57597-62-3

Basic information

• Product Name: 3,3-Dimethoxypropanenitrile
• Synonyms: DMPN;CYANOACETALDEHYDE DIMETHYL ACETAL;3,3-DIMETHOXY-PROPANENITRILE;3,3-DIMETHOXYPROPIONITRILE;1-CYANO-2,2-DIMETHOXYETHANE;3,3-dimethoxypropiononitrile;3,3-DIMETHOXYPROPIONITRILE, TECH.;3 3-DIMETHOXYPROPIONITRILE 96%
• CAS NO: 57597-62-3
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• EINECS: 260-842-1
• Product Categories: API intermediates;C1 to C5;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 57597-62-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 92.5 °C30 mm Hg(lit.)
• Flash Point: 182 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.026 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.639mmHg at 25°C
• Refractive Index: n20/D 1.414(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,3-Dimethoxypropanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-Dimethoxypropanenitrile(57597-62-3)
• EPA Substance Registry System: 3,3-Dimethoxypropanenitrile(57597-62-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/38
• Safety Statements: 23-26-28-37/39-36/37
• WGK Germany: 3
• Hazardous Substances Data: 57597-62-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

InChI:InChI=1/C5H9NO2/c1-7-5(8-2)3-4-6/h5H,3H2,1-2H3

Synthetic route

methanol (67-56-1) + (E)-β-cyanovinyl phenyl sulphone (64326-47-2) → 3,3-dimethoxypropionitrile (57597-62-3)

Conditions	Yield
With sodium methylate for 0.25h;	100%

methanol (67-56-1) + acrylonitrile (107-13-1) → 3,3-dimethoxypropionitrile (57597-62-3)

Conditions	Yield
With methanesulfonic acid; Pd(OAc)2 on carbon; Pd(OAc)2 on carbon - molybdovanadophosphate; oxygen at 60℃; under 760.051 Torr; for 20h; Oxidation; Addition;	96%
With palladium on activated charcoal; oxygen; copper dichloride under 7500.75 Torr; for 8h; Heating;	30%
With carbon dioxide; oxygen; palladium dichloride at 50℃; under 105011 Torr; for 15h;	77.1 % Chromat.

N-(2-Cyano-1-methoxy-ethyl)-N-cyclohexyl-acetamide (98014-05-2) → 3,3-dimethoxypropionitrile (57597-62-3)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 2.5h; Heating;	10%

propiolonitrile (1070-71-9) + sodium methylate (124-41-4) → 3,3-dimethoxypropionitrile (57597-62-3)

Conditions	Yield
With methanol

sodium methylate (124-41-4) + trans-β-chloroacrylonitrile (871-29-4, 3721-37-7, 3721-38-8) → 3,3-dimethoxypropionitrile (57597-62-3)

Conditions	Yield
In ethanol

cyanoacetaldehyde (6162-76-1) + trimethyl orthoformate (149-73-5) → 3,3-dimethoxypropionitrile (57597-62-3)

Conditions	Yield
With toluene-4-sulfonic acid In methanol; dichloromethane at 50℃; for 2h;	3.9 g

acrylonitrile (107-13-1) → 3,3-dimethoxypropionitrile (57597-62-3)

Conditions	Yield
palladium(II) chloride In methanol

methanol (67-56-1) + acrylonitrile (107-13-1) → 3-Methoxypropionitrile (110-67-8) + 3,3-dimethoxypropionitrile (57597-62-3)

Conditions	Yield
With carbon dioxide; oxygen; copper dichloride; palladium dichloride at 57℃; under 97507.8 Torr; for 12h;	A 10.7 % Chromat. B 87.5 % Chromat.

3,3-dimethoxypropionitrile (57597-62-3) + 2,6-dichloro-4-trifluoromethylphenylhydrazine hydrochloride → 3-(2,6-dichloro-4-trifluoromethylphenylhydrazono)propionitrile (111884-98-1)

Conditions	Yield
In tetrachloromethane; water at 75℃; for 10h;	98%

3,3-dimethoxypropionitrile (57597-62-3) + 1-methyl-4-nitrobenzene (99-99-0) → 1-(2-nitrophenyl)-4,4-dimethoxy-2-butanone (69626-62-6)

Conditions	Yield
With piperidine at 110℃; for 4h; Reagent/catalyst;	95.8%

2-amino-1-tert-butyl-4-cyanopyrrole (269726-49-0) + 3,3-dimethoxypropionitrile (57597-62-3) → 6-amino-1-tert-butyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (915726-39-5)

