110-52-1

Basic information

• Product Name: 1,4-Dibromobutane
• Synonyms: 1,4-BUTYLENE DIBROMIDE;1,4-BUTYLENE BROMIDE;1,4-DIBROMOBUTANE;TETRAMETHYLENDIBROMID;TETRAMETHYLENE BROMIDE;TETRAMETHYLENE DIBROMIDE;1,4-Dibrombutan;1,4-dibromo-butan
• CAS NO: 110-52-1
• Molecular Formula: C₄H₈Br₂
• Molecular Weight: 215.91
• EINECS: 203-775-5
• Product Categories: DIBROMOALKANE;Bromine Compounds;alpha,omega-Dibromoalkanes;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;Isoquinolines ,Quinolines ,Quinazolines ,Quinaldines
• Mol File: 110-52-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: −20 °C(lit.)
• Boiling Point: 63-65 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to light yellow-brownish/Liquid
• Density: 1.808 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.544mmHg at 25°C
• Refractive Index: n20/D 1.519(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 0.35g/l
• Water Solubility: immiscible
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
• BRN: 1071199
• CAS DataBase Reference: 1,4-Dibromobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dibromobutane(110-52-1)
• EPA Substance Registry System: 1,4-Dibromobutane(110-52-1)

Safety Data

• Hazard Codes: T,Xi,C
• Statements: 25-37/38-41-36/37/38
• Safety Statements: 26-39-45-37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 2
• RTECS: EJ7565000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 110-52-1(Hazardous Substances Data)

Usage

Chemical Properties

Clear, colorless liquid

Uses

Different sources of media describe the Uses of 110-52-1 differently. You can refer to the following data:
1. 1,4-Dibromo butane was used to investigate the metabolism of two halopropanes: 1,3-dichloropropane and 2,2-dichloropropane. It was used as reagent during the synthesis of diazadioxa oxovanadium(IV) macrocyclic complexes.
2. 1,4-Dibromobutane is used as an intermediate involved in the synthesis of active pharmaceutical ingredient and other organic compounds. It is also used in the investigation of metabolism of two halopropanes such as 1,3-dichloropropane and 2,2-dichloropropane. Further, it acts as a reagent to prepare diazadioxa oxovanadium(IV) macrocyclic complexes.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 3483, 1950 DOI: 10.1021/ja01164a046

General Description

1,4-Dibromobutane reaction with atactic poly(2-vinylpyridine) leads to the formation of long-range 3D molecular ordering in polymer chains.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C4H8Br2/c5-3-1-2-4-6/h1-4H2

Synthetic route

tetrahydrofuran (109-99-9) → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With 1,2-dibromo-1,1,2,2-tetrachloroethane; triphenylphosphine In dichloromethane at 20℃; for 0.15h; Appel Halogenation;	95%
With carbon tetrabromide; triphenylphosphine In chloroform at 20℃; for 240h;	93%
With 2,2,2-tribromo-1,3,2-benzodioxaphosphole In chloroform	86%

cyclopropylcarbinyl bromide (7051-34-5) → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With water; boron tribromide In dichloromethane at 23℃; for 23h; regioselective reaction;	87%
With hydrogen bromide at 170℃; im Rohr;

tetrahydrofuran (109-99-9) → 1,4-dibromo-butane (110-52-1) + 4-bromobutyl phosphite (42023-34-7)

Conditions	Yield
With hydrogen bromide; phosphorus tribromide at 80℃; for 0.666667h;	A 85% B 4%
With hydrogen bromide; phosphorus tribromide at 80℃; for 0.666667h;	A 27% B 53%

Butane-1,4-diol (110-63-4) → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With sulfuric acid; sodium bromide In water for 3h; Heating;	84.8%
With hydrogen bromide at 130℃;
With sulfuric acid; hydrogen bromide

4-methoxy-phenol (150-76-5) → 1,4-dibromo-butane (110-52-1) + 1-(4-methoxyphenoxy)-4-bromobutane (2033-83-2)

