111-25-1

Basic information

• Product Name: 1-Bromohexane
• Synonyms: 1-BROMOHEXANE;HEXYL BROMIDE;Bromohexane;N-HEXYL BROMIDE;N-BROMOHEXANE;1-bromo-hexan;1-Hexyl bromide;1-hexylbromide
• CAS NO: 111-25-1
• Molecular Formula: C₆H₁₃Br
• Molecular Weight: 165.07
• EINECS: 203-850-2
• Product Categories: Industrial/Fine Chemicals;Intermediates;ALKYL BROMIDE;Bromine Compounds;Alkyl Bromides;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Alkyl;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 111-25-1.mol
• Article Data: 45

Chemical Properties

• Melting Point: −85 °C(lit.)
• Boiling Point: 154-158 °C(lit.)
• Flash Point: 135 °F
• Appearance: Clear/Liquid
• Density: 1.176 g/mL at 25 °C(lit.)
• Vapor Density: 5.7 (vs air)
• Vapor Pressure: <10 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.448(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: <1g/l
• Water Solubility: Immiscible with water.
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases. Combustible.
• BRN: 1731290
• CAS DataBase Reference: 1-Bromohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromohexane(111-25-1)
• EPA Substance Registry System: 1-Bromohexane(111-25-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-10
• Safety Statements: 26-36-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 2
• RTECS: MO0925000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 111-25-1(Hazardous Substances Data)

Usage

Chemical nature

1-Bromohexane is organobromine compound with formula Br(CH2)5CH3. It is a colorless liquid.

Synthesis and reactions

Most 1-bromoalkanes are prepared by free-radical addition of hydrogen bromide to the 1-alkene. These conditions lead to anti-Markovnikov addition, giving the 1-bromo derivative. 1-Bromohexane undergoes reactions expected of simple alkyl bromides. It can form Grignard reagents. It reacts with potassium fluoride to give the corresponding fluorocarbons.

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 111-25-1 differently. You can refer to the following data:
1. Intermediate, for introduction of hexyl group.
2. 1-Bromohexane is utilized in the preparation of pharmaceuticals and organic chemicals. It is involved in Grignard reactions as an alkylating agent and in the synthesis of bromo-cyclic compounds.

Synthesis Reference(s)

Chemistry Letters, 7, p. 833, 1978Synthetic Communications, 6, p. 21, 1976 DOI: 10.1080/00397917608062128Tetrahedron, 40, p. 641, 1984 DOI: 10.1016/S0040-4020(01)91092-0

Purification Methods

Shake the bromide with H2SO4, wash with water, dry (K2CO3) and fractionally distil. [Beilstein 1 IV 352.]

InChI:InChI=1/C6H13Br/c1-2-3-4-5-6-7/h2-6H2,1H3

Synthetic route

1-Chlorohexane (544-10-5) → 1-bromo-hexane (111-25-1)

Conditions	Yield
With calcium bromide; tetrahexylammonium bromide at 110℃; for 24h;	92%
With tetrabutylammomium bromide; lithium chloride In toluene at 70℃; Rate constant; Equilibrium constant; effect of nature of the cation of the salt on the equilibrium constant;

hexan-1-ol (111-27-3) → 1-bromo-hexane (111-25-1)

Conditions	Yield
With phosphorus tribromide In tetrahydrofuran at 10℃; for 3h; Large scale;	91.4%
With phosphorus tribromide for 4h; Cooling with ice;	85%
With hydrogen bromide

Pyridine-2-sulfonic acid hexyl ester → 1-bromo-hexane (111-25-1) + C5H4NO3S(1-)*Br(1-)*Mg(2+)

Conditions	Yield
With magnesium bromide ethyl etherate In diethyl ether; dichloromethane at 0℃; for 0.0833333h;	A 88% B n/a

6-Bromo-1-hexene (2695-47-8) → 1-bromo-hexane (111-25-1)

Conditions	Yield
With hydrogen; 1,5-hexadienerhodium(I)-chloride dimer In hexane for 4h; Ambient temperature; pH=7.6;	78%
With hydrogen at 25℃; under 760.051 Torr; for 0.166667h; Catalytic behavior; Reagent/catalyst; Time;

hexan-1-ol (111-27-3) → dihexyl phosphonate (6151-90-2) + 1-bromo-hexane (111-25-1)

