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78-97-7

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78-97-7 Usage

Chemical Properties

Lactonitrile, is soluble in water and alcohol, but insoluble in diethyl ether and carbon disulfide. Lactonitrile is used chiefly to manufacture lactic acid and its derivatives, primarily ethyl lactate.

Uses

Different sources of media describe the Uses of 78-97-7 differently. You can refer to the following data:
1. It is used primarily as a solvent, and as an intermediate in production of ethyl acetate and lactic acid.
2. 2-Hydroxypropanenitrile is a useful compound for efficient lactamide synthesis by fed batch method using nitrile hydratase of Rhodococcus pyridinivorans NIT-36.

Production Methods

Different sources of media describe the Production Methods of 78-97-7 differently. You can refer to the following data:
1. Lactonitrile is derived from acetaldehyde and hydrocyanic acid.
2. Lactonitrile is manufactured from equimolar amounts of acetaldehyde and hydrogen cyanide containing 1.5% of 20% NaOH at ?10–20 °C. The product is stabilized with sulfuric acid. Sulfuric acid hydrolyzes the nitrile to give a mixture of lactic acid and ammonium bisulfate. This mixture can be purified by adding methanol to form methyl lactate which is separated from the ammonium bisulfate. The methyl lactate is distilled, then hydrolyzed back to the aqueous acid. Removal of most of the water yields 90% lactic acid.

General Description

Straw colored liquid. Used as a solvent /intermediate in production of ethyl lactate and lactic acid.

Air & Water Reactions

Water soluble.

Reactivity Profile

Lactonitrile is incompatible with strong acids, strong bases and strong reducing agents. Lactonitrile is also incompatible with strong oxidizers. In the presence of alkali, Lactonitrile evolves toxic compounds. .

Health Hazard

Extremely toxic by oral, skin, or eye contact.

Fire Hazard

Cyanide fumes released when heated to decomposition. Avoid alkali, oxidizing material.

Check Digit Verification of cas no

The CAS Registry Mumber 78-97-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 8 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 78-97:
(4*7)+(3*8)+(2*9)+(1*7)=77
77 % 10 = 7
So 78-97-7 is a valid CAS Registry Number.

78-97-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Lactonitrile

1.2 Other means of identification

Product number -
Other names (RS)-lactonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:78-97-7 SDS

78-97-7Synthetic route

hydrogen cyanide
74-90-8

hydrogen cyanide

acetaldehyde
75-07-0

acetaldehyde

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With triethylamine at 5 - 10℃; Product distribution / selectivity;99%
With triethylamine at 0 - 10℃; pH=2 - 3;99.54%
With sodium acetate; acetic acid; 2-hydroxy-propionitrile
potassium cyanide
151-50-8

potassium cyanide

acetaldehyde
75-07-0

acetaldehyde

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With sodium hydrogensulfite In water at 0℃; for 2h;80%
With acetic acid In diethyl ether; water22%
2-[(tert-butyldimethylsilyl)oxy]propanenitrile
114711-04-5

2-[(tert-butyldimethylsilyl)oxy]propanenitrile

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With P(MeNCH2CH2)3N In dimethyl sulfoxide at 80℃; for 19h; desilylation;80%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

acetaldehyde
75-07-0

acetaldehyde

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With ytterbium(III) chloride; 2,6-bis[4′-isopropyloxazolin-2′-yl]pyridine In acetonitrile for 2h; Ambient temperature;61%
With hydrogenchloride
acrylonitrile
107-13-1

acrylonitrile

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With tetrachloromethane; copper(II) choride dihydrate; chromium(III) acetylacetonate; water at 110℃; for 6h; Sealed tube;46%
With acetic acid; lithium iodide In [D3]acetonitrile at 20℃; for 3h; Irradiation; Inert atmosphere;
hydrogen cyanide
74-90-8

hydrogen cyanide

potassium cyanide
151-50-8

potassium cyanide

acetaldehyde
75-07-0

acetaldehyde

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
at 25 - 30℃;
hydrogen cyanide
74-90-8

