2032-35-1

Basic information

• Product Name: Bromoacetaldehyde diethyl acetal
• Synonyms: 2,2-DIETHOXYETHYL BROMIDE;2-BROMO-1,1-DIETHOXYETHANE;1,1-DIETHOXY-2-BROMOETHANE;BADEA;BROMO ACETYL DIACETAL;BROMOACETAL;BROMOACETALDEHYDE DIETHYL ACETAL;1-Bromo-2,2-diethoxyethane
• CAS NO: 2032-35-1
• Molecular Formula: C₆H₁₃BrO₂
• Molecular Weight: 197.07
• EINECS: 217-989-1
• Product Categories: Pharmaceutical Intermediates;Aromatic Aldehydes & Derivatives (substituted);Aliphatics;Miscellaneous Reagents;Acetals/Ketals/Ortho Esters;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 2032-35-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 66-67 °C18 mm Hg(lit.)
• Flash Point: 125 °F
• Appearance: colorless to light yellow liquid
• Density: 1.31 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.599mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: immiscible
• Sensitive: Moisture Sensitive
• BRN: 635754
• CAS DataBase Reference: Bromoacetaldehyde diethyl acetal(CAS DataBase Reference)
• NIST Chemistry Reference: Bromoacetaldehyde diethyl acetal(2032-35-1)
• EPA Substance Registry System: Bromoacetaldehyde diethyl acetal(2032-35-1)

Safety Data

• Hazard Codes: Xi,T
• Statements: 10-36-36/38-23-22
• Safety Statements: 16-26-45-38-37/39-28A-36/37
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 8-9-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2032-35-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Different sources of media describe the Uses of 2032-35-1 differently. You can refer to the following data:
1. Synthetic building block1,2
2. Bromoacetaldehyde diethyl acetal, is used as a synthetic building block. It is mainly used for synthesis of antibiotics such as erythromycin and cephalosporins and to other drugs. It also can be used as pharmaceutical intermediates. Besides, this chemical can be used to pruduce drugs such as methylthio imidazole, chlorpheniramine and others for thyroid. It also acts as a Useful intermediate for the preparation of other ?-heterosubstituted acetaldehyde acetals.

Preparation

To a flask containing 118.0 gm (1.0 mole) of diethyl acetal and 55 gm (0.55 mole) of calcium carbonate is dropwise added 55 ml (1.0 mole) of bromine over a 30-45 min period while keeping the reaction temperature at 5°-10°C. The reaction mixture is allowed to stand 24 hr, steam is introduced to dissolve the salts, the oil separated, dried over potassium carbonate, and distilled to afford 61-83 gm (31-42%), b.p. 167°-170°C. The product is further purified by shaking with potassium carbonate and distilling it under reduced pressure, b.p. 48°-49°C (3 mm Hg). The pure acetal is unstable and becomes colored in a few hours and black after several days. However, the crude acetal boiling at 167°-170°C is stable for several months.

General Description

May darken in storage

InChI:InChI=1/C6H13BrO2/c1-3-8-6(5-7)9-4-2/h6H,3-5H2,1-2H3

Synthetic route

diethyl acetal (105-57-7) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
With bromine; calcium carbonate 1.) 1 h, 10 deg C; 2.) room temp., 14 h;	60.9%
With bromine; calcium carbonate	51.8%
With bromine

2,4-bis-bromomethyl-6-methyl-[1,3,5]trioxane + ethanol (64-17-5) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
beim Umkrystallisieren;

vinyl acetate (108-05-4) + ethanol (64-17-5) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
With bromine at -10℃;
With bromine at 5 - 30℃; for 10h; Inert atmosphere; Large scale;
With bromine at -10℃;

vinyl acetate (108-05-4) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
With tetrachloromethane; bromine Eintragen des Reaktionsgemisches in Aethanol unter Kuehlung;
In tetrachloromethane; ethanol; water

ethanol (64-17-5) + 2,2,3,4-tetrabromo-butyraldehyde → ethyl bromide (74-96-4) + ethyl bromoacetate (105-36-2) + Bromoacetaldehyde diethyl acetal (2032-35-1) + bromoacetaldehyde (17157-48-1)

α-Chloro-β-bromoethyl ethyl ether (89125-30-4) + sodium ethanolate (141-52-6) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
at 0℃;

α-Chloro-β-bromoethyl ethyl ether (89125-30-4) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
With sodium ethanolate at 0℃;

1,2-dibromoethyl ethyl ether (2983-26-8) + sodium ethanolate (141-52-6) → Bromoacetaldehyde diethyl acetal (2032-35-1)

