36255-44-4

Basic information

• Product Name: 3-BROMOPROPIONALDEHYDE DIMETHYL ACETAL
• Synonyms: 1-BROMO-3,3-DIMETHOXYPROPANE;3-BROMO-1,1-DIMETHOXYPROPANE;3-BROMOPROPIONALDEHYDE DIMETHYL ACETAL;Propane, 3-bromo-1,1-dimethoxy-;3-BROMOPROPIONALDEHYDE DIMETHYL ACETAL, TECH., 90%;3-BROMOPROPIONALDEHYDE DIMETHYL ACETAL (STABILIZED WITH K2CO3) 98+%;1,1-Dimethoxy-3-bromopropane;3-Bromopropanal dimethyl acetal
• CAS NO: 36255-44-4
• Molecular Formula: C₅H₁₁BrO₂
• Molecular Weight: 183.04
• EINECS: 252-936-6
• Product Categories: Acetals/Ketals/Ortho Esters;Organic Building Blocks;Oxygen Compounds;Acetals/Ketals/Ortho Esters;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 36255-44-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 58-60 °C17 mm Hg(lit.)
• Flash Point: 114 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.341 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.54mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: Refrigerator
• Water Solubility: Not miscible or difficult to mix with water.
• BRN: 1697640
• CAS DataBase Reference: 3-BROMOPROPIONALDEHYDE DIMETHYL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMOPROPIONALDEHYDE DIMETHYL ACETAL(36255-44-4)
• EPA Substance Registry System: 3-BROMOPROPIONALDEHYDE DIMETHYL ACETAL(36255-44-4)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 36255-44-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear pale yellow liquid

Uses

3-Bromopropionaldehyde dimethyl acetal was used in the synthesis of spiro cyclobutanones.

InChI:InChI=1/C5H11BrO2/c1-7-5(8-2)3-4-6/h5H,3-4H2,1-2H3

Synthetic route

methanol (67-56-1) + 1,3-dibromo-1-methoxypropane (59635-13-1) → 3-bromopropanal dimethyl acetal (36255-44-4)

Conditions	Yield
for 2h;	70%

methanol (67-56-1) + acrolein (107-02-8) → 3-bromopropanal dimethyl acetal (36255-44-4)

Conditions	Yield
With hydrogen bromide 1.) 0 deg C, 2.) 25 deg C;	70%
With hydrogen bromide In dichloromethane

3,3-dimethoxyprop-1-ene (6044-68-4) → 3-bromopropanal dimethyl acetal (36255-44-4)

Conditions	Yield
With chloro-trimethyl-silane; 4 A molecular sieve; sodium bromide In acetonitrile at 22℃; for 1.5h;	63%

acrolein (107-02-8) + trimethyl orthoformate (149-73-5) → 3-bromopropanal dimethyl acetal (36255-44-4)

Conditions	Yield
With hydrogen bromide

methanol (67-56-1) + hydrogen bromide (10035-10-6, 12258-64-9) + acrolein (107-02-8) → 3-bromopropanal dimethyl acetal (36255-44-4) + 1,3-dibromo-1-methoxypropane (59635-13-1) + 1,1,3-trimethoxypropane (14315-97-0)

Conditions	Yield
at -10℃;

methanol (67-56-1) + acrolein (107-02-8) → 3-bromopropanal dimethyl acetal (36255-44-4) + 1.1.3-trimethoxy-propane; 1.3-dibromo-1-methoxy-propane

Conditions	Yield
With hydrogen bromide at -10℃;

3-bromopropanal (65032-54-4) + trimethyl orthoformate (149-73-5) → 3-bromopropanal dimethyl acetal (36255-44-4)

Conditions	Yield
In methanol

3-bromopropanal dimethyl acetal (36255-44-4) + 6-chloro-N-methoxy-N-methylpyridine-3-carboxamide (149281-42-5) → 6-chloro-3-(4,4-dimethoxy-1-oxobutyl)pyridine (421557-61-1)

Conditions	Yield
Stage #1: 3-bromopropanal dimethyl acetal With magnesium In tetrahydrofuran at 20℃; for 1h; Stage #2: 6-chloro-N-methoxy-N-methylpyridine-3-carboxamide In tetrahydrofuran at -78 - 20℃;	100%

3-bromopropanal dimethyl acetal (36255-44-4) + thioacetic acid (507-09-5) → S-3,3-dimethoxypropyl ethanethioate (128352-00-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at -10 - 20℃; Inert atmosphere;	100%

