6940-78-9

Basic information

• Product Name: 1-Bromo-4-chlorobutane
• Synonyms: 1-BroMo-4-chlorobutane, 99% 25GR;4-Bromobutyl Chloride 4-Chlorobutyl Bromide;1-BroMo-4-chlorobutane, 97+%;1 - broMine - 4 - chlorobutane;BUTANE, 1-BROMO-4-CHLORO-;BROMO(1-)-4-CHLOROBUTANE;1-BROMO-4-CHLOROBUTANE;4-CHLORO-1-BROMOBUTANE
• CAS NO: 6940-78-9
• Molecular Formula: C4H8BrCl
• Molecular Weight: 171.46
• EINECS: 230-089-3
• Product Categories: BROMO CHLORO;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;omega-Haloalkyl Chlorides;organic chemical;Drug Intermediates
• Mol File: 6940-78-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 96-97 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• Boiling Point: 80-82 °C30 mm Hg(lit.)
• Flash Point: 140 °F
• Appearance: Clear/Liquid
• Density: 1.488 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.59mmHg at 25°C
• Refractive Index: n20/D 1.4875(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: SLIGHTLY SOLUBLE
• BRN: 1098275
• CAS DataBase Reference: 1-Bromo-4-chlorobutane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-4-chlorobutane(6940-78-9)
• EPA Substance Registry System: 1-Bromo-4-chlorobutane(6940-78-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 6940-78-9(Hazardous Substances Data)

Usage

Chemical Properties

clear liquid

InChI:InChI=1/C4H8BrCl/c5-3-1-2-4-6/h1-4H2

Synthetic route

4-Chloro-1-butanol (928-51-8) → 4-chlorobutyl bromide (6940-78-9)

Conditions	Yield
With phosphorus tribromide In pyridine 0 deg C, 1 h; r.t., 3 h;	44%
With phosphorus; bromine
With sulfuric acid; water; sodium bromide

benzyloxyacetic acid (30379-55-6) + 1,3-chlorobromopropane (109-70-6) → 4-chlorobutyl bromide (6940-78-9)

Conditions	Yield
Stage #1: benzyloxyacetic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -70 - -30℃; for 1h; Stage #2: 1.3-chlorobromopropane In tetrahydrofuran; hexane at -70 - 20℃; for 2.5h;	32%

tetrahydrofuran (109-99-9) → 1,4-dibromo-butane (110-52-1) + 4-chlorobutyl bromide (6940-78-9)

Conditions	Yield
With water; sodium bromide; sodium chloride anschliessenden Erwaermen des Reaktionsprodukts mit Schwefelsaeure;

1-bromo-butane (109-65-9) → 4-chlorobutyl bromide (6940-78-9)

Conditions	Yield
With chlorine im Licht;
With sulfuryl dichloride; dibenzoyl peroxide

bis-(4-chlorobutyl)ether (6334-96-9) → 4-chlorobutyl bromide (6940-78-9)

Conditions	Yield
With sulfuric acid; water; hydrogen bromide at 150℃;

1,4-dichlorobutane (110-56-5) → 4-chlorobutyl bromide (6940-78-9)

Conditions	Yield
With 1,4-dibromo-butane; tetrabutylammomium bromide at 100℃; for 19.5h;	49.7 % Chromat.

1-bromo-butane (109-65-9) + chlorine (7782-50-5) → 4-chlorobutyl bromide (6940-78-9)

Conditions	Yield
unter Belichtung;

1-bromo-butane (109-65-9) + sulfuryl dichloride (7791-25-5) + dibenzoyl peroxide (94-36-0) → 4-chlorobutyl bromide (6940-78-9)

n-Butyl chloride (109-69-3) → 4-chlorobutyl bromide (6940-78-9) + 1-bromo-1-chlorobutane (514206-33-8) + 2-bromo-4-chloro-butane (141507-40-6) + 2-bromo-1-chlorobutane (79504-01-1)

Conditions	Yield
With carbon tetrabromide; {[PhSiO1.5]2CuO}n at 150℃; for 10h; Product distribution; Further Variations:; Catalysts;

