7252-83-7

Usage

Uses

Used in Pharmaceutical Synthesis:
Bromoacetaldehyde dimethyl acetal is used as a key intermediate in the synthesis of various antibiotics and other drugs. It is particularly useful in the production of erythromycin and cephalosporins, which are essential medications in the treatment of bacterial infections.
Used in Organic Chemistry:
Bromoacetaldehyde dimethyl acetal is used as a starting material in a variety of reactions to provide N-alkylated compounds, lactams, aldehydes, oximes, azides, and acyclic di-/polyselenides. Its reactivity and versatility make it a valuable component in organic chemistry.
Used in Synthesis of 2,3-O-acetal:
Bromoacetaldehyde dimethyl acetal is used as a reactant in the synthesis of 2,3-O-acetal via reaction with 2,3-diol in the presence of 10-camphorsulphonic acid (CSA). This reaction is crucial for the development of new chemical compounds and materials.
Used in Synthesis of Aldehyde Substituted Prodrugs:
Bromoacetaldehyde dimethyl acetal is used to react with 4-hydroxylbenzaldehyde, and the final aldehyde substituted prodrug is generated by TFA-mediated deacetalization. This process is essential for the development of new prodrugs with improved pharmacological properties and enhanced bioavailability.

Reference

Gotkowska, Joanna. "Bromoacetaldehyde Diethyl Acetal." Synlett26.15(2015):2185-2186.

InChI:InChI=1/C4H9BrO2/c1-6-4(3-5)7-2/h4H,3H2,1-2H3

Synthetic route

methanol (67-56-1) + vinyl acetate (108-05-4) → 1-bromo-2,2-dimethoxyethane (7252-83-7)

Conditions	Yield
With bromine at 20℃; Cooling;	77%
With bromine for 48h; Ambient temperature;	55%
With chloroform; bromine at -40℃;
With chloroform; bromine at -40℃;

methanol (67-56-1) + methoxyethene (107-25-5) → 1-bromo-2,2-dimethoxyethane (7252-83-7)

Conditions	Yield
With bromine at -60 - -50℃;

methanol (67-56-1) + 1,2-dibromoethyl ethyl ether (2983-26-8) → 1-bromo-2,2-dimethoxyethane (7252-83-7)

Conditions	Yield
With potassium hydroxide

vinyl acetate (108-05-4) → 1-bromo-2,2-dimethoxyethane (7252-83-7)

Conditions	Yield
With tetrachloromethane Bromierung und Eintragen des Reaktionsgemisches in Methanol unter Kuehlung;

1,1-dimethoxyethane (534-15-6) → 1-bromo-2,2-dimethoxyethane (7252-83-7)

Conditions	Yield
With bromine

paracetaldehyde (123-63-7) → 1-bromo-2,2-dimethoxyethane (7252-83-7)

Conditions	Yield
at -10 - -5℃; Bromieren und Behandeln des Reaktionsproduktes mit absol.Methylalkohol;

methanol (67-56-1) + methoxyethene (107-25-5) + bromine (7726-95-6) → 1-bromo-2,2-dimethoxyethane (7252-83-7)

Conditions	Yield
at -60 - -50℃;

1,2-dibromoethyl ethyl ether (2983-26-8) + methanolic KOH → 1-bromo-2,2-dimethoxyethane (7252-83-7)

1-bromo-2,2-dimethoxyethane (7252-83-7) + potassium phtalimide (1074-82-4) → 2-(2,2-dimethoxyethyl)-1H-isoindole-1,3(2H)-dione (27328-34-3)

Conditions	Yield
With acetamide; potassium iodide at 110 - 140℃; for 3.41667h;	100%
In N,N-dimethyl-formamide at 130 - 135℃; for 20h;	56%
With acetamide at 170℃;
With acetamide; potassium iodide at 130℃; for 5h;

chloraminophenamide (121-30-2) + 1-bromo-2,2-dimethoxyethane (7252-83-7) → 3-bromomethyl-6-chloro-1,1-dioxo-1,2,3,4-tetrahydro-1λ6-benzo[1,2,4]thiadiazine-7-sulfonic acid amide (7181-60-4)