Conditions	Yield
With phosphorus tribromide In diethyl ether at 0 - 25℃; for 6h;	A 12.8% B 75.3%

Bromoform (75-25-2) + 2-(hexyloxy)-1,3-dioxolane (83498-70-8) → [1,3]-dioxolan-2-one (96-49-1) + 1-bromo-hexane (111-25-1) + formic acid-(2-bromo-ethyl ester) (6065-67-4) + hexanal (66-25-1) + 2-bromoethyl hexyl carbonate + 1,2-dibromomethane (74-95-3)

Conditions	Yield
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature;	A n/a B n/a C n/a D n/a E 60% F n/a

Bromoform (75-25-2) + 2-(hexyloxy)-m-dioxane → trimethylene carbonate (2453-03-4) + 1-bromo-hexane (111-25-1) + 3-Brompropylformiat (53452-10-1) + hexanal (66-25-1) + 3-bromopropyl hexyl carbonate + 1,2-dibromomethane (74-95-3)

Conditions	Yield
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature;	A n/a B n/a C n/a D n/a E 56% F n/a

3-bromohexane (3377-87-5) → 1-bromo-hexane (111-25-1)

Conditions	Yield
	50%

2-hexyloxyethanol (112-25-4) → 1-bromo-hexane (111-25-1) + (2-bromo-ethyl)-hexyl ether (82175-70-0)

Conditions	Yield
With dibromo sulfoxide; urea In 1,2-dichloro-benzene at 30 - 50℃; for 14h; Product distribution / selectivity;	A n/a B 13.5%

1-hexene (592-41-6) → 1-bromo-hexane (111-25-1)

Conditions	Yield
With hydrogen bromide unter der Einwirkung von stillen elektrischen Entlandungen;

Acetyl bromide (506-96-7) + ethyl n-hexyl ether (5756-43-4) → ethyl bromide (74-96-4) + 1-bromo-hexane (111-25-1)

Conditions	Yield
at 180℃; im Rohr;

hexane (110-54-3) → 1-bromo-hexane (111-25-1) + 2-bromohexane (3377-86-4, 28941-54-0, 62885-28-3)

Conditions	Yield
With bromine Irradiation.bei gleichzeitiger Belichtung mit einer Uviollampe;
With bromine Irradiation.bei gleichzeitiger Belichtung mit einer Uviollampe;

1-hexene (592-41-6) → 1-bromo-hexane (111-25-1) + 2-bromohexane (3377-86-4, 28941-54-0, 62885-28-3)

Conditions	Yield
With borane; bromine; sodium methylate 1.)THF, 0 deg C, 2.) 0 deg C, 3.) MeOH, 0 deg C; Yield given. Multistep reaction;

1-hexene (592-41-6) → 1-bromo-hexane (111-25-1) + 2-bromohexane (3377-86-4, 28941-54-0, 62885-28-3) + hexan-1-ol (111-27-3)

Conditions	Yield
With borane; bromine In tetrahydrofuran at 20 - 25℃; Product distribution; bromination reaction in presence of various bases; dropwise or simultaneous addition;

hexane (110-54-3) → 3-bromohexane (3377-87-5) + 1-bromo-hexane (111-25-1) + 2-bromohexane (3377-86-4, 28941-54-0, 62885-28-3)

Conditions	Yield
With N-bromo-2,2,6,6-tetramethylpiperidinium perchlorate In trifluoroacetic acid at 5℃; for 8h; Product distribution; Mechanism; Irradiation; different N-bromoammonium perchlorate derivatives;
With N-bromo-2,2,6,6-tetramethylpiperidinium perchlorate In trifluoroacetic acid at 5℃; for 8h; Irradiation; Yield given. Yields of byproduct given;
With bromine; sodium t-butanolate In cyclohexane Heating; Title compound not separated from byproducts;
With N-bromo-N-(t-butyl)-3,5-bis(trifluoromethyl)benzamide In benzene at 20℃; for 4h; Sealed tube; Irradiation; Inert atmosphere; Overall yield = 66.1 %Chromat.;

