62563-07-9

Basic information

• Product Name: 2-(3-BroMopropyl)-1,3-dioxolane
• Synonyms: 2-(3-BroMopropyl)-1,3-dioxolane;4-Bromobutylaldehyde Ethylene Acetal;4-Bromobutanal ethylene acetal;NSC 617308
• CAS NO: 62563-07-9
• Molecular Formula: C₆H₁₁BrO₂
• Molecular Weight: 195
• Mol File: 62563-07-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 88°C/10mmHg(lit.)
• Appearance: /
• Density: 1.44
• Refractive Index: 1.4780-1.4820
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 2-(3-BroMopropyl)-1,3-dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-BroMopropyl)-1,3-dioxolane(62563-07-9)
• EPA Substance Registry System: 2-(3-BroMopropyl)-1,3-dioxolane(62563-07-9)

Safety Data

• Hazardous Substances Data: 62563-07-9(Hazardous Substances Data)

Usage

Description

2-(3-Bromopropyl)-1,3-dioxolane is an organic compound characterized by its unique structure, which features a bromoalkyl group attached to a dioxolane ring. This structure endows it with specific chemical properties that make it a versatile building block in the synthesis of various compounds.

Uses

2-(3-Bromopropyl)-1,3-dioxolane is used as a reactant in the synthesis of compounds that act as therapeutic agents. Its unique structure allows it to be a valuable component in the development of new pharmaceuticals, potentially contributing to the treatment of various medical conditions.
Used in Pharmaceutical Industry:
2-(3-Bromopropyl)-1,3-dioxolane is used as a key intermediate for the synthesis of therapeutic agents. Its incorporation into the molecular structure of these agents can enhance their pharmacological properties, such as potency, selectivity, and bioavailability, ultimately leading to improved treatment outcomes for patients.

Synthetic route

4-bromoethylbutanoate (2969-81-5) + ethylene glycol (107-21-1) → 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9)

Conditions	Yield
Stage #1: Ethyl 4-bromobutyrate With diisobutylaluminium hydride In dichloromethane at -78℃; Stage #2: ethylene glycol With toluene-4-sulfonic acid In toluene at 90℃;	95%
Stage #1: Ethyl 4-bromobutyrate With diisobutylaluminium hydride In hexane; dichloromethane at -70 - -65℃; for 1h; Stage #2: ethylene glycol With toluene-4-sulfonic acid In benzene for 3h; Heating;	88%
With diisobutylaluminium hydride; toluene-4-sulfonic acid In dichloromethane; benzene	85%

4-bromoethylbutanoate (2969-81-5) → 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9)

Conditions	Yield
Stage #1: Ethyl 4-bromobutyrate With diisobutylaluminium hydride In dichloromethane at -78℃; Stage #2: With toluene-4-sulfonic acid; ethylene glycol In benzine; dichloromethane at 90℃;	95%

4-bromobutyraldehyde (38694-47-2) + ethylene glycol (107-21-1) → 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 2.75h; Heating;	90.5%
With toluene-4-sulfonic acid In toluene Heating;	90%
With toluene-4-sulfonic acid In toluene for 1.5h; Reflux;	73%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + (2R,4R)-N-(2,4,6-trimethoxybenzyl)-2-methyl-4-phenyl-1,3-oxazolidine (205526-50-7) → (R)-2-[((R)-4-[1,3]Dioxolan-2-yl-1-methyl-butyl)-(2,4,6-trimethoxy-benzyl)-amino]-2-phenyl-ethanol (205526-51-8)

Conditions	Yield
With magnesium In tetrahydrofuran at 0℃; for 72h;	96.4%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + (2R,4R)-N-(2,4,6-trimethoxybenzyl)-2,4-diphenyl-1,3-oxazolidine (205526-45-0) → (1S,1'R)-1-[N-(2,4,6-trimethoxybenzyl)-N-2'-hydroxy-1'-phenylethylamino]-5,5-ethylenedioxy-1-phenylpentane (205526-46-1)

Conditions	Yield
With magnesium In tetrahydrofuran at 0℃; for 72h;	96.4%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + phosphoric acid diethyl ester (R)-2-iodo-4,4-dimethylcyclohex-2-enyl ester (725739-83-3) → (R)-2-(3-(2-iodo-6,6-dimethylcyclohex-2-en-1-yl)propyl)-1,3-dioxolane (1321556-48-2)

