3140-73-6

Basic information

• Product Name: 2-Chloro-4,6-dimethoxy-1,3,5-triazine
• Synonyms: CDMT;AKOS 89995;2-CHLORO-4,6-DIMETHOXY-1,3,5-TRIAZINE;Chlorodimethoxytriazine;2-CHLORO-4,6-DIMETHOXY-1,3,5-TRIAZINE, 9 7%;2-CHLORO-4,6-DIMETHOXY-1,3,5-TRIAZINE (CDMT);2-CHLORO-4,6-DIMETHOXY-TRIAZINE;2-CHLORO 4,6-DIMETHOX 1,3,5-TRIAZINE
• CAS NO: 3140-73-6
• Molecular Formula: C₅H₆ClN₃O₂
• Molecular Weight: 175.57
• EINECS: 221-541-0
• Product Categories: Starting Raw Materials & Intermediates;Miscellaneous;Biochemistry;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Triazines;TriazinesBuilding Blocks;Aromatics;Heterocycles;Miscellaneous Reagents
• Mol File: 3140-73-6.mol
• Article Data: 25

Chemical Properties

• Melting Point: 71-74 °C(lit.)
• Boiling Point: 99-100 °C (1 mmHg)
• Flash Point: 99-100°C/1mm
• Appearance: White to almost white/Crystalline Powder
• Density: 1.7917 (rough estimate)
• Vapor Pressure: 0.00152mmHg at 25°C
• Refractive Index: 1.5870 (estimate)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Chloroform, Methanol
• PKA: 0.33±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 148988
• CAS DataBase Reference: 2-Chloro-4,6-dimethoxy-1,3,5-triazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4,6-dimethoxy-1,3,5-triazine(3140-73-6)
• EPA Substance Registry System: 2-Chloro-4,6-dimethoxy-1,3,5-triazine(3140-73-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37-36
• RIDADR: UN3077
• WGK Germany: 3
• Hazardous Substances Data: 3140-73-6(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white crystalline powder

Uses

Different sources of media describe the Uses of 3140-73-6 differently. You can refer to the following data:
1. 2-Chloro-4,6-dimethoxy-1,3,5-triazine is used as a peptide coupling agent for the purification of peptides. It is used in the synthesis of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride through coupling with N-methylmorpholine in tetrahydrofuran. Further, it plays an important role in the production of bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether, through reaction with 2-hydroxy-4,6-dimethoxy-1,3,5-triazine. In addition to this, it is involved in the preparation of 2-(4,6-dimethoxy-1,3,5-triazinyl)trialkylammonium salts through reaction with various tertiary amines.
2. 2-Chloro-4,6-dimethoxy-1,3,5-triazine may be used in the following studies:The specific labeling of streptavidin by the modular method for affinity labeling (MoAL). The preparation of bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether, via reaction with 2-hydroxy-4,6-dimethoxy-1,3,5-triazine. The preparation of 2-(4,6-dimethoxy-1,3,5-triazinyl)trialkylammonium salts, via reaction with various tertiary amines. The synthesis of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, via coupling with N-methylmorpholine in THF.

General Description

2-Chloro-4,6-dimethoxy-1,3,5-triazine is a stable, yet highly reactive, peptide coupling agent. It is reported as useful coupling reagent for the purification of peptides. Catalytic amide-forming reactions of 2-chloro-4,6-dimethoxy-1,3,5-triazine has been reported. Procedure for the preparation of multikilogram quantities of 2-chloro-4,6-dimethoxy-1,3,5-triazine has been reported.

InChI:InChI=1/C5H6ClN3O2/c1-10-4-7-3(6)8-5(9-4)11-2/h1-2H3

Synthetic route

methanol (67-56-1) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) → 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6)

Conditions	Yield
With sodium hydrogencarbonate at 25 - 50℃; for 4h;	96%
With sodium hydrogencarbonate In water at 100℃; for 36h; Large scale;	89.5%
With sodium hydrogencarbonate at 0 - 50℃; for 4h;	86%

2,4-dimethoxy-6-hydroxy-1,3,5-triazine (1075-59-8) → 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6)

Conditions	Yield
With N,N-diethylaniline; trichlorophosphate for 3h; Heating;	90%
With N,N-diethylaniline; trichlorophosphate for 3h; Reflux;

1,3,5-trichloro-2,4,6-triazine (108-77-0) → 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water	89.2%
With potassium hydrogencarbonate In methanol; water	88.3%
With potassium hydrogencarbonate In methanol; water; ethyl acetate	87.5%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + sodium methylate (124-41-4) → 2,4-Dichloro-6-methoxy-1,3,5-triazine (3638-04-8) + 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6)

Conditions	Yield
In methanol; toluene at 0℃; for 2h; Substitution;	A 10% B 82%

N-methyl-acetamide (79-16-3) + 2,4-Dichloro-6-methoxy-1,3,5-triazine (3638-04-8) → 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6) + 2-acetamido-4,6-dichloro-1,3,5-triazine + 2-(acetamido)-4-chloro-6-methoxy-1,3,5-triazine

Conditions	Yield
Stage #1: N-methyl-acetamide With sodium hydride In tetrahydrofuran at 0 - 50℃; for 0.75h; Stage #2: 2,4-Dichloro-6-methoxy-1,3,5-triazine In tetrahydrofuran at 0℃; for 2h;	A 31% B 28% C 4%

methanol (67-56-1) + 2,4-Dichloro-6-methoxy-1,3,5-triazine (3638-04-8) → 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6)

Conditions	Yield
With sodium hydrogencarbonate

methanol (67-56-1) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) → 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6) + 2,4,6-trimethoxy-1,3,5-triazine (877-89-4)

