109-65-9

Basic information

• Product Name: 1-Bromobutane
• Synonyms: N-BUTYL BROMIDE;BUTYL BROMIDE;1-BROMOBUTANE;1-Brombutan;1-bromo-butan;1-butylbromide;bromo butane;Butane,1-bromo-
• CAS NO: 109-65-9
• Molecular Formula: C₄H₉Br
• Molecular Weight: 137.02
• EINECS: 203-691-9
• Product Categories: Dyestuff Intermediates;Pharmaceutical Intermediates;Organics;ALKYL BROMIDE;Bromine Compounds;Alkyl Bromides;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes
• Mol File: 109-65-9.mol
• Article Data: 98

Chemical Properties

• Melting Point: -112 °C
• Boiling Point: 100-104 °C(lit.)
• Flash Point: 23 °C
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.276 g/mL at 25 °C(lit.)
• Vapor Density: 4.7 (vs air)
• Vapor Pressure: 150 mm Hg ( 50 °C)
• Refractive Index: n20/D 1.439(lit.)
• Storage Temp.: Flammables area
• Solubility: 0.6g/l
• Explosive Limit: 2.8-6.6%, 100°F
• Water Solubility: 0.608 g/L (30 ºC)
• Stability: Stable. Flammable - note low flash point. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,1553
• BRN: 1098260
• CAS DataBase Reference: 1-Bromobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromobutane(109-65-9)
• EPA Substance Registry System: 1-Bromobutane(109-65-9)

Safety Data

• Hazard Codes: F,Xi,N
• Statements: 11-36/37/38-51/53-10
• Safety Statements: 16-26-60-37/39
• RIDADR: UN 1126 3/PG 2
• WGK Germany: 2
• RTECS: EJ6225000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 109-65-9(Hazardous Substances Data)

Usage

Description

1-Bromobutane, an alkyl halide, is an alkylating agent with a clear colorless to slightly yellow liquid appearance and an aromatic smell. It is denser than water, insoluble in water, and soluble in organic solvents such as alcohol, ether, and chloroform. Its vapors are heavier than air, and it has a flash point of 65°F. 1-Bromobutane's properties, including rotational constants, nuclear quadrupole constants, and centrifugal distortion constants, have been determined through microwave spectral data. Additionally, the rate coefficient for the reaction of 1-bromobutane with hydrogen atoms has been reported to be 2.4±1.2x10^10 cm^3 mol^-1 s^-1.

Uses

1-Bromobutane is used as an intermediate in organic synthesis for various applications. It serves as a solvent for cleaning and degreasing processes. As an alkylating agent, it is involved in the preparation of organometallic compounds, such as n-butyllithium. Furthermore, it plays a role in the synthesis of procaine and tetracaine, which are important in the pharmaceutical industry.
In the chemical industry, 1-bromobutane is used as a derivatization reagent for multiple functional groups (amino, carboxyl, and phenolic hydroxyl groups) of amino acids. This improves the hydrophobicities and basicities of the amino acids, enhancing their properties for various applications.
1-Bromobutane also reacts with magnesium metal to prepare the Grignard reagent, which is essential for forming carbon-carbon bonds in organic synthesis.
In analytical chemistry, 1-bromobutane may be used as an internal standard for the quantification of 1and 2-bromopropane in human urine by headspace gas chromatography. This application aids in the accurate measurement and monitoring of these compounds in biological samples.

Synthesis Reference(s)

Journal of the American Chemical Society, 86, p. 964, 1964 DOI: 10.1021/ja01059a073Organic Syntheses, Coll. Vol. 1, p. 25, 1941Synthesis, p. 326, 1982

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

1-Bromobutane is incompatible with strong bases and oxidizers [USCG, 1999].

Hazard

Flammable, dangerous fire risk.

Health Hazard

Irritating to the eyes, nose, throat, and upper respiratory tract. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. Irritating to the skin.

