2-Cyano-4-methylpyridine supplier

Name
2-CYANO-4-METHYLPYRIDINE
EINECS -0
CAS No. 1620-76-4
Article Data34
CAS DataBase
Density 1.08 g/cm³
Solubility Slightly soluble in water.
Melting Point 88-91 °C
Formula C₇H₆N₂
Boiling Point 261.1 °C at 760 mmHg
Molecular Weight 118.138
Flash Point 99.9 °C
Transport Information UN 3276
Appearance
Safety 26-39
Risk Codes 22-37/38-41
Molecular Structure
Hazard Symbols Xi
Synonyms Picolinonitrile,4-methyl- (6CI,7CI,8CI);4-Methyl-2-cyanopyridine;4-Methyl-2-pyridinecarbonitrile;
PSA 36.68000
LogP 1.26168

Synthetic route

: 1003-67-4
4-methylpyridine-1-oxide

: 7677-24-9
trimethylsilyl cyanide

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
With N,N-Dimethylcarbamoyl chloride In dichloromethane for 120h; Ambient temperature;	100%
Stage #1: 4-methylpyridine-1-oxide; trimethylsilyl cyanide With N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; for 24h; Stage #2: With potassium carbonate In dichloromethane; water for 0.5h;	96%
With triethylamine In acetonitrile at 100 - 110℃; for 20h;	89%

: 108-89-4
picoline

: 151-50-8
potassium cyanide

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
Stage #1: picoline With nitric acid; trifluoroacetic anhydride at 20℃; Stage #2: potassium cyanide With sodium acetate at 20℃; for 12h;	42%

: 151-50-8
potassium cyanide

: 51384-29-3
1-methoxy-4-methylpyridin-1-ium methyl sulfate

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
In ethanol; water at -18 - -12℃; for 3h;	35%

: 1003-67-4
4-methylpyridine-1-oxide

: 77-78-1
dimethyl sulfate

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
In water	6.78%
Behandeln mit Kaliumcyanid in wss. Dioxan;

: 3678-62-4
2-chloro-4-picoline

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
With water; sodium sulfite at 180 - 190℃; Schmelzen des Reaktionsprodukts mit KCN;

: 460-19-5
ethanedinitrile

: 78-79-5
isoprene

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
at 490℃;
at 490℃;

: 1003-67-4
4-methylpyridine-1-oxide

: 151-50-8
potassium cyanide

: 77-78-1
dimethyl sulfate

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
1.) reflux, 5 h, 2.) water, 4 deg C; Yield given. Multistep reaction;

...Expand

: 100-70-9
2-Cyanopyridine

: 67-56-1
methanol

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
With sulfuric acid Irradiation; Co-60 γ-rays;

: 143-33-9
sodium cyanide

1-methoxy-4-methyl-pyridinium-methyl sulfate: 1-methoxy-4-methyl-pyridinium-methyl sulfate

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
With water

: 151-50-8
potassium cyanide

1-methoxy-4-methyl-pyridinium-methyl sulfate: 1-methoxy-4-methyl-pyridinium-methyl sulfate

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
With 1,4-dioxane; water

: 4926-28-7
2-Bromo-4-picoline

CuCN: CuCN

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
unter vermindertem Druck;

: 1003-67-4
4-methylpyridine-1-oxide

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 3 h / 90 - 100 °C 2: 35 percent / H2O; ethanol / 3 h / -18 - -12 °C View Scheme

: 1003-67-4
4-methylpyridine-1-oxide

1,8-Diazabicyclo[5.4.0]undec-7-ene [DBU]: 1,8-Diazabicyclo[5.4.0]undec-7-ene [DBU]

: 7677-24-9
trimethylsilyl cyanide

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
In tetrahydrofuran

...Expand

: 1003-67-4
4-methylpyridine-1-oxide

: 79-44-7
N,N-Dimethylcarbamoyl chloride

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane; water

: 108-89-4
picoline

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid; dihydrogen peroxide / 24 h / Reflux 2.1: N,N-Dimethylcarbamoyl chloride / dichloromethane / 24 h / 20 °C 2.2: 0.5 h View Scheme

: 59576-26-0
2-acetyl-4-methylpyridine

: 1620-76-4
2-Cyano-4-methylpyridin

Conditions

Conditions	Yield
With ammonia; iodine In tetrahydrofuran; water

: 1620-76-4
2-Cyano-4-methylpyridin

: 123811-73-4
4-Methyl-pyridine-2-carboxylic acid; hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride for 24h; Heating;	93%