1,2-dibromoethyl ethyl ether (2983-26-8) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
With potassium hydroxide

ethyl vinyl ether (109-92-2) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
With tetrachloromethane; N-Bromosuccinimide Behandeln des Reaktionsprodukts mit Aethanol;

ethanol (64-17-5) + paracetaldehyde (123-63-7) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
With bromine

paracetaldehyde (123-63-7) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
at -10 - -5℃; Man bromiert, behandelt die Reaktionsfluessigkeit mit ueberschuessigem absol.Alkohol und giesst nach Stehen auf Eis;
With diethyl ether; dihydrogen peroxide; bromine am Licht und Behandeln des Reaktionsprodukts mit Aethanol;

ethanol (64-17-5) + ethyl vinyl ether (109-92-2) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
With tert-butyl hypobromite
With N-Bromosuccinimide at 20℃; for 2h;	180 g

1,2-dibromoethyl ethyl ether (2983-26-8) → ethyl bromide (74-96-4) + ethanol (64-17-5) + (Z)-1-bromo-2-ethoxyethene (23521-49-5) + (E)-1-bromo-2-ethoxyethene (16339-88-1) + Bromoacetaldehyde diethyl acetal (2032-35-1) + 1-ethoxyacetylene (927-80-0)

Conditions	Yield
With N,N-diethylaniline at 98℃; for 2.5h; Product distribution; other bases, var. conditions;

2-methyl-4.6-bis-bromomethyl-1.3.5-trioxane → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
With ethanol

diethyl acetal (105-57-7) + bromine (7726-95-6) → Bromoacetaldehyde diethyl acetal (2032-35-1)

Conditions	Yield
at 40 - 50℃;

p-cresol (106-44-5) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-(2,2-diethoxyethoxy)-4-methylbenzene (66614-56-0)

Conditions	Yield
Stage #1: p-cresol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: Bromoacetaldehyde diethyl acetal In N,N-dimethyl-formamide; mineral oil Reflux;	100%
Stage #1: p-cresol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: Bromoacetaldehyde diethyl acetal In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere;	98%
With potassium hydroxide In N,N-dimethyl acetamide at 20℃; Heating;	96%

Isobutyronitrile (78-82-0) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 2,2-dimethyl-4,4-diethoxybutyronitrile (18240-74-9)

Conditions	Yield
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -68℃; for 1.66667h; Stage #2: Isobutyronitrile In tetrahydrofuran; hexane at -70℃; for 2h; Stage #3: Bromoacetaldehyde diethyl acetal With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone more than 3 stages;	100%
Stage #1: Isobutyronitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran at -20 - 20℃; Reflux;	89%
With lithium diisopropyl amide In N,N,N,N,N,N-hexamethylphosphoric triamide	88%

3-Bromothiophenol (6320-01-0) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-bromo-3-(2,2-diethoxy-ethylsulfanyl)benzene (17347-29-4)

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 120h;	100%
With potassium carbonate In acetone for 2h;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	94%

3-methoxybenzenethiol (15570-12-4) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-[(2,2-diethoxyethyl)sulfanyl]-3-methoxybenzene (96803-85-9)

Conditions	Yield
Stage #1: 3-methoxybenzenethiol With potassium carbonate In acetonitrile at 20℃; Stage #2: Bromoacetaldehyde diethyl acetal In acetonitrile for 15h;	100%
With potassium carbonate In acetone at 20℃; for 3h;	100%
With potassium carbonate In acetone at 20℃; for 3h;	100%

Bromoacetaldehyde diethyl acetal (2032-35-1) → bromoacetaldehyde (17157-48-1)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 25℃; for 6h;	100%
With trifluoroacetic acid In dichloromethane at 20℃; for 6h;	100%
With trifluoroacetic acid In neat (no solvent) at 20℃; for 12h; Inert atmosphere;	55%

4-bromo-phenol (106-41-2) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-bromo-4-(2,2-diethoxyethoxy)benzene (112598-18-2)

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) under a nitrogen atmosphere; Heating / reflux;	100%
Stage #1: 4-bromo-phenol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.333333h; Stage #2: Bromoacetaldehyde diethyl acetal In DMF (N,N-dimethyl-formamide) Heating / reflux;	100%
Stage #1: 4-bromo-phenol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.333333h; Stage #2: Bromoacetaldehyde diethyl acetal In DMF (N,N-dimethyl-formamide) Heating / reflux;	100%