Safety Profile

Moderately toxic by intraperitoneal route. Mddly toxic by inhalation. Dangerous fire hazard when exposed to heat, flame, or oxidizers. Violent reaction with bromobenzene + sodium above 30℃. Can react with oxidizing materials. To fight fire, use CO2, dry chemical, mist or spray. See also BROMIDES.

Synthesis

1-bromobutane is a primary alkyl halide (primary alkyl) and therefore it is produced from bimolecular nucleophilic substitution reactions (Sn2). The preparation method of 1-bromobutane is as follows: stirring n-butanol, sodium bromide, water and sulfuric acid evenly, heating under reflux for 3 hours, steaming out the crude bromobutane, washing with water, treating with cold concentrated sulfuric acid, and distilling to obtain the finished product.Reaction equation: CH3CH2CH2CH2OH+NaBr+H2SO4→CH3CH2CH2CH2Br+Na2SO4+H2OThis halide is easily prepared by reacting butan-1-ol (primary alcohol) with sodium bromide solution and excess of concentrated sulfuric acid. The reaction between sodium bromide and sulphuric acid origins hydrobromic acid.

Shipping

UN1126 & UN23391- & 2-Bromobutane, Hazard Class: 3; Labels: 3—Flammable liquid.

Purification Methods

Wash the bromide with conc H2SO4, water, 10% Na2CO3 and again with H2O. Dry it over CaCl2, CaSO4 or K2CO3, and distil it. Redistil it after drying with P2O5, or pass it through two columns containing 5:1 silica gel/Celite mixture and store it with freshly activated alumina. [Beilstein 1 IV 258.]

Incompatibilities

Vapor may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. May accumulate static electrical charges and cause ignition of its vapors.

InChI:InChI=1/C10H13BrO/c11-8-4-5-9-12-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2

Synthetic route

4-(2-bromo-1-tert-butyl-vinyl)-morpholine (76906-48-4) → 1-bromo-butane (109-65-9) + C10H18LiNO (85429-35-2, 88652-86-2, 88653-14-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; diethyl ether at -70℃; for 0.25h;	A n/a B 100%

((E)-2-Bromo-1-phenyl-vinyl)-dimethyl-amine (85429-30-7) → 1-bromo-butane (109-65-9) + C10H12LiN (85429-36-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; diethyl ether at -70℃; for 0.5h;	A n/a B 100%

phosphoric acid tributyl ester (126-73-8) → 1-bromo-butane (109-65-9)

Conditions	Yield
With salophen(tBu)AlBr In chloroform-d1 at 20℃; for 0.5 - 24h; Product distribution / selectivity;	100%
With (N,N'-ethylenebis(3,5-di-tert-butylsalicylideneimine))AlBr In chloroform-d1 at 20℃; for 0.5 - 24h; Product distribution / selectivity;	12%
With (N,N'-propylenebis(3,5-di-tert-butylsalicylideneimine))AlBr In chloroform-d1 at 20℃; for 0.5 - 24h; Product distribution / selectivity;	7%

1-bromo-4-butene (5162-44-7) → 1-bromo-butane (109-65-9)

Conditions	Yield
With 2,6-bis[1-(2,6-diisopropylphenylimino)ethyl]pyridine cobalt(II) dichloride; diethoxymethylane; sodium triethylborohydride In toluene at -78 - 20℃; for 5h;	96%
With Rh4Co; cetyltrimethylammonim bromide; hydrazine hydrate In toluene at 60℃; for 3h; Schlenk technique; Inert atmosphere;

butan-1-ol (71-36-3) → 1-bromo-butane (109-65-9)

Conditions	Yield
With hydrogen bromide at 160℃; under 11251.1 Torr; for 0.0361111h; Concentration; Pressure; Temperature;	93%
With silica bromide In dichloromethane at 20℃; for 0.166667h;	90%
With bromine for 1h; Heating;	89%

dibromo-tri-n-butylstiborane (16629-56-4) → 1-bromo-butane (109-65-9) + di-n-butylantimonbromide (16629-57-5)

