542-02-9

Basic information

• Product Name: 6-Methyl-1,3,5-triazine-2,4-diamine
• Synonyms: 1,3,5-Triazine-2,4-diamine,6-methyl-;2-Methyl-4,6-diamino-1,3,5-triazine;3,5-Triazine-2,4-diamine,6-methyl-1;5-triazine-2,4-diamine,6-methyl-3;6-METHYL-1,3,5-TRIAZINE-2,4-DIAMINE;ACETOGUANAMINE;2,4-DIAMINO-6-METHYL-1,3,5-TRIAZINE;6-methyl-1,3,5-triazine-2,4-diyldiamine
• CAS NO: 542-02-9
• Molecular Formula: C₄H₇N₅
• Molecular Weight: 125.13
• EINECS: 208-796-3
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Triazines;strong recommend
• Mol File: 542-02-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 274-276 °C(lit.)
• Boiling Point: 443 °C at 760 mmHg
• Flash Point: 252 °C
• Appearance: white solid
• Density: 1.391 g/cm³
• Vapor Pressure: 4.79E-08mmHg at 25°C
• Refractive Index: 1.675
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 4.49±0.10(Predicted)
• Water Solubility: 11.2g/L at 20℃
• Stability: Stable. Incompatible with oxidizing agents, acids.
• BRN: 118348
• CAS DataBase Reference: 6-Methyl-1,3,5-triazine-2,4-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methyl-1,3,5-triazine-2,4-diamine(542-02-9)
• EPA Substance Registry System: 6-Methyl-1,3,5-triazine-2,4-diamine(542-02-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• TSCA: Yes
• Hazardous Substances Data: 542-02-9(Hazardous Substances Data)

Usage

Chemical Properties

white solid

Uses

6-Methyl-1,3,5-triazine-2,4-diamine may be used in the synthesis of s-Bodipy-triazine (BODIPY = 4,4-difluoro-4-borata-3a-azonia-4a-aza-s-indacene). It is a symmetric fluorescent sensor for Cu2+.

Definition

ChEBI: A diamino-1,3,5-triazine that is 1,3,5-triazine-2,4-diamine carrying an additional methyl substituent at position 6.

General Description

6-Methyl-1,3,5-triazine-2,4-diamine butane-1,4-diol monosolvate crystallizes with 6-methyl-1,3,5-triazine-2,4-diamine (DMT) and a molecule of butane-1,4-diol in the asymmetric unit. The DMT molecules form ribbons having centrosymmetric dimer motifs between DMT molecules along the c-axis. DMT and thymine forms a new metastable bicomponent hydrogel, which cage a number of organic solvents.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C4H7N5/c1-2-7-3(5)9-4(6)8-2/h1H3,(H4,5,6,7,8,9)

Synthetic route

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%

dicyandiamide (127099-85-8, 780722-26-1) + acetonitrile (75-05-8) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
With potassium hydroxide In ethanol at 80℃; for 24h;	85%

6-(chloromethyl)-1,3,5-triazine-2,4-diamine (10581-62-1) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
With hydrogenchloride; Lindlar's catalyst Hydrogenation;

acetylguanidine (5699-40-1) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

2,4-bis(trichloromethyl)-6-methyl-1,3,5-triazine (949-42-8) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
With ammonia; N,N-dimethyl-formamide

acetic anhydride (108-24-7) + Biguanide acetate (33668-48-3) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

acetic anhydride (108-24-7) + BIGUANIDE (56-03-1) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

ethyl acetate (141-78-6) + BIGUANIDE (56-03-1) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

dicyanamide; compound with acetamidine + nitrobenzene (98-95-3) + benzene (71-43-2) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

acetamidine hydrochloride (124-42-5) + N-Cyanoguanidine (127099-85-8, 780722-26-1) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
at 225 - 230℃;

N-Cyanoguanidine (127099-85-8, 780722-26-1) + acetonitrile (75-05-8) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
at 225 - 230℃;
With piperidine
With ethylenediamine

urea (57-13-6) + acetonitrile (75-05-8) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
With ammonia at 350℃;

acetate_of guanidine → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
at 228 - 230℃;

ethanol (64-17-5) + acetamidine (143-37-3) + sodium dicyano-amide → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

Conditions	Yield
Erhitzen des Reaktionsprodukts in einem Benzol-Nitrobenzol-Gemisch;

CYANAMID (420-04-2) + N1-acetyl-N3-cyanoguanidine (63071-29-4) + water (7732-18-5) → 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9)

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + benzaldehyde (100-52-7) → 2-amino-4-benzylideneamino-6-methyl[1,3,5]triazine

Conditions	Yield
In neat (no solvent) for 0.0583333h; Microwave irradiation;	95%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 1H,1′H-5,5′-bistetrazole-1,1′-diolate (134293-22-4) → bis-2,4-diamino-6-methyl-1,3,5-triazin 1H,1'H-5,5'-bistetrazole-1,1'-diolate

Conditions	Yield
In water at 20℃;	90%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + chloro-diphenylphosphine (1079-66-9) → C28H25N5P2