Bromotrichloromethane (75-62-7) + 2-(hexyloxy)-1,3-dioxolane (83498-70-8) → [1,3]-dioxolan-2-one (96-49-1) + 1-bromo-hexane (111-25-1) + formic acid-(2-bromo-ethyl ester) (6065-67-4) + hexanal (66-25-1) + 2-bromoethyl hexyl carbonate + 1,2-dibromomethane (74-95-3)

Conditions	Yield
dibenzoyl peroxide at 90℃; for 2h; Rate constant; Product distribution;

ethyl n-hexyl ether (5756-43-4) → 1-bromo-hexane (111-25-1)

Conditions	Yield
With trimethylsilyl bromide for 168h; Heating; Yield given;

n-octyne (629-05-0) + trihexylaluminium (1116-73-0) → 1-bromo-hexane (111-25-1) + 6-methylenetridecane (19780-80-4) + (E)-7-tetradecene (41446-63-3)

Conditions	Yield
With copper(I) bromide In hexane 1.) -78 deg C, 2 h, 2.) 20 deg C, 4 h;	A 2.0 % Chromat. B 57.6 % Chromat. C 5.8 % Chromat.

hexanoxytrimethylsilane (17888-62-9) → 1-bromo-hexane (111-25-1)

Conditions	Yield
With trimethylsilyl bromide for 168h; Heating; Yield given;

1-hexene-3-ol (4798-44-1) → 1-bromo-hexane (111-25-1)

Conditions	Yield
With lithium aluminium tetrahydride; bromine; bis(cyclopentadienyl)titanium dichloride 1.) THF; Yield given. Multistep reaction;

trihexylorthoformate (4459-32-9) → dodecane (112-40-3) + hexyl formate (629-33-4) + hexane (110-54-3) + 1-bromo-hexane (111-25-1) + di-hexyl carbonate (7523-15-1) + hexanal (66-25-1)

Conditions	Yield
With Perbenzoic acid; Bromoform at 89.9℃; Product distribution; Rate constant; Mechanism; other temperatures: 353 deg K; other peroxide: t-butyl peroxide;

n-hexyl mercury chloride (17774-09-3) → 1-bromo-hexane (111-25-1)

Conditions	Yield
With Bromotrichloromethane In benzene at 45℃; for 36h; Irradiation;	56 % Spectr.

hexyldiphenylbismutane (74724-77-9) → bromobenzene (108-86-1) + 1-bromo-hexane (111-25-1)

Conditions	Yield
With bromine In dichloromethane -70 deg C to r.t.;	A 10 % Chromat. B 62 % Chromat.

hexyl 3-methylcyclohexa-1,4-diene-3-carboxylate (162104-75-8) → 1-bromo-hexane (111-25-1) + hexyl benzoate (6789-88-4) + toluene (108-88-3)

Conditions	Yield
With N-Bromosuccinimide; (PhCO2)2O In tetrachloromethane for 16h; Product distribution; Heating; other cyclohexa-1,4-diene-3-carboxylates, 2,5-dihydrofuran-2-carboxylates;	A 3 % Chromat. B 2 % Chromat. C 7 % Chromat.
With N-Bromosuccinimide; dilauryl peroxide In tetrachloromethane for 5h; Mechanism; Product distribution;	A 7 % Chromat. B 4 % Chromat. C 3 % Chromat.

sulfuric acid (7664-93-9) + hexan-1-ol (111-27-3) + sodium bromide → 1-bromo-hexane (111-25-1) + 2-bromohexane (3377-86-4, 28941-54-0, 62885-28-3)

enanthate thallium → 1-bromo-hexane (111-25-1)

Conditions	Yield
With tetrachloromethane; bromine
With tetrachloromethane; bromine

hexane (110-54-3) + bromine (7726-95-6) → 3-bromohexane (3377-87-5) + 1-bromo-hexane (111-25-1) + 2-bromohexane (3377-86-4, 28941-54-0, 62885-28-3)