Conditions	Yield
heating for 4 h at 220°C;	A n/a B 90%
heating for 4 h at 220°C;	A n/a B 74%
heating for 4 h at 220°C;	A n/a B 74%

n-Butyl chloride (109-69-3) → 1-bromo-butane (109-65-9)

Conditions	Yield
With calcium bromide; tetrahexylammonium bromide at 110℃; for 24h;	89%
With benzyl tri-n-butylammonium bromide at 34.9 - 74.9℃; Kinetics; Thermodynamic data; Ea;
With 1-n-butyl-3-methylimidazolim bromide at 70℃; for 5h; Time;

butoxytrimethylsilane (1825-65-6) → 1-bromo-butane (109-65-9)

Conditions	Yield
With Tri-n-butylfluorphosphoniumbromid In dichloromethane at 20℃; for 72h;	84%
With trimethylsilyl bromide; bismuth(III) bromide In neat (no solvent) at 80℃; for 1h;	95 % Chromat.

dibutyl ether (142-96-1) + carbon monoxide (201230-82-2) + 4-Fluorobenzyl bromide (459-46-1) → 1-bromo-butane (109-65-9) + (4-Fluoro-phenyl)-acetic acid butyl ester (104548-37-0)

Conditions	Yield
1,5-hexadienerhodium(I)-chloride dimer; potassium iodide at 75 - 90℃; under 735.5 Torr; overnight or in n-heptane;	A n/a B 83%

dibutyl ether (142-96-1) + carbon monoxide (201230-82-2) + benzyl bromide (100-39-0) → 1-bromo-butane (109-65-9) + butyl phenylacetate (122-43-0)

Conditions	Yield
1,5-hexadienerhodium(I)-chloride dimer at 75 - 90℃; under 760 Torr; Product distribution; overnight, investigation of reactions with variety of benzyl bromides, symmetrical and asymmetrical ethers, with and without KI;	A n/a B 81%
1,5-hexadienerhodium(I)-chloride dimer; potassium iodide at 75 - 90℃; under 735.5 Torr; overnight or in n-heptane;	A n/a B 81%

dibutyl ether (142-96-1) + carbon monoxide (201230-82-2) + p-Methoxybenzyl bromide (2746-25-0) → 1-bromo-butane (109-65-9) + butyl 2-(4-methoxyphenyl)acetate (104548-38-1)

Conditions	Yield
1,5-hexadienerhodium(I)-chloride dimer at 75 - 90℃; under 735.5 Torr; overnight or in n-heptane;	A n/a B 81%

4-(p-chlorophenyl)-1-n-butyl-2,3,5,6-tetraphenylpyridinium bromide (76192-14-8) → 1-bromo-butane (109-65-9)

Conditions	Yield
With 2,4,6-triphenylpyridine at 180 - 220℃; under 0.5 - 1.5 Torr;	75%

tributylarsonium-2,2,3,3,4,4-hexafluorocyclobutane ylide (80351-96-8, 80352-01-8) → 1-bromo-butane (109-65-9) + 1-bromo-2,3,3,4,4-pentafluorocyclobutene (697-08-5)

Conditions	Yield
With bromine Ambient temperature;	A 73% B 70%
With bromine Ambient temperature; also I2;	A 73% B 70%

butyldiphenylbismutane (74724-76-8) → 1-bromo-butane (109-65-9) + bromobenzene (108-86-1)

Conditions	Yield
With bromine In tetrahydrofuran at -70 - 0℃; Product distribution;	A 70% B 56%
With bromine In diethyl ether -70 deg C to r.t.;	A 70 % Chromat. B 56 % Chromat.

dibutyl ether (142-96-1) + carbon monoxide (201230-82-2) + 4-Methylbenzyl bromide (104-81-4) → 1-bromo-butane (109-65-9) + butyl (4-methylphenyl)acetate (93578-99-5)

