420-90-6

Basic information

• Product Name: 3-BROMO-3,3-DIFLUOROPROPENE
• Synonyms: 3-BROMO-3,3-DIFLUOROPROPENE;3,3-DIFLUORO-3-BROMOPROPENE;1-BROMO-1,1-DIFLUOROPROP-2-ENE;1-BROMO-1,1-DIFLUOROPROPENE;3-Bromo-3,3-difluoroprop-1-ene 98%;3-Bromo-3,3-difluoroprop-1-ene98%;1,1-Difluoroallyl bromide;1-Bromo-1,1-difluoro-2-propene
• CAS NO: 420-90-6
• Molecular Formula: C₃H₃BrF₂
• Molecular Weight: 156.96
• EINECS: 810-594-0
• Mol File: 420-90-6.mol

Chemical Properties

• Melting Point: 53-54°C
• Boiling Point: 41-42°C
• Flash Point: -4.642 °C
• Appearance: /
• Density: 1,543 g/cm3
• Vapor Pressure: 411mmHg at 25°C
• Refractive Index: 1.377
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 3-BROMO-3,3-DIFLUOROPROPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-3,3-DIFLUOROPROPENE(420-90-6)
• EPA Substance Registry System: 3-BROMO-3,3-DIFLUOROPROPENE(420-90-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 420-90-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Bromo-3,3-difluoropropene is used as a reagent in chemical synthesis for its reactivity, allowing for the creation of various compounds in the laboratory or industrial processes.
Used in Industrial Applications:
3-Bromo-3,3-difluoropropene is used as an intermediate in industrial applications, where its unique properties contribute to the production of specific products, such as pharmaceuticals or specialty chemicals.
Used in Research and Development:
3-Bromo-3,3-difluoropropene is used as a research compound in the development of new materials and processes, taking advantage of its reactivity and stability to explore novel chemical reactions and applications.

InChI:InChI=1/C3H3BrF2/c1-2-3(4,5)6/h2H,1H2

Synthetic route

1,1-difluoro-1,3-dibromopropane (460-25-3) → 3-bromo-3,3-difluropropene (420-90-6)

Conditions	Yield
With potassium hydroxide

1,1-difluoro-1,3-dibromopropane (460-25-3) → 3-bromo-3,3-difluropropene (420-90-6) + 1,1-difluoro-3-bromo-1-propene (60917-29-5)

Conditions	Yield
With potassium hydroxide at 115 - 130℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With potassium hydroxide In water at 120 - 160℃; Yield given. Yields of byproduct given;
With potassium hydroxide In water at 90 - 110℃; for 3h;

1,1-difluoro-1,3-dibromopropane (460-25-3) + aqueous KOH-solution → 3-bromo-3,3-difluropropene (420-90-6)

Conditions	Yield
at 80℃;

ethene (74-85-1) + dibromodifluoromethane (75-61-6) → 3-bromo-3,3-difluropropene (420-90-6)

3-bromo-3,3-difluropropene (420-90-6) + benzaldehyde (100-52-7) → 2,2-difluoro-1-phenyl-3-buten-1-ol (85864-61-5)

Conditions	Yield
With indium In water at 20℃; for 3h; Addition;	100%
With indium In N,N-dimethyl-formamide for 3h; Ambient temperature;	99%
With ammonium chloride; zinc In tetrahydrofuran allylation;	84%

3-bromo-3,3-difluropropene (420-90-6) + hexanal (66-25-1) → 3,3-difluoro-1-nonen-4-ol (131437-07-5)

Conditions	Yield
With indium In water for 3h;	100%
With zinc In tetrahydrofuran	47%
With indium In N,N-dimethyl-formamide

3-bromo-3,3-difluropropene (420-90-6) + 3-phenyl-propenal (104-55-2) → 4,4-difluoro-1-phenylhexa-1,5-dien-3-ol (88257-89-0)

Conditions	Yield
With indium In water at 20℃; for 3h; Addition;	100%
With zinc In tetrahydrofuran 1.) 0 deg C to RT, 4.5 h; 2.) RT, overnight;	74%

nonan-1-al (124-19-6) + 3-bromo-3,3-difluropropene (420-90-6) → 3,3-difluorododec-1-en-4-ol

Conditions	Yield
With indium In water at 20℃; for 3h; Addition;	100%
With indium In N,N-dimethyl-formamide for 3h; Ambient temperature;	93%

3-bromo-3,3-difluropropene (420-90-6) + 4-cyanobenzaldehyde (105-07-7) → 4-(2,2-difluoro-1-hydroxybut-3-en-1-yl)benzonitrile

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

formaldehyd (50-00-0) + 3-bromo-3,3-difluropropene (420-90-6) → 2,2-difluoro-3-butene-1-ol