3-Bromophenol (591-20-8) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 2-(3-bromophenoxy)acetaldehyde diethyl acetal (204452-94-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 120℃; Cooling with ice;	100%
Stage #1: 3-Bromophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Stage #2: Bromoacetaldehyde diethyl acetal In N,N-dimethyl-formamide; mineral oil at 10 - 120℃; for 6h;	99%
Stage #1: 3-Bromophenol With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: Bromoacetaldehyde diethyl acetal In N,N-dimethyl-formamide at 90℃;	95%

Bromoacetaldehyde diethyl acetal (2032-35-1) + 2-bromo-5-fluorophenol (147460-41-1) → 1-bromo-2-(2,2-diethoxyethoxy)-4-fluorobenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 95℃; for 8h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 135℃; for 7h;	98%
With potassium carbonate In N,N-dimethyl-formamide at 135℃; for 7h;	98%

Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-bromo-4-(2,2-diethoxyethoxy)benzene (112598-18-2)

Conditions	Yield
Stage #1: 4-bromo-phenol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.333333h; Stage #2: Bromoacetaldehyde diethyl acetal In DMF (N,N-dimethyl-formamide) Heating / reflux;	100%
Stage #1: 4-bromo-phenol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.333333h; Stage #2: Bromoacetaldehyde diethyl acetal In DMF (N,N-dimethyl-formamide) Heating / reflux;	100%

2-hydroxybromobenzene (95-56-7) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-bromo-2-(2,2-diethoxyethoxy)benzene (253429-15-1)

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide at 100℃; for 6h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 3h; Inert atmosphere;	93%

N-[5-(benzyloxy)-1H-indazol-3-yl]thiourea (943247-55-0) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 5-(benzyloxy)-N-1,3-thiazol-2-yl-1H-indazol-3-amine (943247-57-2)

Conditions	Yield
In ethanol; water at 20 - 80℃; for 4h;	100%

2-chlorothiphenol (6320-03-2) + Bromoacetaldehyde diethyl acetal (2032-35-1) → (2-chlorophenyl)(2,2-diethoxyethyl)sulfane (936902-05-5)

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating / reflux;	100%
With potassium carbonate In acetone for 3.5h; Reflux;	97%
With potassium carbonate at 40℃; for 2h; Sonication;

2-amino-3,5-dibromopyrazine (24241-18-7) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 6,8-dibromoimidazo[1,2-a]pyrazine (63744-22-9)

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 19h; Reflux;	100%
Stage #1: Bromoacetaldehyde diethyl acetal With hydrogen bromide In water for 2h; Reflux; Stage #2: 2-amino-3,5-dibromopyrazine In isopropyl alcohol for 16h; Reflux;	94%
In tetrahydrofuran; water at 120℃; for 16h;	76%

Bromoacetaldehyde diethyl acetal (2032-35-1) + 5-chlorosalicyclaldehyde (635-93-8) → (4-chloro-2-formylphenoxy)acetaldehyde diethylacetal (1254062-19-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 165℃; for 6h;	100%
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux;	90%
With potassium carbonate In N,N-dimethyl-formamide Reflux;	38%

2,6-diamino-3H-pyrimidin-4-one (100643-27-4, 143504-99-8) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (7355-55-7)

Conditions	Yield
Stage #1: Bromoacetaldehyde diethyl acetal With hydrogenchloride In water at 90℃; for 0.5h; Stage #2: 2,6-diamino-3H-pyrimidin-4-one With sodium acetate In water at 0 - 80℃; for 3.5h;	100%
Stage #1: Bromoacetaldehyde diethyl acetal With hydrogenchloride In water at 90℃; for 0.5h; Stage #2: With sodium acetate In water at 20℃; Stage #3: 2,6-diamino-3H-pyrimidin-4-one In water at 80℃; for 2h;	74%
Stage #1: 2,6-diamino-3H-pyrimidin-4-one; Bromoacetaldehyde diethyl acetal With hydrogenchloride In water at 90℃; for 0.5h; Stage #2: With sodium acetate In water at 0 - 80℃; for 3.5h;	74%
Stage #1: Bromoacetaldehyde diethyl acetal With hydrogenchloride In water at 90℃; for 0.5h; Stage #2: 2,6-diamino-3H-pyrimidin-4-one With sodium acetate In water at 80℃; for 2h;	74%
Stage #1: Bromoacetaldehyde diethyl acetal With hydrogenchloride In water at 90℃; for 0.5h; Stage #2: 2,6-diamino-3H-pyrimidin-4-one With sodium acetate In water at 80℃; for 2h;	42%

4-chloro-3-fluorophenol (348-60-7) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-chloro-4-(2,2-diethoxyethoxy)-2-fluorobenzene (1308669-82-0)