Conditions	Yield
Stage #1: 2-(3-bromopropyl)-1,3-dioxolane With magnesium In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: With copper(l) cyanide In tetrahydrofuran at -40 - 0℃; Inert atmosphere; Stage #3: phosphoric acid diethyl ester (R)-2-iodo-4,4-dimethylcyclohex-2-enyl ester In tetrahydrofuran at -40℃; Inert atmosphere;	96%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + (2R,4R)-N-(2,4,6-trimethoxybenzyl)-2-(2,2-ethylenedioxy-2-phenylethyl)-4-phenyl-1,3-oxazolidine (205440-44-4) → (R)-2-[(S)-4-[1,3]Dioxolan-2-yl-1-(2-phenyl-[1,3]dioxolan-2-ylmethyl)-butylamino]-2-phenyl-ethanol (205440-45-5)

Conditions	Yield
With magnesium In tetrahydrofuran at 0℃; for 48h;	95.8%

cyclohexenone (930-68-7) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → 3-<3-(1,3-dioxolan-2-yl)propyl>cyclohexanone (75506-74-0)

Conditions	Yield
Stage #1: 2-(3-bromopropyl)-1,3-dioxolane With magnesium In tetrahydrofuran at 22 - 24℃; for 1h; Stage #2: cyclohexenone With copper(l) iodide In tetrahydrofuran at -78 - 0℃;	92%
Stage #1: 2-(3-bromopropyl)-1,3-dioxolane With magnesium In tetrahydrofuran at 20℃; for 1.5h; Stage #2: With copper(l) iodide In tetrahydrofuran at -30℃; for 0.5h; Stage #3: cyclohexenone In tetrahydrofuran at -78 - 20℃;	78%
Stage #1: 2-(3-bromopropyl)-1,3-dioxolane With magnesium In tetrahydrofuran at 20℃; for 1.5h; Stage #2: With copper(l) iodide In tetrahydrofuran at -30℃; for 0.5h; Stage #3: cyclohexenone In tetrahydrofuran at -78 - 20℃;	78%

5-ethoxy-pyrrolidin-2-one (39662-63-0) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → C12H21NO4 (1189789-95-4)

Conditions	Yield
Stage #1: 5-ethoxy-pyrrolidin-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 2-(3-bromopropyl)-1,3-dioxolane In tetrahydrofuran; hexane; dimethyl sulfoxide at -78 - 20℃;	92%

(S)-4-(3-iodophenyl)oxazolidin-2-one + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → (S)-3-(3-(1,3-dioxolan-2-yl)propyl)-4-(3-iodophenyl)oxazolidin-2-one

Conditions	Yield
Stage #1: (S)-4-(3-iodophenyl)oxazolidin-2-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-(3-bromopropyl)-1,3-dioxolane In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;	92%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + (1RS,6RS,8SR)-tricyclo<6.3.1.01,6>dodec-3-ene-2,9-dione 9,9-ethylene acetal → (1RS,6RS,8SR)-2-(4,4-ethylenedioxybutyl)-2-hydroxytricyclo<6.3.1.01,6>dodec-3-ene-9-one 9,9-ethylene acetal

Conditions	Yield
With lithium In diethyl ether for 1h; Ambient temperature; Irradiation;	90%

(3R,6aR,10aS,10bR)-6-(tert-Butotxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[3,2-a]isoquinoline + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → (3R,6R,6aR,10aS,10bR)-6-(tert-butotxycarbonyl)-6-[3-(1,3-dioxolan-2-yl)propyl]-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[3,2-a]isoquinoline

Conditions	Yield
Stage #1: (3R,6aR,10aS,10bR)-6-(tert-Butotxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[3,2-a]isoquinoline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: 2-(3-bromopropyl)-1,3-dioxolane With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 18h; Inert atmosphere;	90%

Allyl acetate (591-87-7) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → 2-(hex-5-en-1-yl)-1,3-dioxolane (1005002-50-5)

Conditions	Yield
Stage #1: 2-(3-bromopropyl)-1,3-dioxolane With iodine; magnesium In tetrahydrofuran at 22 - 60℃; for 2h; Inert atmosphere; Stage #2: Allyl acetate With dilithium tetrachlorocuprate In tetrahydrofuran at -20 - 22℃; for 3.5h; Inert atmosphere;	88%

