814-75-5

Basic information

• Product Name: 3-BROMO-2-BUTANONE
• Synonyms: 2-BROMO-3-BUTANONE;3-BROMO-2-BUTANONE;(+-)-alpha-bromoethylmethylketone;1-bromoethylmethylketone;3-bromo-2-butanon;alpha-bromoethylmethylketone;3-bromobutan-2-one;2-Bromobutan-2-one
• CAS NO: 814-75-5
• Molecular Formula: C₄H₇BrO
• Molecular Weight: 151
• EINECS: 212-404-6
• Mol File: 814-75-5.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 36 °C (11 mmHg)
• Flash Point: >100°C
• Appearance: Clear light yellow to brown/Liquid
• Density: 1.416 g/mL at 25 °C
• Vapor Pressure: 5.84mmHg at 25°C
• Refractive Index: 1.458-1.46
• Solubility: Miscible with dichloromethane.
• BRN: 906773
• CAS DataBase Reference: 3-BROMO-2-BUTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-2-BUTANONE(814-75-5)
• EPA Substance Registry System: 3-BROMO-2-BUTANONE(814-75-5)

Safety Data

• Hazard Codes: Xn,C
• Statements: 36/37/38-20/21/22-34-21/24-21/22
• Safety Statements: 36/37/39-26-45
• RIDADR: 1224
• WGK Germany: 2
• RTECS: EL7005000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 814-75-5(Hazardous Substances Data)

Usage

Uses

3-Bromo-2-butanone is involved in the preparation of o-isopropyl S-3-oxobutan-2-yl dithiocarbonate by reaction with potassium o-isopropylxanthate, which on treatment with sulfuric acid gives 4,5-dimethyl-1,3-dithiol-2-one .

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 3369, 1984 DOI: 10.1016/S0040-4039(01)81387-3

InChI:InChI=1/C4H7BrO/c1-3(5)4(2)6/h3H,1-2H3/t3-/m0/s1

Synthetic route

butanone (78-93-3) → 3-bromo-butanone (814-75-5)

Conditions	Yield
With bromine	100%
With bromine In tetrachloromethane Ambient temperature;	71%
With bromine; acetic acid In water at 20 - 70℃; for 17h;	70%

(Z)-2-Bromo-2-butene (3017-68-3) → 3-bromo-butanone (814-75-5)

Conditions	Yield
With sodium hypobromide In acetic acid; acetone at 0℃;	88%

butanone (78-93-3) → 3,3-dibromobutan-2-one (2648-69-3) + 1,1-dibromo-butan-2-one (3479-86-5) + 1-Bromo-2-butanone (816-40-0) + 3-bromo-butanone (814-75-5)

Conditions	Yield
With N-Bromosuccinimide; silica gel In methanol for 0.166667h; Reflux;	A n/a B n/a C 14% D 83%

butanone (78-93-3) → 1-Bromo-2-butanone (816-40-0) + 3-bromo-butanone (814-75-5)

Conditions	Yield
With Oxone; ammonium bromide In methanol at 20℃; for 8h; regioselective reaction;	A 80% B 9%
With 3-bromo-6-chloroimidazo<1,2-b>pyridazine hydrobromide-bromine for 0.5h; Ambient temperature;	A 19% B 58%
With potassium chlorate; bromine at 50℃;

2,3-dimethyl-2-nitro-oxirane (22596-46-9) → 3-bromo-butanone (814-75-5)

Conditions	Yield
With magnesium bromide In diethyl ether at -10℃; for 0.5h;	55%

2-acetoxy-2-butene (6203-88-9) → 3-bromo-butanone (814-75-5)

Conditions	Yield
With tetrachloromethane; bromine anschliessend mit Methanol;

acetic acid (64-19-7) + butanone (78-93-3) → 3-acetoxy-2-butanone (4906-24-5) + 2-oxobutyl acetate (1575-57-1) + 1-Bromo-2-butanone (816-40-0) + 3-bromo-butanone (814-75-5)

Conditions	Yield
With bromine; sodium acetate In water Further byproducts given;

butanone (78-93-3) → 3-acetoxy-2-butanone (4906-24-5) + 2-oxobutyl acetate (1575-57-1) + 1-Bromo-2-butanone (816-40-0) + 3-bromo-butanone (814-75-5)

Conditions	Yield
With bromine; sodium acetate In water; acetic acid Further byproducts given;