Conditions	Yield
1,5-hexadienerhodium(I)-chloride dimer; potassium iodide at 75 - 90℃; under 735.5 Torr; overnight or in n-heptane;	A n/a B 66%

butyl ethyl ether (628-81-9) + carbon monoxide (201230-82-2) + benzyl bromide (100-39-0) → 1-bromo-butane (109-65-9) + ethyl bromide (74-96-4) + butyl phenylacetate (122-43-0) + Ethyl 2-phenylethanoate (101-97-3)

Conditions	Yield
1,5-hexadienerhodium(I)-chloride dimer; potassium iodide at 75 - 90℃; under 735.5 Torr; overnight or in n-heptane;	A n/a B n/a C 64% D 32%

dibutyl ether (142-96-1) → 1-bromo-butane (109-65-9) + Phosphoric acid mono-n-butylester (16456-56-7)

Conditions	Yield
With hydrogen bromide; phosphorus tribromide at 80℃; for 0.666667h;	A 56% B 2%

tributyl-amine (102-82-9) → 1-bromo-butane (109-65-9)

Conditions	Yield
With 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; sodium bromide In acetone Reflux;	55%

2-(ω-bromobutylthio)-4,6-dimethylpyrimidine (15018-33-4) → 1-bromo-butane (109-65-9) + 2-(4-Butoxy-butylsulfanyl)-4,6-dimethyl-pyrimidine + dihydrobromide salt of bis(1,2-dihydro-4,6-dimethyl-2-oxopyrimidinyl-N-butyl) disulfide

Conditions	Yield
With butan-1-ol for 15h; Heating;	A 44.6% B 43.4% C 39.6%

butene-2 (107-01-7) → 1-bromo-butane (109-65-9) + s-butyl bromide (78-76-2, 5787-31-5)

Conditions	Yield
With lithium aluminium tetrahydride; uranium(IV) chloride Product distribution;	A 28% B 42%

n-Butyl chloride (109-69-3) → 1-bromo-butane (109-65-9) + t-butyl bromide (507-19-7) + s-butyl bromide (78-76-2, 5787-31-5)

Conditions	Yield
With hydrogen bromide; ferric(III) bromide In dichloromethane at 25℃; for 15h;	A 5% B 3% C 13%

n-butyllithium (109-72-8, 29786-93-4) → 1-bromo-butane (109-65-9) + octane (111-65-9)

Conditions	Yield
With bromine In tetrahydrofuran; hexane at -78℃; for 1.5h;	A n/a B 10%

n-butane (106-97-8) → 1-bromo-butane (109-65-9) + s-butyl bromide (78-76-2, 5787-31-5)

Conditions	Yield
With N-Bromosuccinimide; 1,1-Dichloroethylene In dichloromethane at 14 - 15℃;	A 0.186% B 0.081 mmol
With CH3CH2CO2Br In trichlorofluoromethane at -100℃; for 0.25h; Irradiation; selectivities for formation of products; influenec of reagents (i-PrCO2Br, t-BuCO2Br); other temperatures;
With N-Bromosuccinimide In dichloromethane at 15℃; Product distribution; Irradiation; influence of addditive - BrCCl3;
With N-Bromosuccinimide; 1,1-Dichloroethylene In dichloromethane at 14 - 15℃;	A 0.081 mmol B 0.186%

1-butylene (106-98-9) → 1-bromo-butane (109-65-9)

Conditions	Yield
With ascaridole; hydrogen bromide
With hydrogen bromide; 1-bromoacetone unter Ausschluss von Licht und Luft;
With hydrogen bromide at -78℃; Irradiation;

n-butyl magnesium bromide (693-03-8) + diethyl sulfate (64-67-5) + diethyl ether (60-29-7) → 1-bromo-butane (109-65-9)

n-butyl magnesium bromide (693-03-8) + diethyl ether (60-29-7) + (3-bromo-1-butyl-prop-2-ynyl)-butyl ether (100399-48-2) → 1-bromo-butane (109-65-9) + butyl-(1-butyl-prop-2-ynyl)-ether (99992-08-2)

n-butyllithium (109-72-8, 29786-93-4) + bromobenzene (108-86-1) + diethyl ether (60-29-7) → 1-bromo-butane (109-65-9) + 1-butylbenzene (104-51-8) + benzene (71-43-2)

butyl para-toluenesulfonate (778-28-9) + diethyl ether (60-29-7) + phenylmagnesium bromide → 1-bromo-butane (109-65-9) + 1-butylbenzene (104-51-8)

butyl para-toluenesulfonate (778-28-9) + phenylmagnesium bromide → 1-bromo-butane (109-65-9)