hydrogen cyanide

acetaldehyde
75-07-0

acetaldehyde

A

acrylonitrile
107-13-1

acrylonitrile

B

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

hydrogen cyanide
74-90-8

hydrogen cyanide

chloroform
67-66-3

chloroform

acetaldehyde
75-07-0

acetaldehyde

Quinine
130-95-0

Quinine

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
at 25℃;
sodium cyanide
143-33-9

sodium cyanide

acetaldehyde
75-07-0

acetaldehyde

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With ammonium chloride In diethyl ether
With Dowex-H+ In water for 24h; Ambient temperature;
1,5-dimethylimidazolidine-2,4-dione
17374-27-5

1,5-dimethylimidazolidine-2,4-dione

A

methylaminopropionitrile
16752-54-8

methylaminopropionitrile

B

α-methylaminodipropionitrile
57768-53-3

α-methylaminodipropionitrile

C

carbamate de l' α-N-methylaminopropionitrile

carbamate de l' α-N-methylaminopropionitrile

D

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With sodium hydrogencarbonate at 30℃; Equilibrium constant; K as a function of pH and concentration of carbonate, borate, phosphate and ammonia;
methylaminopropionitrile
16752-54-8

methylaminopropionitrile

A

1,5-dimethylimidazolidine-2,4-dione
17374-27-5

1,5-dimethylimidazolidine-2,4-dione

B

α-methylaminodipropionitrile
57768-53-3

α-methylaminodipropionitrile

C

carbamate de l' α-N-methylaminopropionitrile

carbamate de l' α-N-methylaminopropionitrile

D

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With sodium carbonate at 50℃; Product distribution;
With sodium hydrogencarbonate at 30℃; Rate constant; Equilibrium constant; k as a function of pH and concentration of carbonate, borate, phosphate and ammonia;
L-threonine
72-19-5

L-threonine

chloroamine-T
127-65-1

chloroamine-T

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With hydrogenchloride; sodium chloride In water at 29.9 - 44.9℃; for 24h; Kinetics; Mechanism; Thermodynamic data; effect of +>, ->, and ; with HClO4 and H2SO4 also; solvent isotope effect; variation of ionic strength and addition of the product, p-toluenesulfonamide; decrease of dielectric constant by methanol; ΔH(excit.), ΔS(excit.), ΔG(excit.);
L-threonine
72-19-5

L-threonine

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With perchloric acid; N-chlorobenzotriazole; chloride In water at 29.9℃; Kinetics; Mechanism;
1-cyanoethyl acetate
15657-96-2

1-cyanoethyl acetate

A

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

B

(S)-O-acetyl-1-cyanoethanol

(S)-O-acetyl-1-cyanoethanol

Conditions
ConditionsYield
With Candida tropicalis at 30℃; for 96h; Quantum yield; Hydrolitic efficiency of other microorganisms; Penicillium notatum, Aspergillus flavas, Pseudomonas fluorescens;
2,2'-iminodipropionitrile
2869-25-2

2,2'-iminodipropionitrile

A

carbamate de l' α-aminopropionitrile

carbamate de l' α-aminopropionitrile

B

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

C

2-aminopropanenitrile
51806-98-5, 95596-57-9, 2134-48-7

2-aminopropanenitrile

D

methyl-5 hydantoine
67337-69-3

methyl-5 hydantoine

Conditions
ConditionsYield
With sodium hydrogencarbonate at 30℃; Equilibrium constant; K as a function of pH and concentration of carbonate, borate, phosphate and ammonia;
L-threonine
72-19-5

L-threonine

A

carbon dioxide
124-38-9

carbon dioxide

B

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With hydrogenchloride; chloroamine-T In water at 29.9 - 44.9℃; Thermodynamic data; Rate constant; Ea, log A, -ΔS(excit.), ΔH(excit.), ΔG(excit.); further acid concentration, further acid and alkaline media;
α-methylaminodipropionitrile
57768-53-3