Conditions	Yield
im Sonnenlichte bei Siedetemperatur;

1-bromo-hexane (111-25-1) + salicylaldehyde (90-02-8) → 2-hexyloxybenzaldehyde (7162-59-6)

Conditions	Yield
With potassium hydroxide; potassium iodide In ethanol for 32h; Heating;	100%
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 20h;	99%
Stage #1: salicylaldehyde With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-bromo-hexane In N,N-dimethyl-formamide at 20℃; for 24h;	75.3%

1-bromo-hexane (111-25-1) + thiophenol (108-98-5) → hexyl phenyl sulfide (943-78-2)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20 - 50℃; for 2.16667h; Inert atmosphere;	100%
With ethanol; sodium ethanolate
With potassium hydroxide
cetyltributylphosphonium bromide
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 12h;

1-bromo-hexane (111-25-1) + triphenylphosphine (603-35-0) → hexyltriphenylphosphonium bromide (4762-26-9)

Conditions	Yield
In toluene for 8h; Reflux;	100%
In acetonitrile for 16h; Heating;	95.6%
In toluene for 120h; Heating;	92%

2-morpholino-3-pentenenitrile (101132-13-2) + 1-bromo-hexane (111-25-1) → 2-hexyl-2-morpholino-3-pentenenitrile (84104-04-1)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran	100%

1-bromo-hexane (111-25-1) + 2-methylbenzene-1,4-diol (95-71-6) → 1,4-Dihexyloxy-2-methylbenzol (157202-49-8)

Conditions	Yield
With potassium hydroxide; Aliquat 336 In 1,2-dimethoxyethane for 24h; Heating;	100%
In ethanol Etherification; Heating;

1-bromo-hexane (111-25-1) + 3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) → non-2-ynyl tetrahydropyran-2-yl ether (83583-29-3)

Conditions	Yield
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; Stage #2: 1-bromo-hexane In tetrahydrofuran	100%
With sodium amide
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane Ambient temperature;
With ammonium chloride; lithium; iron(III) chloride In ammonia

1-bromo-hexane (111-25-1) + 4-hydroxy-benzaldehyde (123-08-0) → 4-(hexyloxy)benzaldehyde (5736-94-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; Williamson ether synthesis;	100%
Stage #1: 4-hydroxy-benzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Stage #2: 1-bromo-hexane In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	99%
With potassium carbonate In acetonitrile Reflux;	96%

1-bromo-hexane (111-25-1) + 4-cyanophenol (767-00-0) → 1-(4-cyanophenyl)oxyhexane (66052-06-0)

Conditions	Yield
In potassium carbonate	100%
With sodium hydride In N,N-dimethyl-formamide 1.) rt, 1 h, 2.) reflux, 12 h;	90%
With potassium carbonate In cyclohexanone for 24h; Heating;	70%

1-bromo-hexane (111-25-1) + ethyl (S)-6-hydroxy-2-methylchroman-2-carboxylate → (S)-6-Hexyloxy-2-methyl-chroman-2-carboxylic acid ethyl ester

Conditions	Yield
With sodium hydride; potassium iodide In N,N-dimethyl-formamide at 80℃; for 48h; Etherification;	100%

4,4'-dichlorodiphenyl disulfide (1142-19-4) + 1-bromo-hexane (111-25-1) → n-Hexyl-p-chlorphenylsulfid (59693-91-3)

Conditions	Yield
Stage #1: 4,4'-dichlorodiphenyl disulfide With aluminium trichloride; zinc In water; N,N-dimethyl-formamide at 65℃; S-S bond cleavage; Stage #2: 1-bromo-hexane In water; N,N-dimethyl-formamide at 65℃; for 18h; Substitution;	100%
With aluminium trichloride; zinc In water; N,N-dimethyl-formamide at 65℃; for 18h;	100 % Chromat.

