143-15-7

Basic information

• Product Name: 1-Bromododecane
• Synonyms: 1-BROMODECANE pure;1-BROMODODECANE pure;Dodecyl bromide, Lauryl bromide;l-Bromododecane;1-BroMododecane, 98% 1LT;1-BroMododecane, 98% 250ML;1-BROMODODECANE FOR SYNTHESIS;1-Bromododecane purum, >=95.0% (GC)
• CAS NO: 143-15-7
• Molecular Formula: C₁₂H₂₅Br
• Molecular Weight: 249.23
• EINECS: 205-587-9
• Product Categories: Bromine chemicals;Bromine Compounds;Alkyl Bromides;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes
• Mol File: 143-15-7.mol

Chemical Properties

• Melting Point: −11-−9 °C(lit.)
• Boiling Point: 134-135 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear/Liquid
• Density: 1.040 g/mL at 20 °C
• Vapor Density: 8.6 (vs air)
• Vapor Pressure: 0.00817mmHg at 25°C
• Refractive Index: n20/D 1.458(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: alcohol: soluble
• Water Solubility: insoluble
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,5389
• BRN: 506159
• CAS DataBase Reference: 1-Bromododecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromododecane(143-15-7)
• EPA Substance Registry System: 1-Bromododecane(143-15-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• F: 19
• TSCA: Yes
• Hazardous Substances Data: 143-15-7(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Synthesis:
1-Bromododecane is used as an intermediate in the production of various organic compounds. Its ability to participate in organic reactions makes it a valuable component in the synthesis of a range of products.
2. Used in Surfactant Production:
As a crucial intermediate, 1-Bromododecane is employed in the manufacturing process of surfactants. Surfactants are essential in various industries, including cosmetics, pharmaceuticals, and cleaning products, due to their ability to reduce surface tension and mix with both water and oil.
3. Used in Pharmaceutical Industry:
1-Bromododecane plays a significant role in the pharmaceutical sector, particularly in the synthesis of disinfectants such as Benzyldodecyldimethylammonium Bromide and domiphen bromide. These disinfectants are used for their antimicrobial properties, ensuring cleanliness and preventing the spread of infections.
4. Used as a Solvent:
Due to its solubility in organic solvents, 1-Bromododecane is also utilized as a solvent in various chemical processes. Its ability to dissolve other substances makes it a useful component in the production of different chemicals and compounds.

Preparation

1-Bromododecane is synthesized by the action of 1-dodecanol and hydrobromic acid. The 1-dodecanol is added to the enameled glass reaction pot, stirred and cooled, and sulfuric acid is slowly added. Stir for 1h, then add hydrobromic acid. The temperature is gradually increased to 90-95℃, and the reaction is stirred for 8h. After the reaction, the temperature is lowered to 30℃ and left for 8h. The acid layer is separated, and the oil layer is adjusted to pH 8 with dilute alkali solution, and the alkali solution is separated and washed with 50% ethanol. Distill under reduced pressure and collect 140-200℃ (3.33kPa) fractions to obtain refined 1-bromododecane.

InChI:InChI=1/C12H25Br/c1-2-3-4-5-6-7-8-9-10-11-12-13/h2-12H2,1H3

Synthetic route

dodecyl benzenesulphonate (121734-15-4) → 1-dodecylbromide (143-15-7)

Conditions	Yield
With lithium bromide In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux;	98%

1-dodecyl alcohol (112-53-8) → 1-dodecylbromide (143-15-7)

Conditions	Yield
With allyl bromide; 1,1'-carbonyldiimidazole In acetonitrile for 2h; Heating;	97%
With hydrogen bromide; 1-dodecylpyridinium bromide for 1.5h; Irradiation;	91%
Stage #1: 1-dodecyl alcohol With copper(l) chloride; diisopropyl-carbodiimide at 20℃; for 0.5h; Stage #2: With N-Bromosuccinimide In 1,2-dichloro-ethane at 80℃; for 4.5h;	90%

1-dodecene (112-41-4) → 1-dodecylbromide (143-15-7)