3-bromopropanal dimethyl acetal (36255-44-4) + benzyl 6-methoxy-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylate → benzyl 4-(3,3-dimethoxypropyl)-6-methoxy-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylate

Conditions	Yield
Stage #1: benzyl 6-methoxy-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylate With sodium hydride; lithium bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling with ice; Stage #2: 3-bromopropanal dimethyl acetal In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling with ice;	100%

3-bromopropanal dimethyl acetal (36255-44-4) → 3-azidopropanal dimethyl acetal

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 90℃; for 24h;	100%

4-chloro-1H-indole (25235-85-2) + 3-bromopropanal dimethyl acetal (36255-44-4) → 4-chloro-1-(3,3-dimethoxypropyl)-1H-indole

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 50℃; for 5h;	99%

3-bromopropanal dimethyl acetal (36255-44-4) + C25H42N2O5Si (1186197-62-5) → C30H52N2O6Si

Conditions	Yield
Stage #1: 3-bromopropanal dimethyl acetal With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: C25H42N2O5Si With lithium chloride In tetrahydrofuran at -60℃; for 16h; Inert atmosphere;	96%

3-bromopropanal dimethyl acetal (36255-44-4) + methyl 4-formylbenzoate (1571-08-0) → methyl 4-(4,4-dimethoxy-1-butenyl)benzoate

Conditions	Yield
Stage #1: 3-bromopropanal dimethyl acetal With triphenylphosphine In tetrahydrofuran at 25℃; for 2h; Stage #2: With potassium tert-butylate In tetrahydrofuran at 5 - 20℃; for 2h; Stage #3: methyl 4-formylbenzoate In tetrahydrofuran at 20℃; for 5h;	96%

3-bromopropanal dimethyl acetal (36255-44-4) + tert-butyl 2-iodophenylcarbamate (161117-84-6) → tert-butyl (3,3-dimethoxypropyl)(2-iodophenyl)carbamate

Conditions	Yield
Stage #1: tert-butyl 2-iodophenylcarbamate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 3-bromopropanal dimethyl acetal In N,N-dimethyl-formamide; mineral oil at 20℃; for 26h; Inert atmosphere;	96%

3-bromopropanal dimethyl acetal (36255-44-4) + <2-<(phenylthio)methyl>allyl>trimethylsilane (116279-69-7) → (6-Bromo-4-methoxy-2-methylene-hexylsulfanyl)-benzene (133620-92-5)

Conditions	Yield
titanium tetrachloride In dichloromethane at -78 - 0℃; other substrates;	95%
titanium tetrachloride In dichloromethane at -78 - 0℃;	95%
With titanium tetrachloride	95%

3-bromopropanal dimethyl acetal (36255-44-4) + vanillin (121-33-5) → 4-(3,3-dimethoxy-propoxy)-3-methoxy-benzaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h;	95%

3-bromopropanal dimethyl acetal (36255-44-4) → 3-bromopropanal (65032-54-4)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 25℃; for 4h;	95%

3-bromopropanal dimethyl acetal (36255-44-4) + 4-(trans-4-n-propylcyclohexyl)cyclohexanone (82832-73-3) → trans-4-[2-(1,3)dioxolan-2-yl-ethyl]-4'-propyl-dicyclohexyl-4-ol

Conditions	Yield
Stage #1: 3-bromopropanal dimethyl acetal With magnesium In tetrahydrofuran at 20 - 30℃; for 1h; Stage #2: 4-(trans-4-n-propylcyclohexyl)cyclohexanone In tetrahydrofuran for 2h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	93.5%

3-bromopropanal dimethyl acetal (36255-44-4) + allenyltributylstannane (53915-69-8) → 6-bromo-4-methoxyhex-1-yne (952110-92-8)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 3h;	93%

(2S,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide (904893-22-7) + 3-bromopropanal dimethyl acetal (36255-44-4) → (2S,3S,4S,5S)-1-hydroxyl-3,4-bis-(benzyloxy)-2-((benzyloxy)methyl)-5-(3,3-dimethoxypropyl)pyrrolidine (1231217-52-9)

Conditions	Yield
Stage #1: 3-bromopropanal dimethyl acetal With magnesium In tetrahydrofuran Heating; Stage #2: (2S,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide In tetrahydrofuran at 0℃;	92%
Stage #1: 3-bromopropanal dimethyl acetal With magnesium In tetrahydrofuran Stage #2: (2S,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole-1-oxide In tetrahydrofuran at 0℃; for 0.5h;	92%