α-methylaminodipropionitrile

A

1,5-dimethylimidazolidine-2,4-dione
17374-27-5

1,5-dimethylimidazolidine-2,4-dione

B

methylaminopropionitrile
16752-54-8

methylaminopropionitrile

C

carbamate de l' α-N-methylaminopropionitrile

carbamate de l' α-N-methylaminopropionitrile

D

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With sodium hydrogencarbonate at 30℃; Equilibrium constant; K as a function of pH and concentration of carbonate, borate, phosphate and ammonia;
potassium cyanide
151-50-8

potassium cyanide

potassium 1-hydroxyethane-1-sulfonate
918-04-7

potassium 1-hydroxyethane-1-sulfonate

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
In water
carbamate de l' α-aminopropionitrile

carbamate de l' α-aminopropionitrile

A

2,2'-iminodipropionitrile
2869-25-2

2,2'-iminodipropionitrile

B

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

C

2-aminopropanenitrile
51806-98-5, 95596-57-9, 2134-48-7

2-aminopropanenitrile

D

methyl-5 hydantoine
67337-69-3

methyl-5 hydantoine

Conditions
ConditionsYield
With sodium hydrogencarbonate at 30℃; Equilibrium constant; K as a function of pH and concentration of carbonate, borate, phosphate and ammonia;
carbamate de l' α-N-methylaminopropionitrile

carbamate de l' α-N-methylaminopropionitrile

A

1,5-dimethylimidazolidine-2,4-dione
17374-27-5

1,5-dimethylimidazolidine-2,4-dione

B

methylaminopropionitrile
16752-54-8

methylaminopropionitrile

C

α-methylaminodipropionitrile
57768-53-3

α-methylaminodipropionitrile

D

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With sodium hydrogencarbonate at 30℃; Equilibrium constant; K as a function of pH and concentration of carbonate, borate, phosphate and ammonia;
sodium carbonate
497-19-8

sodium carbonate

2-aminopropanenitrile
51806-98-5, 95596-57-9, 2134-48-7

2-aminopropanenitrile

A

2,2'-iminodipropionitrile
2869-25-2

2,2'-iminodipropionitrile

B

α-carboxyaminopropionamide
4744-01-8

α-carboxyaminopropionamide

C

α-carboxyaminopropionitrile

α-carboxyaminopropionitrile

D

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

E

methyl-5 hydantoine
67337-69-3

methyl-5 hydantoine

F

alanine amide
4726-84-5

alanine amide

Conditions
ConditionsYield
With ammonia In water at 50℃; Product distribution; Kinetics; pH=8.9 and 9.5;
2-aminopropanenitrile
51806-98-5, 95596-57-9, 2134-48-7

2-aminopropanenitrile

A

2,2'-iminodipropionitrile
2869-25-2

2,2'-iminodipropionitrile

B

carbamate de l' α-aminopropionitrile

carbamate de l' α-aminopropionitrile

C

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

D

methyl-5 hydantoine
67337-69-3

methyl-5 hydantoine

Conditions
ConditionsYield
With sodium carbonate at 50℃; Product distribution;
With sodium hydrogencarbonate at 30℃; Rate constant; Equilibrium constant; k as a function of pH and concentration of carbonate, borate, phosphate and ammonia;
methyl-5 hydantoine
67337-69-3

methyl-5 hydantoine

A

2,2'-iminodipropionitrile
2869-25-2

2,2'-iminodipropionitrile

B

carbamate de l' α-aminopropionitrile

carbamate de l' α-aminopropionitrile

C

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

D

2-aminopropanenitrile
51806-98-5, 95596-57-9, 2134-48-7

2-aminopropanenitrile

Conditions
ConditionsYield
With sodium hydrogencarbonate at 30℃; Equilibrium constant; K as a function of pH and the concentration of carbonate, borate, phosphate and ammonia;
Conditions
ConditionsYield
With perchloric acid; sodium bismuthate; hydrogen fluoride In water at 35℃; for 3h; Kinetics; Further Variations:; Temperatures; Oxidation;
hydrogen cyanide
74-90-8

