16400-32-1

Basic information

• Product Name: 1-BROMO-2-PENTYNE
• Synonyms: 1-BROMO-2-PENTYNE;TIMTEC-BB SBB008834;1-bromopent-2-yne;1-BROMO-2-PENTYNE 97%;2-Pentynyl bromide;Einecs 240-451-2;2-Pentyn-1-yl bromide
• CAS NO: 16400-32-1
• Molecular Formula: C₅H₇Br
• Molecular Weight: 147.01
• EINECS: 240-451-2
• Product Categories: Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 16400-32-1.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 93-94 °C113 mm Hg(lit.)
• Flash Point: 105 °F
• Appearance: Clear yellow/Liquid
• Density: 1.438 g/mL at 25 °C(lit.)
• Vapor Pressure: 7mmHg at 25°C
• Refractive Index: n20/D 1.498(lit.)
• Solubility: Miscible with ether
• CAS DataBase Reference: 1-BROMO-2-PENTYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2-PENTYNE(16400-32-1)
• EPA Substance Registry System: 1-BROMO-2-PENTYNE(16400-32-1)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• Hazardous Substances Data: 16400-32-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 16400-32-1 differently. You can refer to the following data:
1. 1-Bromo-2-pentyne is a brominated alkyne derivative used as a reagent in a wide variety of organic and organometallic compounds.
2. 1-Bromo-2-pentyne acts as a reagent for organic and organometallic compounds. It is also employed in the preparation of stereochemically restricted lactone-type analogs of jasmonic acids, 5-oxa-7-epi-jasmonic acid and 5-oxa-jasmonic acid. Further, it is used to prepare of 4,7-decadienal, 4,7-tridecadienal, 5,8-tetradecadienal and 6,9-dodecadienal synthesis. In addition to this, it plays an important role for the synthesis of 5-ethyl-4-methylene-6-phenyl-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione.
3. 1-Bromo-2-pentyne may be employed for the following syntheses:stereochemically restricted lactone-type analogs of jasmonic acids, 5-oxa-7-epi-jasmonic acid and 5-oxa-jasmonic acid4,7-decadienal, 4,7-tridecadienal, 5,8-tetradecadienal and 6,9-dodecadienal (all-cis)5-ethyl-4-methylene-6-phenyl-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione

Application

1-Bromo-2-pentyne may be employed for the following syntheses:stereochemically restricted lactone-type analogs of jasmonic acids, 5-oxa-7-epi-jasmonic acid and 5-oxa-jasmonic acid 4,7-decadienal, 4,7-tridecadienal, 5,8-tetradecadienal and 6,9-dodecadienal (all-cis)5-ethyl-4-methylene-6-phenyl-3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione.1-Bromo-2-pentyne is an halogenated hydrocarbon.

Synthesis Reference(s)

Synthesis, p. 730, 1974 DOI: 10.1055/s-1974-23426

General Description

1-Bromo-2-pentyne is an halogenated hydrocarbon.

InChI:InChI=1/C5H7Br/c1-2-3-4-5-6/h2,5H2,1H3

Synthetic route

toluene-4-sulfonic acid pent-2-ynyl ester (92666-05-2) → 1-bromo-pent-2-yne (16400-32-1)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium bromide In dichloromethane; water for 6h; Ambient temperature;	95%

2-pent-2-ynyloxy-tetrahydro-pyran (6261-21-8) → 1-bromo-pent-2-yne (16400-32-1)

Conditions	Yield
With bromine; triphenylphosphine In dichloromethane	87%

pent-2-yn-1-ol (6261-22-9) → 1-bromo-pent-2-yne (16400-32-1)

Conditions	Yield
With pyridine; phosphorus tribromide In diethyl ether for 3h; Ambient temperature;	84%
Stage #1: pent-2-yn-1-ol With pyridine; phosphorus tribromide In diethyl ether at -10 - 20℃; for 6h; Inert atmosphere; Reflux; Stage #2: hydroquinone In diethyl ether for 4.5h; Reflux; Inert atmosphere;	84%
With pyridine; phosphorus tribromide In diethyl ether	80%

1-chloropent-2-yne (22592-15-0) → 1-bromo-pent-2-yne (16400-32-1)

Conditions	Yield
With lithium bromide In N,N-dimethyl-formamide at 60℃; for 72h; Substitution;	51%