3-bromopropanal dimethyl acetal (36255-44-4) + methyl 1H-indole-7-carboxylate (93247-78-0) → methyl 1-(3,3-dimethoxypropyl)-1H-indole-7-carboxylate (1262419-90-8)

Conditions	Yield
Stage #1: methyl 1H-indole-7-carboxylate With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 3-bromopropanal dimethyl acetal With potassium iodide In dimethyl sulfoxide for 15h;	92%

3-bromopropanal dimethyl acetal (36255-44-4) + (1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide (172016-00-1) → (1S,2R)-1-phenyl-2-[(S)-1-hydroxy-4,4-dimethoxybutyl]-N,N-diethylcyclopropanecarboxamide (473775-16-5)

Conditions	Yield
Stage #1: 3-bromopropanal dimethyl acetal With iodine; magnesium In tetrahydrofuran at 20℃; for 2h; Stage #2: (1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide In tetrahydrofuran at -15℃; for 2.5h; Grignard reaction; Further stages.;	91%

3-bromopropanal dimethyl acetal (36255-44-4) + (3R)-3-hydroxy-N-methoxy-N-methylbutanamide (379669-02-0) → (R)-6-hydroxy-1,1-dimethoxyheptan-4-one (379669-03-1)

Conditions	Yield
Stage #1: 3-bromopropanal dimethyl acetal With iodine; magnesium In tetrahydrofuran for 1h; Stage #2: (3R)-3-hydroxy-N-methoxy-N-methylbutyramide In tetrahydrofuran at 0 - 20℃; for 1.5h;	91%

3-bromopropanal dimethyl acetal (36255-44-4) + 5-iodo-3-benzoyl-1,3-dihydropyrimidine-2,4-dione (161263-60-1) → 3-benzoyl-(3,3-dimethoxy-propyl)-5-iodo-1H-pyrimidine-2,4-dione

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	91%

3-bromopropanal dimethyl acetal (36255-44-4) + 2-(methylsulfonyl)-10H-phenothiazine (23503-68-6) → C18H21NO4S2

Conditions	Yield
With potassium hydroxide In acetone at 50℃; for 3h;	91%

3-bromopropanal dimethyl acetal (36255-44-4) + 6-cyano-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline → 6-(furan-2-yl)-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline

Conditions	Yield
Stage #1: 3-bromopropanal dimethyl acetal With iodine; magnesium In tetrahydrofuran; ethylene dibromide at 30 - 45℃; Stage #2: 6-cyano-4-[3-chloro-4-(3-fluorobenzyloxy)phenyl]aminoquinazoline In tetrahydrofuran; ethylene dibromide at 10 - 30℃; for 5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethylene dibromide at 50 - 55℃; for 4h;	88.9%

3-bromopropanal dimethyl acetal (36255-44-4) + N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide (14316-14-4) → 3-propanal dimethyl acetal (173602-05-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) room temperature, 1 h, 2.) 70 deg C, 15 h;	88%

propyl cyanide (109-74-0) + 3-bromopropanal dimethyl acetal (36255-44-4) → C9H17NO2 (1582321-73-0)

Conditions	Yield
Stage #1: propyl cyanide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 3-bromopropanal dimethyl acetal In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;	88%

3-bromopropanal dimethyl acetal (36255-44-4) + (6-Bromo-2-oxo-1,2-dihydro-pyridin-4-yl)-acetic acid methyl ester (141807-52-5) → 6-Bromo-4-methoxycarbonylmethyl-2-pyridyl 3,3-dimethoxypropyl ether

Conditions	Yield
With potassium carbonate In acetonitrile for 6h; Heating;	87%

3-bromopropanal dimethyl acetal (36255-44-4) + 5-(4-methyl-1,3-thiazol-2-yl)-3-(phenylcarbonyl)-2,4(1H,3H)-pyrimidinedione (1138450-75-5) → 1-[3,3-bis(methyloxy)propyl]-5-(4-methyl-1,3-thiazol-2-yl)-3-(phenylcarbonyl)-2,4(1H,3H)-pyrimidinedione (1138450-76-6)

Conditions	Yield
With potassium carbonate; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃;	87%

3-bromopropanal dimethyl acetal (36255-44-4) + sodium cyanide (143-33-9) → 4,4-dimethoxybutanenitrile (14618-78-1)