Conditions	Yield
With 2,2,4-trimethylpentane; tetradecafluorohexane; bromine at 20℃; for 2h; Irradiation;	96%
With pyridine; bromine; dichloroaluminum hydride; triethyl borane 1) ether, RT, 2) -78 deg C, 1 h; Yield given. Multistep reaction;

dodecyl mesylate (51323-71-8) → 1-dodecylbromide (143-15-7)

Conditions	Yield
With lithium bromide In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux;	95%
With lithium bromide In acetone for 12h; Heating;
With sodium bromide

1-dodecene (112-41-4) → 1,2-dibromodecane (28467-71-2) + 1-dodecylbromide (143-15-7)

Conditions	Yield
With hexane; bromine at 20℃; for 2h; Irradiation;	A 10% B 90%
With hexane; tetradecafluorohexane; bromine at 20℃; for 2h; Irradiation;	A 68% B 32%

1-dodecylthiol (112-55-0) → 1-dodecylbromide (143-15-7)

Conditions	Yield
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 13h;	80%

1-dodecyl alcohol (112-53-8) + benzoyl chloride (98-88-4) → dodecyl benzoate (2915-72-2) + 1-dodecylbromide (143-15-7)

Conditions	Yield
With diphenylcyclopropenone; sodium bromide In acetone at 40℃; for 13h;	A n/a B 78%

1-fluorododecane (334-68-9) → 1-dodecylbromide (143-15-7) + 1-chlorododecane (112-52-7)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; triethylaluminum; 1,2-dibromomethane In hexane at 20℃; for 24h; Solvent;	A 77% B 22%

C19H34N2O2S (151259-26-6) → toluene-p-sulfonyl bromide (1950-69-2) + 1-dodecylbromide (143-15-7)

Conditions	Yield
With N-Bromosuccinimide In tetrahydrofuran for 16h; Ambient temperature; Irradiation;	A n/a B 65%

dodecane (112-40-3) → 1-dodecylbromide (143-15-7)

Conditions	Yield
Stage #1: dodecane With IrH5(P-(i-Pr)3)2; tert-butylethylene at 150℃; for 6h; Inert atmosphere; Stage #2: With Schwartz's reagent In tetrahydrofuran at 40℃; for 12h; Inert atmosphere; Stage #3: With N-Bromosuccinimide In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; regioselective reaction;	57%

1-fluorododecane (334-68-9) → dodecane (112-40-3) + tetradecane (629-59-4) + 1-dodecylbromide (143-15-7)

Conditions	Yield
With dibromobis(cyclopentadienyl)titanium(IV); triethylaluminum In hexane at 20℃; for 24h; Solvent;	A 31% B 37% C 21%

C18H30Br2Se (102402-79-9) → 1-dodecylbromide (143-15-7)

Conditions	Yield
With bromide Ambient temperature; Yield given;

C18H30Br2Te (83486-03-7) → diphenyl ditelluride (32294-60-3) + 1-dodecylbromide (143-15-7)

Conditions	Yield
With sodium bromide In N,N-dimethyl-formamide at 70℃; Yield given;

2-(8-bromooctyloxy)tetrahydropyran (50816-20-1) → 1-dodecylbromide (143-15-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Li2CuCl4, 2.) PTSA / 1.) THF, room temperature, 12 h, 2.) CH3OH, room temperature, 6 h 2: pyridine / CH2Cl2 / 12 h / Ambient temperature 3: LiBr*H2O / acetone / 12 h / Heating View Scheme

1,8-Octanediol (629-41-4) + primary-secondary glycol C8H18O2 → 1-dodecylbromide (143-15-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / 47percent HBr / benzene / 48 h / Heating 2: 91 percent / PPTS / CH2Cl2 / 2 h / Ambient temperature 3: 1.) Li2CuCl4, 2.) PTSA / 1.) THF, room temperature, 12 h, 2.) CH3OH, room temperature, 6 h 4: pyridine / CH2Cl2 / 12 h / Ambient temperature 5: LiBr*H2O / acetone / 12 h / Heating View Scheme

1-dodecyl alcohol (112-53-8) + Fe2(CO)8CH2 → 1-dodecylbromide (143-15-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / 12 h / Ambient temperature 2: LiBr*H2O / acetone / 12 h / Heating View Scheme