hydrogen cyanide

2cetaldehyde

2cetaldehyde

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
With pyridine; acetic acid; 2-hydroxy-propionitrile
hydrogen cyanide
74-90-8

hydrogen cyanide

water
7732-18-5

water

acetaldehyde
75-07-0

acetaldehyde

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
at 25 - 60℃; Rate constant;
at 25 - 60℃; Equilibrium constant;
hydrogen cyanide
74-90-8

hydrogen cyanide

acetaldehyde
75-07-0

acetaldehyde

K2CO3

K2CO3

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
at 25 - 30℃;
Acetyl cyanide
631-57-2

Acetyl cyanide

hydrogen

hydrogen

A

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

B

propiononitrile
107-12-0

propiononitrile

Conditions
ConditionsYield
at 200 - 225℃; Nickel-Kieselgur-Katalysator;
L-threonine
72-19-5

L-threonine

A

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

B

CO2

CO2

Conditions
ConditionsYield
With formaldehyd; perchloric acid; bromamine T In water at 29.9℃; Kinetics; Mechanism; Thermodynamic data; E(activ.), ΔG(excit.), ΔH(excit.), ΔS(excit.); other temperatures and solvent, effect of acid concentration, no influence of ionic strength and tosylamine addition;
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2-Hydroxy-propionimidic acid ethyl ester hydrochloride

2-Hydroxy-propionimidic acid ethyl ester hydrochloride

Conditions
ConditionsYield
In diethyl ether; ethanol99%
In diethyl ether; ethanol815 g (99%)
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

1-cyanoethyl p-toluenesulfonate
33695-65-7

1-cyanoethyl p-toluenesulfonate

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; toluene at 0 - 25℃;98.34%
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

1-cyanoethyl p-nitrobenzenesulfonate

1-cyanoethyl p-nitrobenzenesulfonate

Conditions
ConditionsYield
With sodium hydroxide at 0 - 10℃;98.34%
4-chlorobenzenesulfonyl chloride
98-60-2

4-chlorobenzenesulfonyl chloride

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

p-chlorobenzenesulfonic acid 1-cyanoethyl ester
33695-77-1

p-chlorobenzenesulfonic acid 1-cyanoethyl ester

Conditions
ConditionsYield
With sodium carbonate at 0 - 25℃;97.52%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2-[(methylsulfonyl)oxy]propanenitrile
6839-20-9

2-[(methylsulfonyl)oxy]propanenitrile

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃; for 24h;96.78%
With triethylamine In dichloromethane at 0℃; for 0.5h; Mesylation;91%
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Ethanesulfonyl chloride
594-44-5

Ethanesulfonyl chloride

2-[(ethylsulfonyl)oxy]propanenitrile

2-[(ethylsulfonyl)oxy]propanenitrile

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In toluene at 0 - 10℃; for 24h;96.01%
With triethylamine In dichloromethane at 0 - 20℃; for 3.5h; Substitution;88%
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

Conditions
ConditionsYield
Stage #1: 2-hydroxy-propionitrile With Caproamide; acetic acid at 50℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: With palladium (II) nitrate at 50℃; for 0.166667h; Schlenk technique; Inert atmosphere;
96%
With CF3O3S(1-)*C36H35ClFeOP3Pt(1+); water; silver trifluoromethanesulfonate In tetrahydrofuran at 40℃; for 12h; Catalytic behavior; Inert atmosphere;93%
With [RuCl2(η3:η3-C10H16){PMe2(OH)}]; water at 20℃; for 72h; Inert atmosphere; Schlenk technique; Sealed tube;85%
benzoyl chloride
98-88-4

benzoyl chloride

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2-benzoyloxy-1-butyronitrile
98777-16-3

