloro-propene
A
bromoallene
B
chloroallene
C
propargyl bromide
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; phenol Yield given; |
prop-2-yn-1-ol methanesulfonate
propargyl bromide
Conditions | Yield |
---|---|
With magnesium bromide In diethyl ether at 15℃; for 1h; |
propynyl radical
propargyl bromide
Conditions | Yield |
---|---|
With bromine at 22.9 - 258.9℃; Kinetics; Irradiation; carrier gas, He, the role of resonance stabilization; |
Conditions | Yield |
---|---|
With pyridine; tributyltin bromide at 50℃; Thermodynamic data; Equilibrium constant; Δ G; |
Conditions | Yield |
---|---|
With pyridine; tributyltin bromide at 50℃; Thermodynamic data; Equilibrium constant; Δ G; |
Conditions | Yield |
---|---|
With phosphorus tribromide |
bromocyane
N-methyl-N-propargylaniline
A
methyl(phenyl)cyanamide
B
propargyl bromide
Conditions | Yield |
---|---|
auf dem Wasserbad; |
2-[N-propargyl-N-(2',6'-dibromo-phenyl)-amino]-2-imidazoline
A
propargyl bromide
B
NC 6
2-[N-propargyl-N-(2',6'-dichloro-4'-bromo-phenyl)-amino]-2-imidazoline
A
propargyl bromide
B
St 871
2-[N-propargyl-N-(2'-chloro-3'-methyl-phenyl)-amino]-2-imidazoline
A
propargyl bromide
B
(2-chloro-3-methyl-phenyl)-(4,5-dihydro-1H-imidazol-2-yl)-amine
2-[N-propargyl-N-(2',6'-diethyl-phenyl)-amino]-2-imidazoline
A
propargyl bromide
B
NC 5
2-[N-propargyl-N-(3'-methoxyphenyl)-amino]-2-imidazoline
A
2-[N-(3'-methoxy-phenyl)-amino]-2-imidazoline
B
propargyl bromide
(2-chloro-4-methyl-phenyl)-(4,5-dihydro-1H-imidazol-2-yl)-prop-2-ynyl-amine
A
propargyl bromide
B
Tolonidine
(2-chloro-6-methyl-phenyl)-(4,5-dihydro-1H-imidazol-2-yl)-prop-2-ynyl-amine
A
propargyl bromide
B
(2-chloro-6-methyl-phenyl)-(4,5-dihydro-1H-imidazol-2-yl)-amine
2-[N-propargyl-N-(2',5'-dichloro-phenyl)-amino]-2-imidazoline
A
propargyl bromide
B
(2,5-dichloro-phenyl)-(4,5-dihydro-1H-imidazol-2-yl)-amine
(2,4-dichloro-phenyl)-(4,5-dihydro-1H-imidazol-2-yl)-prop-2-ynyl-amine
A
propargyl bromide
B
NC 8
Conditions | Yield |
---|---|
With zinc In tetrahydrofuran for 0.5h; | 100% |
Stage #1: propargyl bromide With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at -78℃; for 0.333333h; Stage #2: benzophenone In diethyl ether at -78 - 20℃; for 2h; Stage #3: With hydrogen cation In diethyl ether | 96% |
Stage #1: benzophenone; propargyl bromide With dysprosium; sodium iodide; mercury dichloride In tetrahydrofuran at -14 - 20℃; Propargylation; Stage #2: With hydrogenchloride In water Hydrolysis; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 100% |
Stage #1: aniline With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; | 100% |
With potassium carbonate In acetonitrile at 20℃; Sealed tube; Inert atmosphere; | 99% |
propargyl bromide
diethyl malonate
diethyl 2,2-di(prop-2-yn-1-yl)malonate
Conditions | Yield |
---|---|
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; mineral oil for 2h; Inert atmosphere; Cooling with ice; Stage #2: propargyl bromide In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; | 100% |
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 20℃; for 15h; | 94% |
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 16h; | 90% |
propargyl bromide
2-acetylaminomalonic acid diethyl ester
diethyl α-acetamido-α-propargylmalonate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 18h; | 100% |
With caesium carbonate In acetonitrile at 20℃; for 18h; | 99% |
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutyl ammonium fluoride In benzene a) 0 deg C, 30 min, b) r.t., 2h; | 100% |
With triethylamine In diethyl ether at 20℃; for 2h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran | 100% |
With potassium carbonate In acetone Reflux; | 100% |
Stage #1: ortho-cresol With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃; for 60h; | 100% |
With potassium carbonate In acetone Reflux; | 100% |
With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃; for 12h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 100% |
Stage #1: p-cresol With potassium carbonate In N,N-dimethyl-formamide for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 24h; Schlenk technique; Inert atmosphere; | 99% |
With caesium carbonate In acetonitrile | 93% |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 0 - 20℃; for 1h; | 100% |
(i) Na, liq. NH3, (ii) /BRN= 605309/; Multistep reaction; | |
With sodium ethanolate In ethanol |
(2-furyl)methyl alcohol