Conditions	Yield
	A n/a B 82%

1,4-bis-isopentyloxy-butane (873988-92-2) → 1,4-dibromo-butane (110-52-1) + 1-bromo-4-isopentyloxy-butane (51748-48-2)

Conditions	Yield
With hydrogen bromide

Cyclopropylmethanol (2516-33-8) → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With hydrogen bromide

4-bromophenyl butyl ether (1200-03-9) → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With hydrogen bromide

1,4-diphenoxybutane (3459-88-9) → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With hydrogen bromide
With hydrogen bromide at 130 - 140℃; im Rohr;

uvariadiamide (31991-78-3) → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With phosphorus pentabromide
With bromine; phosphorus trichloride
With phosphorus pentabromide im Vakuum;

tetrahydrofuran (109-99-9) + methanesulfonyl bromide (41138-92-5) → 1,4-dibromo-butane (110-52-1) + 4,4'-dibromo-di-n-butyl ether (7239-41-0) + busulfan (55-98-1) + 1-bromo-4-methanesulfonyloxy-butane (40671-33-8)

Conditions	Yield
zinc(II) chloride at 75℃; for 5h;

1-bromo-butane (109-65-9) → 1,4-dibromo-butane (110-52-1) + 1,1-dibromobutane (62168-25-6) + 1,3-dibromobutane (107-80-2) + 1,2-dibromobutane (533-98-2, 130232-89-2, 130232-90-5)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 15℃; Product distribution; Irradiation; CH2CCl2; influence of additive - BrCCl3;

trifluoro-acetic acid, 1,4-butanediyl ester (31528-89-9) → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With lithium bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 4h; Heating; Yield given;

2-(ω-bromobutylthio)-4,6-dimethylpyrimidine (15018-33-4) → thiophene (110-01-0) + 1,4-dibromo-butane (110-52-1) + 2-bromo-4,6-dimethylpyrimidine (16879-39-3) + 1,4-bis(4',6'-dimethylpyrimidinyl-2'-thio)butane (14961-47-8)

Conditions	Yield
at 165 - 205℃; under 15 Torr; Further byproducts given;	A 2.5 g B 4.8 g C 8.5 g D 9.5 g
at 165 - 205℃; under 15 Torr;	A 2.5 g B 4.8 g C 8.5 g D 9.5 g

tetrahydrofuran (109-99-9) + hydrogen bromide (10035-10-6, 12258-64-9) → 1,4-dibromo-butane (110-52-1)

n-benzoylpyrrolidine (3389-54-6) + phosphorus pentabromide (7789-69-7) → 1,4-dibromo-butane (110-52-1) + benzonitrile (100-47-0)

Conditions	Yield
Beim Erwaermen und nachfolgendem Destillieren des Reaktionsprodukts im Vakuum.;

adipate silver → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With tetrachloromethane; bromine

butanediol-(1.4)-diisopentyl ether → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
With hydrogen bromide

pseudobutylene bromide → 1,4-dibromo-butane (110-52-1)

Conditions	Yield
at 220 - 230℃; im Rohr;

1,4-dibromo-butane (110-52-1) + bis(phenylsulfonyl)methane (3406-02-8) → 1,1-bis(benzenesulphonyl)cyclopentane (88073-51-2)

Conditions	Yield
tetrabutylammomium bromide In sodium hydroxide at 25 - 30℃; for 3h;	100%
With sodium hydride In N,N-dimethyl-formamide at 70 - 80℃; for 1h;	88%

1,4-dibromo-butane (110-52-1) + tert‐butyl 3‐aminopiperidine‐1‐carboxylate (144243-24-3) → 1-(tert-butoxycarbonyl)-3-(1-pyrrolidinyl)piperidine (144243-26-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 72h;	100%

1,4-dibromo-butane (110-52-1) + p-chlorobenzyl cyanide (140-53-4) → 1-(4-chlorophenyl)cyclopentane-1-carbonitrile (64399-26-4)