8-bromooctanol (50816-19-8) → 1-dodecylbromide (143-15-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 91 percent / PPTS / CH2Cl2 / 2 h / Ambient temperature 2: 1.) Li2CuCl4, 2.) PTSA / 1.) THF, room temperature, 12 h, 2.) CH3OH, room temperature, 6 h 3: pyridine / CH2Cl2 / 12 h / Ambient temperature 4: LiBr*H2O / acetone / 12 h / Heating View Scheme

n-Dodecylamine (124-22-1) + 2) HCl → 1-dodecylbromide (143-15-7)

Conditions	Yield
Multi-step reaction with 3 steps 2: 1.) base, 2.) O-(2,4-dinitrophenyl)hydroxylamine 3: 65 percent / NBS / tetrahydrofuran / 16 h / Ambient temperature; Irradiation View Scheme

N-dodecyl-4-methylbenzenesulfonamide (1635-09-2) → 1-dodecylbromide (143-15-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) base, 2.) O-(2,4-dinitrophenyl)hydroxylamine 2: 65 percent / NBS / tetrahydrofuran / 16 h / Ambient temperature; Irradiation View Scheme

n-dodecyl(phenyl)telluride (75250-42-9) → 1-dodecylbromide (143-15-7) + calcium oxide

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine / CCl4 / Ambient temperature 2: sodium bromide / dimethylformamide / 70 °C View Scheme

ethylene glycol mono-n-dodecyl ether (4536-30-5) → 2-bromoethyl n-dodecyl ether (22732-79-2) + 1-dodecylbromide (143-15-7)

Conditions	Yield
With pyridine; phosphorus tribromide at -10 - 25℃; for 2h;	A 85 %Spectr. B 15 %Spectr.

4-hydroxy-benzaldehyde (123-08-0) + 1-dodecylbromide (143-15-7) → 4-n-dodecyloxybenzaldehyde (24083-19-0)

Conditions	Yield
Stage #1: 4-hydroxy-benzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃; for 1h; Stage #2: 1-dodecylbromide In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide	99%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere;	98%

1-dodecylbromide (143-15-7) + triphenylphosphine (603-35-0) → dodecyltriphenylphosphonium bromide (15510-55-1)

Conditions	Yield
In toluene Reflux;	100%
In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 48h;	96.1%
In tetrahydrofuran for 12h; sealed tube, bath temperature 250 deg C;	88%

diphenyl diselenide (1666-13-3) + 1-dodecylbromide (143-15-7) → dodecyl phenyl selenide (42066-69-3)

Conditions	Yield
With indium(III) bromide; zinc In N,N-dimethyl-formamide at 100℃; for 1h;	100%
With ruthenium trichloride; zinc In N,N-dimethyl-formamide at 100℃; for 1h;	98%
With RhCl(PPh3)3; hydrogen; triethylamine In tetrahydrofuran at 50℃; under 760 Torr; for 24h;	97%

benzene-1,2-diol (120-80-9) + 1-dodecylbromide (143-15-7) → 1,2-bisdodecyloxybenzene (42244-53-1)

Conditions	Yield
With potassium carbonate In acetone for 48h; Williamson ether synthesis; Reflux;	100%
With potassium carbonate In acetone for 48h; Heating;	95%
With potassium carbonate; potassium iodide In acetone for 48h; Reflux;	95%

methyl galloate (99-24-1) + 1-dodecylbromide (143-15-7) → methyl [3,4,5-tris(n-dodecan-1-yloxy)]benzoate (123126-39-6)

Conditions	Yield
Stage #1: methyl galloate With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2h; Stage #2: 1-dodecylbromide In N,N-dimethyl-formamide at 80℃;	100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere;	98%
With 18-crown-6 ether; potassium carbonate In acetone Reflux;	96%

1-dodecylbromide (143-15-7) + thiophenol (108-98-5) → (n-dodecylthio)benzene (56056-49-6)

Conditions	Yield
Stage #1: thiophenol With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1-dodecylbromide In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	100%
With potassium hydroxide
With potassium hydroxide In ethanol for 5h; Ambient temperature;
With potassium carbonate In acetone for 15h; Heating;

1-dodecylbromide (143-15-7) + methyl 4-hydroxylbenzoate (99-76-3) → methyl 4-(dodecyloxy)benzoate (40654-49-7)