Conditions	Yield
With diethyl ether

pyridine (110-86-1) + 1-bromo-butane (109-65-9) → 1-butylpyridinium bromide (874-80-6)

Conditions	Yield
at 100℃; for 40h; Sealed tube;	100%
at 120 - 150℃; under 517.162 - 1654.92 Torr; for 0.3h; Microwave irradiation; Autoclave;	97%
In acetonitrile at 84.99℃; for 48h;	97.6%

picoline (108-89-4) + 1-bromo-butane (109-65-9) → N-butyl-4-methylpyridinium bromide (65350-59-6)

Conditions	Yield
Darkness;	100%
Darkness;	100%
In ethanol for 24h; Reflux;	100%

1-bromo-butane (109-65-9) + potassium thioacetate (10387-40-3) → S-butyl ethanethioate (928-47-2)

Conditions	Yield
In tetrahydrofuran Reflux;	100%
With ethanol

1-bromo-butane (109-65-9) → dibutyl diselenide (20333-40-8)

Conditions	Yield
With selenium; sodium tetrahydroborate In ethanol; N,N-dimethyl-formamide for 1h;	100%
With selenium; sodium tetrahydroborate In ethanol; N,N-dimethyl-formamide for 0.5h; Inert atmosphere;	90%
With selenium; potassium hydroxide In water at 60℃; for 0.5h; Green chemistry;	90%

1-methyl-1H-imidazole (616-47-7) + 1-bromo-butane (109-65-9) → 1-n-butyl-3-methylimidazolim bromide (85100-77-2)

Conditions	Yield
In toluene for 3h; Alkylation; Heating;	100%
ultrasound;	100%
at 50℃; for 12h; Inert atmosphere;	100%

1-bromo-butane (109-65-9) + methyldiallylamine (2424-01-3) → N,N-diallyl-N-methyl-N-butylammonium bromide (69419-83-6)

Conditions	Yield
In acetonitrile at 96℃; for 24h;	100%
In acetone for 96h; Ambient temperature;	42%

1-bromo-butane (109-65-9) + Methyl 4-hydroxyphenylacetate (14199-15-6) → (4-butoxy-phenyl)-acetic acid methyl ester (29056-06-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80 - 100℃; for 3h;	100%
With potassium tert-butylate In dimethyl sulfoxide for 0.5h;	68%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;

1-bromo-butane (109-65-9) + indole-2,3-dione (91-56-5) → N-butylisatin (4290-91-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;	100%
With caesium carbonate In N,N-dimethyl-formamide at 140℃; Microwave irradiation;	93%
With potassium carbonate In N,N-dimethyl-formamide for 0.05h; microwave irradiation;	90%

1-bromo-butane (109-65-9) + ethyl acetoacetate (141-97-9) → ethyl 3-oxooctanoate (10488-95-6)

Conditions	Yield
Stage #1: ethyl acetoacetate With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: 1-bromo-butane In tetrahydrofuran; hexane at -78 - 20℃; for 14h; Further stages.;	100%
Stage #1: ethyl acetoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: With n-butyllithium In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #3: 1-bromo-butane In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	73%
	70%
With n-butyllithium; sodium hydride In tetrahydrofuran; pentane at 0 - 20℃; for 14h;	38%
Stage #1: ethyl acetoacetate With n-butyllithium; sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 1-bromo-butane at 0 - 25℃; Inert atmosphere;