Conditions	Yield
Stage #1: 2-amino-1-tert-butyl-4-cyanopyrrole; 3,3-dimethoxypropionitrile With hydrogenchloride In ethanol for 2h; Heating / reflux; Stage #2: With sodium hydroxide In water	93%

3,3-dimethoxypropionitrile (57597-62-3) + 2-amino-2'-chloro-3,5-dimethylbenzophenone → 4-(2-chlorophenyl)-6,8-dimethyl-3-quinolinecarbonitrile

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 3h; Heating;	92%

3,3-dimethoxypropionitrile (57597-62-3) → N-hydroxy-3,3-dimethoxypropanimidamide (197075-61-9)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydrogencarbonate In methanol for 16h; Reflux;	87%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In methanol at 80℃; for 15h;	4.5 g

Methyl formate (107-31-3) + 3,3-dimethoxypropionitrile (57597-62-3) → 3,3-dimethoxy-2-formyl-propanenitrile sodium salt (105161-33-9)

Conditions	Yield
With sodium hydride In diethyl ether at 20℃; for 48h;	86%
With sodium methylate In toluene at 35 - 40℃; for 6h; Product distribution / selectivity;	55 %Chromat.

3,3-dimethoxypropionitrile (57597-62-3) + 1-amino-4-bromo-1H-pyrrole-2-carboxylic acid methyl ester (1208361-39-0) → 6-bromo-4-hydroxypyrrolo[1,2-b]pyridazine-3-carbonitrile (1400580-13-3)

Conditions	Yield
Stage #1: 3,3-dimethoxypropionitrile; 1-amino-4-bromo-1H-pyrrole-2-carboxylic acid methyl ester With toluene-4-sulfonic acid In tetrahydrofuran at 80℃; for 6h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 80℃; for 10h;	85%

3,3-dimethoxypropionitrile (57597-62-3) + tert-butyl 3-thienylcarbamate (19228-91-2) → [2-((E)-2-Cyano-vinyl)-thiophen-3-yl]-carbamic acid tert-butyl ester

Conditions	Yield
With hydrogenchloride In dichloromethane for 2h; Ambient temperature;	83%

3,3-dimethoxypropionitrile (57597-62-3) → 2-hydroxyimino-3-oxopropionitrile (571178-16-0)

Conditions	Yield
Stage #1: 3,3-dimethoxypropionitrile With sodium nitrite In water at -5℃; Stage #2: With hydrogenchloride In water at -5 - 20℃; for 2.5h;	76%

furfural (98-01-1) + 3,3-dimethoxypropionitrile (57597-62-3) → (E)-2-formyl-3-(furan-2-yl)acrylonitrile (148840-19-1)

Conditions	Yield
With sodium In methanol for 72h; Ambient temperature;	75%

3,3-dimethoxypropionitrile (57597-62-3) → 3-aminopropionaldehyde dimethyl acetal (60185-84-4)

Conditions	Yield
With methanol; sodium for 2h; Heating;	71%

3,3-dimethoxypropionitrile (57597-62-3) + formic acid ethyl ester (109-94-4) → sodium (E)-2-cyano-3,3-dimethoxy-prop-1-en-1-olate (105161-33-9)

Conditions	Yield
With sodium hydride In diethyl ether at 20℃; for 48h;	70%

3,3-dimethoxypropionitrile (57597-62-3) + 2-amino-4'-methylbenzophenone (36192-63-9) → 4-(4-methylphenyl)-3-quinolinecarboxylate (149323-56-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 6h; Heating;	69%

3-thiophene carboxaldehyde (498-62-4) + 3,3-dimethoxypropionitrile (57597-62-3) → 2-(Dimethoxymethyl)-3-(thien-3-yl)acrylonitrile

Conditions	Yield
With sodium methylate In methanol at 20℃;	69%
With sodium methylate In methanol	65 g (69%)

3,3-dimethoxypropionitrile (57597-62-3) + benzaldehyde (100-52-7) → (E)-2-Dimethoxymethyl-3-phenyl-acrylonitrile (163921-40-2)

Conditions	Yield
With sodium methylate In methanol Ambient temperature;	68%

3,3-dimethoxypropionitrile (57597-62-3) + benzaldehyde (100-52-7) → 2-(dimethoxymethyl)-3-phenylacrylonitrile