1-methoxy-2-pentyne (18495-20-0) → 1-bromo-pent-2-yne (16400-32-1)

Conditions	Yield
With Acetyl bromide; zinc dibromide at 60 - 65℃;

tetra-N-methyl-phosphorodiamidic acid pent-2-ynyl ester (53799-89-6) → 1-bromo-pent-2-yne (16400-32-1)

Conditions	Yield
With phosphorus tribromide In diethyl ether for 4h; Heating;

methylmagnesium bromide (75-16-1) + 1,4-dibromobut-2-yne (2219-66-1) → 1-bromo-pent-2-yne (16400-32-1)

Conditions	Yield
at 0 - 5℃;

1-bromo-pent-2-yne (16400-32-1) + methyl-malonic acid dimethylester (609-02-9) → dimethyl methyl(2-pentynyl)malonate (863297-78-3)

Conditions	Yield
Stage #1: methyl-malonic acid dimethylester With sodium hydride In tetrahydrofuran for 0.25h; Stage #2: 1-bromo-pent-2-yne In tetrahydrofuran at 0 - 20℃;	100%

1-bromo-pent-2-yne (16400-32-1) + S-(2-bromo-5-hydroxybenzyl)ethanethioate (1609496-75-4) → 4-bromo-3-((pent-2-yn-1-ylthio)methyl)phenol (1609496-76-5)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 0.5h;	100%

1-bromo-pent-2-yne (16400-32-1) + 3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) + ethylmagnesium bromide (925-90-6) → 2,5-octadiyn-1-ol tetrahydropyranyl ether (117606-23-2)

Conditions	Yield
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne; ethylmagnesium bromide In tetrahydrofuran; diethyl ether for 0.5h; Inert atmosphere; Reflux; Stage #2: 1-bromo-pent-2-yne With copper(l) iodide In tetrahydrofuran; diethyl ether	100%

1-bromo-pent-2-yne (16400-32-1) + 2-((2-bromo-5-methoxybenzyl)thio)-1H-benzimidazole → 2-((2-bromo-5-methoxybenzyl)thio)-1-(pent-2-yn-1-yl)-1H-benzimidazole

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 18h;	100%

1-bromo-pent-2-yne (16400-32-1) + 2-Iodophenol (533-58-4) → 1-iodo-2-(pent-2-yn-1-yloxy)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	100%

1-bromo-pent-2-yne (16400-32-1) + 4-bromo-3,5-dimethylphenol (7463-51-6) → 2-Bromo-1,3-dimethyl-5-(2-pentynyloxy)benzene (925441-93-6)

Conditions	Yield
Stage #1: 4-bromo-3,5-dimethylphenol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 1-bromo-pent-2-yne In N,N-dimethyl-formamide at 20℃; for 3h;	99%

1-bromo-pent-2-yne (16400-32-1) + C13H17NO2S (1266485-95-3) → C18H23NO2S (1266485-96-4)

Conditions	Yield
Stage #1: C13H17NO2S With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Reflux; Stage #2: 1-bromo-pent-2-yne In N,N-dimethyl-formamide at 20℃; for 1.5h;	99%

1-bromo-pent-2-yne (16400-32-1) + 3-hydroxy-6-methylflavone (6971-18-2) → 6-methyl-3-(pent-2-ynyloxy)-2-phenyl-4H-chromen-4-one (1429665-09-7)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 60℃;	99%

1-bromo-pent-2-yne (16400-32-1) + S-(2-bromo-5-methoxybenzyl)ethanethioate (1609496-74-3) → (2-bromo-5-methoxybenzyl)(pent-2-yn-1-yl)sulfide (1609496-73-2)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 1h;	99%

1-bromo-pent-2-yne (16400-32-1) + S-(2-bromobenzyl)ethanethioate (1256085-49-0) → (2-bromobenzyl)(pent-2-yn-1-yl)sulfide (1609496-72-1)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 1h;	99%
With potassium hydroxide In ethanol at 20℃; for 1h;	99%

1-bromo-pent-2-yne (16400-32-1) + C27H23Cl2N3NiO3 → C32H29Cl2N3NiO3

Conditions	Yield
With sodium methylate; magnesium sulfate In neat (no solvent) at 20℃; for 0.333333h; Milling; diastereoselective reaction;	99%