1-bromo-butane (109-65-9) + methyl N-(diphenylmethylene)glycinate (81167-39-7) → methyl 2-((diphenylmethylene)amino)hexanoate (203855-78-1)

Conditions	Yield
With MeO-PEG; potassium carbonate In acetonitrile for 36h; Heating;	100%

1-bromo-butane (109-65-9) + 4-(4-methoxyphenyl)piperidine hydrochloride → 1-butyl-4-(4-methoxyphenyl)piperidine

Conditions	Yield
With potassium carbonate In acetonitrile for 48h; Alkylation; Heating;	100%

4-tert-butylpyridine (3978-81-2) + 1-bromo-butane (109-65-9) → 4-(tert-butyl)-1-butylpyridin-1-ium bromide

Conditions	Yield
In ethanol for 16h;	100%
In ethanol Heating;	68%

1-bromo-butane (109-65-9) + p-phenylpyridine (939-23-1) → 1-butyl-4-phenylpyridin-1-ium bromide

Conditions	Yield
In ethanol for 16h;	100%
In ethanol Heating;	98%
In ethanol for 24h; Reflux;

1-bromo-butane (109-65-9) + trimethylstannyl sodium (16643-09-7) → n-butyltrimethyltin (1527-99-7)

Conditions	Yield
In tetrahydrofuran Kinetics; 0°C in N2-atmosphere, then stored at -10°C; various yields for various conditions;	100%
In not given	43%
In not given	43%

1-bromo-butane (109-65-9) + 2,7-dibromo-9H-carbazole (136630-39-2) → 2,7-dibromo-9-butyl-9H-carbazole (654675-88-4)

Conditions	Yield
Stage #1: 2,7-dibromo-9H-carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromo-butane In N,N-dimethyl-formamide; mineral oil at 20℃; for 16h; Inert atmosphere;	100%
Stage #1: 2,7-dibromo-9H-carbazole With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 0.5h; Stage #2: 1-bromo-butane In N,N-dimethyl-formamide at 23℃; for 12h;	96%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 10h;	92%

1-bromo-butane (109-65-9) + 2,6-bis(1H-benzo[d]imidazol-1-yl)pyridine (1030366-99-4) → 2,6-bis(3-butylbenzimidazol-1-ium)pyridine dibromide

Conditions	Yield
In benzonitrile at 160℃; for 30h;	100%
In N,N-dimethyl-formamide at 100℃;	595 mg

4-iodopyrazole (3469-69-0) + 1-bromo-butane (109-65-9) → 1-butyl-4-iodo-1H-pyrazole (918487-10-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 70℃;	100%
With sodium hydride In tetrahydrofuran at 70℃;	100%

1-bromo-butane (109-65-9) + (±)-cis-5-(2-hydroxyethyl)cyclopent-2-enol (133969-91-2) → 1-butyloxy-(+/-)-cis-5-(2-butyloxyethyl)cyclopent-2-ene

Conditions	Yield
Stage #1: (±)-cis-5-(2-hydroxyethyl)cyclopent-2-enol With potassium hydride In tetrahydrofuran at 0℃; Stage #2: 1-bromo-butane In tetrahydrofuran at 0 - 20℃;	100%

1-bromo-butane (109-65-9) + C19H20N2 (946415-03-8) → C23H29N2(1+)*I(1-) (1255528-52-9)

Conditions	Yield
With sodium iodide In acetone at 20℃; for 18h;	100%

1-bromo-butane (109-65-9) + N-methyl-N-[4-(diphenylphosphino)benzyl]pyrrolidinium bromide (1229444-44-3) → 2Br(1-)*C28H36NP(2+)

Conditions	Yield
In toluene at 95 - 100℃; for 50h;	100%

1-bromo-butane (109-65-9) + ethyl 2-((((4-methoxybenzyl)oxy)carbonyl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (1315321-39-1) → ethyl 2-(butyl(((4-methoxybenzyl)oxy)carbonyl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (1315321-43-7)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	100%