1-bromo-butane (109-65-9) → 4-chlorobutyl bromide (6940-78-9) + 1-bromo-3-chlorobutane (56481-42-6) + 1-bromo-2-chlorobutane (108200-18-6)

Conditions	Yield
With perchloric acid; 1-chloro-cis-2,6-dimethylpiperidine In dichloromethane; water at 0℃; for 2h; Irradiation; Sealed tube; Inert atmosphere; Overall yield = 53 percent;

4-chlorobutyl bromide (6940-78-9) + silver trifluoromethanesulfonate (2923-28-6) → 4-chlorobutanol-1-trifluoromethanesulfonate (103935-55-3)

Conditions	Yield
In tetrachloromethane for 0.166667h;	100%

4-chlorobutyl bromide (6940-78-9) + 2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazin-4-one 1,1-dioxide (232945-10-7) → 5-(4-chlorobutyl)-2-methyl-2,3,4,5-tetrahydropyrrolo[2,3-e][1,2]thiazin-4-one 1,1-dioxide (232945-13-0)

Conditions	Yield
With potassium carbonate In butanone	100%

4-chlorobutyl bromide (6940-78-9) + 5-phenylpentanoic acid-methoxy-methyl-amide → C15H21ClO (1032445-82-1)

Conditions	Yield
Stage #1: 4-chlorobutyl bromide With magnesium In tetrahydrofuran; diethyl ether for 0.5h; Heating / reflux; Stage #2: 5-phenylpentanoic acid-methoxy-methyl-amide In tetrahydrofuran; diethyl ether at 5 - 55℃; for 3.5h;	100%
Stage #1: 4-chlorobutyl bromide With magnesium In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: In tetrahydrofuran; diethyl ether for 0.5h; Stage #3: 5-phenylpentanoic acid-methoxy-methyl-amide In tetrahydrofuran; diethyl ether at 5 - 55℃; for 3.5h;	100%

4-chlorobutyl bromide (6940-78-9) + N-methoxy-N-methyl-4-phenylbutanamide (177756-65-9) → 8-Chloro-1-phenyl-octan-4-one (78429-24-0)

Conditions	Yield
Stage #1: 4-chlorobutyl bromide With magnesium In diethyl ether at 20℃; for 1h; Heating / reflux; Stage #2: N-methoxy-N-methyl-4-phenylbutyramide In tetrahydrofuran; diethyl ether at 0 - 50℃; for 4.25h;	100%
Stage #1: 4-chlorobutyl bromide With magnesium In diethyl ether at 20℃; for 1h; Reflux; Stage #2: N-methoxy-N-methyl-4-phenylbutyramide In tetrahydrofuran; diethyl ether at 0 - 50℃;	100%

4-chlorobutyl bromide (6940-78-9) + N(1)-ethyl-N(1),N(3)-bis(2-nitrobenzenesulfonyl)propane-1,3-diamine (1111643-45-8) → N(1)-(4-chlorobutyl)-N(3)-ethyl-N(1),N(3)-bis(2-nitrobenzenesulfonyl)propane-1,3-diamine (1111643-57-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 65h;	100%

4-chlorobutyl bromide (6940-78-9) + N-hydroxyphthalimide (524-38-9) → 2-(2-chlorobutoxy)isoindoline-1,3-dione (59376-94-2)

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

4-chlorobutyl bromide (6940-78-9) + C120H176O16 (1370520-18-5) → C152H232Cl8O16 (1350521-16-2)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 60℃; Inert atmosphere;	100%

4-chlorobutyl bromide (6940-78-9) + 2-hydroxypyrazolo<1,5-α>pyridine (59942-87-9) → 2-(4-chlorobutoxy)pyrazolo[1,5-a]pyridine (1451182-03-8)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 20℃; for 18h;	100%
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 18h;	100%

4-chlorobutyl bromide (6940-78-9) + tert-Butyl N-(4-methyl-pyridin-2-yl)carbamate (90101-20-5) → tert-butyl (4-azidobutyl)(4-methylpyridin-2-yl)carbamate

Conditions	Yield
Stage #1: tert-Butyl N-(4-methyl-pyridin-2-yl)carbamate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Stage #2: 4-chlorobutyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Stage #3: With sodium azide In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	100%

