2,6-Diaminopyridine supplier

Name
2,6-Diaminopyridine
EINECS 205-507-2
CAS No. 141-86-6
Article Data40
CAS DataBase
Density 1.251 g/cm³
Solubility water: 9.9 g/100 mL (20 ºC)

Melting Point 117-122 ºC(lit.)

Formula C₅H₇N₃

Boiling Point 285 ºC at 760 mmHg

Molecular Weight 109.131

Flash Point 161.3 ºC

Transport Information 2811

Appearance off-white crystal powder/granuale

Safety 26-45-37/39-28A-36

Risk Codes 22-36/37/38-25

Molecular Structure

Hazard Symbols Xn,T,Xi

Synonyms Pyridine, 2,6-diamino-;DAP;2,6-pyridinediamine;1H-pyridine-2,6-diamine;DAP (amine);pyridine-2,6-diamine;2,6-Diamino Pyridine;Di-ammonium phosphat (DAP);pyridine-2,6-diyldiamine;2,6-Diamino Pyridine,141-86-6;

PSA 64.93000

LogP 1.40840

Synthetic route

626-05-1
2,6-Dibromopyridine

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water; ethylene glycol at 110 - 140℃; for 16h; 96%

With copper(I) oxide; potassium carbonate; ammonium hydroxide; N,N-dimethylethylenediamine In ethylene glycol at 60℃; for 16h; Inert atmosphere; 68%

With ammonia; water at 200℃;

626-05-1
2,6-Dibromopyridine

A

141-86-6
2,6-Diaminopyridine

B

19798-81-3
2-Amino-6-bromopyridine

Conditions

Conditions Yield

With ammonia In water at 190℃; under 18751.9 Torr; for 6h; A n/a
B 88.9%

With ammonium hydroxide at 180℃;

With copper(I) oxide; potassium carbonate; ammonium hydroxide; N,N-dimethylethylenediamine In ethylene glycol at 60℃; for 16h; Inert atmosphere;

70826-08-3
N2,N6-dibenzylpyridine-2,6-diamine

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With sulfuric acid for 24h; Ambient temperature; 82%

110-86-1
pyridine

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With p-toluidine; sodium amide; decalin In water under 2250.23 Torr; for 0.00555556h; Pressure; Microwave irradiation; 78%

With vaseline oil; sodium amide at 125 - 180℃;

With sodium amide

45644-21-1
6-chloropyridin-2-amine

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With ammonia; copper(l) iodide In water at 150℃; under 6050.79 - 21875.9 Torr; for 8h; Product distribution / selectivity; 69%

With ammonium acetate; ammonia; copper(l) iodide In water at 150℃; under 6050.79 - 21875.9 Torr; for 8h; Product distribution / selectivity; 81 %Chromat.

62679-42-9
N-(2-pyridylmethylene)-2,6-diaminopyridine

A

141-86-6
2,6-Diaminopyridine

B

76274-25-4
3-(2-pyridylmethylene)-2,6-diaminopyridine

C

76274-26-5
3-(6-methyl-2-pyridylmethylene)-2,6-diaminopyridine

D

76274-23-2
3-(6-methyl-2-pyridulmethylene)-5-(2-pyridylmethylene)-2,6-diaminopyryridine

Conditions

Conditions Yield

With N-(6-methyl-2-pyridylmethylene)-2,6-diaminopyridine at 300℃; for 0.2h; A 18.3%
B 19.4%
C 17.7%
D 30.7%

...Expand

70826-10-7
N-(6-methyl-2-pyridylmethylene)-2,6-diaminopyridine

A

141-86-6
2,6-Diaminopyridine

B

76274-25-4
3-(2-pyridylmethylene)-2,6-diaminopyridine

C

76274-26-5
3-(6-methyl-2-pyridylmethylene)-2,6-diaminopyridine

D

76274-23-2
3-(6-methyl-2-pyridulmethylene)-5-(2-pyridylmethylene)-2,6-diaminopyryridine

Conditions

Conditions Yield

With N-(2-pyridylmethylene)-2,6-diaminopyridine at 300℃; for 0.2h; A 18.3%
B 19.4%
C 17.7%
D 30.7%