1-bromo-butane (109-65-9) + carbon dioxide (124-38-9) + phenylacetylene (536-74-3) → phenylpropiolic acid n-butyl ester (80220-93-5)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; under 1520.1 Torr; for 16h; Reagent/catalyst;	100%
Stage #1: carbon dioxide; phenylacetylene With caesium carbonate In dimethyl sulfoxide at 60℃; for 24h; Sealed tube; Inert atmosphere; Stage #2: 1-bromo-butane In dimethyl sulfoxide at 60℃; for 24h;	98%
With caesium carbonate In N,N-dimethyl-formamide at 60℃; under 1520.1 Torr; for 6h;	92%

1-bromo-butane (109-65-9) + 2-hydroxy-4-methoxypyridine-3-carbonitrile (21642-98-8) → 1-n-butyl-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (1056381-91-9)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	100%
With potassium carbonate In acetonitrile at 100℃; for 16h;

1-bromo-butane (109-65-9) + 2-(2-((3-(1H-imidazol-1-yl)propyl)amino)-2-oxoethoxy)-N,N-di-n-octyl-acetamide (1442467-58-4) → 3-n-butyl-1-(3-(2-(2-(di-n-octylamino)-2-oxoethoxy)acetamido)propyl)-1H-imidazol-3-ium bromide (1442467-59-5)

Conditions	Yield
In acetonitrile at 0 - 85℃; Inert atmosphere;	100%

1-bromo-butane (109-65-9) + 3,4,5-triphenylpyrazole (18076-30-7) → 1-butyl-3,4,5-triphenyl-1H-pyrazole

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 5h;	100%

1-bromo-butane (109-65-9) + (R)-(-)-[1-phenylethyl]-1H-imidazole (844658-92-0) → (R)-1-butyl-3-(1-phenylethyl)imidazolium bromide

Conditions	Yield
In toluene Reflux;	100%

1-bromo-butane (109-65-9) + L,L-selenohomocystine → (2S)-2-amino-4-(butylselanyl)butanoic acid (1601474-70-7)

Conditions	Yield
With sodium tetrahydroborate; sodium hydroxide In tetrahydrofuran; water at 20℃; for 5h; pH=5 - 7; Inert atmosphere;	100%

Upstream product

• 629-04-9 1-Bromoheptane 
• 544-40-1 Dibutyl sulfide 
• 1191-30-6 5-bromopentanal 
• 38563-45-0 Diphenylbutylarsine 
• 2348-55-2 sec-Butyl-Radikal 
• 142-96-1 dibutyl ether 
• 10035-10-6 hydrogen bromide 
• 108-24-7 acetic anhydride 
• 4945-48-6 1-butyl-piperidine 
• 506-68-3 bromocyane 
• 106-98-9 1-butylene 
• 512-85-6 ascaridole 
• 598-31-2 1-bromoacetone 
• 7726-95-6 bromine 

Downstream Products

• 767-10-2 1-butylpyrrolidine 
• 2294-76-0 2-pentylpyridine 
• 1455-20-5 2-butylthiophene 
• 7133-16-6 cyclopentyl n-butyl sulfide 
• 25394-31-4 (1R,2S)-2-(butyl(methyl)amino)-1-phenylpropan-1-ol 
• 178552-51-7 3-butoxy-benzoic acid ethyl ester 
• 23563-26-0 4-n-butoxyacetanilide 
• 91560-97-3 (4-bromo-3,5-dimethyl-phenyl)-butyl ether 
• 18232-09-2 2-(butylthio)cyclohexa-2,5-diene-1,4-dione 
• 613-29-6 N-Dibutylaniline 
• 87282-11-9 N,N-dibutyl-2,5-dimethyl-aniline 
• 55019-66-4 (2-benziloyloxy-ethyl)-butyl-dimethyl-ammonium; bromide 
• 875846-14-3 3-butoxy-5-nitro-benzoic acid 
• 102310-68-9 methyl 3,4,5-tris(n-butan-1-yloxy)benzoate 