4-chlorobutyl bromide (6940-78-9) + C14H16N2O4 → 2-(4-(4-chlorobutoxy)-5-(cyclopropylmethoxy)-2-nitrophenyl)-2-methylpropanenitrile

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃;	100%

4-chlorobutyl bromide (6940-78-9) → 1-azido-4-chloro-butane (671821-46-8)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 20℃;	99%
With sodium azide In N,N-dimethyl-formamide at 20℃; for 24h;	95%
With sodium azide In N,N-dimethyl-formamide at 20℃; for 20h;	94%

4-chlorobutyl bromide (6940-78-9) + methyl cyclopentane carboxylate (4630-80-2) → 1-(4-Chlorobutyl)cyclopentanecarboxylic acid, methyl ester (182886-55-1)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; ammonium chloride; lithium diisopropyl amide	99%
Stage #1: methyl cyclopentane carboxylate With lithium diisopropyl amide In tetrahydrofuran at -70 - -50℃; for 1h; Stage #2: 4-chlorobutyl bromide at -70 - 20℃; for 15h;	64%
	64%

4-chlorobutyl bromide (6940-78-9) + 9-bromo-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-dione → N-(4-chlorobutyl)-1-bromo-dibenzo[e,h]bicyclo[2.2.2]octane-2,3-dicarboximide

Conditions	Yield
With potassium carbonate In acetonitrile for 51h; Heating;	99%

4-chlorobutyl bromide (6940-78-9) + N‐methoxy‐N‐methyl‐2‐phenoxyacetamide (91012-53-2) → C12H15ClO2 (1032357-38-2)

Conditions	Yield
Stage #1: 4-chlorobutyl bromide With magnesium In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; Heating / reflux; Stage #2: N‐methoxy‐N‐methyl‐2‐phenoxyacetamide In tetrahydrofuran; diethyl ether at 5 - 50℃; for 4h;	99%

4-chlorobutyl bromide (6940-78-9) + N-(tert-butoxycarbonyl)-N'-(2-nitrobenzenesulfonyl)-1,3-propanediamine (240423-18-1) → {3-[(4-chlorobutyl)(2-nitrobenzenesulfonyl)amino]propyl}carbamic acid tert-butyl ester (1111643-42-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 20h;	99%

4-chlorobutyl bromide (6940-78-9) + thiophenol (108-98-5) → 1-chloro-4-(phenylthio)butane (14633-31-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;	98%
With potassium carbonate In dimethyl sulfoxide at 20 - 50℃; for 2.16667h; Inert atmosphere;	94%
Stage #1: thiophenol With sodium hydroxide In ethanol; water at 20℃; for 0.166667h; Stage #2: 4-chlorobutyl bromide In ethanol; water at 25℃; for 8h;	92%

4-chlorobutyl bromide (6940-78-9) + β-naphthol (135-19-3) → 4-(2-naphthyloxy)-1-chlorobutane (653573-32-1)

Conditions	Yield
With potassium carbonate In acetone for 6h; Heating / reflux;	98%
With potassium carbonate In acetone for 6h; Heating / reflux;	98%
With potassium carbonate In acetone Heating;	98%

4-chlorobutyl bromide (6940-78-9) + 1-(3-chloro-propyl)-5-pyridin-3-yl-1H-pyrimidine-2,4-dione (952402-42-5) → 3-benzoyl-1-(4-chloro-butyl)-5-iodo-1H-pyrimidine-2,4-dione (952402-43-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	98%

4-chlorobutyl bromide (6940-78-9) + 5-hydroxy-1,3-dihydro-1-isoindolone (252061-66-8) → 5-(4-chloro-butoxy)-2,3-dihydro-isoindol-1-one (1007455-38-0)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 18h; Heating / reflux;	98%

4-chlorobutyl bromide (6940-78-9) + 2-ethylhept-6-enenitrile → C13H22ClN (1256484-04-4)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃;	98%

4-chlorobutyl bromide (6940-78-9) + 3-(4-((benzyl(ethyl)amino)methyl)phenyl)-7-hydroxy-2H-chromen-2-one (1008798-50-2) → 3-(4-{[benzyl(ethyl)amino]methyl}phenyl)-7-(4-chlorobutoxy)-2H-chromen-2-one