Conditions	Yield
With sodium methylate In methanol at 20℃; for 72.25h;	68%

3,3-dimethoxypropionitrile (57597-62-3) + methyl 2-(2,6-dichlorophenyl)acrylate (1203555-33-2) → methyl 2-(2,6-dichlorophenyl)-4-cyano-5,5-dimethoxypentanoate (1203555-38-7)

Conditions	Yield
Stage #1: 3,3-dimethoxypropionitrile; methyl 2-(2,6-dichlorophenyl)acrylate With potassium tert-butylate In tetrahydrofuran at -78℃; for 0.0833333h; Michael addition; Stage #2: With acetic acid In tetrahydrofuran	68%

acetic acid methyl ester (79-20-9) + 3,3-dimethoxypropionitrile (57597-62-3) → 2-(dimethoxymethyl)-3-oxo-butanenitrile sodium salt

Conditions	Yield
With sodium hydride In diethyl ether at 20℃; for 48h;	65%

2-methyl-3-(trifluoromethyl)benzaldehyde (878001-20-8) + 3,3-dimethoxypropionitrile (57597-62-3) → (2E)-2-[bis(methyloxy)methyl]-3-[2-methyl-3-(trifluoromethyl)phenyl]-2-propenenitrile (1420468-43-4)

Conditions	Yield
With sodium methylate In methanol at 20℃;	64%

3,3-dimethoxypropionitrile (57597-62-3) + benzaldehyde (100-52-7) → [E]-α-cyanocinnamaldehyde (56069-64-8)

Conditions	Yield
Stage #1: 3,3-dimethoxypropionitrile; benzaldehyde at 20℃; for 8h; Stage #2: With hydrogenchloride at 20℃; for 2h;	64%

N-(thiophen-3-yl)acetamide (42602-67-5) + 3,3-dimethoxypropionitrile (57597-62-3) → N-[2-((E)-2-Cyano-vinyl)-thiophen-3-yl]-acetamide

Conditions	Yield
With hydrogenchloride In dichloromethane for 2h; Ambient temperature;	63%

3,3-dimethoxypropionitrile (57597-62-3) + 3-chloro-N-(2-fluoro-2-methylpropyl)-7-hydrazino-8,9-dihydro-7H-cyclopenta[h]isoquinoline-5-sulfonamide → 7-(5-aminopyrazol-1-yl)-3-chloro-N-(2-fluoro-2-methylpropyl)-8,9-dihydro-7H-cyclopenta[h]isoquinoline-5-sulfonamide

Conditions	Yield
With hydrogenchloride In ethanol at 80℃; Sealed tube;	62%

dibenzoazepine (256-96-2) + 3,3-dimethoxypropionitrile (57597-62-3) → 3-(5H-dibenzo[b,f]azepin-5-yl)propanenitrile

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 16h; Inert atmosphere;	60%

3,3-dimethoxypropionitrile (57597-62-3) + 2,6-dichloro-4-(trifluoromethyl)phenyl hydrazine (86398-94-9) → 3-(2,6-dichloro-4-trifluoromethylphenylhydrazono)propionitrile (111884-98-1)

Conditions	Yield
With hydrogenchloride at 80℃; for 2h;	59%

3-aminothiophene (17721-06-1) + 3,3-dimethoxypropionitrile (57597-62-3) → thieno[3,2-b]pyridine-6-carbonitrile (116538-95-5)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 12h; Ambient temperature;	57%

3,3-dimethoxypropionitrile (57597-62-3) + acetic anhydride (108-24-7) → N-(3,3-dimethoxypropyl)acetamide (1262142-10-8)

Conditions	Yield
With methanol; nickel(II) sulphate; sodium tetrahydroborate at 20℃;	56%
With hydrogen In tetrahydrofuran at 60℃; under 3040.2 Torr; for 6h;	35%

3,3-dimethoxypropionitrile (57597-62-3) + 1,2,4-trimethoxy-benzene (135-77-3) → 3,3-bis(2,4,5-trimethoxyphenyl)propanenitrile (1431862-18-8)

Conditions	Yield
With trifluorormethanesulfonic acid In acetonitrile at 0 - 20℃; for 24h;	55%

3,3-dimethoxypropionitrile (57597-62-3) + methyl 2-(2,6-dichlorophenyl)acrylate (1203555-33-2) + guanidine hydrogen carbonate (124-46-9, 20734-13-8, 100224-74-6, 593-85-1) → 2-amino-6-(2,6-dichlorophenyl)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one (1203555-39-8)

