631-57-2

Basic information

• Product Name: PYRUVONITRILE
• Synonyms: 2-OXOPROPIONITRILE;ACETYL CYANIDE;PYRUVONITRILE;2-Oxopropanenitrile;alpha-Oxopropionitrile;Oxopropionitrile;Oxypropionitrile;Propanenitrile, 2-oxo-
• CAS NO: 631-57-2
• Molecular Formula: C₃H₃NO
• Molecular Weight: 69.06
• EINECS: 211-159-2
• Product Categories: Pharmaceutical Intermediates;Building Blocks;C1 to C5;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 631-57-2.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 92-93 °C(lit.)
• Flash Point: 58 °F
• Appearance: Colorless to brown/Liquid
• Density: 0.974 g/mL at 25 °C(lit.)
• Vapor Pressure: 51.9mmHg at 25°C
• Refractive Index: n20/D 1.376(lit.)
• Storage Temp.: 2-8°C
• Solubility: Soluble in ether and acetonitrile.
• BRN: 1737633
• CAS DataBase Reference: PYRUVONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: PYRUVONITRILE(631-57-2)
• EPA Substance Registry System: PYRUVONITRILE(631-57-2)

Safety Data

• Hazard Codes: F,T,N
• Statements: 11-23/25-51/53-37/38
• Safety Statements: 45-61-36/37-16
• RIDADR: UN 3273 3/PG 2
• WGK Germany: 3
• F: 8-10-13
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 631-57-2(Hazardous Substances Data)

Usage

Uses

Pyruvonitrile was used in the synthesis of cuprate-carbonyl π-complexes by reaction with Me2CuLi in THF.

General Description

The infrared spectra of pyruvonitrile was studied.

InChI:InChI=1/C3H3NO/c1-3(5)2-4/h1H3

Synthetic route

bis(dimethylamino)malononitrile (63442-64-8) → Acetyl cyanide (631-57-2) + 1,1-dicyanoethyl acetate (7790-01-4) + Cyan-N,N,N',N'-tetramethylformamidinium-chlorid (70976-82-8)

Conditions	Yield
With acetyl chloride In diethyl ether for 6h; Product distribution; Ambient temperature; further acyl chlorides;	A 23% B 61% C 96%
With acetyl chloride In diethyl ether for 6h; Ambient temperature;	A 23% B 61% C 96%

bis(dimethylamino)malononitrile (63442-64-8) + acetyl chloride (75-36-5) → Acetyl cyanide (631-57-2) + 1,1-dicyanoethyl acetate (7790-01-4) + Cyan-N,N,N',N'-tetramethylformamidinium-chlorid (70976-82-8)

Conditions	Yield
In diethyl ether for 6h; Ambient temperature;	A 23% B 61% C 96%

trimethylsilyl cyanide (7677-24-9) + acetyl chloride (75-36-5) → Acetyl cyanide (631-57-2)

Conditions	Yield
With zinc(II) iodide at 100℃; for 2h; Inert atmosphere; Neat (no solvent); neat (no solvent);	90%

methyl 2-oxo-2-phenylacetate (15206-55-0) + ethyl cyanoformate (623-49-4) → Acetyl cyanide (631-57-2)

Conditions	Yield
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	88%

diethyl phosphorocyanidate (33326-12-4) + acetyl chloride (75-36-5) → diethyl phosphorylchloridite (589-57-1) + Acetyl cyanide (631-57-2)

Conditions	Yield
triethylamine at 70 - 80℃; for 0.5h;	A 65% B 32%

chloro-trimethyl-silane (75-77-4) + potassium cyanide (151-50-8) + acetyl chloride (75-36-5) → Acetyl cyanide (631-57-2) + 2-<(trimethylsilyl)oxy>propenenitrile (54276-53-8)

Conditions	Yield
With zinc(II) iodide; PEG400 In dichloromethane for 2h; Heating;	A 55% B 15%

1-triphenylphosphoranylidene-2-propanone (1439-36-7) → Acetyl cyanide (631-57-2) + triphenylphosphine oxide-nitric acid complex (18365-29-2)