2-bromo-1-methylpropypperoxy radical (144698-91-9) → 3-bromo-2-butanol (5798-80-1) + 3-Bromo-but-2-yl-hydroperoxide (199802-42-1) + 3-bromo-butanone (814-75-5)

Conditions	Yield
at 24.9℃; under 400 Torr; Rate constant; Mechanism; (irradiation of a C4H8/Br2/O2/N2-mixture);

water (7732-18-5) + bromine (7726-95-6) + butanone (78-93-3) + CaCO3 → 3-bromo-butanone (814-75-5)

Conditions	Yield
at 50℃;

phosphorus pentabromide (7789-69-7) + butanone (78-93-3) + petroleum ether → 3-bromo-butanone (814-75-5)

Conditions	Yield
at 50℃;

2-bromo-1-methylpropypperoxy radical (144698-91-9) → 3-bromo-2-butanol (5798-80-1) + 3-bromo-butanone (814-75-5)

Conditions	Yield
at 1.85℃; Kinetics; Further Variations:; Temperatures;

iso-butanol (78-92-2, 15892-23-6) → butanone (78-93-3) + 1-Bromo-2-butanone (816-40-0) + 3-bromo-butanone (814-75-5)

Conditions	Yield
With sodium bromate; sulfuric acid; sodium bromide In water at 60℃; for 0.166667h; Microwave irradiation;

iso-butanol (78-92-2, 15892-23-6) → butanone (78-93-3) + 3-bromo-butanone (814-75-5)

Conditions	Yield
With sodium bromate; sulfuric acid; sodium bromide In water at 33 - 35℃; for 0.833333h; Microwave irradiation;

N-(3-nitrophenyl)formamide (102-38-5) + 3-bromo-butanone (814-75-5) → N-(1-methyl-2-oxo-propyl)-N-(3-nitrophenyl)formamide (333793-39-8)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) for 72h;	100%

Cbz-L-proline thioamide (63808-47-9) + 3-bromo-butanone (814-75-5) → benzyl (S)-2-(4,5-dimethyl-thiazol-2-yl)-pyrrolidine-1-carboxylate

Conditions	Yield
In ethanol for 4h; Heating / reflux;	100%
In ethanol at 20 - 80℃;	100%
In ethanol

2-Iodophenol (533-58-4) + 3-bromo-butanone (814-75-5) → 3-(2-Iodo-phenoxy)-butan-2-one (30343-28-3)

Conditions	Yield
With potassium carbonate In acetone for 8h; Reflux;	100%

(S)-1-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)thiourea (939039-51-7) + 3-bromo-butanone (814-75-5) → (S)-N-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)-4,5-dimethylthiazol-2-amine

Conditions	Yield
In ethanol at 90℃; for 1h;	99%

2,4-Diamino-1,3,5-triazin-6-yl-thioharnstoff (90440-15-6) + 3-bromo-butanone (814-75-5) → 2,4-Diamino-6-(4,5-dimethyl-thiazol-2-yl-amino)-1,3,5-triazinhydrobromid

Conditions	Yield
In ethanol for 14h; Heating;	98%

potassium O-ethyl 1-13C-dithiocarbonate + 3-bromo-butanone (814-75-5) → O-ethyl S-3-oxobut-2-yl 1-13C-dithiocarbonate (243844-92-0)

Conditions	Yield
In ethanol at 0℃; for 3h; Substitution;	98%

3-bromo-butanone (814-75-5) + phenol (108-95-2) → 3-phenyloxy-2-butanone (6437-85-0)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 20℃; for 16h;	98%
With potassium carbonate In acetone at 75℃; Inert atmosphere;	61%
With potassium iodide; potassium carbonate In butanone

4-methoxyphenylacetamide (3424-93-9) + 3-bromo-butanone (814-75-5) → 2-(4-methoxy-phenyl)-4,5-dimethyl-oxazole (124811-80-9)

Conditions	Yield
With silver(I) trifluoromethoxide In ethyl acetate at 50℃; for 4h; Darkness;	98%

2-iodo-3-(methyloxy)phenol (121980-50-5) + 3-bromo-butanone (814-75-5) → 3-(2-iodo-3-methoxyphenoxy)butan-2-one

Conditions	Yield
With potassium carbonate In acetone at 80℃; for 8h; Inert atmosphere; Schlenk technique;	98%

potassium phtalimide (1074-82-4) + 3-bromo-butanone (814-75-5) → 2-(1-methyl-2-oxo-propyl)-isoindole-1,3-dione (2028-33-3)