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile for 24h; Heating;	100%
With potassium carbonate In N,N-dimethyl-formamide for 20h; Inert atmosphere; Reflux;	98%
Stage #1: methyl 4-hydroxylbenzoate With potassium carbonate In acetonitrile at 70℃; Inert atmosphere; Stage #2: 1-dodecylbromide In acetonitrile for 12h; Reflux; Inert atmosphere;	96%

1-dodecylbromide (143-15-7) → dodecane (112-40-3)

Conditions	Yield
With sodium tetrahydroborate; 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; PE-Sn(Bu)2Cl In toluene at 110℃; for 16h; Rate constant; Product distribution; other polyethylene- and polystyrene-bound tin halides, other alkyl and aryl bromides and iodides, var. amounts of catalyst;	100%
With triethyl borane; tri-n-butyl-tin hydride In hexane; toluene at -78℃; for 0.5h;	100%
With ytterbium(II) iodide In tetrahydrofuran at 60℃; for 8h; Irradiation;	99%

1-dodecylbromide (143-15-7) → dodecyl azide (13733-78-3)

Conditions	Yield
With sodium azide In methanol Reflux;	100%
With sodium azide In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	100%
With sodium azide; Aliquat 336 In formamide at 100℃; Rate constant; Product distribution; further solvent;	99%

terephthalic acid (100-21-0) + 1-dodecylbromide (143-15-7) → bis-dodecyl benzene-1,4-dicarboxylate (18749-84-3)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene for 18h; Esterification; Heating;	100%

1-dodecylbromide (143-15-7) + 5,11,17,23-tetra-tert-butyl-26,28-bis((dimethyl(thiocarbamoyl))oxy)calix<4>arene-25,27-diol (162716-19-0, 173400-90-3, 173400-91-4, 297749-65-6) → C74H114N2O4S2 (297163-55-4, 297749-66-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 8h; Etherification; Heating;	100%

4-bromo-phenol (106-41-2) + 1-dodecylbromide (143-15-7) → 1-bromo-4-dodecyloxybenzene (123883-51-2)

Conditions	Yield
With potassium carbonate Williamson's etherification;	100%
With potassium hydroxide In dimethyl sulfoxide at 50℃; Inert atmosphere;	96%
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	95.3%

1-dodecylbromide (143-15-7) + β,β-dimethyl-N,N-dimethyl-4-piperidineethanamine (167649-35-6) → N,N,β,β-tetramethyl-1-dodecyl-4-piperidineethanamine

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile for 8h; Heating;	100%

di(p-tolyl) disulfide (103-19-5) + 1-dodecylbromide (143-15-7) → dodecyl 4-methylphenyl sulfide (94435-76-4)

Conditions	Yield
With RhCl(PPh3)3; hydrogen; triethylamine In tetrahydrofuran at 50℃; under 760 Torr; for 24h;	100%
With hydrogen; triethylamine In tetrahydrofuran at 65℃; under 760.051 Torr; for 24h; Temperature; Solvent; Time; Inert atmosphere; Green chemistry;	93%

1-methyl-1H-imidazole (616-47-7) + 1-dodecylbromide (143-15-7) → 1-dodecyl-3-methylimidazol-1-ium bromide

Conditions	Yield
In neat (no solvent) at 60℃; for 24h; Inert atmosphere;	100%
at 130℃; for 0.133333h; Microwave irradiation; Neat (no solvent);	98%
In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;	94%

lithium acetylide-ethylenediamine complex (1216963-74-4) + 1-dodecylbromide (143-15-7) → 1-tetradecyne (765-10-6)

Conditions	Yield
In dimethyl sulfoxide at 23℃; for 12h;	100%

1-dodecylbromide (143-15-7) + n-octyl 4,6-O-benzylidene-β-D-glucopyranoside (118249-73-3) → octyl 4,6-O-benzyliden-2,3-di-O-dodecyl-β-D-glucopyranoside

Conditions	Yield
Stage #1: n-octyl 4,6-O-benzylidene-β-D-glucopyranoside With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 1-dodecylbromide In N,N-dimethyl-formamide at 20℃; for 2h; Further stages.;	100%