Conditions	Yield
With hydrogen bromide In 1,4-dioxane; water at 100 - 120℃; for 0.333333h;	100%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 4-bromo-N-(3-bromo-4-hydroxyphenethyl)thiophene-2-carboxamide (1174651-00-3) → 4-bromo-N-(3-bromo-4-(2,2-dimethoxyethoxy)phenethyl)thiophene-2-carboxamide (1174651-01-4)

Conditions	Yield
With caesium carbonate; potassium iodide In N,N-dimethyl-formamide at 120℃; under 760.051 Torr; for 1h; Inert atmosphere; Microwave irradiation;	100%
With caesium carbonate; potassium iodide In N,N-dimethyl-formamide Reflux;	70%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2-(3,4-dimethoxyphenyl)-7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-8-methoxy-[1]benzopyrano[3,4-b]pyrrol-4(3H)-one → 3-(2,2-dimethoxyethyl)-2-(3,4-dimethoxyphenyl)-7-isopropoxy-1-(3-isopropoxy-4-methoxyphenyl)-8-methoxy-[1]benzopyrano[3,4-b]pyrrol-4(3H)-one

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 14h; Inert atmosphere;	100%

1-bromo-2,2-dimethoxyethane (7252-83-7) + tert-Butyl-((R)-4-[1,3]dithian-2-yl-2,2-dimethyl-pentyloxy)-diphenyl-silane (159751-66-3) → tert-Butyl-{(R)-4-[2-(2,2-dimethoxy-ethyl)-[1,3]dithian-2-yl]-2,2-dimethyl-pentyloxy}-diphenyl-silane (159751-67-4)

Conditions	Yield
With tert.-butyl lithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide	99%

1-bromo-2,2-dimethoxyethane (7252-83-7) + (3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide (128019-40-9, 149510-73-6, 136465-81-1) → N-tert-butyl-2-(2,2-dimethoxyethyl)decahydro-3-isoquinoline carboxamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Heating;	99%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2-amino-3,5-dibromopyrazine (24241-18-7) → 6,8-dibromoimidazo[1,2-a]pyrazine (63744-22-9)

Conditions	Yield
Stage #1: 1-bromo-2,2-dimethoxyethane; 2-amino-3,5-dibromopyrazine In water at 20℃; for 2h; Reflux; Stage #2: With sodium hydrogencarbonate In water for 0.25h;	99%
Stage #1: 1-bromo-2,2-dimethoxyethane; 2-amino-3,5-dibromopyrazine With hydrogen bromide In ethanol; water at 20℃; for 21h; Heating / reflux; Stage #2: With sodium carbonate In dichloromethane; water	95%
In water at 100℃; for 2h;	91%
Stage #1: 1-bromo-2,2-dimethoxyethane With hydrogen bromide In water at 120℃; for 1h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In water; isopropyl alcohol for 0.5h; Inert atmosphere; Stage #3: 2-amino-3,5-dibromopyrazine In water; isopropyl alcohol for 16h; Inert atmosphere; Reflux;	30 g
Stage #1: 1-bromo-2,2-dimethoxyethane With hydrogen bromide In water at 55℃; for 2h; Stage #2: 2-amino-3,5-dibromopyrazine In isopropyl alcohol at 78℃; for 16h;	12.0 g

1-bromo-2,2-dimethoxyethane (7252-83-7) + 3,4-methylenedioxyphenylethylamine (1484-85-1) → C13H19NO4 (1160948-79-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;	99%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → C13H18O6

Conditions	Yield
With caesium carbonate In acetonitrile for 40h; Reflux;	99%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 3-hydroxy-5-methoxy-benzoic acid methyl ester (19520-74-2) → C13H18O6

Conditions	Yield
With caesium carbonate In acetonitrile for 40h; Reflux;	99%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2-Iodophenol (533-58-4) → 1-(2,2-dimethoxyethoxy)-2-iodobenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Reflux;	99%

1-bromo-2,2-dimethoxyethane (7252-83-7) + triphenylphosphine (603-35-0) → 2-triphenylphosphoniumacetaldehyde dimethyl acetal bromide

Conditions	Yield
In acetonitrile at 60 - 65℃; for 3h; Solvent; Inert atmosphere; Green chemistry;	98.9%
In toluene at 120℃; for 24h;	54%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 4-bromo-2-hydroxyphenylthioamide → 5-bromo-2-(2-thiazolyl)phenol