2-benzoyloxy-1-butyronitrile

Conditions
ConditionsYield
In pyridine at 20℃; for 2h;96%
With triethylamine In dichloromethane at 0 - 20℃;85%
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2-hydroxypropanethioamide

2-hydroxypropanethioamide

Conditions
ConditionsYield
With hydrogenchloride; thiophosphate sodium salt hydrate In water; water-d2 at 50℃; for 24h; pH=6.5; Sealed tube;96%
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-cyanoethyl benzenesulfonate
10531-15-4

1-cyanoethyl benzenesulfonate

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0 - 20℃; for 24h;95.2%
trifluoromethane sulfonyl chloride
421-83-0

trifluoromethane sulfonyl chloride

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

1-cyanoethyl trifluoromethanesulfonate
1403873-31-3

1-cyanoethyl trifluoromethanesulfonate

Conditions
ConditionsYield
With potassium carbonate at 0 - 25℃; for 20h;94.13%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2-[(tert-butyldimethylsilyl)oxy]propanenitrile
114711-04-5

2-[(tert-butyldimethylsilyl)oxy]propanenitrile

Conditions
ConditionsYield
With triethylamine; 2,8,9-Trimethyl-2,5,8,9-tetraaza-1-phospha-bicyclo[3.3.3]undecane 1-oxide In [D3]acetonitrile at 25℃; for 6h;94%
With P(MeNCH2CH2)3N; triethylamine In acetonitrile at 24℃; for 0.2h;90%
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;70%
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

1-cyanoethyl 4-bromobenzoate
1569086-99-2

1-cyanoethyl 4-bromobenzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;94%
ClNH4

ClNH4

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

alanine amide
4726-84-5

alanine amide

Conditions
ConditionsYield
With sodium hydroxide In ammonium hydroxide; acetone92%
n-vinylformamide
13162-05-5

n-vinylformamide

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

N-[α-(α'-cyanoethoxy)ethyl]formamide

N-[α-(α'-cyanoethoxy)ethyl]formamide

Conditions
ConditionsYield
With boron trifluoride at 0℃; for 18h; Addition;91%
oxalyl dichloride
79-37-8

oxalyl dichloride

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

3,5-dichloro-6-methyl-2(H)-1,4-oxazin-2-one
125849-94-7

3,5-dichloro-6-methyl-2(H)-1,4-oxazin-2-one

Conditions
ConditionsYield
With triethylamine hydrochloride In chlorobenzene at 90℃; for 3h;90%
With triethylamine hydrochloride In chlorobenzene at 90℃; for 3h; Inert atmosphere;90%
Stage #1: oxalyl dichloride; 2-hydroxy-propionitrile In chlorobenzene at 0℃;
Stage #2: With triethylamine hydrochloride In chlorobenzene at 0 - 90℃; Inert atmosphere;
81%
ethanol
64-17-5

ethanol

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2-Hydroxy-propionimidic acid ethyl ester hydrochloride

2-Hydroxy-propionimidic acid ethyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at -5 - 26℃; for 18h;90%
With hydrogenchloride In diethyl ether at 0 - 5℃; for 48h;
4-methoxy-aniline
104-94-9

4-methoxy-aniline

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2-((4-methoxyphenyl)amino)propanenitrile

2-((4-methoxyphenyl)amino)propanenitrile

Conditions
ConditionsYield
In ethanol for 18h; Reflux;90%
With titanium(IV) isopropylate In toluene at 40℃; for 18h; Inert atmosphere; Glovebox;56%
ethyl vinyl ether
109-92-2

ethyl vinyl ether

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2-<(1'-ethoxy)ethoxy> propionitrile
53411-95-3

2-<(1'-ethoxy)ethoxy> propionitrile

Conditions
ConditionsYield
With hydrogenchloride at 80℃; for 3h;88%
With acid
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2,N-dihydroxy-propionamidine
52046-55-6