3-amino-4-chloro-benzoic acid (2840-28-0) + 1-dodecylbromide (143-15-7) → n-dodecyl 3-amino-4-chlorobenzoate (6195-20-6)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In water; xylene at 140℃; for 5h; Product distribution / selectivity;	100%
With potassium carbonate In methanol; water; ethyl acetate; N,N-dimethyl-formamide	95%

1,2-dimethyl-1H-imidazole (1739-84-0) + 1-dodecylbromide (143-15-7) → 1-dodecyl-2,3-dimethylimidazol-1-ium bromide (61546-10-9)

Conditions	Yield
In neat (no solvent) at 60℃; for 24h; Inert atmosphere;	100%
at 20℃; Inert atmosphere;	90%
at 140℃; for 0.133333h; Microwave irradiation; Neat (no solvent);

1-dodecylbromide (143-15-7) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → tetradodecyl perylene-3,4,9,10-tetracarboxylate

Conditions	Yield
Stage #1: perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride With potassium hydroxide In water Stage #2: 1-dodecylbromide With potassium iodide	100%
With Aliquat 336; potassium iodide; potassium hydroxide Inert atmosphere;	96%
With 1-dodecyl alcohol; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; for 12h;	86%

1-dodecylbromide (143-15-7) → cetyl azide (66143-67-7)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 20℃; for 12h;	100%

1-methyl-1,3-dihydro-imidazole-2-thione (60-56-0) + 1-dodecylbromide (143-15-7) → 2-Dodecylsulfanyl-1-methyl-1H-imidazole; hydrobromide (50968-39-3)

Conditions	Yield
In acetonitrile for 24h; Reflux;	100%

1-methyl-1H-imidazole (616-47-7) + iron(III) chloride hexahydrate + 1-dodecylbromide (143-15-7) → C16H31N2(1+)*BrCl3Fe(1-)

Conditions	Yield
Stage #1: 1-methyl-1H-imidazole; 1-dodecylbromide In neat (no solvent) Reflux; Inert atmosphere; Stage #2: iron(III) chloride hexahydrate Inert atmosphere;	100%

N-(benzyloxycarbonyl)acetamide potassium salt + 1-dodecylbromide (143-15-7) → N-(benzyloxycarbonyl)-N-dodecylacetamide

Conditions	Yield
With 18-crown-6 ether In N,N-dimethyl-formamide at 20℃; for 24.5h;	100%
With 18-crown-6 ether In acetonitrile at 20℃; for 24h; Reagent/catalyst; Temperature;	100%

1-dodecylbromide (143-15-7) + 1-(2-methoxyphenyl)-imidazole (10040-93-4) → 1‐(2‐methoxyphenyl)‐3‐dodecyl‐imidazolium bromide

Conditions	Yield
In tetrahydrofuran at 70℃;	100%

1-dodecylbromide (143-15-7) + 1-o-tolyl-1H-imidazole (25371-93-1) → 1‐(2‐methylphenyl)‐3‐dodecyl‐imidazolium bromide

Conditions	Yield
In tetrahydrofuran at 70℃;	100%

caprolactam (105-60-2) + 1-dodecylbromide (143-15-7) → Azone (59227-89-3)

Conditions	Yield
With sodium hydroxide In water; toluene	99.6%
With sodium hydroxide In toluene	95%
With sodium hydroxide; tetrabutylammomium bromide; potassium carbonate In cyclohexane	92.8%

1-dodecylbromide (143-15-7) → 1-Iodododecane (4292-19-7)

Conditions	Yield
With sodium iodide In acetone at 20℃; for 55.5h; Inert atmosphere;	99%
With 1,3-di-n-octyl-2-phenylimidazolium bromide; potassium iodide In toluene at 40℃; for 20h;	68%
With sodium iodide; (β-CD) - epichlorohydrin copolymer In water at 90℃; Rate constant; catalytic activity, EP/β-CD ratio, concentration of catalyst, various nucleophiles, reactivity order of nucleophiles;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1-dodecylbromide (143-15-7) → JE 188

Conditions	Yield
In ethyl acetate at 20℃; for 24h;	99%
In acetone at 20 - 50℃; for 1.5h;	66%
In diethyl ether for 48h; Ambient temperature;	37%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1-dodecylbromide (143-15-7) → N,N'-didodecyl-1,4-diazoniabicyclo<2.2.2>octane bromide

