1973-04-2

Basic information

• Product Name: 2,4-Dichloro-6-methyl-1,3,5-triazine
• Synonyms: 2,4-Dichloro-6-methyl-1,3,5-triazine;2,4-Dichloro-6-methyl-1,3,5-triazine1
• CAS NO: 1973-04-2
• Molecular Formula: C₄H₃Cl₂N₃
• Molecular Weight: 163.99272
• Mol File: 1973-04-2.mol
• Article Data: 29

Chemical Properties

• Melting Point: 97-98 °C
• Boiling Point: 345.3°Cat760mmHg
• Flash Point: 193.4°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 0.000124mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: -0.71±0.10(Predicted)
• CAS DataBase Reference: 2,4-Dichloro-6-methyl-1,3,5-triazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-6-methyl-1,3,5-triazine(1973-04-2)
• EPA Substance Registry System: 2,4-Dichloro-6-methyl-1,3,5-triazine(1973-04-2)

Safety Data

• Hazard Codes: T+,C
• Statements: 14-22-26-34-43
• Safety Statements: 26-28-36/37/39-45
• RIDADR: UN 2923 6.1(8) / PGII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1973-04-2(Hazardous Substances Data)

Usage

Uses

2,4-Dichloro-6-methyltriazine is a reagent used to prepare triazinyl-amines as inhibitors of HIV-1 reverse transcriptase. It is also used in the synthesis of anilinotriazine corticotropin releasing hormone antagonists.

InChI:InChI=1/C4H3Cl2N3/c1-2-7-3(5)9-4(6)8-2/h1H3

Synthetic route

acetonitrile (75-05-8) + cyanogen chloride (506-77-4) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
With hydrogenchloride; aluminum (III) chloride In water; 1,2-dichloro-ethane at -5 - 5℃; for 8h; Reagent/catalyst; Solvent;	99%
With hydrogenchloride; aluminum (III) chloride In dichloromethane at -5 - 5℃; under 750.075 Torr; for 12h;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + methylmagnesium bromide (75-16-1) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
In diethyl ether; dichloromethane at 0 - 22℃; for 3h; Inert atmosphere;	90%
In diethyl ether; dichloromethane at 0 - 20℃;	89%
In diethyl ether; dichloromethane at -10 - -5℃; for 4h;	87%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + methylmagnesium chloride (676-58-4) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
In dichloromethane at -20 - -15℃; for 4.5h;	65%
In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;
In dichloromethane at 20℃; for 0.5h;

1,3,5-trichloro-2,4,6-triazine (108-77-0) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
With methylmagnesium bromide; magnesium sulfate In dichloromethane; water	65%

sodium dicyanamide (1934-75-4) + acetyl chloride (75-36-5) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
With hydrogenchloride In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; acetic acid methyl ester	37%

4-amino-2-(3-methyl-but-2-enyloxy)-benzonitrile (915774-28-6) + 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) → 4-(4-chloro-6-methyl-[1,3,5]triazin-2-ylamino)-2-(3-methyl-but-2-enyloxy)-benzonitrile (933045-45-5)

Conditions	Yield
With sodium hydrogencarbonate	98%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + N-({2-[(trifluoromethyl)oxy]phenyl}methyl)-2,3-dihydro-1H-indole-5-carboxamide (1141898-92-1) → 1-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-N-({2-[(trifluoromethyl)oxy]phenyl}methyl)-2,3-dihydro-1H-indole-5-carboxamide (1141899-73-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; for 1h; Product distribution / selectivity;	91%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
With ammonia In acetone at 40 - 45℃;	87%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 4-Isopropylaniline (99-88-7) → C13H15ClN4

Conditions	Yield
In acetone at 20℃; for 1h;	85%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + C20H40N3(1+)*Br(1-) → C24H42ClN6(1+)*Br(1-)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3.25h;	83%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 1-methyl-3-(2-hydroxyethyl)imidazolium bromide (97513-90-1) → C10H13ClN5O(1+)*Br(1-)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3.25h;	83%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + benzaldehyde (100-52-7) → (E)-6-styryl-1,3,5-triazine-2,4-diol