2-benzothiazol-2-ylsulfanyl-6-morpholin-4-yl-6-oxo-hexanoic acid methyl ester (70203-09-7) + 1-bromo-pent-2-yne (16400-32-1) → 2-(Benzothiazol-2-ylsulfanyl)-2-(4-morpholin-4-yl-4-oxo-butyl)-hept-4-ynoic acid methyl ester (72844-46-3)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone Heating;	98%

1-bromo-pent-2-yne (16400-32-1) + indole-2,3-dione (91-56-5) → 1-Pent-2-ynyl-1H-indole-2,3-dione (180968-93-8)

Conditions	Yield
With lithium hydride In N,N-dimethyl-formamide 20 deg C, 4 h; 60 deg C, 1 h;	98%

1-bromo-pent-2-yne (16400-32-1) + dimethyl allylmalonate (40637-56-7) → dimethyl 2-allyl-2-(pent-2-ynyl)malonate (191801-56-6)

Conditions	Yield
Stage #1: dimethyl allylmalonate With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: 1-bromo-pent-2-yne In tetrahydrofuran at 20℃; for 11h; Further stages.;	98%
With sodium hydride In mineral oil at 20℃; for 0.5h; Schlenk technique; Inert atmosphere;	91%
Stage #1: dimethyl allylmalonate With sodium hydride In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: 1-bromo-pent-2-yne In tetrahydrofuran; hexane at 20℃; for 12.25h;	72%

1-bromo-pent-2-yne (16400-32-1) + 6-hydroxy-2,3-dihydro-1H-indolizin-5-one (253195-68-5) → 6-(pent-2-ynyloxy)-2,3-dihydroindolizin-5(1H)-one (1426932-78-6)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 20h; Reflux;	98%

1-bromo-pent-2-yne (16400-32-1) + 1-methylalizarin (6170-06-5) → 1-methoxy-2-(pent-2-ynyloxy)anthracene-9,10-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;	98%

1-bromo-pent-2-yne (16400-32-1) + 3-hydroxy-2-phenylpropene (6006-81-1) → C14H16O

Conditions	Yield
Stage #1: 3-hydroxy-2-phenylpropene With sodium hydride at 0 - 20℃; for 0.5h; Williamson Ether Synthesis; Inert atmosphere; Stage #2: 1-bromo-pent-2-yne at 20℃; Williamson Ether Synthesis; Inert atmosphere;	98%

2-benzothiazol-2-ylsulfanyl-hexanedioic acid dimethyl ester (70203-07-5) + 1-bromo-pent-2-yne (16400-32-1) → dimethyl 2-(2-pentynyl)-2-(2-benzothiazolylthio)adipate (72844-41-8)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone for 24h; Heating;	97%

1-bromo-pent-2-yne (16400-32-1) + 4-hydroxy-2,3,6-trimethylbenzaldehyde (41827-90-1) → 4-(2-Pentynyloxy)-2,3,6-trimethylbenzaldehyde (925441-96-9)

Conditions	Yield
Stage #1: 4-hydroxy-2,3,6-trimethylbenzaldehyde With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 1-bromo-pent-2-yne In N,N-dimethyl-formamide at 20℃; for 3h;	97%

1-bromo-pent-2-yne (16400-32-1) + N-(2,2-dimethoxyethyl)-p-toluenesulfonamide (58754-95-3) → N-(2,2-dimethoxyethyl)-4-methyl-N-pent-2-ynylbenzenesulfonamide (1290143-97-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;	97%

1-bromo-pent-2-yne (16400-32-1) + 2-(hept-1-yn-1-yl)-1-(4-hydroxybut-2-yn-1-yl)cyclohex-2-en-1-ol → 2-(hept-1-yn-1-yl)-1-(4-(pent-2-yn-1-yloxy)but-2-yn-1-yl)cyclohex-2-en-1-ol

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane; water at 40℃; for 3.5h; Williamson Ether Synthesis;	97%

1-bromo-pent-2-yne (16400-32-1) + 2-(phenylselanyl)cyclohex-2-en-1-one (57204-95-2) + LiMe2Cu → (2S,3S)-3-Methyl-2-pent-2-ynyl-cyclopentanone

Conditions	Yield
	96%

1-Chloro-4-iodobenzene (637-87-6) + 1-bromo-pent-2-yne (16400-32-1) → 1-chloro-4-(1-ethyl-propa-1,2-dienyl)-benzene