Conditions	Yield
With potassium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 16h;	100%

homoalylic alcohol (627-27-0) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 4-(2,2-diethoxyethoxy)but-1-ene (1343915-25-2)

Conditions	Yield
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran; mineral oil at 0 - 68℃; for 66h; Inert atmosphere;	100%
Stage #1: homoalylic alcohol With sodium hydride In water at 0℃; for 1h; Stage #2: Bromoacetaldehyde diethyl acetal In water at 0 - 80℃; for 24h; Temperature;	100%
Stage #1: homoalylic alcohol In tetrahydrofuran at 0℃; for 1h; Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran at 70℃; for 48h; Temperature;	96.3%
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran; mineral oil at 0 - 68℃; for 66h;	77 g

Bromoacetaldehyde diethyl acetal (2032-35-1) + 4,4-difluoropiperidine hydrochloride → 1-(2,2-diethoxyethyl)-4,4-difluoropiperidine (1432664-77-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 100℃; for 24h;	100%

6-bromopyridazin-3-amine (88497-27-2) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 6-bromoimidazo[1,2-b]pyridazine (1159977-65-7)

Conditions	Yield
In ethanol; water at 80℃; for 16h;	100%

4-bromo-3-fluorophenol (121219-03-2) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-bromo-4-(2,2-diethoxyethoxy)-2-fluorobenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 135℃; for 7h;	100%
With caesium carbonate In N,N-dimethyl-formamide at 85℃; for 3h;

4,4'-Dihydroxybiphenyl (92-88-6) + Bromoacetaldehyde diethyl acetal (2032-35-1) → C24H34O6

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide for 5h; Reflux;	100%

Bromoacetaldehyde diethyl acetal (2032-35-1) + 5-Bromo-2-fluorophenol (112204-58-7) → 4-bromo-2-(2,2-diethoxyethoxy)-1-fluorobenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 95℃; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 135℃; for 7h;
With potassium carbonate In N,N-dimethyl-formamide at 135℃; for 7h;

5-nitro-N-(3-(trifluoromethoxy)benzyl)-1H-imidazole-2-carboxamide + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-(2,2-diethoxyethyl)-4-nitro-N-(3-(trifluoromethoxy)benzyl)-1H-imidazole-2-carboxamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 1h; Microwave irradiation;	100%

N-(1-(4-fluorophenyl)ethyl)-5-nitro-1H-imidazole-2-carboxamide + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-(2,2-diethoxyethyl)-N-(1-(4-fluorophenyl)ethyl)-4-nitro-1Himidazole-2-carboxamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 1h; Microwave irradiation;	100%

N-(4-methylphenethyl)-5-nitro-1H-imidazole-2-carboxamide + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-(2,2-diethoxyethyl)-N-(4-methylphenethyl)-4-nitro-1H-imidazole-2-carboxamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 1h; Microwave irradiation;	100%

phenylmethanethiol (100-53-8) + Bromoacetaldehyde diethyl acetal (2032-35-1) → [(2,2-diethoxyethyl)sulfanylmethyl]benzene (91905-68-9)

Conditions	Yield
Stage #1: phenylmethanethiol With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran for 4h; Heating;	99%
Stage #1: phenylmethanethiol With sodium alkoxide Stage #2: Bromoacetaldehyde diethyl acetal at 70℃; for 3h;	92%
With sodium hydride In various solvent(s) 1.) 0 deg C, 30 min, 2.) r.t., 18 h;	85%
With sodium hydride In tetrahydrofuran reflux, 3 h then r.t., overnight;	67%

para-nitrobenzenethiol (1849-36-1) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-[(2,2-diethoxyethyl)sulfanyl]-4-nitrobenzene (81146-79-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux;	99%
With ethanol; sodium ethanolate

para-bromobenzenethiol (106-53-6) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 1-bromo-4-[(2,2-diethoxyethyl)sulfanyl]benzene (96804-05-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	99%
With potassium carbonate In acetone at 20℃; for 15h;	91%
	82%

Hexanethiol (111-31-9) + thiophenol (108-98-5) + Bromoacetaldehyde diethyl acetal (2032-35-1) → hexylmercaptoacetaldehyde diethyl acetal (249906-56-7)

Conditions	Yield
Stage #1: Hexanethiol; thiophenol With sodium hydride In tetrahydrofuran for 2h; Metallation; Heating; Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran for 48h; Condensation; Heating;	99%

Bromoacetaldehyde diethyl acetal (2032-35-1) → 1,1-diethoxy-2-ethylsulfanyl-ethane (77113-06-5)