Conditions	Yield
With hydrogenchloride; water at 100℃; for 12h;	79%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + cis-4-amino-N-{[2-(trifluoromethyl)phenyl]methyl}cyclohexane carboxamide → cis-4-[(4-chloro-6-methyl-1,3,5-triazin-2-yl)amino]-N-{[2-(trifluoromethyl)phenyl]methyl}cyclohexanecarboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3h;	78%

acetonitrile (75-05-8) + cyanogen chloride (506-77-4) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
With hydrogenchloride; aluminum (III) chloride In water; 1,2-dichloro-ethane at -5 - 5℃; for 8h; Reagent/catalyst; Solvent;	99%
With hydrogenchloride; aluminum (III) chloride In dichloromethane at -5 - 5℃; under 750.075 Torr; for 12h;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + methylmagnesium bromide (75-16-1) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
In diethyl ether; dichloromethane at 0 - 22℃; for 3h; Inert atmosphere;	90%
In diethyl ether; dichloromethane at 0 - 20℃;	89%
In diethyl ether; dichloromethane at -10 - -5℃; for 4h;	87%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + methylmagnesium chloride (676-58-4) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
In dichloromethane at -20 - -15℃; for 4.5h;	65%
In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;
In dichloromethane at 20℃; for 0.5h;

1,3,5-trichloro-2,4,6-triazine (108-77-0) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
With methylmagnesium bromide; magnesium sulfate In dichloromethane; water	65%

sodium dicyanamide (1934-75-4) + acetyl chloride (75-36-5) → 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2)

Conditions	Yield
With hydrogenchloride In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; acetic acid methyl ester	37%

4-amino-2-(3-methyl-but-2-enyloxy)-benzonitrile (915774-28-6) + 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) → 4-(4-chloro-6-methyl-[1,3,5]triazin-2-ylamino)-2-(3-methyl-but-2-enyloxy)-benzonitrile (933045-45-5)

Conditions	Yield
With sodium hydrogencarbonate	98%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + N-({2-[(trifluoromethyl)oxy]phenyl}methyl)-2,3-dihydro-1H-indole-5-carboxamide (1141898-92-1) → 1-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-N-({2-[(trifluoromethyl)oxy]phenyl}methyl)-2,3-dihydro-1H-indole-5-carboxamide (1141899-73-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 40℃; for 1h; Product distribution / selectivity;	91%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
With ammonia In acetone at 40 - 45℃;	87%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 4-Isopropylaniline (99-88-7) → C13H15ClN4

Conditions	Yield
In acetone at 20℃; for 1h;	85%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + C20H40N3(1+)*Br(1-) → C24H42ClN6(1+)*Br(1-)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3.25h;	83%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 1-methyl-3-(2-hydroxyethyl)imidazolium bromide (97513-90-1) → C10H13ClN5O(1+)*Br(1-)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3.25h;	83%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + benzaldehyde (100-52-7) → (E)-6-styryl-1,3,5-triazine-2,4-diol

Conditions	Yield
With hydrogenchloride; water at 100℃; for 12h;	79%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + cis-4-amino-N-{[2-(trifluoromethyl)phenyl]methyl}cyclohexane carboxamide → cis-4-[(4-chloro-6-methyl-1,3,5-triazin-2-yl)amino]-N-{[2-(trifluoromethyl)phenyl]methyl}cyclohexanecarboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3h;	78%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + sodium thiomethoxide (5188-07-8) → 2-chloro-4-methyl-6-(methylthio)-1,3,5-triazine (78504-09-3)

Conditions	Yield
In toluene at 0℃; for 1.25h; Inert atmosphere;	78%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + Cyclopropylamine (765-30-0) → 2-chloro-4-cyclopropylamino-6-methyl-1,3,5-triazine (148312-27-0)

Conditions	Yield
With potassium carbonate In chloroform	75%

2-chloro-1H-benzoimidazole (4857-06-1) + 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) → 2-chloro-1-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-1H-benzo[d]imidazole (1239980-99-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	73%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane	55%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) → 4-chloro-6-methyl-1,3,5-triazin-2-amine (21320-62-7)

Conditions	Yield
With ammonia In methanol; toluene at 22℃; for 4h; Inert atmosphere;	73%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + N-ethyl-2-bromo-4-isopropylaniline → N-(2-bromo-4-isopropylphenyl)-N-ethyl-2-chloro-6-methyl-1,3,5-triazin-4-amine (169882-09-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane	68%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane for 3h; Heating / reflux;	68%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 2h; Heating;	67%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 2-bromo-4-(dimethylamino)aniline (107100-00-5) → N-<2-bromo-4-(dimethylamino)phenyl>-4-chloro-6-methyltriazin-2-amine (224195-03-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane for 16h; Ambient temperature;	57%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 2-Amino-2-methyl-1-propanol (124-68-5) → 2-(4-chloro-6-methyl-1,3,5-triazin-2-ylamino)-2-methylpropan-1-ol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 0℃; for 0.333333h;	57%

morpholine (110-91-8) + 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 6-bromo-1,2,3,4-tetrahydroisoquinoline (226942-29-6) → 4-(4-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-6-methyl-1,3,5-triazin-2-yl)morpholine