Conditions	Yield
at 20℃; for 0.233333h; Ionic liquid;	96%
In N,N-dimethyl-formamide at 20℃;

caprinaldehyde (112-31-2) + 3-bromo-butanone (814-75-5) → C14H28O2 (1007572-49-7)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; manganese In tetrahydrofuran at 20℃; for 6h;	96%

3-bromo-butanone (814-75-5) → butanone (78-93-3)

Conditions	Yield
With Methyltrichlorosilane; sodium iodide In acetonitrile for 2h; Ambient temperature;	95%
With ammonium oxalate; aluminium In methanol for 1.5h; Heating;	87%
With tetrakis(triphenylphosphine) palladium(0); 1,1,1,2,2,2-hexamethyldisilane at 150℃; for 9.5h;	100 % Spectr.
With bismuth; ammonium fluoride-hydrogen fluoride In water at 20℃; for 2h;	100 % Spectr.

O-methylresorcine (150-19-6) + 3-bromo-butanone (814-75-5) → 3-(3-methoxyphenyloxy)-butan-2-one (93351-44-1)

Conditions	Yield
With potassium carbonate In acetone at 80℃; for 8h; Inert atmosphere; Schlenk technique;	95%

isopropylxanthic acid (108-25-8) + 3-bromo-butanone (814-75-5) → carbonodithioic acid O-(isopropyl) S-(1-methyl-2-oxopropyl) ester (958649-73-5)

Conditions	Yield
In acetone at 20℃; for 1h;	94%

4-((8-azabicyclo[3.2.1]oct-3-yl)oxy)-6-fluoroquinoline dihydrochloride + 3-bromo-butanone (814-75-5) → 3-(3-((6-fluoroquinolin-4-yl)oxy)-8-azabicyclo[3.2.1]octane-8-yl)butan-2-one

Conditions	Yield
With triethylamine In acetonitrile at 30℃;	94%

Thallous Phenyl Selenide (72017-00-6) + 3-bromo-butanone (814-75-5) → diphenyl diselenide (1666-13-3) + 3-(phenylselanyl)butan-2-one (72017-05-1)

Conditions	Yield
In diethyl ether for 24h;	A 4% B 91%

potassium isopropylxanthate (140-92-1) + 3-bromo-butanone (814-75-5) → carbonodithioic acid O-(isopropyl) S-(1-methyl-2-oxopropyl) ester (958649-73-5)

Conditions	Yield
In acetone for 0.5h;	91%
In dichloromethane at 60℃; for 6h; Inert atmosphere;	50.1 g

thallium thiophenoxide (57340-80-4) + 3-bromo-butanone (814-75-5) → 3-phenylsulfanyl-butan-2-one (13023-53-5, 132187-18-9, 132187-19-0) + diphenyldisulfane (882-33-7)

Conditions	Yield
In diethyl ether for 24h;	A 90% B 5%

N-acetyl-5-amino-2,3-dimethylindoline (137601-19-5, 137601-21-9) + 3-bromo-butanone (814-75-5) → 1-(2,3,6,7-Tetramethyl-3,5-dihydro-2H-pyrrolo[2,3-f]indol-1-yl)-ethanone (137601-17-3, 137601-23-1)

Conditions	Yield
With acetic acid In butan-1-ol for 24h; Heating;	90%

phenanthridine (229-87-8) + 3-bromo-butanone (814-75-5) → 5-(1-methyl-2-oxo-propyl)-phenanthridinium bromide

Conditions	Yield
In acetonitrile Heating;	90%

S-tert-butyl sodium trithiocarbonate (71127-42-9) + 3-bromo-butanone (814-75-5) → 2-(3-oxobutyl) tert-butyl trithiocarbonate (71988-74-4)

Conditions	Yield
In acetone at 20℃; for 2h;	89%

3-bromo-butanone (814-75-5) → (2R,3S)-dimethylthiirane (5954-71-2) + 2(R),3(R)(2(S),3(S))-dimethylthiirane (70492-83-0)

Conditions	Yield
With aluminum oxide; sodium tetrahydroborate; O,O-Diethyl hydrogen phosphorodithioate for 0.05h; microwave irradiation;	A n/a B 88%

1,1-Diphenylethylene (530-48-3) + 3-bromo-butanone (814-75-5) → 3-methyl-5,5-diphenylpent-4-en-2-one