Conditions	Yield
With Nitrogen dioxide In dichloromethane Ambient temperature; Yields of byproduct given;	A 40% B n/a
With Nitrogen dioxide In dichloromethane Ambient temperature; Yield given;	A 40% B n/a

pyridine (110-86-1) + hydrogen cyanide (74-90-8) + acetyl chloride (75-36-5) → Acetyl cyanide (631-57-2) + pyridine hydrochloride (628-13-7)

Ketene (463-51-4) + hydrogen cyanide (74-90-8) → Acetyl cyanide (631-57-2)

Conditions	Yield
With pyrographite at 350℃;

hydrogen cyanide (74-90-8) + acetic anhydride (108-24-7) → Acetyl cyanide (631-57-2)

Conditions	Yield
With silica gel at 350 - 365℃;
With pyrographite at 240 - 270℃;

hydrogen cyanide (74-90-8) + acetyl chloride (75-36-5) → Acetyl cyanide (631-57-2)

Conditions	Yield
With pyridine

silver(I) cyanide (506-64-9) + acetyl chloride (75-36-5) → Acetyl cyanide (631-57-2)

Conditions	Yield
at 100℃;

acetyl chloride (75-36-5) + propanone 1-oxime (306-44-5) → Acetyl cyanide (631-57-2)

acrylonitrile (107-13-1) → Acetyl cyanide (631-57-2)

Conditions	Yield
With palladium dichloride at 30℃;

propanone 1-oxime (306-44-5) → Acetyl cyanide (631-57-2)

Conditions	Yield
With carbon disulfide; phosphorus pentoxide

Acetyl bromide (506-96-7) + copper(I) cyanide (544-92-3) → Acetyl cyanide (631-57-2)

acetonyltriphenylphosphonium chloride (1235-21-8) → Acetyl cyanide (631-57-2)

Conditions	Yield
(i) HCl, CHCl3, (ii) iPrONO; Multistep reaction;

copper(I) cyanide (544-92-3) + acetyl chloride (75-36-5) → Acetyl cyanide (631-57-2)

Conditions	Yield
In acetonitrile

rac-oxiranecarbonitrile (4538-51-6) → Acetyl cyanide (631-57-2)

cyanide(1-) (57-12-5) + 9-acetyl-9-cyanofluorene (81477-52-3) → Acetyl cyanide (631-57-2) + 9-cyanofluorenide anion (12564-43-1)

Conditions	Yield
In dimethyl sulfoxide Rate constant;

3-cyano-3-methyl-1,2,4-trioxolane (130558-79-1) → formaldehyd (50-00-0) + Acetyl cyanide (631-57-2)

Conditions	Yield
With 2,3-dimercapto-succinic acid In chloroform at -20℃;

1-(phenylhydrazono)-1-(phenylthio)-2-propanone (132401-43-5) → Acetyl cyanide (631-57-2) + 4-aminophenyl phenyl sulfide (1135-14-4)

Conditions	Yield
With PPA Mechanism; also 1-phenyl-2-(phenylhydrazono)-2-(phenylthio)ethanal and α-(phenylthio)benzalphenylhydrazone;

4-azido-3,5-dimethylisoxazole → Acetyl cyanide (631-57-2) + acetonitrile (75-05-8)

Conditions	Yield
In 1,1,2,2-tetrachloroethylene at 50 - 90℃; Rate constant; Kinetics; E** and ΔS** determined, other solvents used;

trimethylsilyl cyanide (7677-24-9) + acetyl chloride (75-36-5) → chloro-trimethyl-silane (75-77-4) + Acetyl cyanide (631-57-2)

Conditions	Yield
Ambient temperature;

2-Benzylsulfanyl-2-hydroxy-propionitrile (110823-07-9) + phenylmethanethiol (100-53-8) → Acetyl cyanide (631-57-2)