2,N-dihydroxy-propionamidine

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride In ethanol at 20℃;87%
With hydroxylamine hydrochloride; sodium ethanolate
With hydroxylamine hydrochloride; water; sodium carbonate
methanol
67-56-1

methanol

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

methyl lactate
547-64-8

methyl lactate

Conditions
ConditionsYield
With hydrogenchloride; water at -10 - -5℃; for 4h; Reflux;85.58%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

1-cyanoethyl trifluoromethanesulfonate
1403873-31-3

1-cyanoethyl trifluoromethanesulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 0.25h; Inert atmosphere;82%
ammonium carbonate
506-87-6

ammonium carbonate

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

A

α-ureido-propionamide
39121-77-2

α-ureido-propionamide

B

methyl-5 hydantoine
67337-69-3

methyl-5 hydantoine

Conditions
ConditionsYield
In water at 50℃; for 4h; pH=7.9;A 20%
B 80%
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

2-hydroxypropiophenone
5650-40-8

2-hydroxypropiophenone

Conditions
ConditionsYield
In diethyl ether for 0.25h; Heating;80%
(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

2-[(2,6-dimethylimidazo[1,2-a]pyridine-3-yl)amino]propanenitrile
1176904-05-4

2-[(2,6-dimethylimidazo[1,2-a]pyridine-3-yl)amino]propanenitrile

Conditions
ConditionsYield
Stage #1: (5-methyl-pyridin-2-yl)amine; 2-hydroxy-propionitrile With silica-gel-supported sulfuric acid at 20℃;
Stage #2: With ammonia In water
80%
2-hydroxy-propionitrile
78-97-7

2-hydroxy-propionitrile

diethyl malonate
105-53-3

diethyl malonate

ethyl 4-amino-2,5-dihydro-5-methyl-2-oxo-3-furancarboxylate
139003-80-8

ethyl 4-amino-2,5-dihydro-5-methyl-2-oxo-3-furancarboxylate

Conditions
ConditionsYield
With tin(IV) chloride In ethyl acetate for 48h; Ambient temperature;79%

78-97-7Relevant articles and documents

Photochemical reductive homologation of hydrogen cyanide using sulfite and ferrocyanide

Xu, Jianfeng,Ritson, Dougal J.,Ranjan, Sukrit,Todd, Zoe R.,Sasselov, Dimitar D.,Sutherland, John D.

supporting information, p. 5566 - 5569 (2018/06/04)

Photoredox cycling during UV irradiation of ferrocyanide ([FeII(CN)6]4-) in the presence of stoichiometric sulfite (SO32-) is shown to be an extremely effective way to drive the reductive homologation

2 - methyl malonic acid diester synthetic method of the compound

-

Paragraph 0033-0036, (2017/08/10)

The invention discloses a synthetic method of 2-diester methylmalonate compounds, and relates to the technical field of carboxylic ester preparation. The synthetic method comprises steps as follows: C, sulfonic acid 2-ethyl N-cyanoethanimideate IV and cyanide react under the action of a solvent and a catalyst, and 2-methyl malononitrile V is obtained; D, 2-methyl malononitrile V and ROH react under the action of the solvent and concentrated sulfuric acid, and products of 2-diester methylmalonate compounds I are obtained, wherein MCN is cyanide, M is Na or K, ROH is alkyl alcohol, alkenyl alcohol or a fluoride group containing alcohol, is benzyl alcohol or benzyl alkyl, halogen or nitro substituted benzyl alcohol, or is phenol or C1-C5 containing alkyl, halogen or nitro substituted phenol. The method is unique, the reaction conditions are mild, the reaction process is basically free of by-products, the yield is high, adopted raw materials have extensive sources, and acetaldehyde can be used as the raw material; the synthetic method is applicable to industrial production.

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles

Kadunce, Nathaniel T.,Reisman, Sarah E.

supporting information, p. 10480 - 10483 (2015/09/28)

A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild conditions at room temperature and precludes the need to pregenerate organometallic nucleophiles.

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