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); disodium hydrogenphosphate In acetonitrile at 20℃; for 72h; Inert atmosphere; Sealed tube; Irradiation;	88%

m-chlorophenylhydrazine hydrochloride (2312-23-4) + potassium thioacyanate (333-20-0) + 3-bromo-butanone (814-75-5) → 1-(3-chloro-phenylamino)-4,5-dimethyl-1H-imidazole-2-thiol

Conditions	Yield
Stage #1: potassium thioacyanate; 3-bromo-butanone With acetic acid for 0.5h; Stage #2: m-chlorophenylhydrazine hydrochloride With acetic acid	87%

7-nitro-1H-indole-2-carbothioic acid amide (913286-15-4) + 3-bromo-butanone (814-75-5) → 2-(4,5-dimethyl-1,3-thiazol-2-yl)-7-nitro-1H-indole (913286-34-7)

Conditions	Yield
In ethanol; N,N-dimethyl acetamide at 100℃; for 48h;	87%

2-methyl-4-phenylthiosemicarbazide (14223-71-3) + 3-bromo-butanone (814-75-5) → 2-phenylimino-3,5,6-trimethyl-2,3-dihydro-6H-1,3,4-selenadiazine hydrobromide

Conditions	Yield
In ethanol 1h, 0 deg C; 10min, reflux;	86%
In ethanol at 0℃; for 1.16667h; Reflux;	86%

(E)-3-phenylpropenal (14371-10-9) + 3-bromo-butanone (814-75-5) → (3E,5E)-3-Methyl-6-phenylhexa-3,5-dien-2-one (19520-38-8)

Conditions	Yield
With 1-phenylphospholane-1-oxide; diphenylsilane; N-ethyl-N,N-diisopropylamine In toluene at 100℃; for 24h; Wittig Olefination; Inert atmosphere;	86%

benzaldehyde (100-52-7) + 3-bromo-butanone (814-75-5) → 4-hydroxy-3-methyl-4-phenyl-2-butanone (74676-21-4)

Conditions	Yield
With tin; water at 80℃; for 4h;	85%

Upstream product

• 78-93-3 butanone 
• 22596-46-9 2,3-dimethyl-2-nitro-oxirane 
• 144698-91-9 2-bromo-1-methylpropypperoxy radical 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 7789-69-7 phosphorus pentabromide 
• 78-92-2 iso-butanol 
• 3017-68-3 (Z)-2-Bromo-2-butene 
• 64-19-7 acetic acid 
• 6203-88-9 2-acetoxy-2-butene 

Downstream Products

• 62614-92-0 3-cyclohexylidene-butan-2-one 
• 3581-91-7 4,5-Dimethylthiazole 
• 2302-39-8 4,5-dimethylimidazole 
• 20662-83-3 4,5-dimethyl-oxazole 
• 98484-92-5 (4,5-dimethylthiazol-2-yl)hydrazine 
• 36810-74-9 3-(N-ethyl-anilino)-butan-2-one 
• 2289-75-0 4,5-dimethyl-1,3-thiazole-2-amine 
• 91-55-4 2,3-dimethylindole 
• 28128-12-3 (methyl)(phenyl)aminoacetone 
• 45529-92-8 2-amino-4,5-dimethyloxazole 
• 22072-35-1 2,3,6-trimethylindole 
• 117668-69-6 3-(m-tolylamino)butan-2-one 
• 27862-73-3 3-(N-methyl-anilino)-butan-2-one 
• 20662-84-4 2,4,5-trimethyloxazole 

Relevant articles and documents

Preparation method of 3-methyl-3-penten-2-one

The invention discloses a preparation method of 3-methyl-3-penten-2-one. The preparation method comprises the following steps: with butanone as a raw material, performing 3-position halogenation to obtain 3-halobutanone (1), then performing a ketalation reaction to obtain 3-halobutanonediol (2), then performing a Grignard reaction to obtain a Grignard reagent, performing nucleophilic addition on the Grignard reagent and acetaldehyde, and performing intramolecular dehydration under the conditions of acid catalysis and heating to obtain a target product, namely the 3-methyl-3-penten-2-one (3). The preparation method has the advantages of easy obtainment of the raw material, a wide raw material source, simpleness, low preparation cost and suitability for industrial production; by the preparation method, the problems of high preparation cost and difficult industrial production in the prior art are solved.

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