Conditions	Yield
With tributyl-amine In water for 2h; Heating;	86%

3-bromopropanal dimethyl acetal (36255-44-4) + 8-benzyloxy-5-bromo-6-(tert-butyloxycarbonylamino)quinoline (1098620-18-8) → 8-benzyloxy-5-bromo-6-[N-(tert-butyloxycarbonyl)-N-(3,3-dimethoxypropyl)amino]quinoline (1098620-19-9)

Conditions	Yield
Stage #1: 8-benzyloxy-5-bromo-6-(tert-butyloxycarbonylamino)quinoline With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.583333h; Inert atmosphere; Cooling; Stage #2: 3-bromopropanal dimethyl acetal In N,N-dimethyl-formamide at 20℃; for 68h; Inert atmosphere;	86%

3-bromopropanal dimethyl acetal (36255-44-4) + 3',5'-O-bis(tert-butyldimethylsilyl)-N2-dimethylaminomethylene-2'-deoxyguanosine → 3',5'-O-bis(tert-butyldimethylsilyl)-1-(3,3-dimethoxypropyl)-N2-dimethylaminomethylene-2'-deoxyguanosine

Conditions	Yield
Stage #1: 3',5'-O-bis(tert-butyldimethylsilyl)-N2-dimethylaminomethylene-2'-deoxyguanosine With caesium carbonate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 3-bromopropanal dimethyl acetal In tetrahydrofuran at 70℃;	85%

3-bromopropanal dimethyl acetal (36255-44-4) + (1-Oxopropyl)methyldiphenylsilane dimethylhydrazone (1025874-29-6) → (5,5-Dimethoxy-2-methyl-1-oxopentyl)methyldiphenylsilane dimethylhydrazone

Conditions	Yield
With lithium diisopropyl amide 1.) THF, 0 deg C, 2 h; HMPA, 0 deg C, 10 min, 2.) -78 deg C, 2 h;	83%

3-bromopropanal dimethyl acetal (36255-44-4) + 8-benzyloxy-6-(tert-butyloxycarbonylamino)-5-iodoquinoline (444564-97-0) → 8-benzyloxy-6-[N-(tert-butyloxycarbonyl)-N-(3,3-dimethoxypropyl)amino]-5-iodoquinoline (444564-98-1)

Conditions	Yield
Stage #1: 8-benzyloxy-6-(tert-butyloxycarbonylamino)-5-iodoquinoline With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3-bromopropanal dimethyl acetal In N,N-dimethyl-formamide at 20℃; for 22h; Inert atmosphere;	83%

3-bromopropanal dimethyl acetal (36255-44-4) + 3β-hydroxy-14β-hydrogen-15β,16β-methanoisoandrost-5-en-17-one (1093661-36-9) → 14β-hydrogen-17α-(3′,3′-dimethoxy-1-propanyl)-15β,16β-methano-isoandrostane-3β,17β-diol (1093661-37-0)

Conditions	Yield
Stage #1: 3-bromopropanal dimethyl acetal With iodine; magnesium In tetrahydrofuran for 4h; Inert atmosphere; Stage #2: 3β-hydroxy-14β-hydrogen-15β,16β-methanoisoandrost-5-en-17-one In tetrahydrofuran at 20℃; Inert atmosphere;	83%

Upstream product

• 107-02-8 acrolein 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 59635-13-1 1,3-dibromo-1-methoxypropane 
• 65032-54-4 3-bromopropanal 
• 10035-10-6 hydrogen bromide 
• 6044-68-4 3,3-dimethoxyprop-1-ene 

Downstream Products

• 99167-50-7 (3,3-dimethoxy-propyl)-[2]pyridyl-amine 
• 192311-04-9 2-(3,3-dimethoxypropyl)cyclohexanone 
• 473775-16-5 (1S,2R)-1-phenyl-2-[(S)-1-hydroxy-4,4-dimethoxybutyl]-N,N-diethylcyclopropanecarboxamide 
• 1231217-52-9 (2S,3S,4S,5S)-1-hydroxyl-3,4-bis-(benzyloxy)-2-((benzyloxy)methyl)-5-(3,3-dimethoxypropyl)pyrrolidine 
• 937047-87-5 (R)-3-(4.4-dimethoxybutyryl)-piperidine-1-carboxylic acid benzyl ester 
• 4454-02-8 1,1,5,5-tetramethoxy-pentane 
• 54286-89-4 1,1,6,6-tetramethoxyhexane 
• 27098-65-3 3-phenylsulfanyl-propionaldehyde 

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