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

4-chlorobutyl bromide (6940-78-9) + 4,5,6,6a-tetrahydro-3aH-cyclopenta[c]pyrrole-1,3-dione (5763-44-0) → 2-(4-chlorobutyl)tetrahydrocyclopenta[c]pyrrole-1,3(2H,3aH)-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	98%

Upstream product

• 109-99-9 tetrahydrofuran 
• 928-51-8 4-Chloro-1-butanol 
• 110-56-5 1,4-dichlorobutane 
• 109-65-9 1-bromo-butane 
• 30379-55-6 benzyloxyacetic acid 
• 109-70-6 1.3-chlorobromopropane 
• 109-69-3 n-Butyl chloride 
• 7791-25-5 sulfuryl dichloride 
• 94-36-0 dibenzoyl peroxide 
• 7782-50-5 chlorine 
• 6334-96-9 bis-(4-chlorobutyl)ether 

Downstream Products

• 1610-39-5 1,2,3,4,5,6,7,8,9,10,11,12-dodecahydrotriphenylene 
• 36871-49-5 2-(5-chloro-pentyl)-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine 
• 120758-23-8 benzyl 4-chlorobutyl sulfide 
• 99840-22-9 4-chloro-1-[(4-chlorobutyl)thiomethyl]benzene 
• 127625-85-8 2-(4-chlorobutyl)-2H-naphth<1,8-cd>isothiazole 1,1-dioxide 
• 4238-01-1 2-(4-Chlor-butoxy)-1-nitro-benzol 
• 177531-36-1 (4-chlorobutyl)diphenylphosphine sulfide 
• 107-46-0 Hexamethyldisiloxane 
• 40702-18-9 allylidenecyclopentane 
• 164934-25-2 3-(4-chlorobutoxy)xanthen-9-one 
• 220926-88-5 N-(tert-butoxycarbonyl)-N-(4-chlorobutyl)cinnamylamine 
• 231610-94-9 ethyl 4-chlorobutyl(phenyl)phosphinate 
• 234090-69-8 2-(4-chlorobutyl)-6-<4-<2-(2-methoxyphenoxy)ethyl>-1-piprazinyl>-3(2H)-pyridazinone 
• 234090-64-3 4-chloro-2-(4-chlorobutyl)-5-<4-<2-(2-methoxyphenoxy)ethyl>-1-piprazinyl>-3(2H)-pyridazinone 

Relevant articles and documents

Practical and Selective sp3 C?H Bond Chlorination via Aminium Radicals

The introduction of chlorine atoms into organic molecules is fundamental to the manufacture of industrial chemicals, the elaboration of advanced synthetic intermediates and also the fine-tuning of physicochemical and biological properties of drugs, agrochemicals and polymers. We report here a general and practical photochemical strategy enabling the site-selective chlorination of sp3 C?H bonds. This process exploits the ability of protonated N-chloroamines to serve as aminium radical precursors and also radical chlorinating agents. Upon photochemical initiation, an efficient radical-chain propagation is established allowing the functionalization of a broad range of substrates due to the large number of compatible functionalities. The ability to synergistically maximize both polar and steric effects in the H-atom transfer transition state through appropriate selection of the aminium radical has provided the highest known selectivity in radical sp3 C?H chlorination.

Carbon tetrabromide - A new brominating agent for alkanes and arylalkanes

Quantitative catalytic bromination of alkanes, cycloalkanes, and arylalkanes with carbon tetrabromide as brominating agent was accomplished for the first time.

10,11-Methanodibenzosuberane derivatives

10,11-Methanodibenzosuberane derivatives, i.e., the compounds of Formula I: STR1 wherein: A is --CH2 --CH2 --, --CH2 --CHRa --CH2 --, or --CH2 --CHRa --CHRb --CH2 --, where one of Ra or Rb is H, OH, or lower acyloxy, and the other is H; R1 is H, F, Cl or Br; R2 is H, F, Cl or Br; and R3 is heteroaryl or phenyl optionally substituted with F, Cl, Br, CF3, CN, NO2 or OCHF2 ; and the pharmaceutically acceptable salts thereof, are useful chemosensitizing agents, e.g., for cancer chemotherapy, particularly for treating multidrug resistance.