Conditions	Yield
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 0 - 20℃; for 3.5h; Solvent; Temperature;	100%
Stage #1: p-chlorobenzyl cyanide With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	82%
Stage #1: p-chlorobenzyl cyanide With sodium hydroxide In N,N-dimethyl-formamide for 0.5h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 50 - 55℃; for 4h;	76%
Stage #1: p-chlorobenzyl cyanide With sodium hydroxide In N,N-dimethyl-formamide for 0.5h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 50 - 55℃; for 4h;	76%
With sodium hydride In diethyl ether; dimethyl sulfoxide	61%

1,4-dibromo-butane (110-52-1) + methyl 3-oxonon-8-ene-1-carboxylate (128738-23-8) → methyl 1-hept-6-enoylcyclopentanecarboxylate (171925-00-1)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide Ambient temperature;	100%

1,4-dibromo-butane (110-52-1) → pyrrolidin-1-ol (5904-62-1)

Conditions	Yield
With hydroxylamine hydrochloride; triethylamine for 1.5h; Heating;	100%
With hydroxylamine hydrochloride; triethylamine for 1h; Heating;
With hydroxylamine hydrochloride; triethylamine for 1h; Inert atmosphere; Reflux;

Wang-benzaldehyde resin, imine with glycine ethyl ester + 1,4-dibromo-butane (110-52-1) → 1-amino-cyclopentanecarboxylic acid ethyl ester hydrochloride (22649-37-2)

Conditions	Yield
Stage #1: Wang-benzaldehyde resin, imine with glycine ethyl ester; 1,4-dibromo-butane In 1-methyl-pyrrolidin-2-one for 1h; Stage #2: With tert-butylimino-tri(pyrrolidino)phosphorane In 1-methyl-pyrrolidin-2-one at 20℃; for 14h; Stage #3: With hydrogenchloride In tetrahydrofuran for 5h;	100%

1,4-dibromo-butane (110-52-1) + tri-n-butyl phosphite (102-85-2) → dibutyl(4-bromobutyl)phosphonate

Conditions	Yield
at 118℃; for 6h;	100%

1,4-dibromo-butane (110-52-1) + (4-bromo-2-fluorophenyl)acetonitrile (114897-91-5) → 2-(4-bromo-2-chloro-phenyl)-2-methyl-propionitrile(4-bromo-2-fluorophenyl)acetonitrile (749930-45-8)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water at 50℃; for 3h;	100%

1,4-dibromo-butane (110-52-1) + 1-(4-iodo-phenoxymethyl)-cyclopropylamine (868609-61-4) → 1-[1-(4-brom-phenoxymethyl)-cyclopropyl]-pyrrolidine (868609-62-5)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 24h;	100%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 24h;

1,4-dibromo-butane (110-52-1) → tetrahydropyridazine dihydrochloride (89990-53-4, 124072-89-5)

Conditions	Yield
Stage #1: t-butoxycarbonylhydrazine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide Stage #3: With hydrogenchloride In 1,4-dioxane; diethyl ether at 20℃; for 1h;	100%

1,4-dibromo-butane (110-52-1) + (+)-(aR)-7,7'-dihydroxy-8,8'-biquinolyl (914288-77-0, 914288-78-1, 829666-42-4) → C22H18N2O2 (1062259-42-0)

Conditions	Yield
Stage #1: (-)-(aS)-7,7'-dihydroxy-8,8'-biquinolyl With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.416667h; Williamson synthesis; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 42h; Williamson synthesis;	100%

1,4-dibromo-butane (110-52-1) + 4-amino-o-xylene (95-64-7) → 1-(3,4-dimethylphenyl)pyrrolidine

Conditions	Yield
With sodium dodecyl-sulfate; sodium hydrogencarbonate In water at 80℃; for 1h; Inert atmosphere;	100%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;

1,4-dibromo-butane (110-52-1) + pyridine-2-acetonitrile (2739-97-1) → 1-(pyridin-2-yl)cyclopentanecarbonitrile (400727-04-0)