Conditions	Yield
In acetonitrile at 80℃; for 48h;	99%
In methanol for 36h; Heating;
In acetonitrile

Upstream product

• 112-53-8 1-dodecyl alcohol 
• 112-41-4 1-dodecene 
• 102402-79-9 C₁₈H₃₀Br₂Se 
• 1635-09-2 N-dodecyl-4-methylbenzenesulfonamide 
• 124-22-1 n-Dodecylamine 
• 50816-19-8 8-bromooctanol 
• 629-41-4 1,8-Octanediol 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 112-55-0 1-dodecylthiol 
• 151259-26-6 C₁₉H₃₄N₂O₂S 
• 51323-71-8 dodecyl mesylate 
• 83486-03-7 C₁₈H₃₀Br₂Te 
• 112-40-3 dodecane 
• 75250-42-9 n-dodecyl(phenyl)telluride 

Downstream Products

• 1541-81-7 4-dodecyl-morpholine 
• 82394-21-6 1,4-didodecylpiperazine 
• 47034-41-3 4-ethyl-4-dodecyl-morpholinium; bromide 
• 15411-40-2 N,N'-didodecyl ethylenediamine 
• 111562-07-3 4-dimethylcarbamoyl-1-dodecyl-1-methyl-piperazinium; bromide 
• 24083-19-0 4-n-dodecyloxybenzaldehyde 
• 16613-87-9 2-(N-dodecylamino)ethanol 
• 70664-40-3 3-dodecyl-3,6-dimethyl-6-phenyl-[1,3]oxazinanium; bromide 
• 4861-61-4 2-dodecylthiophene 
• 88016-57-3 2-(2-Dodecyloxy-phenyl)-1H-benzoimidazole 
• 129117-49-3 N-dodecyl-N-methylmonoazonium 15-crown-5 bromide 
• 3482-63-1 n-dodecyl methyl ether 
• 184434-98-8 2-Dodecyloxy-1,4-dimethyl-benzene 
• 94846-71-6 5,10,15,20-tetrakis(dodecyloxyphenyl)-21H,23H-porphyrin 

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The halogenation of alcohols under mild conditions expedited by the presence of substoichiometric amounts of thiourea additives is presented. The amount of thiourea added dictates the pathway of the reaction, which may diverge from the desired halogenation reaction toward oxidation of the alcohol, in the absence of thiourea, or toward starting material recovery when excess thiourea is used. Both bromination and chlorination were highly efficient for primary, secondary, tertiary, and benzyl alcohols and tolerate a broad range of functional groups. Detailed electron paramagnetic resonance (EPR) studies, isotopic labeling, and other control experiments suggest a radical-based mechanism. The fact that the reaction is carried out at ambient conditions, uses ubiquitous and inexpensive reagents, boasts a wide scope, and can be made highly atom economic, makes this new methodology a very appealing option for this archetypical organic reaction.

Promotion of Appel-type reactions by N-heterocyclic carbenes

N-Heterocyclic carbenes (NHCs) have been extensively used as a versatile class of catalysts and ligands in organocatalytic and organometallic chemistry. However, there are only a small number of synthetic applications where they act as reagents. Here we demonstrate that NHCs can be used as stoichiometric redox reagents for Appel-type halogenation reactions of alcohols. This new reactivity reveals a fresh and interesting aspect and enriches the chemistry of NHCs in an underexplored area. The potential of performing this chemical transformation at the catalytic level using an NHC-oxide derivative is also investigated.

Nucleophilic Substitutions of Alcohols in High Levels of Catalytic Efficiency

A practical method for the nucleophilic substitution (SN) of alcohols furnishing alkyl chlorides, bromides, and iodides under stereochemical inversion in high catalytic efficacy is introduced. The fusion of diethylcyclopropenone as a simple Lewis base organocatalyst and benzoyl chloride as a reagent allows notable turnover numbers up to 100. Moreover, the use of plain acetyl chloride as a stoichiometric promotor in an invertive SN-type transformation is demonstrated for the first time. The operationally straightforward protocol exhibits high levels of stereoselectivity and scalability and tolerates a variety of functional groups.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Halogen Exchange Reaction of Aliphatic Fluorine Compounds with Organic Halides as Halogen Source

The halogen exchange reaction of aliphatic fluorine compounds with organic halides as the halogen source was achieved. Treatment of alkyl fluorides (primary, secondary, or tertiary fluorides) with a catalytic amount of titanocene dihalides, trialkyl aluminum, and polyhalomethanes (chloro or bromo methanes) as the halogen source gave the corresponding alkyl halides in excellent yields under mild conditions. In the case of a fluorine/iodine exchange, no titanocene catalyst is needed. Only C-F bonds are selectively activated under these conditions, whereas alkyl chlorides, bromides, and iodides are tolerant to these reactions.