Conditions	Yield
With indium; lithium iodide In N,N-dimethyl-formamide	100%
With lithium iodide In N,N-dimethyl-formamide at 22℃; for 12h;

(E)-2-Heptenal (18829-55-5) + 3-bromo-3,3-difluropropene (420-90-6) → (E)-3,3-Difluoro-deca-1,5-dien-4-ol

Conditions	Yield
With indium In N,N-dimethyl-formamide for 3h; Ambient temperature;	99%

3-bromo-3,3-difluropropene (420-90-6) + 3-Butyl-acrolein (2463-63-0) → 3,3-difluorodeca-1,5-dien-4-ol

Conditions	Yield
With indium In N,N-dimethyl-formamide at 20℃; for 3h; Addition;	99%

3-bromo-3,3-difluropropene (420-90-6) + tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate (155396-71-7) → C15H19F2NO2 (1095387-06-6)

Conditions	Yield
Stage #1: 3-bromo-3,3-difluropropene With zinc(II) chloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate In N,N-dimethyl-formamide at 20℃; for 1h;	99%

3-bromo-3,3-difluropropene (420-90-6) + thiophenol (108-98-5) → (3,3-difluoro-2-propen-1-yl)phenyl sulfide

Conditions	Yield
Stage #1: thiophenol With sodium hydride In 1,4-dioxane at 0℃; for 0.25h; Inert atmosphere; Sonication; Stage #2: 3-bromo-3,3-difluropropene In 1,4-dioxane at 0 - 20℃; for 1h; Inert atmosphere;	99%
Stage #1: thiophenol With sodium hydride for 0.0833333h; Inert atmosphere; Stage #2: 3-bromo-3,3-difluropropene at 20℃; for 1h; Inert atmosphere;	99%

3-bromo-3,3-difluropropene (420-90-6) + C10H17O4(1-)*Na(1+) → tert-butyl ethyl 2-(3,3-difluoroprop-2-enyl)isobutan-1,3-dioate

Conditions	Yield
With palladium diacetate; triphenylphosphine In tetrahydrofuran at 40℃; for 2h; Alkylation;	98%

3-bromo-3,3-difluropropene (420-90-6) + (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → C14H23F2NO4 (1056467-63-0)

Conditions	Yield
With indium; lithium iodide In N,N-dimethyl-formamide	98%

3-bromo-3,3-difluropropene (420-90-6) + 4-hydroxy-benzaldehyde (123-08-0) → 2,2-difluoro-1-(p-hydroxyphenyl)but-3-en-1-ol

Conditions	Yield
With indium In N,N-dimethyl-formamide for 3h; Ambient temperature;	97%
With indium In N,N-dimethyl-formamide at 20℃; for 3h; Addition;	97%

3-bromo-3,3-difluropropene (420-90-6) + sodium diethyl methylmalonate (18424-77-6) → diethyl 2-(3,3-difluoroprop-2-enyl)isobutan-1,3-dioate (288302-72-7)

Conditions	Yield
With palladium diacetate; triphenylphosphine In tetrahydrofuran at 40℃; for 2h; Alkylation;	97%

3-bromo-3,3-difluropropene (420-90-6) + 3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) → 1-(tert-butyldiphenylsilyloxy)-4,4-difluoro-5-hexen-3-ol (1310565-93-5)

Conditions	Yield
Stage #1: 3-bromo-3,3-difluropropene With indium In water at 20℃; for 0.166667h; Stage #2: 3-(tert-butyldiphenylsilyloxy)-1-propanal In tetrahydrofuran; water for 5h;	97%
Stage #1: 3-bromo-3,3-difluropropene With indium; lithium iodide In water at 20℃; for 0.166667h; Stage #2: 3-(tert-butyldiphenylsilyloxy)-1-propanal In tetrahydrofuran; water at 20℃; for 5h;	97%
With indium In tetrahydrofuran; water at 20℃; for 2h;	93%
With indium In tetrahydrofuran; water at 20 - 60℃; Inert atmosphere;	90%
With indium	90%

3-bromo-3,3-difluropropene (420-90-6) + 2-hydroxybromobenzene (95-56-7) → 1-bromo-2-((1’,1’-difluoroallyl)oxy)benzene (1565823-27-9)

Conditions	Yield
With palladium diacetate; sodium hydride; triphenylphosphine In tetrahydrofuran at 0 - 40℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Tsuji-Trost Allylation; Inert atmosphere; regioselective reaction;	97%
With palladium diacetate; sodium hydride; triphenylphosphine In tetrahydrofuran at 0 - 40℃; Tsuji-Trost Allylation; Inert atmosphere;	83%

3-bromo-3,3-difluropropene (420-90-6) + 7-bromo-2-(pyridin-2-yl)isoquinolin-1(2H)-one → 7-bromo-3-(3,3-difluoroallyl)-2-(pyridin-2-yl)isoquinolin-1(2H)-one