Conditions	Yield
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25h; Inert atmosphere;	100%
Stage #1: pyridine-2-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: 1,4-dibromo-butane In tetrahydrofuran at -78 - 20℃; for 10h;	96%
With sodium hydride In diethyl ether; dimethyl sulfoxide at 0 - 20℃; for 4.5h;	82%

1,4-dibromo-butane (110-52-1) + methyl 3,5-difluorobenzoate → 1-(3,5-difluorophenyl)cyclopentanol (1344015-79-7)

Conditions	Yield
Stage #1: 1,4-dibromo-butane With magnesium In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: methyl 3,5-difluorobenzoate In tetrahydrofuran at 0 - 20℃; for 1h; Stage #3: With ammonium chloride In tetrahydrofuran	100%
Stage #1: 1,4-dibromo-butane With magnesium In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: methyl 3,5-difluorobenzoate In tetrahydrofuran at 0 - 20℃; for 1h;	100%
Stage #1: 1,4-dibromo-butane With magnesium In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: methyl 3,5-difluorobenzoate In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	100%

1,4-dibromo-butane (110-52-1) + dimethyl amine (124-40-3) → N,N,N',N'-tetramethyl-1,4-butanediamine (111-51-3)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 24h;	100%
In chloroform at 20℃; for 24h;	100%

1,4-dibromo-butane (110-52-1) + Tocopherol (59-02-9) → (R)-6-(4-bromobutoxy)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman (1451385-71-9)

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; Inert atmosphere; Darkness;	100%
Stage #1: Tocopherol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	50%
Stage #1: Tocopherol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃;	47%

2-hydroxypyridin (142-08-5) + 1,4-dibromo-butane (110-52-1) → C14H16N2O2 (82791-51-3)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 5.5h;	100%

1,4-dibromo-butane (110-52-1) + N-(tert-butoxycarbonyl)-N'-(2-nitrobenzenesulfonyl)-1,3-propanediamine (240423-18-1) → C32H48N6O12S2

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; caesium carbonate In acetonitrile at 0 - 60℃; for 2h; Inert atmosphere;	100%

1,4-dibromo-butane (110-52-1) + 4-chloro-3-fluorophenol (348-60-7) → 4-(4-bromobutoxy)-1-chloro-2-fluorobenzene

Conditions	Yield
With potassium carbonate In acetone Reflux;	100%

1,4-dibromo-butane (110-52-1) + 4-chloro-2-fluorophenol (348-62-9) → 4-(4-bromobutoxy)-1-chloro-3-fluorobenzene

Conditions	Yield
With potassium carbonate In acetone Reflux;	100%

1,4-dibromo-butane (110-52-1) + salicylonitrile (611-20-1) → 2-(4-bromobutoxy)benzonitrile

Conditions	Yield
With potassium carbonate In acetone Reflux;	100%

1,4-dibromo-butane (110-52-1) + 3,3'-dinitro-[1,1'-biphenyl]-4,4’-diol (66041-61-0) → C20H22Br2N2O6

Conditions	Yield
Stage #1: 3,3'-dinitro-[1,1'-biphenyl]-4,4’-diol With potassium carbonate In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: 1,4-dibromo-butane In tetrahydrofuran for 24h; Inert atmosphere; Reflux;	99.6%

1,4-dibromo-butane (110-52-1) + N,N'-bis(4-methoxyphenyl)iminoformamide (1152-75-6, 141417-87-0) → C19H24N2O3

Conditions	Yield
With potassium carbonate In acetonitrile at 100℃;	99.4%

1,4-dibromo-butane (110-52-1) + methyl 4-{[4-(methoxycarbonyl)phenyl]-amino}methyleneaminobenzoate (67126-75-4) → C21H24N2O5

Conditions	Yield
With potassium carbonate In acetonitrile at 100℃;	99.4%

1,4-dibromo-butane (110-52-1) + gentitein (529-49-7) → C17H15BrO5

Conditions	Yield
Stage #1: gentitein With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 20h;	99.3%
Stage #1: gentitein With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 12.5h;

1,4-dibromo-butane (110-52-1) + 7-chloro-1,3-dihydroxy-9H-xanthen-9-one (100334-95-0) → C17H14BrClO4