propargyl bromide
2-((prop-2-yn-1-yloxy)methyl)furan
Conditions | Yield |
---|---|
Stage #1: (2-furyl)methyl alcohol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; Reagent/catalyst; | 100% |
With para-chlorotoluene; lithium In tetrahydrofuran at -35 - 20℃; for 10h; Heating / reflux; | 93% |
Stage #1: (2-furyl)methyl alcohol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene at 23℃; for 4h; | 86% |
1H-indol-2-ylcarboxaldehyde
propargyl bromide
1-(prop-2-yn-1-yl)-1H-indole-2-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 1H-indol-2-ylcarboxaldehyde With sodium hydride In N,N-dimethyl-formamide Inert atmosphere; Schlenk technique; Cooling with ice; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Schlenk technique; Cooling with ice; | 100% |
Stage #1: 1H-indol-2-ylcarboxaldehyde With sodium hydride In N,N-dimethyl-d6-formamide Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene for 6.5h; | 97% |
With sodium hydride In N,N-dimethyl-formamide | 75% |
(+/-)-5-phenyl-2-pyrrolidinone
propargyl bromide
N-propargyl-5-phenyl-2-pyrrolidone
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In tetrahydrofuran at 0 - 20℃; for 6h; | 100% |
7-hydroxy-4-methyl-chromen-2-one
propargyl bromide
7-propargyloxy-4-methyl-2H-chromen-2-one
Conditions | Yield |
---|---|
With potassium carbonate In toluene; acetonitrile at 60℃; Inert atmosphere; | 100% |
With potassium carbonate In acetone for 4h; Heating; | 97% |
With potassium carbonate In toluene; acetonitrile at 60℃; for 12h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
Stage #1: indole-2,3-dione With potassium carbonate In N,N-dimethyl-formamide for 0.333333h; Cooling with ice; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 3h; | 100% |
With KF-Celite In 2-methyltetrahydrofuran for 3h; Reflux; chemoselective reaction; | 95% |
With potassium carbonate In N,N-dimethyl-formamide | 95% |
tetramethylene glutarimide
propargyl bromide
8-Propargyl-8-azaspiro<4.5>decane-7,9-dione
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 10h; Heating; | 100% |
With potassium carbonate In acetone Heating; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Reflux; | 100% |
With potassium carbonate In acetone Reflux; | 100% |
With potassium carbonate for 6h; Reflux; | 100% |
Conditions | Yield |
---|---|
With aluminum oxide In diethyl ether at 20℃; for 96h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h; | 85% |
With potassium carbonate In N,N-dimethyl-formamide; toluene at 20℃; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran | 100% |
With potassium carbonate In N,N-dimethyl-formamide; toluene at 25℃; for 16h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 98% |
With potassium carbonate In acetonitrile for 6h; Reflux; | 97% |
methyl 4-hydroxylbenzoate
propargyl bromide
methyl 4-(2-propynoxy)benzoate
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone; toluene for 72h; Reflux; | 100% |
With potassium carbonate In acetone Inert atmosphere; | 99% |
With potassium carbonate In acetone at 65℃; for 18h; Inert atmosphere; | 98% |
isovanillin
propargyl bromide
4-methoxy-3-(prop-2-yn-1-yloxy)benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; | 100% |
With potassium carbonate In acetone Reflux; | 97% |
With potassium carbonate In N,N-dimethyl-formamide for 4h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone; toluene for 24h; Williamson Ether Synthesis; Reflux; | 100% |
Stage #1: 4-nitro-phenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere; | 100% |
Stage #1: 4-nitro-phenol With potassium carbonate In acetonitrile at 20℃; for 0.166667h; Stage #2: propargyl bromide In acetonitrile Reflux; | 100% |
ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate
propargyl bromide
8-Ethoxycarbonyl-8-(prop-2-ynyl)-1,4-dioxaspiro[4.5]decane
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran 1.) -78 to 0 deg C, 2.) -78 deg C, 15 min; | 100% |
With lithium diisopropyl amide In tetrahydrofuran Yield given; | |
Stage #1: ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate With lithium diisopropyl amide In tetrahydrofuran at -70℃; for 1h; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran at -70 - 20℃; for 12h; Inert atmosphere; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; toluene at 60℃; for 2h; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere; | 100% |
With potassium carbonate In acetone | 99% |