Conditions	Yield
In chloroform-d1 at 29.9℃; under 750.06 Torr; Equilibrium constant; other pressures;

cyanide(1-) (57-12-5) + 2,4-dinitrophenyl acetate (4232-27-3) → Acetyl cyanide (631-57-2) + 2,4-dinitrophenolate (20350-26-9)

Conditions	Yield
In dimethyl sulfoxide Rate constant;

water (7732-18-5) + acrylonitrile (107-13-1) + palladium(II)-chloride + oxygen → Acetyl cyanide (631-57-2)

pyridine (110-86-1) + acetyl chloride (75-36-5) + liquid hydrocyanic acid → Acetyl cyanide (631-57-2) + pyridine hydrochloride (628-13-7)

methacrylonitrile (126-98-7) + oxygen → formaldehyd (50-00-0) + Acetyl cyanide (631-57-2) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + carbon monoxide

Conditions	Yield
at 40 - 45℃; UV-Licht.Irradiation;

Acetyl cyanide (631-57-2) → 2-oxopropanethioamide (31787-50-5)

Conditions	Yield
Stage #1: Acetyl cyanide With hydrogen sulfide In tetrahydrofuran at -10℃; Stage #2: With triethylamine In tetrahydrofuran at -3 - 4℃;	98%
With hydrogen sulfide; triethylamine In tetrahydrofuran at -10 - 4℃;	98%
Stage #1: Acetyl cyanide With hydrogen sulfide In tetrahydrofuran at -10℃; Stage #2: With triethylamine In tetrahydrofuran at -3 - 4℃;	98%

ethyl-2-azidoacetate (637-81-0) + Acetyl cyanide (631-57-2) → 5-acetyltetrazole-1-acetic acid ethyl ester (120869-84-3)

Conditions	Yield
at 80℃; under 7500600 Torr; for 12h;	98%

heptanal (111-71-7) + Acetyl cyanide (631-57-2) → 1-cyanoheptyl-1 acetate

Conditions	Yield
tri-n-butyltin cyanide at 20℃; for 4h;	98%

Acetyl cyanide (631-57-2) + 2-Phenylpropanal (34713-70-7) → Acetic acid 1-cyano-2-phenyl-propyl ester

Conditions	Yield
tri-n-butyltin cyanide at 20℃; for 4h;	98%

Acetyl cyanide (631-57-2) + dimethyl 2,2-di(but-2-yn-1-yl)malonate (107428-05-7) → dimethyl 3-acetyl-1,4-dimethyl-5,7-dihydro-6H-cyclopenta[c]pyridine-6,6-dicarboxylate

Conditions	Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 80℃; for 40h;	98%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis(di(pentafluorophenyl)phosphino)ethane In toluene for 24h; Reflux; Inert atmosphere;	89%

Acetyl cyanide (631-57-2) + triethyl phosphite (122-52-1) → diethyl-(1-dichlorophosphinoxy-1-cyaoethyl)phosphonate

Conditions	Yield
With phosphorus trichloride at 20℃; for 1h;	97%

Acetyl cyanide (631-57-2) + cyclohexanecarbaldehyde (2043-61-0) → 1-cyano-1-cyclohexylmethyl acetate (171774-99-5)

Conditions	Yield
tri-n-butyltin cyanide at 20℃; for 5h;	96%
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃; for 6h; Inert atmosphere;	88%
With potassium carbonate In acetonitrile for 3h; Ambient temperature;	79%
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In 1,2-dichloro-ethane at 0 - 20℃; Inert atmosphere;	71%

Acetyl cyanide (631-57-2) + 2-aza-3-phenyl-1-(3-pyridyl)prop-1-ene (141120-47-0) → N-benzyl-N-(cyano-pyridin-3-yl-methyl)-acetamide

Conditions	Yield
With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea In dichloromethane at 0℃; for 24h; Strecker reaction;	96%

Acetyl cyanide (631-57-2) + p-methoxyphenylhydroxylamine (4546-20-7) → N-Acetoxy-4-methoxyaniline (126875-69-2)