Ruthenium bipyridyl tethered porous organosilica: A versatile, durable and reusable heterogeneous photocatalyst

A versatile heterogeneous photocatalysis protocol was developed by using ruthenium bipyridyl tethered porous organosilica (Ru-POS). The versatility of the Ru-POS catalyst in organo-photocatalysis was explored by (i) oxidative aromatization of Hantzsch ester, (ii) reductive dehalogenation of alkyl halides, and (iii) functional group interconversion (FGI) of alcohols to alkyl halides. This journal is

Synthesis of some acyclic quaternary ammonium compounds. Alkylation of secondary and tertiary amines in a two-phase system

A series of acyclic symmetrical and asymmetrical quaternary ammonium chlorides of the general formula R1R2R3N+AR4Cl- (R1 = Me, Bu; R2 = n-C12H25, PhCH2, C n H2n+1(OCH2CH2) m, n = 9 and 12, m = 1 and 2; R3 = n-C12H25, PhCH2, HOCH2CH2,-OOCCH2; R4 = n-C12H25, PhCH2; A = (CH2CH2O)1,2, CH2C(O)O) was synthesized by the alkylation of tertiary amines in a two-phase system containing water. A convenient method for the synthesis of the initial symmetrical and asymmetrical tertiary amines of the general formula MeNR1R2 (R1 = Me, Bu; R2 = n-C12H25, PhCH2, CnH2n+1(OCH2CH2) m, n = 9 and 12, m = 1 and 2) in an organic phase-aqueous phase heterogeneous system, which allows the use of aqueous solutions of alkali and amines, was developed. The improved method for the preparation of intermediate ethylene glycol and diethylene glycol monoethers is monoalkylation of glycols in dioxane using solid KOH in a two-phase system.

Efficient procedures to prepare primary and secondary alkyl halides from alkanols via the corresponding sulfonates under mild conditions

The study presented herein shows that sulfonate/halide exchange can be advantageously performed in THF to avoid several side reactions such as elimination and epimerization when the reaction is performed from a chiral alkyl sulfonate or a substrate having a C-H acidic chiral center. The main limitation of this procedure was found to be the conversion of secondary alkyl sulfonates to alkyl chlorides. In this case, the addition of a catalytic amount of manganese chloride clearly accelerates the rate and the efficiency of the reaction. Copyright

Arylsulfur trifluorides: Improved method of synthesis and use as in situ deoxofluorination reagents

Building on recent results of Umemoto and Winter, an improved method of synthesis of arylsulfur trifluorides, including the excellent, new deoxofluorination reagent Fluolead, is hereby reported. The method utilizes Br2 and KF as oxidizing and fluorinating reagents for efficient, high yield conversion of aryl disulfides and mercaptans to arylsulfur trifluorides. It has also been shown that both Fluolead and mesitylsulfur trifluoride may be generated in acetonitrile and used as in situ deoxofluorination reagents for conversion of either aldehydes or ketones to their respective gem-difluoro compounds. An analysis of the probable mechanism of action, including computational efforts, allows postulation of a rationale for the highly variable reactivities of different arylsulfur trifluorides as deoxofluorination reagents.

A photoirradiative phase-vanishing method: Efficient generation of HBr from alkanes and molecular bromine and its use for subsequent radical addition to terminal alkenes

A triphasic phase-vanishing (PV) system comprised of an alkane, perfluorohexanes, and bromine was successfully combined by photoirradiation to efficiently generate hydrogen bromide, which underwent radical addition with 1-alkenes in the hydrocarbon layer to afford terminal bromides in high yields. Georg Thieme Verlag Stuttgart.