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → (R)-tert-butyl 5-(1,3-dioxolan-2-yl)-2-(diphenylmethyleneamino)pentanoate (1416352-41-4)

Conditions	Yield
With cesiumhydroxide monohydrate; (R)-4,4-dibutyl-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepinium bromide In toluene at -40℃; for 16h; enantioselective reaction;	87%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + isobutyric Acid (79-31-2) → 5-[1,3]Dioxolan-2-yl-2,2-dimethyl-pentanoic acid

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran	86%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-(4-((3-(1,3-dioxolan-2-yl)propyl)amino)phenyl)ethanol + 2-(4-(bis(3-(1,3-dioxolan-2-yl)propyl)amino)phenyl)ethanol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In acetonitrile at 20℃; for 20h; Inert atmosphere; Reflux;	A 83% B 13%

5-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylhexanamide (1078697-21-8) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → 8'-(tert-butyldimethylsilyloxy)-9'-(tert-butyldiphenylsilyloxy)-1'-(1,3-dioxolan-2-yl)nonan-4'-one (1078697-20-7)

Conditions	Yield
With iodine; magnesium; ethylene dibromide In tetrahydrofuran at 33℃; for 3h; Barbier reaction; Inert atmosphere;	80%

(3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline (864967-37-3) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → (3R,6R,6aR,10aS,10bR)-6-[3-(1,3-dioxolan-2-yl)propyl]-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[3,2-a]isoquinoline (1428872-47-2)

Conditions	Yield
Stage #1: (3R,6aR,10aS,10bR)-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[2,3-a]isoquinoline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 2-(3-bromopropyl)-1,3-dioxolane With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	80%

1-(1,1,1-trifluoroprop-2-en-2-yl)-4-methoxybenzene (69843-08-9) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → 2-(6,6-difluoro-5-(4-methoxyphenyl)hex-5-en-1-yl)-1,3-dioxolane

Conditions	Yield
With 3,4,7,8-Tetramethyl-o-phenanthrolin; (η(5)-indenyl)trichlorotitanium; nickel dibromide; zinc In N,N-dimethyl acetamide at 60℃; for 24h; Schlenk technique; Inert atmosphere;	79%

(E,E)-sorbyl acetate (57006-69-6) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → 2-(5E,7E)-(nona-5,7-diene-1-yl)-1,3-dioxolane (550334-68-4)

Conditions	Yield
Stage #1: 2-(3-bromopropyl)-1,3-dioxolane With magnesium; ethylene dibromide In tetrahydrofuran at -40 - 30℃; for 1.5h; Stage #2: (E,E)-sorbyl acetate With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -40 - 20℃; for 15h;	78%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + ethyl acetoacetate (141-97-9) → 2-Acetyl-5-[1,3]dioxolan-2-yl-pentanoic acid ethyl ester

Conditions	Yield
With sodium hydroxide; sodium ethanolate Heating;	76%

ethyl 2-cyano-2-(cyclohepta-2,4,6-trien-1-yl)acetate (1875-60-1) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → 2-Cyano-2-cyclohepta-2,4,6-trienyl-5-[1,3]dioxolan-2-yl-pentanoic acid ethyl ester

Conditions	Yield
With sodium ethanolate In ethanol Heating;	75%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + tetrahydrothiopyran-4-one-3-carboxylic acid allyl ester (126573-38-4) → 3-(3-[1,3]Dioxolan-2-yl-propyl)-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester (180573-65-3)

Conditions	Yield
With sodium hydride; sodium iodide In acetone for 24h; Heating;	75%

4-bromo-phenol (106-41-2) + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → 2-[3-(4-bromo-phenoxy)-propyl]-[1,3]dioxolane

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h;	75%

4-(2-phenyl-1-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)but-1-en-1-yl)phenol + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → 2-(4-(1-(4-(3-(1,3-dioxolan-2-yl)propoxy)phenyl)-2-phenylbut-1-en-1-yl)phenoxy)tetrahydro-2H-pyran

Conditions	Yield
With potassium carbonate In acetonitrile at 75℃; for 20h;	74%

methyl (naphthalen-2-ylmethyl) oxalate + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → C17H20O2