Conditions	Yield
With triethylamine In tetrahydrofuran Reflux; Inert atmosphere;	89%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 3,9-dichloro-2,4,8,10-tetraoxa-3,9-diphospaspiro <5,5>undecane 3,9-dioxide (714-87-4) → C13H20N10O6P2

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 90℃; for 6h;	89%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 2-chloro-4-(1,3-thiazol-2-yl)pyrimidine (83726-80-1) → 6-methyl-N2-(4-(thiazol-2-yl)pyrimidin-2-yl)-1,3,5-triazine-2,4-diamine

Conditions	Yield
With sodium t-butanolate In tetrahydrofuran at 10 - 20℃; for 2h;	89%

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

Conditions	Yield
With hydrogenchloride In water Further stages;	86%

hydrogenchloride (7647-01-0) + 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + bismuth (III) nitrate pentahydrate + water (7732-18-5) → 3C4H7N5*3H(1+)*H2O*BiCl6(3-)

Conditions	Yield
In ethanol at 20℃;	80%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 5-chloro-2-hydroxybenzoic acid (321-14-2) → C7H5ClO3*C4H7N5*H2O

Conditions	Yield
In methanol; water at 20℃; for 336h;	79%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 1,5-pentanedioic acid (110-94-1) → C18H22N10O4 (1401592-22-0)

Conditions	Yield
With hydrogenchloride In ethanol; water at 85 - 90℃;	78%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + Adipic acid (124-04-9) → C20H26N10O4 (1401592-24-2)

Conditions	Yield
With hydrogenchloride In ethanol; water at 85 - 90℃;	78%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + ethanol (64-17-5) + naphthalene-1,4-dicarboxylic acid (605-70-9) + silver nitrate → bis(2,4-diamino-6-methyl-1,3,5-tetrazine)(naphthalene-1,4-dicarboxylate)dicopper(II) - ethanol (1/2)

Conditions	Yield
With NH3 In methanol; ethanol Sonication; AgNO3, 2,4-diamino-6-methyl-1,3,5-triazine and naphthalene-1,4-dicarboxylic acid (1:1:1) in CH3OH/C2H5OH in the presence of NH3 sonicated at 50°C; crystd. at room temp. for 1 week, washed (H2O), dried (air), elem. anal.;	77%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + Eudesmic acid (118-41-2) → C10H12O5*C4H7N5

Conditions	Yield
In water; acetone at 20℃; for 336h; Sealed tube;	77%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + Pyridine-2,3-dicarboxylic acid (89-00-9) → C7H5NO4*C4H7N5

Conditions	Yield
In ethanol; water; N,N-dimethyl-formamide at 20℃; for 240h;	76%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 2,3,5,6-tetrafluoroterephthalic acid (652-36-8) → C8H2F4O4*2C4H7N5

Conditions	Yield
In 1,4-dioxane; water for 0.25h;	75%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + cyclopentane-1,2,3,4-tetracarboxylic acid (3724-52-5) → C9H10O8*2C4H7N5

Conditions	Yield
In water; acetone at 20℃; for 336h; Sealed tube;	75%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + terephthalic acid (100-21-0) → C8H6O4*2C4H7N5

Conditions	Yield
In methanol; water at 20℃; for 240h; Sealed tube;	75%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + benzene-1,2-dicarboxylic acid (88-99-3) → C4H7N5*C8H6O4 (1293397-54-2)

Conditions	Yield
In methanol; water at 20℃; for 336h;	74%
In water at 120℃; for 72h; Autoclave;	58.4%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + picryl fluoride (364-44-3) → 6-methyl-[1,3,5]triazine-2,4-diyldiamine; picrate (121105-41-7)

Conditions	Yield
In dimethyl sulfoxide at 80℃; for 48h;	73%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + malonic acid (141-82-2) → C14H14N10O4 (1401592-18-4)

Conditions	Yield
With hydrogenchloride In ethanol; water at 85 - 90℃;	72%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + succinic acid (110-15-6) → C16H18N10O4 (1401592-21-9)

Conditions	Yield
With hydrogenchloride In ethanol; water at 85 - 90℃;	70%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + Chlorodiisopropylphosphane (40244-90-4) → N2,N4-bis(diisopropylphosphanyl)-6-methyl-1,3,5-triazine-2,4-diamine

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 60℃; for 16h; Glovebox; Inert atmosphere; Sealed tube;	70%
With triethylamine In tetrahydrofuran at 0 - 60℃; Inert atmosphere; Sealed tube;
With triethylamine In tetrahydrofuran at 60℃; Inert atmosphere; Sealed tube;

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 3-Formylchromone (17422-74-1) → 3-[(E)-2-(4,6-diamino-1,3,5-triazin-2-yl)vinyl]-4H-chromen-4-one (1020416-75-4)

Conditions	Yield
With chloro-trimethyl-silane In N,N-dimethyl-formamide Heating;	67%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 2,4-dichlorobenzaldeyhde (874-42-0) → 2,4-diamino--6-<2-(2,4-dichlorophenyl)ethenyl>-1,3,5-triazine (131454-72-3)