Conditions	Yield
With triethylamine In tetrahydrofuran-d8 at -78℃; for 0.0833333h;	95%
In tetrahydrofuran at -78℃; for 0.0833333h;

Acetyl cyanide (631-57-2) + butyraldehyde (123-72-8) → 2-acetoxybutanenitrile (2983-06-4)

Conditions	Yield
With potassium carbonate In acetonitrile for 1h; Ambient temperature;	95%

Acetyl cyanide (631-57-2) + (E)-N-benzyl-1-(4-methoxyphenyl)methanimine (130517-94-1) → N-benzyl-N-[cyano-(4-methoxy-phenyl)-methyl]-acetamide

Conditions	Yield
With chiral 1,2-diaminocyclohexane based reagent In toluene at -40℃;	95%

4-heptanone (123-19-3) + Acetyl cyanide (631-57-2) + aniline (62-53-3) → 2-phenylamino-2-propyl-pentanenitrile

Conditions	Yield
With N,N-dimethyl-cyclohexanamine In water at 20℃; for 5h; Strecker reaction;	95%

3-octanone (106-68-3) + Acetyl cyanide (631-57-2) + aniline (62-53-3) → C15H22N2 (1202243-48-8)

Conditions	Yield
With N,N-dimethyl-cyclohexanamine In water at 20℃; for 5h; Strecker reaction;	95%

Acetyl cyanide (631-57-2) + cyclohexanone (108-94-1) + aniline (62-53-3) → 1-(phenylamino)cyclohexanecarbonitrile (64269-06-3)

Conditions	Yield
With N,N-dimethyl-cyclohexanamine In water at 20℃; for 5h; Strecker reaction;	95%

Acetyl cyanide (631-57-2) + benzaldehyde (100-52-7) + aniline (62-53-3) → 2-anilino-2-phenylacetonitrile (4553-59-7)

Conditions	Yield
With N,N-dimethyl-cyclohexanamine In water at 20℃; for 1h; Strecker reaction;	95%

Acetyl cyanide (631-57-2) + 4-methoxy-benzaldehyde (123-11-5) + aniline (62-53-3) → 2-anilino-2-(p-methoxyphenyl)acetonitrile (15190-69-9)

Conditions	Yield
With N,N-dimethyl-cyclohexanamine In water at 20℃; for 1h; Strecker reaction;	95%

Acetyl cyanide (631-57-2) + propionaldehyde (123-38-6) + aniline (62-53-3) → 2-(phenylamino)butane nitrile (85599-84-4)

Conditions	Yield
With N,N-dimethyl-cyclohexanamine In water at 20℃; for 1h; Strecker reaction;	95%

Acetyl cyanide (631-57-2) + aniline (62-53-3) + acetone (67-64-1) → 2-methyl-2-(N-phenylamino)propanenitrile (2182-38-9)

Conditions	Yield
With N,N-dimethyl-cyclohexanamine In water at 20℃; for 48h; Strecker reaction;	95%

Acetyl cyanide (631-57-2) + benzyloxyacetoaldehyde (60656-87-3) → Acetic acid 2-benzyloxy-1-cyano-ethyl ester (123283-19-2)

Conditions	Yield
tri-n-butyltin cyanide at 20℃; for 4h;	94%

Acetyl cyanide (631-57-2) + loukacinol A → 13-acetoxyloukacinol A

Conditions	Yield
In triethylamine; acetonitrile at 20℃; for 2.5h; Acetylation;	94%

Acetyl cyanide (631-57-2) + (E)-N-benzylidenebenzylamine (27845-50-7) → N-benzyl-N-(cyano-phenyl-methyl)-acetamide

Conditions	Yield
With chiral 1,2-diaminocyclohexane based reagent In toluene at -40℃;	94%

Acetyl cyanide (631-57-2) + 4-methyl-benzaldehyde (104-87-0) → α-acetoxy-2-(4-methylphenyl)acetonitrile (75599-81-4)

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃; for 24h; Inert atmosphere;	94%
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In 1,2-dichloro-ethane at 0 - 20℃; Inert atmosphere;	65%