Conditions	Yield
Stage #1: 7-chloro-1,3-dihydroxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 20h;	99.2%
Stage #1: 7-chloro-1,3-dihydroxy-9H-xanthen-9-one With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 12.5h;

1,4-dibromo-butane (110-52-1) + C17H16N2O4 → C21H24N2O5

Conditions	Yield
With potassium carbonate In acetonitrile at 100℃;	99.1%

1,4-dibromo-butane (110-52-1) + 9H-fluorene (86-73-7) → Spirofluorene> (14966-37-1)

Conditions	Yield
Stage #1: 9H-fluorene With n-butyllithium In tetrahydrofuran at -78℃; for 0.75h; Stage #2: 1,4-dibromo-butane In tetrahydrofuran at -78 - 20℃; for 4h;	99%
With potassium tert-butylate In dimethyl sulfoxide for 2h; cooled (water bath);

1,4-dibromo-butane (110-52-1) + N,N-dimethylhexadecylamine (112-69-6) → butane-1,4-diyl bis(N,N-dimethyl-N-hexadecylammonium) dibromide (29908-17-6)

Conditions	Yield
In ethanol at 80℃; for 48h;	99%
In acetonitrile for 0.5h; Heating;	94%
In ethanol; ethyl acetate for 48h; Reflux; Inert atmosphere;	59%

1,4-dibromo-butane (110-52-1) + (1R,2S)-norephedrine (492-41-1) → (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol (56571-91-6, 56571-92-7, 123620-80-4, 127641-25-2)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Heating;	99%
With sodium hydrogencarbonate In toluene at 110 - 118℃; for 20h;	97%
With sodium hydrogencarbonate In toluene for 32h; Heating;	97%

Upstream product

• 3389-54-6 n-benzoylpyrrolidine 
• 1927-71-5 4-phenoxybutan-1-ol 
• 13179-96-9 1,4-dimethoxybutane 
• 3459-88-9 1,4-diphenoxybutane 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 109-99-9 tetrahydrofuran 
• 109-65-9 1-bromo-butane 
• 7789-69-7 phosphorus pentabromide 
• 1200-03-9 4-bromophenyl butyl ether 
• 10035-10-6 hydrogen bromide 
• 31991-78-3 uvariadiamide 
• 7726-95-6 bromine 
• 7719-12-2 phosphorus trichloride 
• 1393448-68-4 C₂₀H₃₁BrN₂O₃ 

Downstream Products

• 16450-38-7 5-azoniaspiro<4.4>nonane bromide 
• 69506-86-1 1,1'-(1,4-butanediyl)bis(imidazole) 
• 80038-65-9 1-[4-(1-quinoliniumyl)butyl]quinolinium dibromide 
• 28247-15-6 ethyl 1-acetylcyclopropane-1-carboxylate 
• 77-57-6 1-phenyl-1-cyclopentanecarbonitrile 
• 32040-07-6 1-(3-methoxyphenyl)pyrrolidine 
• 16837-07-3 2-(4-bromo-butoxy)-phenol 
• 2955-88-6 1-pyrrolidineethanol 
• 110-63-4 Butane-1,4-diol 
• 2033-81-0 1-(4-bromobutoxy)-4-chlorobenzene 
• 100617-29-6 1-(1-methyl-2-phenyl-ethyl)-pyrrolidine 
• 2033-83-2 1-(4-methoxyphenoxy)-4-bromobutane 
• 7333-63-3 4-bromobutylphosphonium bromide 
• 15546-42-6 [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide 

Related news

Low frequency skeletal vibrations and rotational isomers of solid 1,4-Dibromobutane (cas 110-52-1) and 1,5-dibromopentane studied by neutron inelastic scattering08/23/2019

The neutron inelastic spectra of solid 1,4-dibromobutane and 1,5-dibromopentane have been taken at several temperatures. The observed neutron spectra are assigned to the skeletal bending and torsion modes on the basis of normal coordinate calculations, in which only intramolecular valence force ...detailed