1-methyl-1H-imidazole (616-47-7) + 1-bromo-hexane (111-25-1) → 1-hexyl-3-methyl-1-imidazolium bromide (85100-78-3)

Conditions	Yield
at 140℃; Continuous flow; neat (no solvent);	100%
In dichloromethane at 20℃; for 0.25h; Cooling with ice;	99.87%
In toluene at 65℃; for 5h;	98%

9H-fluorene (86-73-7) + 1-bromo-hexane (111-25-1) → 9,9-dihexyl-9H-fluorene (123863-97-8)

Conditions	Yield
Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: 1-bromo-hexane In tetrahydrofuran at -78 - 20℃; for 12h; Further stages.;	100%
With tetra-(n-butyl)ammonium iodide; sodium hydroxide	100%
Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 0.75h; Stage #2: 1-bromo-hexane In tetrahydrofuran at -78 - 20℃; for 3h;	99%

1-bromo-hexane (111-25-1) + 2-bromo-9H-fluorene (1133-80-8) → 2-bromo-9,9-dihexyl-9H-fluorene (226070-05-9)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dimethyl sulfoxide	100%
Stage #1: 2-bromo-9H-fluorene With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1-bromo-hexane In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	100%
Stage #1: 2-bromo-9H-fluorene With potassium iodide; potassium hydroxide In dimethyl sulfoxide for 0.333333h; Heating; Inert atmosphere; Stage #2: 1-bromo-hexane In dimethyl sulfoxide at 20℃; for 3.6h; Inert atmosphere;	100%

1-bromo-hexane (111-25-1) + truxene (548-35-6) → 5,5,10,10,15,15-hexahexyltruxene (600172-85-8)

Conditions	Yield
Stage #1: truxene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: 1-bromo-hexane In tetrahydrofuran at -78 - 20℃;	100%
Stage #1: truxene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 1-bromo-hexane In tetrahydrofuran at 20℃; Inert atmosphere;	95%
Stage #1: truxene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Inert atmosphere; Stage #2: 1-bromo-hexane In tetrahydrofuran; hexane at -78 - 20℃; for 12h;	95%

1-bromo-hexane (111-25-1) + 2-(trifluoromethyl)phenol (444-30-4) → 1-(hexyloxy)-2-(trifluoromethyl)benzene (872123-27-8)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 2.5h;	100%
With potassium carbonate In various solvent(s) Heating;	75%

1-vinylimidazole (1072-63-5) + 1-bromo-hexane (111-25-1) → 1-vinyl-3-hexyl-1H-imidazol-3-ium bromide

Conditions	Yield
at 110℃; Continuous flow; neat (no solvent);	100%
Microwave irradiation;	82.6%
In tetrahydrofuran at 60℃; for 48h;	51.63%

C76H21N3O2 (1008131-36-9) + 1-bromo-hexane (111-25-1) → Br(1-)*C82H34N3O2(1+) (1008131-37-0)

Conditions	Yield
at 100℃; for 48h;	100%

C72H21N3 (1008131-33-6) + 1-bromo-hexane (111-25-1) → Br(1-)*C78H34N3(1+) (1008131-34-7)

Conditions	Yield
at 100℃; for 48h;	100%

5-fluoro-1H-indole-2,3-dione (443-69-6) + 1-bromo-hexane (111-25-1) → 5-fluoro-1-hexyl-isatin (85511-62-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 140℃; Microwave irradiation;	100%

1-bromo-hexane (111-25-1) + 5-chloroindole 2,3-dione (17630-76-1) → 5-chloro-1-hexyl-isatin (79183-52-1)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 140℃; Microwave irradiation;	100%

1-bromo-hexane (111-25-1) + 6-Hydroxy-1-tetralone (3470-50-6) → 6-(hexyloxy)-3,4-dihydronaphthalen-1(2H)-one (62324-94-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃;	100%

1-bromo-hexane (111-25-1) + 4-nitro-benzoic acid (62-23-7) → 4-nitrophenyl hexanoate (6268-24-2)

Conditions	Yield
With potassium carbonate In acetone for 48h; Reflux;	100%

1-bromo-hexane (111-25-1) + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-70-3) → 2-(4-(hexyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (921937-76-0)

Conditions	Yield
With potassium carbonate at 120℃; for 11h; Inert atmosphere;	100%
With potassium carbonate In acetone Reflux;	64%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In tetrahydrofuran for 3h; Reflux;