Conditions	Yield
With sodium; ethanethiol In ethanol	99%

Upstream product

• 105-57-7 diethyl acetal 
• 7726-95-6 bromine 
• 2983-26-8 1,2-dibromoethyl ethyl ether 
• 64-17-5 ethanol 
• 109-92-2 ethyl vinyl ether 
• 123-63-7 paracetaldehyde 
• 141-52-6 sodium ethanolate 
• 89125-30-4 α-Chloro-β-bromoethyl ethyl ether 
• 108-05-4 vinyl acetate 

Downstream Products

• 81146-79-4 1-[(2,2-diethoxyethyl)sulfanyl]-4-nitrobenzene 
• 67264-31-7 (2-anilino-ethyl)-phosphonic acid diethyl ester 
• 60558-61-4 (2-Phenylamino-ethyl)-phosphonic acid 
• 51830-50-3 1,1-diethoxy-2-(4-methylphenylthio)ethane 
• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 
• 137601-28-6 N-(1-Acetyl-2,3-dihydro-1H-indol-5-yl)-N-(2,2-diethoxy-ethyl)-2,2,2-trifluoro-acetamide 
• 94851-02-2 <(2-hydroxyethyl)amino>ethanal diethyl acetal 
• 76534-71-9 (2-aminoethoxy)ethanal diethyl acetal 
• 117516-63-9 1-(2,2-diethoxyethoxy)-2-methylbenzene 
• 62897-80-7 2-bromo-1,1-bis-(4-methoxy-phenyl)-ethane 
• 23230-01-5 2,3-dihydro-1,4-dithiin 
• 4360-63-8 2-bromomethyl-1,3-dioxolane 
• 69148-92-1 N-ethylamino-acetaldehyde diethyl acetal 
• 75934-28-0 p-toluidino-acetaldehyde diethylacetal 

Relevant articles and documents

Thiohemiacetal formation by inhibitory aldehydes at the active site of papain.

Papain is strongly inhibited by aldehydes resembling carboxylic acids, released by hydrolysis of specific substrates (Westerik, J. O''C., and Wolfenden, R. (1972), J. Biol. Chem. 247, 8195-8197). Inhibitory complexes might involve binding of the aldehyde intact or as a covalent hydrate, or the aldehyde might undergo covalent addition of an active site sulfhydryl group to form a thiohemiacetal derivative. In an attempt to distinguish between these possibilities, benzamidoacetaldehyde-1-d has been synthesized, and its properties compared with those of the undeuterated inhibitor. After correction for differences in hydration, the observed effect on inhibition is found to be compatible with formation of a thiohemiacetal. In keeping with this conclusion, benzamidoethanol (a partial analogue of the covalent hydrate) and benzamide, N-methylbenzamide and N-ethylbenzamide (somewhat similar to the free aldehyde in size and hydrophobic character) are found to exhibit negligible affinity for the active site.

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2-mercapto-1-methyl imidazole industrial production method

The invention relates to an industrialization production method of antithyroid drug 2-mercapto-1-methylimidazole. The method comprises: (a) reacting vinyl acetate with bromine in absolute ethyl alcohol, regulating a pH value into alkalescence after reaction, obtaining a bromoacetaldehyde diethyl acetal crude product after extraction and desolventization, and directly adding the bromoacetaldehyde diethyl acetal crude product into a next step of reaction; (b) performing aminolysis reaction of bromoacetaldehyde diethyl acetal and methylamine aqueous solution, and after completing reaction, obtaining methylamino acetal through distilling, separating and purifying after extraction and de-watering; (3) dropping hydrochloric acid into aqueous solution of methylamino acetal and potassium rhodanide; removing water in the reaction solution by reduced pressure distillation after reaction, removing a part insoluble in ethyl acetate from the obtained solid, dissolving residual solid into water with pH being 1-2, crystallizing to obtain 2-mercapto-1-methylimidazole with purity higher than 99%, and then vacuum-drying to obtain a finished product. The production method has a short product line, can obtain 2-mercapto-1-methylimidazole with high purity, and has a strong industrialization prospect.

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.

CHEMISTRY OF ENOL ETHERS. LXXXVIII. CONDENSATION OF THE TETRAETHYLACETAL OF MALONALDEHYDE WITH β-SUBSTITUTED ENOL ALKYL ETHERS

The action of β-substituted enol ethers on the tetraethylacetal of malonaldehyde gave the acetals of 1,5- and 1,7-dialdehydes.The nature of the substituent in the enol ether was found to affect the regioselectivity of the reaction: condensation with ethers containig an electron-wthdrawing substituent leads to 1,5-dialdehyde acetals, while condensation with ethers containig a strong electron donor substituent leads to 1,7-dialdehyde acetals.