Related news

Vapour pressures at 10 different temperatures between 278.15 and 323.15 K for binary mixtures of 1-Bromobutane (cas 109-65-9) with ethanol or 1-hexanol08/21/2019

Vapour pressures of 1-bromobutane+ethanol, or + 1-hexanol at 10 different temperatures between 278.15 and 323.15 K were measured by a static method. The reduction of the vapour pressures to obtain activity coefficients and excess molar Gibbs energies was carried out by fitting the vapour pressur...detailed

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Convergent synthesis of a deuterium-labeled serine dipeptide lipid for analysis of biological samples

Bacterial serine dipeptide lipids are known to promote inflammatory processes and are detected in human tissues associated with periodontal disease or atherosclerosis. Accurate quantification of bacterial serine lipid, specifically lipid 654 [((S)-15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-l-serine, (3S)-l-serine] isolated from Porphyromonas gingivalis, in biological samples requires the preparation of a stable isotope internal standard for sample supplementation and subsequent mass spectrometric analysis. This report describes the convergent synthesis of a deuterium-substituted serine dipeptide lipid, which is an isotopically labeled homologue that represents a dominant form of serine dipeptide lipid recovered in bacteria.

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STABILIZATION IN THE ORDER I>Br>Cl AMONG TRIMETHYLSILYLMETHYL HALIDES, COMPARED TO CARBON ANALOGS. POSSIBLE ROLE OF ELECTRONEGATIVITY IN ORGANOSILICON CHEMISTRY

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Tributylarsonium-2,2,3,3,4,4-hexafluorocyclobutane Ylide. Preparation and Cleavage

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A study of the lithiation of 2,6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010

Mono-lithiation of 2,6-dibromopyridine by n-BuLi is complicated by deprotonation of the pyridine ring by the resulting mono-lithium species. This problem can be eliminated by a reverse addition, but this causes formation of the undesired dilithio species. However, rapid lithium-halogen exchange between 2,6-dibromopyridine and 2,6-dilithiopyridine produces 2-bromo-6-lithiopyridine cleanly. Thus, using reverse addition, the mono-lithiated pyridine can be generated in 98% yield.

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Method of preparing 1-bromobutane continuously

The invention discloses a method of preparing 1-bromobutane continuously. 1-bromobutane is produced continuously by carrying out a reaction within a short time in a micro reactor without a catalyst bytaking normal butanol and hydrobromic acid as raw materials. Two strands of materials enter the micro reactor through a metering pump and are preheated, mixed and reacted to obtain a coarse product 1-bromobutane. Compared with the prior art, a catalyst sulfuric acid is not used, so that treatment of sulfuric acid at the back end is reduced, the separation process is simplified, the environmentalpollution is reduced, the utilization ratio of hydrobromic acid is high, the conversion rate of reactants is high, and the selectivity and yield of a target product are relatively high and the like. The method is simple and safe to operate, can be used for producing 1-bromobutane continuously with a high yield, and has a good industrial application prospect.

Why is cis/trans stereoinversion with Li+(THF)4 migration across the phenyl ring of α-lithiostyrene accelerated by two ortho-methyl groups?

Common wisdom might anticipate that two methyl groups placed on a molecular migration route should act as an impediment. However, the “conducted tour” migration of Li+(THF)4 across the aryl ring (“π-route”) during the cis/trans stereoinversion of α-arylvinyllithiums had been found to occur with practically equal velocities in the presence of either one or two ortho-alkyl substituents. We now report that the omission of both ortho-methyl groups retards the stereoinversion process. In order to arrive at an answer to the title question, we investigate the aggregation equilibria and microsolvation states of ortho, ortho′-unsubstituted α-lithiostyrenes by means of approved secondary NMR criteria. Beyond such necessary knowledge about the ground-state properties, we provide kinetic evidence showing that the retarded cis/trans stereoinversion of α-lithiostyrene proceeds by the pseudomonomolecular, ionic mechanism with Li+(THF)4 migration.