: 1620-76-4
2-Cyano-4-methylpyridin

: 925-90-6
ethylmagnesium bromide

: 1-(4-methylpyridin-2-yl)propan-1-one

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin; ethylmagnesium bromide In tetrahydrofuran; diethyl ether at -15 - 20℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethylene glycol at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;	87%
Stage #1: 2-Cyano-4-methylpyridin; ethylmagnesium bromide In diethyl ether at -15 - 20℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water at 20℃; for 0.25h; Inert atmosphere;	77%
In tetrahydrofuran

: 1620-76-4
2-Cyano-4-methylpyridin

: 129768-95-2
1-(4-methylpyridin-2-yl)methanamine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere;	86%
Stage #1: 2-Cyano-4-methylpyridin With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol; water for 14h; Stage #2: With sodium hydroxide In methanol; water pH=12;

: 1620-76-4
2-Cyano-4-methylpyridin

: 64-17-5
ethanol

: 58997-09-4
ethyl 4-methyl-2-pyridinecarboxylate

Conditions

Conditions	Yield
With hydrogenchloride Reflux;	86%

: 1620-76-4
2-Cyano-4-methylpyridin

: 4021-08-3
4-methylpicolinic acid

Conditions

Conditions	Yield
With hydrogenchloride In water for 24h; Heating / reflux;	85%
With sodium carbonate; sodium sulfite In sulfuric acid; water	53.8%
With water; potassium hydroxide for 1h; Reflux;	3.26 g
With hydrogenchloride

: 1620-76-4
2-Cyano-4-methylpyridin

: 5470-49-5
4-methanesulfonylphenylamine

: 177662-59-8
4-methyl-N-[4-(methylsulfonyl)phenyl]-2-pyridinecarboximidamide

Conditions

Conditions	Yield
Stage #1: 4-methanesulfonylphenylamine With trimethylaluminum In 1,2-dichloro-ethane; toluene at 0℃; for 1.5h; Stage #2: 2-Cyano-4-methylpyridin In 1,2-dichloro-ethane; toluene for 20h; Heating / reflux;	85%

: 1620-76-4
2-Cyano-4-methylpyridin

: 23491-49-8
2-amino-4-<5'-(4''-methylpiperazin-1''-yl)benzimidazol-2'-yl>aniline

: 1339044-77-7
4-methyl-2-(5'-(5''-(4'''-methylpiperazin-1'''-yl)benzimidazol-2''-yl)benzimidazol-2'-yl)pyridine

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin With methanol; sodium methylate at 40℃; for 2h; Inert atmosphere; Stage #2: 2-amino-4-<5'-(4''-methylpiperazin-1''-yl)benzimidazol-2'-yl>aniline With acetic acid In methanol for 21h; Reflux; Inert atmosphere; Stage #3: With ammonia In water for 0.75h;	83%

: 1620-76-4
2-Cyano-4-methylpyridin

: 4-methylpyridinyl-2-hydrazonamide

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol at 0 - 40℃; for 23h;	78.4%

: 1620-76-4
2-Cyano-4-methylpyridin

: 873692-91-2
[2-(3-bromo-benzo[b]thiophen-2-yl)-ethyl]dimethyl-amine

: [2-(2-dimethylaminoethyl)benzo[b]thiophen-3-yl]pyridin-2-ylmethanone

Conditions

Conditions	Yield
Stage #1: [2-(3-bromo-benzo[b]thiophen-2-yl)-ethyl]dimethyl-amine With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In cyclohexane; toluene at -78 - 60℃; for 0.5h; Stage #2: 2-Cyano-4-methylpyridin In cyclohexane; toluene at -78℃; for 0.5h; Stage #3: With hydrogenchloride; methanol; sodium hydroxide; water more than 3 stages;	78%

: 1620-76-4
2-Cyano-4-methylpyridin

: 4-(5-morpholin-4-yl-1(3)H-benzoimidazol-2-yl)-benzene-1,2-diamine

: 1339045-14-5
2-(5'-(5''-morpholinobenzimidazol-2''-yl)benzimidazol-2'-yl)-4-methylpyridine

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin With methanol; sodium methylate at 40℃; for 1.5h; Inert atmosphere; Stage #2: 4-(5-morpholin-4-yl-1(3)H-benzoimidazol-2-yl)-benzene-1,2-diamine With acetic acid In methanol for 18h; Reflux; Inert atmosphere; Stage #3: With ammonia In water	73%

: 1620-76-4
2-Cyano-4-methylpyridin

: 102477-61-2
1,3,5-tris(4-methyl-2-pyridyl)-2,4,6-triazine

Conditions

Conditions	Yield
With sodium hydride In mineral oil at 125℃; for 24h; Inert atmosphere;	71%

: 1620-76-4
2-Cyano-4-methylpyridin

: 170487-39-5
2-cyano-4-methylpyridine N-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Cooling;	71%