Cycloalkylation of phenylacetonitrile with 1,4-Dibromobutane (cas 110-52-1) catalyzed by aqueous sodium hydroxide and a new phase transfer reagent, Dq-Br08/20/2019

The kinetics of cycloalkylation of phenylacetonitrile (PAN) with an excess of 1,4-dibromobutane has been studied under phase transfer catalysis (PTC) conditions using aqueous sodium hydroxide as the base and 2-benzilidine-N,N,N,N′,N′,N′-hexaethylpropane-1,3-diammonium dibromide (Dq-Br) as a n...detailed

Relevant articles and documents

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Syntheses of [13C,15N]-Labeled Polyamines

[1,4-13C2, 1,4-15N2]butanediamine (1), a key compound in the syntheses of [5,8-13C2, 1,4,8-15N3]spermidine (2) and [5,8-13C2, 1,4,8,12-15N4]spermine (3), has been prepared as part of a 6-step process from 1,2-dibromoethane using potassium [13C]cyanide and potassium [15N]phthalimide. In the course of the syntheses, it was found that 1,4-dibromobutane was generated from tetrahydrofuran when bromination using triphenylphosphine and tetrabromomethane took place. A high-yield preparation of monobenzyloxycarbonyl (Z) derivative of 1, a precursor for 2, was obtained using a water-soluble Z reagent, Z-DSP, in a two-phase system of alkaline solution and chloroform. All the steps for 1, 2, and 3, were aimed at minimizing the loss of stable isotopes.

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Continuous method for preparation of dihalogenated alkane from diol compound

The invention discloses a continuous method for preparation of dihalogenated alkane from a diol compound. A diol compound and haloid acid are used as the substrate, a microchannel reactor is utilizedto synthesize dihalogenated alkane continuously. Synthesis of the dihalogenated alkane includes the steps of: inputting the diol compound and haloid acid into a mixer respectively by a metering pump at room temperature, conducting premixing, then sending the mixture into a high-temperature section of the microchannel reactor at for reaction, and controlling the reaction temperature by an externalcirculating heat exchange system; at the end of the reaction, letting the product flow out from an outlet of the microchannel reactor and enter a cooling section, letting the cooled material enter a liquid separation kettle for standing and liquid separation, and collecting an organic layer; and preheating the organic layer, then feeding the preheated organic layer into a rectifying tower by a metering pump, controlling the temperature and reflux ratio of a reboiler, and collecting fractions at a specific temperature, thus obtaining the target product in a product collecting tank. The method provided by the invention has the characteristics of high reaction efficiency, safety, environmental protection, convenience and rapidity.

1,2-Dibromotetrachloroethane: An efficient reagent for many transformations by modified Appel reaction

An efficient and facile method has been developed for the synthesis of alkyl bromides from various alcohols under mild conditions using a triphenylphosphine (PPh 3) /1,2-dibromotetrachloroethane (DBTCE) complex in excellent yields and very short time (5 min). This method can also be applied for the transformation of chiral alcohols to their corresponding bromides in very high enantiomeric excess. The PPh 3 /DBTCE complex is also successfully applied to ring-opening reactions of cyclic ethers in mild conditions. Esterification, amidation, and formation of acid anhydrides under very mild experimental conditions are also successfully accomplished by following a modification of the Appel reaction protocol in this work.

Mild one-step synthesis of dibromo compounds from cyclic ethers

A novel one-step method for mildly converting cyclic ethers into dibromo compounds is reported. Alcohols, oximes, aldehydes, and ketones are known to react under Appel or Corey-Fuchs reaction conditions, but apparently these have never been applied to oxetanes or larger cyclic ethers. Treatment of 3,3-dimethyloxetane (1) with tetrabromomethane and triphenylphosphine gave the corresponding dibromo compound 1,3-dibromo-2,2-dimethylpropane (2). The less-strained homologue oxolane (6) was also reacted giving 1,4-dibromobutane (7) in a 93% yield. Mechanistic interpretations are offered to explain the observed reaction rates of the conversions described.