1-bromo-hexane (111-25-1) + tert-butyl 3-{7-fluoro-6-hydroxy-2H-spiro[1-benzofuran-3,4'-piperidine]-1'-yl}propanoate (1355089-63-2) → tert-butyl 3-{7-fluoro-6-(hexyloxy)-2H-spiro[1-benzofuran-3,4'-piperidine]-1'-yl}propanoate (1355089-67-6)

Conditions	Yield
Stage #1: 1-bromo-hexane; tert-butyl 3-{7-fluoro-6-hydroxy-2H-spiro[1-benzofuran-3,4'-piperidine]-1'-yl}propanoate With potassium carbonate In acetonitrile at 75℃; Stage #2: In acetonitrile	100%

1-bromo-hexane (111-25-1) + 2,6-difluorophenol (28177-48-2) → 2,4-difluoro-3-hexyloxybenzene (1562104-17-9)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 80℃; for 4h;	100%
With potassium carbonate In acetonitrile for 24h; Reflux;	84%

5-bromo-2-pyridylamine (1072-97-5) + 1-bromo-hexane (111-25-1) → 5-bromo-N,N-dihexylpyridin-2-amine

Conditions	Yield
With sodium hydride In tetrahydrofuran at 50℃;	100%
With sodium hydride In tetrahydrofuran at 50℃; Reflux;

1-bromo-hexane (111-25-1) + 5-Bromo-1H-indole-2,3-dione (87-48-9) → C14H16BrNO2

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 110℃; for 16h;	100%

7-Azaindole (271-63-6) + 1-bromo-hexane (111-25-1) → C13H18N2 (418795-22-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃;	100%

1-bromo-hexane (111-25-1) + 2,3,6-trifluorophenol (113798-74-6) → C12H15F3O

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	100%

1-bromo-hexane (111-25-1) + (E)-N'-(1H-imidazol-2-yl)-N,N-dimethylformimidamide → (E)-N'-(1-hexyl-1H-imidazol-2-yl)-N,N-dimethylformimidamide

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 40℃;	100%

Upstream product

• 506-96-7 Acetyl bromide 
• 5756-43-4 ethyl n-hexyl ether 
• 110-54-3 hexane 
• 111-27-3 hexan-1-ol 
• 592-41-6 1-hexene 
• 75-25-2 Bromoform 
• 83498-70-8 2-(hexyloxy)-1,3-dioxolane 
• 544-10-5 1-Chlorohexane 
• 75-62-7 Bromotrichloromethane 
• 629-05-0 n-octyne 
• 1116-73-0 trihexylaluminium 
• 17888-62-9 hexanoxytrimethylsilane 
• 4798-44-1 1-hexene-3-ol 
• 4459-32-9 trihexylorthoformate 

Downstream Products

• 110533-46-5 2-(3,4-dichloro-trans-styryl)-1-hexyl-pyridinium; bromide 
• 6911-41-7 2-hexylsulfanylthiophene 
• 1142-39-8 para-hexyloxybenzoic acid 
• 154845-72-4 4-hexyloxy-benzoic acid ethyl ester 
• 74320-07-3 1-(4-methylphenylsulfonyl)-hexane 
• 15440-98-9 1-(hexyloxy)-4-nitrobenzene 
• 57792-40-2 1-(hexyloxy)-4-methylbenzene 
• 59693-90-2 n-hexyl 4-methoxyphenyl sulfide 
• 30752-19-3 1-bromo-4-hexyloxylbenzene 
• 5398-10-7 diethyl 2-hexylmalonate 
• 6294-31-1 hexyl sulfide 
• 629-64-1 diheptyl ether 
• 63957-53-9 N,N-diethyl-N,N'-dihexyl-N',N'-dimethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; dibromide 
• 101262-37-7 3-ethoxy-2-hexyloxy-toluene 

Related news

High-pressure phase equilibria for the synthesis of ionic liquids in compressed CO2 for 1-hexyl-3-methylimidazolium bromide with 1-Bromohexane (cas 111-25-1) and 1-methylimidazole08/20/2019