2-hydroxybromobenzene
propargyl bromide
1-bromo-2-(prop-2-yn-1-yloxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In toluene; acetonitrile at 60℃; for 16h; | 100% |
With potassium carbonate In N-methyl-acetamide; hexane; water; ethyl acetate | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14h; | 98% |
ethyl N-diphenylmethylene glycine
propargyl bromide
ethyl 2-[(diphenylmethylidene)amino]pent-4-ynoate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 20h; Heating; | 100% |
With potassium carbonate In acetonitrile Alkylation; Heating; | 86% |
With potassium carbonate In acetonitrile Alkylation; | 86% |
(E)-3-trimethylsilyl-2-propenal
propargyl bromide
(E)-6-trimethylsilyl-hex-5-en-1-yn-4-ol
Conditions | Yield |
---|---|
With zinc; titanium tetrachloride In tetrahydrofuran for 0.5h; Ambient temperature; | 100% |
With zinc; titanium tetrachloride In tetrahydrofuran | |
With titanium tetrachloride; zinc In tetrahydrofuran at 0℃; Yield given; |
3-α-Naphthylpropargylpyrrolidine
propargyl bromide
1-(3-Naphthalen-1-yl-prop-2-ynyl)-1-prop-2-ynyl-pyrrolidinium; bromide
Conditions | Yield |
---|---|
In diethyl ether | 100% |
[3-(α-naphthyl)-2-propynyl]dipropylamine
propargyl bromide
Dipropylpropargyl<3-(α-naphthyl)propargyl>ammonium bromide
Conditions | Yield |
---|---|
In diethyl ether | 100% |
1-(3-(naphthalen-1-yl)prop-2-ynyl)piperidine
propargyl bromide
1-(3-Naphthalen-1-yl-prop-2-ynyl)-1-prop-2-ynyl-piperidinium; bromide
Conditions | Yield |
---|---|
In diethyl ether | 100% |
The Propargyl bromide, with the CAS registry number 106-96-7 and EINECS registry number 203-447-1, has the systematic name and IUPAC name of 3-bromoprop-1-yne. And the molecular formula of this chemical is C3H3Br. It is a kind of yellow solution, and belongs to the following product categories: Alkyl bromide; Acetylenes; Functionalized Acetylenes. It is a kind of light sensitive chemical, and should be stored in the refrigerator. What's more, it is denser than water and insoluble in water, but soluble in alcohol, ether, chloroform, carbon tetrachloride and carbon disulfide. And its vapors are heavier than air.
The physical properties of Propargyl bromide are as following: (1)ACD/LogP: 1.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.32; (4)ACD/LogD (pH 7.4): 1.32; (5)ACD/BCF (pH 5.5): 5.96; (6)ACD/BCF (pH 7.4): 5.96; (7)ACD/KOC (pH 5.5): 124.88; (8)ACD/KOC (pH 7.4): 124.88; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.485; (14)Molar Refractivity: 21.5 cm3; (15)Molar Volume: 75 cm3; (16)Polarizability: 8.52×10-24cm3; (17)Surface Tension: 35.1 dyne/cm; (18)Density: 1.586 g/cm3; (19)Flash Point: 17.1 °C; (20)Enthalpy of Vaporization: 31.64 kJ/mol; (21)Boiling Point: 90 °C at 760 mmHg; (22)Vapour Pressure: 64.6 mmHg at 25°C.
Preparation of Propargyl bromide: It can be prepared by propargyl alcohol and phosphonium bromide. Add hydrogen bromide and the solution into the reaction bulb, and drop propargyl alcohol with stirring in the presence of catalyst of CuBr and Cu. Heat up after propargyl alcohol is over, and then rectify it, the Propargyl bromide is obtained.
CH≡C—CH2OH+PBr3 → CH≡C—CH2Br
Uses of Propargyl bromide: It is used in organic syntheses, preparation of resins and perfume intermediates. It is also used to prepare several derivatives of acetylene. What's more, it is also used in the synthesise of antifungal drug.
You should be cautious while dealing with this chemical. It is a kind of highly flammable chemical, and irritates eyes, respiratory system and skin. It is also toxic if swallowed, and has possible risk of harm to the unborn child. Therefore, you had better take the following instructions: Wear suitable, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Keep away from sources of ignition - No smoking; After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer); In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: BrCC#C
(2)InChI: InChI=1/C3H3Br/c1-2-3-4/h1H,3H2
(3)InChIKey: YORCIIVHUBAYBQ-UHFFFAOYAE
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | oral | 29ug/kg (0.029mg/kg) | "Pesticide Index," Frear, E.H., ed., State College, PA, College Science Pub., 1969Vol. 4, Pg. 76, 1969. | |
rat | LD50 | oral | 53mg/kg (53mg/kg) | Bulletin of the Entomological Society of America. Vol. 12, Pg. 161, 1966. |
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