Conditions	Yield
With manganese; nickel dibromide; tris(para-trifluoromethyl)phenyl phosphine In dimethyl sulfoxide; N,N-dimethyl-formamide at 30℃; for 24h;	73%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + 1-bromo-2-(3-methylbut-3-en-1-yl)benzene (130955-17-8) → C17H24O2

Conditions	Yield
With nickel(II) bromide dimethoxyethane; (R,R)-4,4'-bis(phenylmethyl)-2,2',5,5'-tetrahydro-2,2'-bioxazole; zinc In N,N-dimethyl acetamide at 40℃; for 10h; Inert atmosphere; Sealed tube; enantioselective reaction;	71%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → 3-iodopropionaldehyde ethylene acetal (58135-25-4)

Conditions	Yield
With lithium iodide In tetrahydrofuran Finkelstein reaction; Heating;	68%

C22H33NO5 + 2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) → C26H38O6

Conditions	Yield
Stage #1: 2-(3-bromopropyl)-1,3-dioxolane With iodine; magnesium In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: C22H33NO5 In tetrahydrofuran at 20℃; Inert atmosphere;	68%

2-(3-bromopropyl)-1,3-dioxolane (62563-07-9) + 1-bromo-2-(3-methylbut-3-en-1-yl)benzene (130955-17-8) → C17H24O2

Conditions	Yield
With pyridine-2-yl-N-cyanoamidine; nickel dibromide; zinc In N,N-dimethyl acetamide at 55℃; for 10h;	67%

Upstream product

• 38694-47-2 4-bromobutyraldehyde 
• 107-21-1 ethylene glycol 
• 2969-81-5 Ethyl 4-bromobutyrate 

Downstream Products

• 205526-51-8 (R)-2-[((R)-4-[1,3]Dioxolan-2-yl-1-methyl-butyl)-(2,4,6-trimethoxy-benzyl)-amino]-2-phenyl-ethanol 
• 205526-46-1 (1S,1'R)-1-[N-(2,4,6-trimethoxybenzyl)-N-2'-hydroxy-1'-phenylethylamino]-5,5-ethylenedioxy-1-phenylpentane 
• 205440-45-5 (R)-2-[(S)-4-[1,3]Dioxolan-2-yl-1-(2-phenyl-[1,3]dioxolan-2-ylmethyl)-butylamino]-2-phenyl-ethanol 
• 204845-24-9 (4S,1'R)-2-{4-[N-(2,4,6-trimethoxybenzyl)-N-(2'-hydroxy-1'-phenylethyl)amino]heptyn-5-yl}-1,3-dioxolane 
• 75506-74-0 3-<3-(1,3-dioxolan-2-yl)propyl>cyclohexanone 
• 125736-43-8 5-[1,3]Dioxolan-2-yl-2-hydroxy-pentanoic acid benzyl ester 
• 125736-47-2 (2R,5R)-1-Benzyl-5-(4-[1,3]dioxolan-2-yl-butyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 125736-44-9 5-[1,3]Dioxolan-2-yl-2-trifluoromethanesulfonyloxy-pentanoic acid benzyl ester 
• 1078697-20-7 8'-(tert-butyldimethylsilyloxy)-9'-(tert-butyldiphenylsilyloxy)-1'-(1,3-dioxolan-2-yl)nonan-4'-one 
• 1321556-50-6 (R)-6-(3-(1,3-dioxolan-2-yl)propyl)-5,5-dimethylcyclohex-1-enecarbaldehyde 
• 1321556-48-2 (R)-2-(3-(2-iodo-6,6-dimethylcyclohex-2-en-1-yl)propyl)-1,3-dioxolane 
• 1416352-41-4 (R)-tert-butyl 5-(1,3-dioxolan-2-yl)-2-(diphenylmethyleneamino)pentanoate 
• 1428872-55-2 (4R,4aR,6S,7S,8aS)-7-(benzyloxy)-4-[3-(1,3-dioxolan-2-yl)propyl]-6,4-(iminomethano)-2-(7-octenoyl)-9-(p-toluenesulfonyl)perhydroisoquinoline 
• 1428872-54-1 (4R,4aR,6S,7S,8aS)-7-(benzyloxy)-4-[3-(1,3-dioxolan-2-yl)propyl]-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline 

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