Conditions	Yield
With bromopentacarbonylmanganese(I); N-cyclohexyl-cyclohexanamine In 1,4-dioxane at 90℃; for 22h;	97%

3-bromo-3,3-difluropropene (420-90-6) + 4-methoxy-1-(pyridin-2-yl)-1H-indole → 2-(3,3-difluoroallyl)-4-methoxy-1-(pyridin-2-yl)-1H-indole

Conditions	Yield
With bromopentacarbonylmanganese(I); sodium acetate In 1,4-dioxane at 90℃; for 22h;	97%

3-bromo-3,3-difluropropene (420-90-6) + 3-methyl-1-(pyridine-2-yl)-1H-indole (116359-75-2) → 2-(3,3-difluoroallyl)-3-methyl-1-(pyridin-2-yl)-1H-indole

Conditions	Yield
With bromopentacarbonylmanganese(I); sodium acetate In 1,4-dioxane at 90℃; for 22h;	97%

3-bromo-3,3-difluropropene (420-90-6) + benzyloxyacetoaldehyde (60656-87-3) → 1-(benzyloxy)-3,3-difluoropent-4-en-2-ol (275377-30-5)

Conditions	Yield
With indium In N,N-dimethyl-formamide at 20℃; for 6h; sonification;	96%
With indium In N,N-dimethyl-formamide at 20℃; for 5h; allylation; Sonication;	80%

3-bromo-3,3-difluropropene (420-90-6) + 2-bromo-4-chlorophenol (695-96-5) → 2-bromo-4-chloro-1-(1,1-difluoroallyloxy)benzene (1565823-30-4)

Conditions	Yield
With palladium diacetate; sodium hydride; triphenylphosphine In tetrahydrofuran at 0 - 40℃; for 1h; Tsuji-Trost Allylation; Inert atmosphere; regioselective reaction;	96%

3-bromo-3,3-difluropropene (420-90-6) + pivalaldehyde (630-19-3) → 4,4-Difluoro-2,2-dimethyl-hex-5-en-3-ol (73557-51-4)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane; pentane at -95℃;	95%

3-bromo-3,3-difluropropene (420-90-6) + methyl chloroacetate (96-34-4) → 1-Chloro-3,3-difluoro-pent-4-en-2-one (85882-51-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane; pentane at -95℃;	95%

3-bromo-3,3-difluropropene (420-90-6) + 4-bromo-benzaldehyde (1122-91-4) → 1-(p-bromophenyl)-2,2-difluorobut-3-en-1-ol (189949-30-2)

Conditions	Yield
With indium In N,N-dimethyl-formamide for 3h; Ambient temperature;	95%
With indium In N,N-dimethyl-formamide at 20℃; for 3h; Addition;	95%

furfural (98-01-1) + 3-bromo-3,3-difluropropene (420-90-6) → 2,2-difluoro-1-(furan-2-yl)but-3-en-1-ol (275377-29-2)

Conditions	Yield
With indium In N,N-dimethyl-formamide at 20℃; for 4h; sonification;	95%
With indium In N,N-dimethyl-formamide at 20℃; allylation; Sonication;	77%

3-bromo-3,3-difluropropene (420-90-6) + 3-bromo-4-hydroxybenzonitrile (2315-86-8) → 3-bromo-4-(1,1-difluoroallyloxy)benzonitrile

Conditions	Yield
With palladium diacetate; sodium hydride; triphenylphosphine In tetrahydrofuran at 0 - 40℃; for 0.5h; Tsuji-Trost Allylation; Inert atmosphere; regioselective reaction;	95%

5-chloro-2H-[1,2'-bipyridin]-2-one (109822-12-0) + 3-bromo-3,3-difluropropene (420-90-6) → 5-chloro-6-(3,3-difluoroallyl)-2H-[1,2'-bipyridin]-2-one

Conditions	Yield
With bromopentacarbonylmanganese(I); N-cyclohexyl-cyclohexanamine In 1,4-dioxane at 90℃; for 22h;	95%

3-bromo-3,3-difluropropene (420-90-6) + 5-methoxy-1-(pyridine-2-yl)-1H-indole → 2-(3,3-difluoroallyl)-5-methoxy-1-(pyridin-2-yl)-1H-indole

Conditions	Yield
With bromopentacarbonylmanganese(I); sodium acetate In 1,4-dioxane at 90℃; for 22h;	95%

3-bromo-3,3-difluropropene (420-90-6) + methyl salicylate (119-36-8) → methyl 2-((1’,1’-difluoroallyl)oxy)benzoate

Conditions	Yield
With palladium diacetate; sodium hydride; triphenylphosphine In tetrahydrofuran at 0 - 40℃; Tsuji-Trost Allylation; Inert atmosphere;	95%