Conditions	Yield
With toluene-4-sulfonic acid In ethanol; water at 100℃; for 12h;	98.2%

1-bromo-2,2-dimethoxyethane (7252-83-7) + thiophenol (108-98-5) → 2-(phenylthio)acetaldehyde dimethyl acetal (99172-76-6)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h;	98%
With 1-pentyl-3-methylimidazolium bromide at 25 - 30℃; for 0.2h;	95%
With sodium hydride In tetrahydrofuran at 0 - 20℃;	84%
With ethanol; sodium ethanolate; sodium iodide
With sodium hydroxide In methanol at 20℃; for 18h; Product distribution / selectivity; Inert atmosphere;

1-bromo-2,2-dimethoxyethane (7252-83-7) + phenylmethanethiol (100-53-8) → benzylmercaptoacetaldehyde dimethyl acetal (6304-94-5)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃;	98%
With ethanol; sodium ethanolate

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2-Naphthalenethiol (91-60-1) → [2]naphthylsulfanyl-acetaldehyde dimethylacetal

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃;	98%
With sodium ethanolate; sodium iodide

1-bromo-2,2-dimethoxyethane (7252-83-7) + benzylamine (100-46-9) → N-benzyl-2,2-dimethoxyethylamine (54879-88-8)

Conditions	Yield
at 80℃; for 18h; Inert atmosphere; sealed tube;	98%

1-bromo-2,2-dimethoxyethane (7252-83-7) + potassium (2-phenylethynyl)trifluoroborate → (4-bromo-3-methoxybut-1-ynyl)benzene (1201652-07-4)

Conditions	Yield
With boron trifluoride diethyl etherate In acetonitrile at 0 - 23℃; Inert atmosphere;	98%

1-bromo-2,2-dimethoxyethane (7252-83-7) + ethyl 3-(2-bromo-4,5-dimethoxyphenyl)-4,5-bis(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylate → C35H40BrNO10

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 16h; Schlenk technique; Sealed tube;	98%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 6-bromoguaiacol (28165-49-3) → 1-bromo-2-(2,2-dimethoxyethoxy)-3-methoxybenzene

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 8h;	98%
With caesium carbonate In N,N-dimethyl-formamide at 80℃;	98%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2‐bromo‐1‐fluoro‐3‐methoxybenzene (446-59-3) → 2-bromo-1-(2,2-dimethoxyethoxy)-3-methoxybenzene

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere;	98%

Thiophene-2-thiol (7774-74-5) + 1-bromo-2,2-dimethoxyethane (7252-83-7) → 2-(2,2-dimethoxy-ethylsulfanyl)-thiophene (98558-44-2)

Conditions	Yield
With potassium carbonate In acetone	97%
With ethanol; sodium ethanolate

1-bromo-2,2-dimethoxyethane (7252-83-7) + (1S,2R)-1,2-diphenylethane-1,2-diol (579-43-1) → 2ξ-bromomethyl-4r,5c-diphenyl-[1,3]dioxolane (5436-03-3, 138922-97-1, 138923-00-9)

Conditions	Yield
With Dowex-x8 (H+) resin	97%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 3,4-difluorophenol (2713-33-9) → 4-(2,2-Dimethoxyethoxy)-1,2-difluorobenzene (342435-26-1)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 120℃; for 4h;	97%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 3,4-dimethoxyphenol (2033-89-8) → C12H18O5

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 16h;	97%

1-bromo-2,2-dimethoxyethane (7252-83-7) + methyl 5-amino-6-bromopyrazine-2-carboxylate (1076198-49-6) → methyl 8-bromoimidazo[1,2-a]pyrazine-6-carboxylate

Conditions	Yield
In acetonitrile at 150℃; for 2h; Concentration; Microwave irradiation; Sealed tube;	97%
In acetonitrile at 150℃; for 2h; Microwave irradiation; Sealed tube;	9%

1-bromo-2,2-dimethoxyethane (7252-83-7) + isopropylamine (75-31-0) → 2-(isopropyl)acetaldehyde dimethyl acetal (60912-32-5)

Conditions	Yield
at 80℃; for 18h; Inert atmosphere; sealed tube;	96%
In neat (no solvent) at 80℃; Sealed tube;	92%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2,5-Dimethyl-1,4-benzenedithiol (104014-86-0) → 1,4-Bis(2,2-dimethoxyethylthio)-2,5-dimethylbenzene (104014-87-1)