Acetyl cyanide (631-57-2) + 1-trimethylsilyloxy-2-methyl-1-cyclohexene (19980-35-9) → 2-Hydroxy-2-(1-methyl-2-oxo-cyclohexyl)-propionitrile (78747-30-5)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 2h;	93.5%

Acetyl cyanide (631-57-2) + (Z)-3-trimethylsiloxy-2-pentene (51425-54-8) → rac-2-hydroxy-2,3-dimethyl-4-oxo-hexanenitrile (78747-29-2)

Conditions	Yield
With titanium tetrachloride In dichloromethane at -80℃; for 1.5h; Mukaiyama aldol reaction;	93%
With titanium tetrachloride In dichloromethane at -78℃; for 2h;	85%

Acetyl cyanide (631-57-2) + (R)-Carvone (6485-40-1, 2244-16-8) → (5R)-6-acetyl-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone (886537-41-3)

Conditions	Yield
Stage #1: (R)-Carvone With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: Acetyl cyanide In tetrahydrofuran; hexane	93%

Acetyl cyanide (631-57-2) + 3-Phenoxybenzaldehyde (39515-51-0) → alpha-cyano-3-phenoxybenzyl acetate (61066-87-3)

Conditions	Yield
With triethylamine at 20℃; for 1h;	93%

Acetyl cyanide (631-57-2) + phenylthiotrimethylsilane (4551-15-9) → 2-phenylthio-2-<(trimethylsilyl)oxy>propanenitrile

Conditions	Yield
	92%

Upstream product

• 110-86-1 pyridine 
• 74-90-8 hydrogen cyanide 
• 75-36-5 acetyl chloride 
• 463-51-4 Ketene 
• 107-13-1 acrylonitrile 
• 306-44-5 propanone 1-oxime 
• 130558-79-1 3-cyano-3-methyl-1,2,4-trioxolane 
• 7677-24-9 trimethylsilyl cyanide 
• 63442-64-8 bis(dimethylamino)malononitrile 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 7732-18-5 water 
• 126-98-7 methacrylonitrile 
• 87988-95-2 4-azido-5-methylisoxazole 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 7790-01-4 1,1-dicyanoethyl acetate 
• 114-83-0 1-acetyl-2-phenylhydrazine 
• 90770-98-2 1-(3-phenyl-[1,2,4]oxadiazol-5-yl)-ethanone 
• 37760-56-8 2-acetoxy-2-(3-phenyl-[1,2,4]oxadiazol-5-yl)-propionitrile 
• 72876-49-4 1-Cyanovinyl-p-nitrobenzoat 
• 77426-90-5 α,α-diethoxybenzeneacetonitrile 
• 129803-30-1 Cyano-(3-pyridyl)methyl Acetate 
• 37513-99-8 2-acetyldimedone 
• 194021-87-9 5-Acetyl-3,5-dimethyl-[1,2,4]trioxolane-3-carbonitrile 
• 622010-78-0 C₉H₁₁NO₂ 
• 13058-70-3 3-nitrobutan-2-one 
• 74-90-8 hydrogen cyanide 
• 75-05-8 acetonitrile 
• 121054-03-3 2-hydroxy-4-phenylbutanenitrile 

Relevant articles and documents

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Method for synthesizing sucrose-6-acetic ester

The present invention discloses a method of synthesizing sucrose-6-acetic ester, comprising the following steps: adding sucrose into a polar aprotic solvent, and stirring the solvent to dissolve it, then generate a suspension solution of sucrose; adding a acetylation agent acetylnitrile into said suspension solution and stirring the solution; adding water into the aforesaid reaction solution, and then concentrating it to generate a concentrated product; adding a crystalline solvent into the concentrated product, stirring to dissolve it, and depositing for crystallization, then filtering and drying it to get a product of sucrose-6-acetic ester. The benefit of the present invention is that the method of synthesizing sucrose-6-acetic ester has simple operation, mild reaction condition, high selectivity, high yield, and is suitable for industrial production.