Conditions	Yield
With sodium hydrogencarbonate In water; water-d2 at 40℃; Product distribution; influence of reaction conditions (base amount and temperature) on the yield of the products;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + sodium methylate (124-41-4) → 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6)

Conditions	Yield
at -30℃; Substitution;

methanol (67-56-1) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) + NaHCO3 <2 mol> → 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6)

2-(4-methoxybenzoyloxy)-4,6-dimethoxy-1,3,5-triazine (132353-25-4) → 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate / acetonitrile / 10 h / 50 °C / Inert atmosphere 2: N,N-diethylaniline; trichlorophosphate / 3 h / Reflux View Scheme

Upstream product

• 67-56-1 methanol 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 3638-04-8 2,4-Dichloro-6-methoxy-1,3,5-triazine 
• 79-16-3 N-methyl-acetamide 
• 132353-25-4 2-(4-methoxybenzoyloxy)-4,6-dimethoxy-1,3,5-triazine 
• 1075-59-8 2-hydroxy-4,6-dimethoxy-1,3,5-triazine 
• 124-41-4 sodium methylate 

Downstream Products

• 263276-09-1 S-ethyl 3-(4-hydroxyphenyl)-2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]propionate 
• 912338-16-0 C₃₂H₅₀N₄O₄ 
• 1061675-59-9 C₂₀H₂₇N₅O₂ 
• 132243-78-8 methyl phenoxy>acetate 
• 112226-61-6 halofenozide 
• 23875-76-5 N'-tert-butyl-N-(4-chlorobenzoyl)hydrazine 
• 127013-92-7 3-phenyl-3-methyl-2-(4,6-dimethoxy-S-triazin-2-ylthio)butyric acid 
• 95693-76-8 lometrexol 
• 170508-01-7 (R)-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)-2-(N-triphenylmethylamino)-propanamide 
• 169318-08-5 N-{[4-(2,6-diamino-4-chloro-5-pyrimidinyl)propyl]benzoyl}-L-glutamic acid di-t-butyl ester 
• 169318-03-0 N-{[4-(2,6-diamino-4-chloro-5-pyrimidinyl)propyl]benzoyl}-L-glutamic acid diethyl ester 
• 198703-19-4 dimethyl N-(2-iodo-1-triphenylmethylimidazol-4-ylcarbonyl)-L-glutamate 
• 146943-43-3 N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester 
• 40501-14-2 (4,6-dimethoxy-[1,3,5]triazin-2-yl)-(4-methyl-2-nitro-phenyl)-amine 

Relevant articles and documents

Understanding the effect of an amino group on the selective and ultrafast detection of TNP in water using fluorescent organic probes

We have designed and developed three single-molecule fluorescent probes differing in the number of amino groups, namely 5-((4,6-Diamino-1,3,5-triazin-2-yl)amino)isophthalic acid (H2ATAIA, 1), 5-((4-amino-6-methoxy-1,3,5-triazin-2-yl)amino)isophthalic acid (H2AMTAIA, 2) and 5-((4,6-dimethoxy-1,3,5-triazin-2-yl)amino)isophthalic acid (H2DMTAIA, 3), from cheap and readily available starting materials via simple procedures in high yields for demonstrating their application in highly selective and ultrafast sensing of 2,4,6-trinitrophenol (TNP) in water (slurry mode). Probes 1-3 have been characterized by various analytical techniques, such as melting point, FTIR, UV-vis and NMR (1H and 13C) spectroscopy and high resolution mass spectrometry (HRMS). It is quite evident that the effect of an amino group is more prominent compared to a methoxy group towards the selective detection of TNP over other potentially interfering nitro compounds. The detection limit for the diamino derivative was found to be 120 ppb compared to those with one amino or no amino group (0.8 ppm and 1.2 ppm, respectively). We also report the ideal real time detection of TNP through a contact mode or instant spot via paper strips. Spectral overlap, time-resolved fluorescence studies, quantum yield, Stern-Volmer plots, field emission scanning electron microscopy (FESEM) and DFT calculations have been used to establish their mechanism of action. Furthermore, competitive nitro-analyte tests demonstrate that the selectivity for TNP is more in 1 compared to 2 and 3. To the best of our knowledge, we have demonstrated for the first time molecular decoding of TNP based on the dual read-out identification scheme constructed from life-time and quantum yield. These probes have been found to be highly photostable in the presence of acidic TNP as well as recyclable without much loss of sensitivity up to five cycles. These results vividly depict that these are excellent candidates for environmental monitoring.

An improved procedure for the large scale preparation of 2-chloro-4,6-dimethoxy-1,3,5-triazine

A robust process for the preparation of multikilogram quantities of 2-chloro-4,6-dimethoxy-1,3,5-triazine (1) is described.

Solvent-Directed Click Reaction between Active Methylene Compounds and Azido-1,3,5-triazines

A novel solvent-directed click reaction between active methylene compounds and azido-1,3,5-triazines has been developed. In aqueous solution, the regiospecific trisubstituted 1,2,3-triazole products are quickly synthesized in high yields under mild conditions and easy to separate without column chromatography. This click reaction is controlled by the protonation of a nitrogen anion intermediate, and the postulated mechanism is substantiated by DFT calculations.

Intrinsically Safe and Shelf-Stable Diazo-Transfer Reagent for Fast Synthesis of Diazo Compounds

We report a crystalline compound 2-azido-4,6-dimethoxy-1,3,5-triazine (ADT) as an intrinsically safe, highly efficient, and shelf-stable diazo-transfer reagent. Because the decomposition of ADT is an endothermal process (ΔH = 30.3 kJ mol-1), ADT is intrinsically nonexplosive, as proved by thermal, friction, and impact tests. The diazo-transfer reaction based on ADT gives diazo compounds in excellent yields within several minutes at room temperature. ADT is very stable upon >1 year storage under air at room temperature.