Conditions	Yield
With sodium ethanolate In ethanol for 3h; Heating;	96%

6-hydroxyquinoline (580-16-5) + 1-bromo-2,2-dimethoxyethane (7252-83-7) → 6-(2,2-dimethoxyethoxy)quinoline (1029714-98-4)

Conditions	Yield
Stage #1: 6-hydroxyquinoline With sodium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 1-bromo-2,2-dimethoxyethane In tetrahydrofuran; N,N-dimethyl-formamide for 6h; Heating / reflux;	96%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 3-Trifluoromethylphenol (98-17-9) → C11H13F3O3 (1190883-14-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140 - 150℃;	96%

Upstream product

• 67-56-1 methanol 
• 107-25-5 methoxyethene 
• 108-05-4 vinyl acetate 
• 2983-26-8 1,2-dibromoethyl ethyl ether 
• 534-15-6 1,1-dimethoxyethane 
• 123-63-7 paracetaldehyde 
• 7726-95-6 bromine 

Downstream Products

• 274-76-0 imidazo[1,2-a]pyridine 
• 858816-12-3 (4-methoxy-phenylsulfanyl)-acetaldehyde dimethylacetal 
• 855242-32-9 1,3-bis-(2,2-dimethoxy-ethylsulfanyl)-benzene 
• 109845-99-0 1,4-bis-(2,2-dimethoxy-ethylsulfanyl)-benzene 
• 57860-49-8 3-methyl-1-(2,2-dimethoxy-ethyl-sulfanyl)-benzene 
• 103181-65-3 (2-methoxy-phenylsulfanyl)-acetaldehyde dimethylacetal 
• 859034-01-8 2-(2,2-dimethoxy-ethylsulfanyl)-benzoic acid 
• 858816-10-1 (3-methoxy-4-methyl-phenylsulfanyl)-acetaldehyde dimethylacetal 
• 860687-79-2 1-chloro-2,4-bis-(2,2-dimethoxy-ethylsulfanyl)-benzene 
• 24332-20-5 methoxyacetaldehyde dimethylacetal 
• 27328-34-3 2-(2,2-dimethoyxethyl)-1H-isoindole-1,3(2H)-dione 
• 85168-86-1 ethoxy-acetaldehyde dimethylacetal 
• 78102-16-6 bis-(2,2-dimethoxy-ethyl)-sulfane 
• 56548-04-0 bis(dimethoxyethyl)amine 

Relevant academic research and scientific papers

Synthesis of functionalized tetrahydro-1,3-diazepin-2-ones and 1-carbamoyl-1H-pyrroles via ring expansion and ring expansion/ring contraction of tetrahydropyrimidines

A general approach to 6-phenylthio-substituted 2,3,4,5-tetrahydro-1H-1,3- diazepin-2-ones based on the ring expansion reaction of 1,2,3,4- tetrahydropyrimidin-2-ones under the action of nucleophiles has been developed. The first step of the synthesis was preparation of N-[(2-benzoyloxy-1-tosyl) ethyl]urea by three-component condensation of 2-benzoyloxyethanal, urea and p-toluenesulfinic acid. Nucleophilic substitution of the tosyl group in the obtained sulfone with sodium enolates of α-phenylthioketones followed by cyclization-dehydration, and debenzoylation gave 4-hydroxymethyl-5-phenylthio-1, 2,3,4-tetrahydropyrimidin-2-ones which were transformed into the 4-mesyloxymethyl-derivatives. Treatment of the latter with nucleophilic reagents, such as NaCN, sodium diethyl malonate, PhSNa, MeONa, NaBH4, sodium succinimide, or potassium phthalimide, afforded the target multi-functionalized diazepinones. The obtained 6-phenylthio-diazepinones and their 6-tosyl-substituted analogues were converted into 3-substituted 1-carbamoyl-1H-pyrroles under acidic conditions as a result of ring contraction. Effective one-pot synthesis of the latter from 4-mesyloxymethyl-pyrimidines was realized using a ring expansion/ring contraction sequence.

Scavenger assisted combinatorial process for preparing libraries of tertiary amine compounds

This invention relates to a novel solution phase process for the preparation of tertiary amine combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.