: 1620-76-4
2-Cyano-4-methylpyridin

: 112245-13-3
(S)-tert-leucinol

: 1257527-18-6
(S)-4-(tert-butyl)-2-(4-methylpyridin-2-yl)-4,5-dihydrooxazole

Conditions

Conditions	Yield
With zinc trifluoromethanesulfonate In toluene for 24h; Inert atmosphere; Schlenk technique; Reflux;	70%

: 1620-76-4
2-Cyano-4-methylpyridin

: 100-59-4
phenylmagnesium chloride

: 847923-56-2
C-(5-methyl-pyridin-2-yl)-C-phenyl-methylamine

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin; phenylmagnesium chloride In tetrahydrofuran; toluene at 0 - 5℃; for 1h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; 2-methyl-propan-1-ol; toluene at 20℃;	69%

: 1620-76-4
2-Cyano-4-methylpyridin

: 153993-99-8
4-(bromomethyl)pyridine-2-carbonitrile

Conditions

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 77℃; for 4h;	67%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Heating; photolysis;	250 mg
Stage #1: 2-Cyano-4-methylpyridin With acetic acid In tetrachloromethane at 20 - 50℃; Stage #2: With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 50 - 80℃; for 18h;
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; Inert atmosphere;

: 1620-76-4
2-Cyano-4-methylpyridin

: 4892-02-8
Methyl thiosalicylate

: 501376-13-2
2-(4-Methyl-2-pyridyl)-4H-1,3-benzothiazine-4-one

Conditions

Conditions	Yield
With triethylamine In toluene for 8h; Heating / reflux;	64%

: 1620-76-4
2-Cyano-4-methylpyridin

: 87555-65-5
N'-(6,7-dihydroquinolin-8(5H)-ylidene)-4-(pyridine-2-yl)piperazine-1-carbothiohydrazide

: 1538612-17-7
4-methyl-N'-(4-(pyridin-2-yl)piperazine-1-carbonothioyl)picolinohydrazonamide

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin With sodium In methanol for 0.5h; Stage #2: N'-(6,7-dihydroquinolin-8(5H)-ylidene)-4-(pyridine-2-yl)piperazine-1-carbothiohydrazide In methanol for 4h; Reflux;	63%
Stage #1: 2-Cyano-4-methylpyridin With methanol; sodium for 0.5h; Stage #2: N'-(6,7-dihydroquinolin-8(5H)-ylidene)-4-(pyridine-2-yl)piperazine-1-carbothiohydrazide for 1h; Stage #3: With methanol for 4h; Reflux;	63%

: 1620-76-4
2-Cyano-4-methylpyridin

: 1339045-98-5
2-amino-4-(5'-(4''-hydroxypiperidin-1''-yl)benzimidazol-2'-yl)aniline

: 1339045-73-6
2-(5'-(5''-(4'''-hydroxypiperidin-1'''-yl)benzimidazol-2''-yl)benzimidazol-2'-yl)-4-methylpyridine

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin With methanol; sodium methylate at 40 - 45℃; for 1.83333h; Inert atmosphere; Stage #2: 2-amino-4-(5'-(4''-hydroxypiperidin-1''-yl)benzimidazol-2'-yl)aniline With acetic acid In methanol for 19h; Reflux; Inert atmosphere; Stage #3: With ammonia In water pH=8 - 9;	61%

: 1620-76-4
2-Cyano-4-methylpyridin

: 100-58-3
phenylmagnesium bromide

: 18103-76-9
phenyl(4-methylpyridin-2-yl)methanimine

Conditions

Conditions	Yield
In toluene at -40 - 20℃; for 12h;	60%

: 1620-76-4
2-Cyano-4-methylpyridin

: 420-37-1
trimethoxonium tetrafluoroborate

: N,4-dimethyl-2-pyridinium-carbonitrile tetrafluoroborate

Conditions

Conditions	Yield
In acetone at 20℃; for 17h;	59%

: 1620-76-4
2-Cyano-4-methylpyridin

: 917-64-6
methyl magnesium iodide

: 59576-26-0
2-acetyl-4-methylpyridine

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin; methyl magnesium iodide In diethyl ether; benzene at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: With water; ammonium chloride In diethyl ether; benzene Inert atmosphere;	52%
With diethyl ether; benzene Behandeln des Reaktionsgemisches mit wss.Ammoniumchlorid-Loesung;

: 1620-76-4
2-Cyano-4-methylpyridin

: 85148-98-7
4-Dichloromethyl-2-cyanopyridine

Conditions

Conditions	Yield
With sulfuryl dichloride; dibenzoyl peroxide In tetrachloromethane for 24h; Heating; Irradiation;	47%