The use of carbon dioxide in the synthesis of ionic liquids (ILs) has many advantages over conventional solvents. Here, the high-pressure phase equilibria (including CO2 solubility, volume expansion, and mixture critical points) are measured and modeled for the system involved in the synthesis o...detailed

Relevant articles and documents

Facile hydrogenation of carbon-carbon double bonds using catalytic noble nanoparticles immobilized in microfluidic reactors

Facile hydrogenation of carbon-carbon double bonds was achieved in a poly(dimethylsiloxane) (PDMS) microfluidic reactor with immobilized noble nanoparticles, using the conversion of 6-bromo-1-hexene to 1-bromo-hexane as a model reaction. The microreactor was used to measure the intrinsic catalytic activity and turnover frequencies (TOF) of palladium (Pd), platinum (Pt) and ruthenium (Ru) nanocatalysts. The TOF of reactions run with immobilized nanocatalysts in the microfluidic reactor were hundreds of times larger than those measured in identical reactions in batch reactors. The combination of well-defined nanocatalysts and microfluidics significantly enhances hydrogen diffusion to catalytic sites, thus eliminating mass transfer limitations and enabling evaluation of the intrinsic catalytic activity. The system provides an excellent platform for high throughput screening of catalysts, and for conducting mechanistic studies of reaction kinetics.

Synthesis of the sex pheromone of Lygus lineolaris (Heteroptera miridae)

We propose a new synthesis of the sex pheromone of Lygus lineolaris (Heteroptera miridae) that uses a phase-transfer version of the Wittig - Horner reaction to produce a monoene synthon of the principal component of the pheromone, E-2-hexenylbutyrate.

Anion nucleophilicity in ionic liquids: A comparison with traditional molecular solvents of different polarity

The nucleophilic reactivity of a homogeneous series of anions (halides, pseudohalides and organic anions) in the ionic liquids [hexmim] [ClO 4] and [hexmim] [PF6] has been measured in their reaction with n-alkyl methanesulfonates, and compared with that found in traditional molecular solvents of different polarity, that is, chlorobenzene, DMSO, and MeOH.

A preparing method of diethylamino hydroxybenzoyl hexylbenzoate

The present invention relates to a method for the preparation of diethylamino hydroxybenzoyl hexyl benzoate. Specifically, the present invention relates to a method for preparing diethylamino hydroxybenzoyl hexyl benzoate which is easy to manufacture and commercially available in mass production, and diethylamino hydroxybenzoyl hexyl benzoate crystalline particles prepared thereby. According to the present invention, diethylamino hydroxybenzoyl hexyl benzoate crystalline particles having excellent UV blocking effect can be obtained in a stable and high yield.COPYRIGHT KIPO 2020

Synthesis and mass spectra of rearrangement bio-signature metabolites of anaerobic alkane degradation via fumarate addition

Metabolite profiling in anaerobic alkane biodegradation plays an important role in revealing activation mechanisms. Apart from alkylsuccinates, which are considered to be the usual biomarkers via fumarate addition, the downstream metabolites of C-skeleton rearrangement can also be regarded as biomarkers. However, it is difficult to detect intermediate metabolites in both environmental samples and enrichment cultures, resulting in lacking direct evidence to prove the occurrence of fumarate addition pathway. In this work, a synthetic method of rearrangement metabolites was established. Four compounds, namely, propylmalonic acid, 2-(2-methylbutyl)malonic acid, 2-(2-methylpentyl)malonic acid and 2-(2-methyloctyl)malonic acid, were synthesized and determined by four derivatization approaches. Besides, their mass spectra were obtained. Four characteristic ions were observed at m/z 133 + 14n, 160 + 28n, 173 + 28n and [M - (45 + 14n)]+ (n = 0 and 2 for ethyl and n-butyl esters, respectively). For methyl esterification, mass spectral features were m/z 132, 145 and [M - 31]+, while for silylation, fragments were m/z 73, 147, 217, 248, 261 and [M - 15]+. These data provide basis on identification of potential rearrangement metabolites in anaerobic alkane biodegradation via fumarate addition.