Conditions	Yield
With methanesulfonic acid at 110℃; for 2.5h;	66%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + pivaloyl chloride (3282-30-2) → N-[4-(2,2-Dimethyl-propionylamino)-6-methyl-[1,3,5]triazin-2-yl]-2,2-dimethyl-propionamide (180986-97-4)

Conditions	Yield
With pyridine for 1.25h; Heating;	66%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 4-nitrophenol acetate (830-03-5) → 4-nitro-phenol (100-02-7) + N-(amino-methyl-[1,3,5]triazin-2-yl)-acetamide (30355-53-4)

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 17.5h;	A n/a B 60%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 3,5-dichlorobenzaldehyde (10203-08-4) → 2,4-diamino--6-<2-(3,5-dichlorophenyl)ethenyl>-1,3,5-triazine (131454-65-4)

Conditions	Yield
With methanesulfonic acid at 110℃; for 2.5h;	59%

2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) + 2-Trifluoromethylbenzaldehyde (447-61-0) → 2,4-diamino--6-<2-(2-trifluoromethylphenyl)ethenyl>-1,3,5-triazine (139979-25-2)

Conditions	Yield
With methanesulfonic acid at 110℃; for 2.5h;	54%

3-pyridinecarboxaldehyde (500-22-1) + 2-methyl-4,6-diamino-1,3,5-triazine (542-02-9) → 2-amino-4-hydroxy--6-<2-(3-pyridyl)ethenyl>-1,3,5-triazine (131454-55-2) + 2,4-diamino--6-<2-(3-pyridyl)ethenyl>-1,3,5-triazine (124173-70-2)

Conditions	Yield
With methanesulfonic acid at 110℃; for 2.5h;	A n/a B 51%
With methanesulfonic acid at 110℃; for 2h;	A 12% B n/a

Upstream product

• 10581-62-1 6-(chloromethyl)-1,3,5-triazine-2,4-diamine 
• 141-78-6 ethyl acetate 
• 56-03-1 BIGUANIDE 
• 98-95-3 nitrobenzene 
• 71-43-2 benzene 
• 124-42-5 acetamidine hydrochloride 
• 127099-85-8 N-Cyanoguanidine 
• 75-05-8 acetonitrile 
• 57-13-6 urea 
• 127099-85-8 dicyandiamide 
• 64-17-5 ethanol 
• 143-37-3 acetamidine 
• 1973-04-2 2,4-dichloro-6-methyl-1,3,5-triazine 
• 420-04-2 CYANAMID 

Downstream Products

• 121105-41-7 6-methyl-[1,3,5]triazine-2,4-diyldiamine; picrate 
• 933-19-7 6-methyl-1,3,5-triazine-2,4(1H,3H)-dione 
• 1293397-54-2 C₄H₇N₅*C₈H₆O₄ 
• 139979-26-3 2,4-diamino--6-<2-(4-cyanophenyl)ethenyl>-1,3,5-triazine 
• 100-02-7 4-nitro-phenol 
• 30355-53-4 N-(amino-methyl-[1,3,5]triazin-2-yl)-acetamide 
• 131454-72-3 2,4-diamino--6-<2-(2,4-dichlorophenyl)ethenyl>-1,3,5-triazine 
• 139979-28-5 2,4-diamino--6-<2-(4-methoxyphenyl)ethenyl>-1,3,5-triazine 
• 139979-24-1 2,4-diamino--6-styryl-1,3,5-triazine 

Relevant articles and documents

Design and development of 1,3,5-triazine derivatives as protective agent against spinal cord injury in rat via inhibition of NF-?B

Spinal cord injury (SCI) is a chronic disease causing motor and sensory loss in the affected individuals. The SCI has a huge impact on the lives of patients that makes them susceptible to life-long disability. However, the current clinical modalities are ineffective to cope the aftermath of SCI. Thus, in the present study, we aimed to develop a series of 1,3,5-triazine derivatives as a protective agent against SCI. The molecules were developed by facile synthetic route and obtained in excellent yield. The compounds were tested for their efficacy to inhibit the transcription of NF-κB in RAW 264.7 cells, where they displayed mild to potent activity. Compound 8a was identified as most potent NF-κB inhibitor among the tested analogues. The effect of compound 8a was further scrutinized against the SCI injury in rats induced by contusion injury. It has been found that compound 8a improves motor function of rats together with reduction in inflammation and edema in spinal cord of rats. It also showed to inhibit oxidative stress and inflammation in the SCI rats. In a western blot analysis, after SCI induction, compound 8a inhibited NF-κB and its upstream regulator TLR4 in a dose-dependent manner. Collectively, our study provides a novel class of agent that provide protective action against SCI.

Hydroxide-Catalyzed Synthesis of Heterocyclic Aromatic Amine Derivatives from Nitriles

A generalized method for synthesizing a wide variety of heterocyclic aromatic amine derivatives from nitriles by use of hydroxide catalysts is presented.Nitrile dimers (3-aminocrotononitrile and dicyandiamide) and a dimer analog (anthranilonitrile) react with monomeric nitriles in the presence of hydroxide to form respectively, aminopyrimidines, diaminotriazines and aminoquinazolines.