3397-62-4

Basic information

• Product Name: 2-CHLORO-4,6-DIAMINO-1,3,5-TRIAZINE
• Synonyms: TIMTEC-BB SBB004112;6-CHLORO-1,3,5-TRIAZINE-2,4-DIAMINE;6-CHLORO-2,4-DIAMINO-S-TRIAZINE;2,4-DIAMINO-6-CHLORO-1,3,5-TRIAZINE;2 4-DIAMINO-6-CHLORO-SYM-TRIAZINE;2-CHLORO-4,6-DIAMINO-1,3,5-TRIAZINE;2-CHLORO-4,6-DIAMINO-S-TRIAZINE;2-CHLORO-2,6-DIAMINO-1,3,5-TRIAZINE
• CAS NO: 3397-62-4
• Molecular Formula: C₃H₄ClN₅
• Molecular Weight: 145.55
• EINECS: 222-260-6
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;A;A-BAlphabetic;Alpha sort;AR to AZEnvironmental Standards;Herbicides;MetabolitesPesticides&Metabolites;Pesticides&Metabolites;Triazines;Amines, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 3397-62-4.mol
• Article Data: 22

Chemical Properties

• Melting Point: >320 °C(lit.)
• Boiling Point: 237.97°C (rough estimate)
• Flash Point: 11 °C
• Appearance: white to pale yellow crystalline powder
• Density: 1.700
• Vapor Pressure: 1.14E-09mmHg at 25°C
• Refractive Index: 1.6110 (estimate)
• Storage Temp.: APPROX 4°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.90±0.10(Predicted)
• BRN: 124340
• CAS DataBase Reference: 2-CHLORO-4,6-DIAMINO-1,3,5-TRIAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-4,6-DIAMINO-1,3,5-TRIAZINE(3397-62-4)
• EPA Substance Registry System: 2-CHLORO-4,6-DIAMINO-1,3,5-TRIAZINE(3397-62-4)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 36/37/38-20/21/22-39/23/24/25-23/24/25-11
• Safety Statements: 22-24/25-45-36/37-16-7
• RIDADR: UN1230 3/PG 2
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3397-62-4(Hazardous Substances Data)

Usage

Chemical Properties

white to pale yellow crystalline powder

Uses

Different sources of media describe the Uses of 3397-62-4 differently. You can refer to the following data:
1. Desethyldesisopropyl Atrazine is a metabolite of Atrazine (A794600).
2. Atrazine-desethyl-desisopropyl may be used as an analytical reference standard for the quantification of the analyte in environmental samples using different chromatography techniques

InChI:InChI=1/C3H4ClN5/c4-1-7-2(5)9-3(6)8-1/h(H4,5,6,7,8,9)

Synthetic route

1,3,5-trichloro-2,4,6-triazine (108-77-0) → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4)

Conditions	Yield
With ammonium hydroxide In 1,2-dichloro-ethane at 3 - 42℃; for 6h; Temperature; Solvent;	96%
With ammonia In water; acetone at 10℃; for 4h; Heating;	95%
With ammonia In water; acetone at 60℃; for 4h;	91%

terbuthylazine (5915-41-3) → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + deethylterbuthylazine (30125-63-4) + 2-chloro-4-acetamido-6-tert-butylamino-1,3,5-triazine + Deisopropylatrazine (1007-28-9)

Conditions	Yield
With dihydrogen peroxide In water at 25℃; Quantum yield; Oxidation; UV-irradiation;

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine (1912-24-9) → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + Deisopropylhydroxyatrazine (7313-54-4) + Deethylatrazine (6190-65-4) + Hydroxyatrazine (2163-68-0) + 2-amino-4-hydroxy-6-(isopropylamino)-s-triazine + Deisopropylatrazine (1007-28-9)

Conditions	Yield
With titanium(IV) oxide In perchloric acid; water Mechanism; Irradiation; other reagent;

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine (1912-24-9) → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + Deethylatrazine (6190-65-4) + Deisopropylatrazine (1007-28-9)

Conditions	Yield
manganese(IV) oxide In diethyl ether at 30℃; for 72h; Product distribution; Further Variations:; Reagents; Temperatures; Dealkylation;

Deethylatrazine (6190-65-4) → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 2-amino-4-hydroxy-6-(isopropylamino)-s-triazine + 6-Amino-4-acetamido-2-chloro-s-triazine

Conditions	Yield
In water for 60h; pH=6.5; Product distribution; Kinetics; Further Variations:; also in the presence of NaNO3; Decomposition; Photolysis;

Deisopropylatrazine (1007-28-9) → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + Deisopropylhydroxyatrazine (7313-54-4) + 6-Amino-4-acetamido-2-chloro-s-triazine

Conditions	Yield
In water for 60h; pH=6.5; Product distribution; Kinetics; Further Variations:; also in the presence of NaNO3; Decomposition; Photolysis;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + ammonia (7664-41-7) + acetone (67-64-1) → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4)

potassium-salt of N,N'-dicyano-guanidine → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4)