Synthesis of Branched Biolubricant Base Oil from Oleic Acid

The mature manufacturing of synthetic lubricants (poly-α-olefins, PAO) proceeds through oligomerization, polymerization, and hydrogenation reactions of petrochemical ethylene. In this work, we utilize the inexpensive bio-derived oleic acid as raw material to synthesize a crotch-type C45 biolubricant base oil via a full-carbon chain synthesis without carbon loss. It contains several cascade chemical processes: oxidation of oleic acid to azelaic acid (further esterification to dimethyl azelate) and nonanoic acid (both C9 chains). The latter is then selectively hydrogenated to nonanol and brominated to the bromo-Grignard reagent. In a next step, a C45 biolubricant base oil is formed by nucleophilic addition (NPA) of excessive C9 bromo-Grignard reagent with dimethyl azelate, followed by subsequent hydrodeoxygenation. The specific properties of the prepared biolubricant base oil are almost equivalent to those of the commercial lubricant PAO6 (ExxonMobil). This process provides a new promising route for the production of value-added biolubricant base oils.

An efficient conversion of alcohols to alkyl bromides using pyridinium based ionic liquids: A green alternative to appel reaction

Pyridinium based ionic liquids namely 4-alkylpyridinium bromides were prepared and used for the conversion of alcohols to alkyl bromides in the presence of p-toluenesulphonic acid in the absence of volatile organic compounds. This solvent free procedure promises to be a much improved and environmentally benign alternative to the Appel reaction.

Facile continuous process for gas phase halogen exchange over supported alkyl phosphonium salts

Chloride-bromide halogen exchange was realized when a mixture of an alkyl chloride and an alkyl bromide were reacted over a supported molten alkyl phosphonium catalyst. Conversion was found to be near equilibrium in a tubular flow reactor at 150 °C and 1500 GHSV. The catalyst was prepared by impregnation of alumina or silica support and found to be highly stable for relatively long periods of time. A pathway for the catalytic cycle is proposed.

B(C6F5)3-Catalyzed Chemoselective Defunctionalization of Ether-Containing Primary Alkyl Tosylates with Hydrosilanes

Catalytic C(sp3)?O bond cleavage promoted by B(C6F5)3 /Et3SiH proceeds preferentially with primary tosylates in the presence of primary and secondary silyl ethers and aryl ethers. This reactivity difference enables the chemoselective defunctionalization of several 1,n-diols, and the efficiency of the new procedure is highlighted by the selective deoxygenation of the hydroxymethyl group of an orthogonally protected carbohydrate. Tosylates with an adjacent phenyl group are cleaved with anchimeric assistance.

Mild partial deoxygenation of esters catalyzed by an oxazolinylborate-coordinated rhodium silylene

An electrophilic, coordinatively unsaturated rhodium complex supported by borate-linked oxazoline, oxazoline-coordinated silylene, and N-heterocyclic carbene donors [{κ3-N,Si,C-PhB(OxMe2)(OxMe2SiHPh)ImMes}Rh(H)CO][HB(C6F5)3] (2, OxMe2 = 4,4-dimethyl-2-oxazoline; ImMes = 1-mesitylimidazole) is synthesized from the neutral rhodium silyl {PhB(OxMe2)2ImMes}RhH(SiH2Ph)CO (1) and B(C6F5)3. The unusual oxazoline-coordinated silylene structure in 2 is proposed to form by rearrangement of an unobserved isomeric cationic rhodium silylene species [{PhB(OxMe2)2ImMes}RhH(SiHPh)CO][HB(C6F5)3] generated by H abstraction. Complex 2 catalyzes reductions of organic carbonyl compounds with silanes to give hydrosilylation products or deoxygenation products. The pathway to these reactions is primarily influenced by the degree of substitution of the organosilane. Reactions with primary silanes give deoxygenation of esters to ethers, amides to amines, and ketones and aldehydes to hydrocarbons, whereas tertiary silanes react to give 1,2-hydrosilylation of the carbonyl functionality. In contrast, the strong Lewis acid B(C6F5)3 catalyzes the complete deoxygenation of carbonyl compounds to hydrocarbons with PhSiH3 as the reducing agent.