Conditions	Yield
With indium; lithium iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃;	96%

isovanillin (621-59-0) + 1-bromo-pent-2-yne (16400-32-1) → 4-methoxy-3-(pent-2-ynyloxy)benzaldehyde (1001289-44-6)

Conditions	Yield
With potassium carbonate In acetone for 16h; Reflux;	96%

1-bromo-pent-2-yne (16400-32-1) + 2-bromothiophenol (6320-02-1) → (2-bromophenyl)(pent-2-yn-1-yl)sulfide (1609496-70-9)

Conditions	Yield
With triethylamine In toluene for 4h; Reflux;	96%
With triethylamine In toluene for 4h; Reflux;	96%

N-(2-Formyl-phenyl)-4-methyl-benzenesulfonamide (6590-65-4) + 1-bromo-pent-2-yne (16400-32-1) → N-(2-formylphenyl)-4-methyl-N-(pent-2-yn-1-yl)benzenesulfonamide

Conditions	Yield
With potassium carbonate In acetonitrile at 75℃; for 24h; Inert atmosphere;	96%

1-bromo-pent-2-yne (16400-32-1) + diethyl malonate (105-53-3) → ethyl 2-carbethoxy-hept-4-yn-1-oate (98442-18-3)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane	95%
With potassium carbonate In acetone at 20℃; for 24h;	57%
Stage #1: diethyl malonate With sodium ethanolate In ethanol at 20℃; for 0.166667h; Stage #2: 1-bromo-pent-2-yne In ethanol at 20℃; for 2h; Further stages.;	31%

1-bromo-pent-2-yne (16400-32-1) + 3-Phenyl-2-propyn-1-ol (1504-58-1) → (3-(pent-2-yn-1-yloxy)prop-1-yn-1-yl)benzene (1292284-06-0)

Conditions	Yield
Stage #1: 3-Phenyl-2-propyn-1-ol With sodium hydride In tetrahydrofuran at 0℃; for 0.75h; Inert atmosphere; Stage #2: 1-bromo-pent-2-yne In tetrahydrofuran Inert atmosphere;	95%

1-bromo-pent-2-yne (16400-32-1) + N-allyl-4-bromobenzenesulfonamide (830-41-1) → N-allyl-4-bromo-N-(but-2-yn-1-yl)benzenesulfonamide

Conditions	Yield
Stage #1: 1-bromo-pent-2-yne; N-allyl-4-bromobenzenesulfonamide With potassium carbonate In acetonitrile for 8h; Reflux; Stage #2: In acetonitrile at 20℃; for 14h;	95%

Upstream product

• 22592-15-0 1-chloropent-2-yne 
• 6261-21-8 2-pent-2-ynyloxy-tetrahydro-pyran 
• 75-16-1 methylmagnesium bromide 
• 2219-66-1 1,4-dibromobut-2-yne 
• 53799-89-6 tetra-N-methyl-phosphorodiamidic acid pent-2-ynyl ester 
• 18495-20-0 1-methoxy-2-pentyne 
• 6261-22-9 pent-2-yn-1-ol 
• 92666-05-2 toluene-4-sulfonic acid pent-2-ynyl ester 

Downstream Products

• 22644-09-3 4Z,7Z-decadienal 
• 50329-15-2 pent-2-ynyl-triphenylphosphine bromide 
• 1180643-01-9 C₁₇H₂₃NOS 
• 1180642-93-6 C₁₅H₁₉NOS 
• 1159685-55-8 N-[2-fluoro-3-(2-pentynyloxy)phenyl]methyl-quinoline-6-carboxamide 
• 1159685-60-5 N-[3-(2-pentynyloxy)phenyl]methyl-quinoline-6-carboxamide 
• 1094528-33-2 C₂₀H₂₈O₄ 
• 865762-72-7 2-ethyl-1-(4-methoxylphenyl)buta-2,3-dien-1-ol 
• 865762-71-6 2-ethyl-1-(4-methylphenyl)buta-2,3-dien-1-ol 
• 1072809-20-1 (S_S)-(2-(2-ethylbuta-2,3-dienyl)phenyl)-p-tolyl-sulfoxide 
• 1051385-35-3 C₁₄H₁₂O₂ 
• 68480-23-9 methyl 2-oxo-1-(pent-2-yn-1-yl)cyclopentanecarboxylate 

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