Conditions	Yield
With hydrogenchloride; water

1,3,5-trichloro-2,4,6-triazine (108-77-0) → 4,6-dichloro-1,3,5-triazin-2-amine (933-20-0) + 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4)

Conditions	Yield
With ammonia In diethyl ether 0°C;

Simazine (122-34-9) → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + Deisopropylatrazine (1007-28-9)

Conditions	Yield
With titanium(IV) oxide In water for 0.25h; pH=6; UV-irradiation;

ammeline (645-92-1) → 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4)

Conditions	Yield
With thionyl chloride In toluene at 5 - 65℃; for 0.5h; Temperature;	21.91 g

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + Cyclopropylamine (765-30-0) → cyromazine (66215-27-8)

Conditions	Yield
With sodium hydroxide at 70 - 85℃; for 6h; pH=9.5; pH-value; Temperature;	96.37%
With potassium carbonate In water at 95 - 100℃; for 4h; pH=7.5 - 8.5; Temperature; Reagent/catalyst;	90.1%
With sodium hydroxide at -10 - 10℃; for 10h; Temperature;	24.47 g

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + dimethyl amine (124-40-3) → 2,4-diamino-6-dimethylamino-1,3,5-triazine (1985-46-2)

Conditions	Yield
With sodium hydroxide In water for 4h; Reflux;	96%
In water at 120℃; for 2h; Microwave irradiation; Inert atmosphere;	90%
With ethanol

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + N-butylamine (109-73-9) → 2-n-butylamino-4,6-diamino-1,3,5-triazine (5606-24-6)

Conditions	Yield
In water	96%
With sodium hydroxide
In water at 10 - 85℃; for 6h;

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-[4-(4,6-diamino-[1,3,5]triazin-2-ylamino)-phenyl]-ethanol (291755-52-7)

Conditions	Yield
With sodium hydroxide Condensation; Heating;	96%
With sodium hydroxide for 3.5h; Heating;

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + glycine (56-40-6) → 2-(4,6-diamino-1,3,5-triazin-2-ylamino)ethanoic acid (945035-83-6)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 80℃; for 48h;	95%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + rac-Ala-OH (302-72-7) → 2-(4,6-diamino-1,3,5-triazin-2-ylamino)propanoic acid (118767-71-8)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 150℃; for 4h; Microwave irradiation;	95%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + Boc-Lys-OH (13734-28-6) → (S)-2-((tert-butoxycarbonyl)amino)-6-((4,6-diamino-1,3,5-triazin-2-yl)amino)hexanoic acid (1354418-23-7)

Conditions	Yield
Stage #1: 2-Chloro-4,6-diamino-1,3,5-triazine; Boc-Lys-OH With sodium hydroxide In water at 85℃; Stage #2: With hydrogenchloride In water at 0℃; pH=5;	95%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 4-Aminoacetophenone (99-92-3) → 1-((4-(4,6-diamino-1,3,5-triazin-2-ylamino))phenyl)ethanone

Conditions	Yield
In 1,4-dioxane for 20h; Reflux; Inert atmosphere;	93%
With hydrogenchloride

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + acetic anhydride (108-24-7) → 2,4-diacetylamino-6-chloro-1,3,5-triazine

Conditions	Yield
at 120℃; for 1h;	93%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + N-acetyl-p-phenylenediamine (122-80-5) → 2-(4-acetylaminophenyl)-4,6-diamino-1,3,5-triazine (57230-73-6)

Conditions	Yield
With sodium hydroxide In water for 4.5h; Heating;	92%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + bis(4-aminophenyl)disulfide (722-27-0) → bis(4-melaminophenyl)disulfide

Conditions	Yield
With hydrogenchloride In water at 100℃; for 1h;	91.2%

1,4-dioxane (123-91-1) + 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 1-aminooctadecane (124-30-1) → 2,4-diamino-6-octadecyl-amino-1,3,5-triazine (21840-04-0)

Conditions	Yield
With sodium hydroxide In water; toluene	91%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + quinolin-5-ylboronic acid (355386-94-6) → 2,4-diamino-6-quinolyl-1,3,5-triazine

Conditions	Yield
Stage #1: 2-Chloro-4,6-diamino-1,3,5-triazine; quinolin-5-ylboronic acid With sodium carbonate; tetrakis-(triphenylphosphino)-palladium(0) In 1,4-dioxane for 48h; Suzuki cross-coupling reaction; Heating; Stage #2: In tetrahydrofuran for 1h;	90%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 4-amino-n-butyric acid (56-12-2) → 4-(4,6-diamino-1,3,5-triazin-2-ylamino)butanoic acid (1193812-77-9)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 80℃; for 48h;	90%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 4-bromo-aniline (106-40-1) → 2-N-(4-bromophenyl)-1,3,5-triazine-2,4,6-triamine (93167-96-5)