Conditions	Yield
Stage #1: 2,4-dichloro-6-methyl-1,3,5-triazine; 6-bromo-1,2,3,4-tetrahydroisoquinoline With triethylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h; Inert atmosphere; Stage #2: morpholine In 1-methyl-pyrrolidin-2-one at 20℃; for 2h;	54%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + (S)-1-Aminoindane (10277-74-4, 34698-41-4, 61341-86-4, 61949-83-5) → 4-chloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-6-methyl-1,3,5-triazin-2-amine (1007125-33-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; toluene at 0℃; for 0.5h;	53%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamide (791012-39-0) → 1-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamide (1141896-03-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.25h;	52%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 2-chloro-4-(3R,5S-dimethyl-piperazine-1-yl)-6-(1-methoxy-ethyl)-[1,3,5]triazine → 2-chloro-4-[2-(4-chloro-6-methyl-[1,3,5]triazine-2-yl)-3R,5S-dimethyl-piperazine-1-yl]-6-(1-methoxy-ethyl)-[1,3,5]triazine (465530-95-4)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;	49%

2-chloro-4-(3,5-dimethyl-piperazin-1-yl)-6-(1-methoxy-ethyl)-[1,3,5]triazine (465530-94-3) + 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) → 2-chloro-4-[2-(4-chloro-6-methyl-[1,3,5]triazine-2-yl)-3R,5S-dimethyl-piperazine-1-yl]-6-(1-methoxy-ethyl)-[1,3,5]triazine (465530-95-4)

Conditions	Yield
With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 20℃;	49%

2-chloro-4-(3,5-dimethyl-piperazin-1-yl)-6-(1-methoxy-ethyl)-[1,3,5]triazine (465530-94-3) + 2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) → 2-chloro-4-[2-(4-chloro-6-methyl-[1,3,5]triazine-2-yl)-3R,5S-dimethyl-piperazin-1-yl]-6-(1-methoxy-ethyl)-[1,3,5]triazine

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide	49%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 4-trifluoromethylphenylamine (455-14-1) → 4-chloro-6-methyl-N-[4-trifluoromethylphenyl]-1,3,5-triazin-2-amine (852062-22-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 140℃; for 0.0555556h; Microwave irradiation;	48%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → C13H20ClN5O2 (1258197-15-7)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;	47%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃;	47%

2,4-dichloro-6-methyl-1,3,5-triazine (1973-04-2) + (S)-4-((R)-1-fluoroethyl)oxazolidin-2-one → (R)-3-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-4-((S)-1-fluoroethyl)oxazolidin-2-one

Conditions	Yield
Stage #1: (S)-4-((R)-1-fluoroethyl)oxazolidin-2-one With sodium hydride; N-ethyl-N,N-diisopropylamine In diethyl ether; mineral oil at 0℃; for 0.25h; Stage #2: 2,4-dichloro-6-methyl-1,3,5-triazine In diethyl ether; mineral oil at 0℃; for 0.5h;	41.2%

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 75-16-1 methylmagnesium bromide 
• 75-05-8 acetonitrile 
• 506-77-4 cyanogen chloride 
• 1934-75-4 sodium dicyanamide 
• 75-36-5 acetyl chloride 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 30894-86-1 2-chloro-4-diazomethyl-6-methyl-[1,3,5]triazine 
• 287491-84-3 2-(4-benzylidene-piperidin-1-yl)-4-chloro-6-methyl-[1,3,5]triazine 
• 933045-45-5 4-(4-chloro-6-methyl-[1,3,5]triazin-2-ylamino)-2-(3-methyl-but-2-enyloxy)-benzonitrile 
• 1141899-73-1 1-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-N-({2-[(trifluoromethyl)oxy]phenyl}methyl)-2,3-dihydro-1H-indole-5-carboxamide 
• 57639-19-7 4?chloro?N,6?dimethyl?1,3,5?triazin?2?amine 
• 1141895-74-0 1-[4-chloro-6-methyl-1,3,5-triazin-2-yl]-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide 
• 1141896-03-8 1-(4-chloro-6-methyl-1,3,5-triazin-2-yl)-N-[(2,4-dichlorophenyl)methyl]-4-piperidinecarboxamide 
• 542-02-9 2-methyl-4,6-diamino-1,3,5-triazine 
• 1917-34-6 2,4-dihydroxy-6-styrenyl-1,3,5-triazine 

Relevant articles and documents

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NOVEL 2,4,6-TRISUBSTITUTED S-TRIAZINE COMPOUND, PREPARATION METHOD THEREFOR, AND USE THEREOF

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