Conditions	Yield
Stage #1: 3,3-dimethoxypropionitrile; methyl 2-(2,6-dichlorophenyl)acrylate With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: With acetic acid In tetrahydrofuran Stage #3: guanidine hydrogen carbonate With pyridine at 180℃; for 1h; Microwave irradiation;	53%

Upstream product

• 1070-71-9 propiolonitrile 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 107-13-1 acrylonitrile 
• 6162-76-1 cyanoacetaldehyde 
• 149-73-5 trimethyl orthoformate 
• 98014-05-2 N-(2-Cyano-1-methoxy-ethyl)-N-cyclohexyl-acetamide 
• 64326-47-2 (E)-β-cyanovinyl phenyl sulphone 
• 871-29-4 trans-β-chloroacrylonitrile 

Downstream Products

• 1203555-38-7 methyl 2-(2,6-dichlorophenyl)-4-cyano-5,5-dimethoxypentanoate 
• 1203555-35-4 (E)-methyl 2-(2,6-dichlorophenyl)-4-cyano-5-methoxypent-4-enoate 
• 1203555-36-5 (Z)-methyl 2-(2,6-dichlorophenyl)-4-cyano-5-methoxypent-4-enoate 
• 1203555-39-8 2-amino-6-(2,6-dichlorophenyl)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one 
• 1203555-45-6 6-(2,6-dichlorophenyl)-5,6-dihydro-2-(phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 1203555-37-6 methyl 2-(2-bromophenyl)-4-cyano-5-methoxypent-4-enoate 
• 1203555-43-4 2-amino-6-(2-bromophenyl)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one 
• 1203555-42-3 2-amino-5,6-dihydro-6-(2-methoxyphenyl)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 1203555-41-2 2-amino-5,6-dihydro-6-o-tolylpyrido[2,3-d]pyrimidin-7(8H)-one 
• 1203555-48-9 5,6-dihydro-2-(phenylamino)-6-o-tolylpyrido[2,3-d]pyrimidin-7(8H)-one 
• 1203555-46-7 5,6-dihydro-6-(naphthalen-1-yl)-2-(phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 105161-33-9 sodium (E)-2-cyano-3,3-dimethoxy-prop-1-en-1-olate 
• 69626-62-6 1-(2-nitrophenyl)-4,4-dimethoxy-2-butanone 
• 56069-64-8 [E]-α-cyanocinnamaldehyde 

Relevant articles and documents

Ozonolysis of olefins, VI: Cyanoacetaldehyde by ozonolysis of (E)-1,4-dicyano-2-butene or allyl cyanide

A new route for the preparation of cyanoacetaldehyde (3-oxopropanenitrile, 1) and its stable dimethyl acetal (3,3-dimethoxypropanenitrile, 2), which both are valuable intermediates for organic syntheses, is described. It starts from (E)-1,4-dicyano-2-butene or allyl cyanide (3-butenenitrile), respectively, which are ozonized at -40°C and further treated with dimethyl sulfide to give a solution of 1. This solution can either be used directly for further reactions or be transformed into the dimethyl acetal 2. The overall yield of 2 is 67 to 71%. The acetal can be hydrolyzed again by treatment with Amberlyst-15 to give 1.

Palladium-catalyzed aerobic oxidation of terminal olefins with electron-withdrawing groups in scCO2

Product control of palladium-catalyzed aerobic oxidation of terminal olefins with electron-withdrawing groups can be achieved through modifying reaction conditions. When the oxidant, such as CuCl2/O2, benzoquinone/O2 or O2, was present in scCO2, aerobic oxidation of terminal olefins goes smoothly. With enough MeOH and sufficient oxygen, acetalization preponderated over cyclotrimerization, while with little MeOH as co-solvent in scCO2 or no MeOH in DMF and an appropriate pressure of O2, cyclotrimerization of terminal olefins became the dominated reaction. When oxygen is absent and triethylamine was added into the reaction system, palladium-catalyzed C-N bond formation occurs to produce β-amino acid derivatives as the sole product.

Nitrilase from rhodococcus rhodochrous ncimb 11216

The invention relates to nucleic acid sequences which code for a polypeptide having nitrilase activity, to nucleic acid constructs comprising the nucleic acid sequences, and to vectors comprising the nucleic acid sequences or the nucleic acid constructs. The invention further relates to amino acid sequences which are encoded by the nucleic acid sequences, and to microorganisms comprising the nucleic acid sequences, the nucleic acid constructs or vectors comprising the nucleic acid sequences or the nucleic acid constructs. The invention additionally relates to an enzymatic process for preparing carboxylic acids from the corresponding nitrites.