Conditions	Yield
Stage #1: 2-Chloro-4,6-diamino-1,3,5-triazine; 4-bromo-aniline In water Reflux; Stage #2: With sodium hydroxide In water for 6.5h; Reflux;	90%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + Propargylamine (2450-71-7) → C6H8N6

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 80℃;	88%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 1-amino-2-propene (107-11-9) → N2-propenyl-1,3,5-triazine-2,4,6-triamine (6494-74-2)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 80℃; Inert atmosphere;	85%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) → 4,6-diamino-1,3,5-triazine-2(1H)-thione (767-17-9)

Conditions	Yield
With sodium thiosulfate In ethanol; water Heating;	84%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + aniline yellow (60-09-3) → C15H14N8 (1403756-48-8)

Conditions	Yield
Stage #1: 2-Chloro-4,6-diamino-1,3,5-triazine With hydrogenchloride In 1-methyl-pyrrolidin-2-one; water at 40℃; for 0.5h; Stage #2: aniline yellow In 1-methyl-pyrrolidin-2-one at 100℃; for 5h;	84%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + cystamine dihydrochioride (56-17-7) → C10H18N12S2 (500999-67-7)

Conditions	Yield
With sodium hydroxide In water Reflux;	81%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + propan-1-ol-3-amine (156-87-6) → 3-(4,6-diamino-1,3,5-triazin-2-ylamino)propan-1-ol (91313-29-0)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water at 140℃; for 0.416667h; Microwave irradiation;	80%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 1,4-diaminobutane (110-60-1) → N2-(4-aminobutyl)-1,3,5-triazine-2,4,6-triamine (223494-85-7)

Conditions	Yield
at 130℃;	80%
In ethanol for 18h; Reflux; Inert atmosphere;	58%
at 130℃; for 12h;

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 4-fluoroboronic acid (1765-93-1) → 2,4-diamino-6-(4-fluorophenyl)-1,3,5-triazine (30530-44-0)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane Suzuki cross-coupling reaction; Heating;	77%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 1,12-Diaminododecane (2783-17-7) → C18H34N12

Conditions	Yield
With sodium hydrogencarbonate In ethanol at 80℃; for 19h;	77%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 4-methoxyphenylboronic acid (5720-07-0) → 6-(4-methoxyphenyl)-[1,3,5]-triazine-2,4-diamine (30354-91-7)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane Suzuki cross-coupling reaction; Heating;	76%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + n-Dodecylamine (124-22-1) → 2,4-diamino-6-dodecylamino-1,3,5-triazine (5606-11-1)

Conditions	Yield
With sodium carbonate In 1,4-dioxane for 6h; Reflux;	75%
With sodium hydrogencarbonate In 1,4-dioxane for 6h; Heating;	60%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + N-Boc-1,3-diaminopropane (75178-96-0) → tert-butyl 3-(4,6-diamino-1,3,5-triazin-2-ylamino)propylcarbamate (1158040-48-2)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water at 140℃; for 0.166667h; Microwave irradiation;	75%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 4-methylphenylboronic acid (5720-05-8) → 2,4-diamino-6-(4-methylphenyl)-1,3,5-triazine (19338-12-6)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane Suzuki cross-coupling reaction; Heating;	73%

Upstream product

• 1007-28-9 Deisopropylatrazine 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 645-92-1 ammeline 
• 122-34-9 Simazine 
• 7664-41-7 ammonia 
• 67-64-1 acetone 
• 6190-65-4 Deethylatrazine 
• 1912-24-9 6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine 
• 5915-41-3 terbuthylazine 

Downstream Products

• 64381-89-1 6-aziridin-1-yl-[1,3,5]triazine-2,4-diyldiamine 
• 2827-43-2 6-pyrrolidin-1-yl-[1,3,5]triazine-2,4-diamine 
• 5606-32-6 6-piperidino-[1,3,5]-triazine-2,4-diamine 
• 2827-42-1 2,4-diamino-6-morpholino-1,3,5-triazine 
• 30360-74-8 2,4-diamino-6-(benzyloxy)-s-triazine 
• 645-92-1 ammeline 
• 291755-52-7 2-[4-(4,6-diamino-[1,3,5]triazin-2-ylamino)-phenyl]-ethanol 
• 5606-25-7 2,4-diamino-6-cyclohexylamino-1,3,5-triazine 
• 109114-20-7 N-mono-(5-hydroxy-3-oxapentyl)-melamine 
• 21840-04-0 2,4-diamino-6-octadecyl-amino-1,3,5-triazine 
• 5606-23-5 N-ethyl-[1,3,5]triazine-2,4,6-triamine 
• 66215-27-8 cyromazine 
• 504-08-5 2,4-diamino-1,3,5-triazine 
• 114155-23-6 bis-[4-(4,6-diamino-[1,3,5]triazin-2-ylamino)-phenyl]-sulfone 

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