3-bromo-3,3-difluropropene (420-90-6) + methyl 3-hydroxybenzoate (19438-10-9) → methyl-3-((1’,1’-difluoroallyl)oxy)benzoate

Conditions	Yield
With palladium diacetate; sodium hydride; triphenylphosphine In tetrahydrofuran at 0 - 40℃; Tsuji-Trost Allylation; Inert atmosphere;	95%

Upstream product

• 460-25-3 1,1-difluoro-1,3-dibromopropane 
• 74-85-1 ethene 
• 75-61-6 dibromodifluoromethane 

Downstream Products

• 88257-89-0 (1E)-4,4-difluoro-1-phenylhexa-1,5-dien-3-ol 
• 125982-92-5 1-(1,1-difluoro-2-propenyl)-2-cyclohexen-1-ol 
• 125982-91-4 1,1,1,3,3-pentafluoro-2-phenyl-4-penten-2-ol 
• 131437-10-0 1,1,1,3,3-pentafluoro-2-(4-methylphenyl)-4-penten-2-ol 
• 131437-08-6 4,4-difluoro-2-phenyl-5-hexen-3-ol 
• 73557-48-9 1-(1,1-difluoro-2-propenyl)cyclohexanol 
• 85864-61-5 2,2-difluoro-1-phenyl-3-buten-1-ol 
• 85882-51-5 1-Chloro-3,3-difluoro-pent-4-en-2-one 
• 132496-65-2 1-(1,1-difluoro-2-propenyl)-2-methylcyclohexanol 
• 88257-89-0 4,4-difluoro-1-phenylhexa-1,5-dien-3-ol 
• 73557-49-0 3,3-Difluoro-2-phenyl-pent-4-en-2-ol 
• 64545-26-2 3,3-difluoro-3-(dimethylphenylsilyl)propene 
• 4938-52-7 1-hepten-3-ol 
• 85864-60-4 4,4-Difluoro-hexa-1,5-dien-3-ol 

Related news

Indium-Mediated Reaction of 3-BROMO-3,3-DIFLUOROPROPENE (cas 420-90-6) and Bromodifluoromethylacetylene Derivatives with Aldehydes07/13/2019

Aldehydes reacted with 3-bromo-3,3-difluoropropene at the α-position in the presence of indium to afford 1-substituted-2,2-difluorobut-3-en-1-ols. Ketones and other electrophiles are inert under the examined conditions. The reaction of bromodifluoromethylacetylene derivatives with an aldehyde i...detailed

Relevant articles and documents

Infrared and Raman spectra, conformational stability, vibration assignment, and ab initio calculations for 3-bromo-3,3-difluoropropene

The infrared spectra (3200-50 cm-1) of gaseous and solid and Raman spectra (3200-10 cm-1) of the liquid with qualitative depolarization ratios and solid 3-bromo-3,3-difluoropropene CH2=CHCBrF2 have been recorded

Method of synthesizing fluorinated diene alcohols

Disclosed are fluorinated diene alcohols perferably having a fluorine content of at least about 45 weight percent and having a plurality of moieties of the formula CFx and a plurality of moieties of the formula CHx, where each x is independently 1, 2 or 3 and where each CFx moiety is not directly bonded to another CFx moiety. Methods of synthesizing fluorinated diene alcohol compounds are also disclosed comprising reacting at least one C2-C3 alkene halide with at least one reactant of the formula (II): where Z is OH, OR6, OC(O)R7, or a halogen, R6 is a C1-C6 branched or straight chain alkyl, and R7 is a C1-C6 branched or straight chain alkyl or fluoroalkyl,

gem-(DIFLUOROALLYL)LITHIUM: PREPARATION BY LITHIUM-HALOGEN EXCHANGE AND UTILIZATION IN ORGANOSILICON AND ORGANIC SYNTHESIS.

gem-(Difluoroallyl)lithium may be generated by lithium-bromine exchange between n-butyllithium and CH//2 equals CHCF//2Br at minus 95 degree C by using an in situ procedure. When this preparation is carried out in the presence of chlorosilanes, aldehydes, ketones, and esters, products are formed, often in good yield. The factors determining the regioselectivity in addition to C equals O of unsymmetrically substituted allylic lithium reagents are discussed.

gem-Difluoroallyllithium: Improved Synthesis Brings Improved Applicability

The action of n-butyllithium in hexane on CF2BrCH=CH2/CF2=CHCH2Br (5:2 to 20:1 mixture) in 5:1:1 THF/Et2O/pentane at -95 deg C generates gem-difluoroallyllithium which may be trapped, generally in good yield, by an in situ procedure using triorganochlorosilanes (R3SiCF2CH=CH2) and aldehydes and ketones (RR'C(OH)CF2CH=CH2).