: 1620-76-4
2-Cyano-4-methylpyridin

: 6507-37-5
azepane-1-carbothioic acid hydrazide

: 1538612-13-3
4-methyl-N'-(azepane-1-carbonothioyl)picolinohydrazonamide

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin With sodium In methanol for 0.5h; Stage #2: azepane-1-carbothioic acid hydrazide In methanol for 4h; Reflux;	45%
Stage #1: 2-Cyano-4-methylpyridin With methanol; sodium for 0.5h; Stage #2: azepane-1-carbothioic acid hydrazide for 1h; Stage #3: With methanol for 4h; Reflux;	45%

: 1620-76-4
2-Cyano-4-methylpyridin

: 53547-60-7
4-methyl-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h;	41%
Multi-step reaction with 2 steps 1: hydrogenchloride / Reflux 2: diisobutylaluminium hydride / dichloromethane / 0.08 h / -60 °C View Scheme

: 1620-76-4
2-Cyano-4-methylpyridin

: 6499-15-6
4-morpholinothiosemicarbazide

: 1538612-03-1
4-methyl-N'-(morpholine-4-carbonothioyl)picolinohydrazonamide

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin With sodium In methanol for 0.5h; Stage #2: 4-morpholinothiosemicarbazide In methanol for 4h; Reflux;	41%
Stage #1: 2-Cyano-4-methylpyridin With methanol; sodium for 0.5h; Stage #2: 4-morpholinothiosemicarbazide for 1h; Stage #3: With methanol for 4h; Reflux;	41%

: 1620-76-4
2-Cyano-4-methylpyridin

: 102854-88-6
diisobutyl aluminium hydride

: 53547-60-7
4-methyl-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
In dichloromethane; toluene at -78℃; for 2h;	37%

: 1620-76-4
2-Cyano-4-methylpyridin

: 41197-43-7
thiomorpholine-4-carbothiohydrazide

: 1538612-08-6
4-methyl-N'-(thiomorpholine-4-carbonothioyl)picolinohydrazonamide

Conditions

Conditions	Yield
Stage #1: 2-Cyano-4-methylpyridin With sodium In methanol for 0.5h; Stage #2: thiomorpholine-4-carbothiohydrazide In methanol for 4h; Reflux;	32%
Stage #1: 2-Cyano-4-methylpyridin With methanol; sodium for 0.5h; Stage #2: thiomorpholine-4-carbothiohydrazide for 1h; Stage #3: With methanol for 4h; Reflux;	32%

2-Cyano-4-methylpyridine Specification

The 2-Cyano-4-methylpyridine, with the CAS registry number 1620-76-4, has the systematic name of 4-methylpyridine-2-carbonitrile. It belongs to the the product categories of Pyridines and Heterocyclic Compounds. And the molecular formula of the chemical is C₇H₆N₂.

The characteristics of this chemical are as followings: (1)ACD/LogP: 0.97; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.97; (4)ACD/LogD (pH 7.4): 0.97; (5)ACD/BCF (pH 5.5): 3.22; (6)ACD/BCF (pH 7.4): 3.22; (7)ACD/KOC (pH 5.5): 80.46; (8)ACD/KOC (pH 7.4): 80.46; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 36.68 Å²; (13)Index of Refraction: 1.531; (14)Molar Refractivity: 33.74 cm³; (15)Molar Volume: 108.9 cm³; (16)Polarizability: 13.37×10^-24cm³; (17)Surface Tension: 47.9 dyne/cm; (18)Density: 1.08 g/cm³; (19)Flash Point: 99.9 °C; (20)Enthalpy of Vaporization: 49.89 kJ/mol; (21)Boiling Point: 261.1 °C at 760 mmHg; (22)Vapour Pressure: 0.0117 mmHg at 25°C.

Preparation of 2-Cyano-4-methylpyridine: This chemical can be prepared by 4-methyl-pyridine-1-oxide and trimethyl-silanecarbonitrile. The reaction will need reagent DBU, and the menstruum tetrahydrofuran. The reaction time is 5 hours with heating, and the yield is about 44%.

Uses of 2-Cyano-4-methylpyridine: It can react to produce C₇H₇NO₂^.ClH. This reaction will need reagent 6 NHCl. The reaction time is 24 hours with heating, and the yield is about 93%.

You should be cautious while dealing with this chemical. It irritats to eyes and respiratory system, and is harmful if swallowed, what's more, it has risk of serious damage to eyes. Therefore, you had better take the following instructions: Wear suitable protective eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: N#Cc1nccc(c1)C
(2)InChI: InChI=1/C7H6N2/c1-6-2-3-9-7(4-6)5-8/h2-4H,1H3
(3)InChIKey: LQAWSWUFSHYCHP-UHFFFAOYAC

Product Name

2-CYANO-4-METHYLPYRIDINE

Synthetic route

2-Cyano-4-methylpyridine Specification

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