...Expand

62679-42-9
N-(2-pyridylmethylene)-2,6-diaminopyridine

A

141-86-6
2,6-Diaminopyridine

B

68752-24-9
3,5-di(2-pyridylmethylene)-2,6-diaminopyryridine

C

76274-25-4
3-(2-pyridylmethylene)-2,6-diaminopyridine

Conditions

Conditions Yield

at 300℃; for 0.2h; A 12.1%
B 27.5%
C 23.3%

...Expand

544-13-8
Glutaronitrile

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With ammonia; palladium 10% on activated carbon at 200℃; under 87917.5 Torr; for 45h; Product distribution / selectivity; Autoclave; 17.3%

With ammonia; 0.5% Pd on alumina In ethanol at 309℃; Product distribution / selectivity; Gas phase;

With ammonia In ethanol at 160℃; Product distribution / selectivity;

4945-49-7
glutarimide

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With ammonia; palladium 10% on activated carbon at 200℃; for 45h; Product distribution / selectivity; 10%

With ammonia; 5%-palladium/activated carbon at 200℃; for 45h; Product distribution / selectivity; 0.7%

110-86-1
pyridine

A

141-86-6
2,6-Diaminopyridine

B

Conditions

Conditions Yield

With sodium amide; 2,3-Dimethylaniline

Conditions

Conditions Yield

With 4-methylisopropylbenzene; sodium amide at 210℃;

504-29-0
2-aminopyridine

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With Isopropylbenzene; sodium amide at 200℃;

59-67-6
nicotinic acid

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With sodium amide; paraffin oil at 200℃;

55-22-1
pyridine-4-carboxylic acid

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With sodium amide; paraffin oil at 200℃;

54903-86-5
2,6-diamino-3-bromopyridine

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With sodium hydroxide; water; nickel Hydrogenation.und Aethanol;

4663-97-2
pyridine-2,6-dicarboxylic acid diamide

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With water; bromine

98-92-0
nicotinamide

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With sodium amide; paraffin oil at 200℃;

4936-27-0
ethyl 2,6-pyridinedicarbamate

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With potassium hydroxide

Pyridine-2,6-diamine; compound with ethanol

A

141-86-6
2,6-Diaminopyridine

B

64-17-5
ethanol

Conditions

Conditions Yield

In 2,2,4-trimethylpentane at 20℃; Equilibrium constant;

5-Methyl-1-propyl-1H-pyrimidine-2,4-dione; compound with pyridine-2,6-diamine

A

141-86-6
2,6-Diaminopyridine

B

22919-49-9
5-methyl-1-propyl-1H-pyrimidine-2,4-dione

Conditions

Conditions Yield

In chloroform-d1 at 24.9℃; Equilibrium constant; association constant;

98-92-0
nicotinamide

sodium amide

paraffin oil

paraffin oil

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

at 200℃;

...Expand

110-86-1
pyridine

sodium amide

vaseline oil

vaseline oil

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

at 125 - 180℃;

...Expand

5683-33-0
2-(Dimethylamino)pyridine

sodium amide

A

141-86-6
2,6-Diaminopyridine

B

124-40-3
dimethyl amine

Conditions

Conditions Yield

at 190℃;

...Expand

5441-02-1
N,N'-(2,6-pyridinediyl)bis(acetamide)

80-48-8
methyl p-toluene sulfonate

A

141-86-6
2,6-Diaminopyridine

B
p-toluenesulfonate/s of 1-methyl-2-imino-6-acetylimino-1.2.3.6-tetrahydro-pyridine

p-toluenesulfonate/s of 1-methyl-2-imino-6-acetylimino-1.2.3.6-tetrahydro-pyridine

Conditions

Conditions Yield

Alkohol;

...Expand

110-86-1
pyridine

109-89-7
diethylamine

A

141-86-6
2,6-Diaminopyridine

B
pyridyl-2-ylamine

pyridyl-2-ylamine

Conditions

Conditions Yield

With potassium amide; sodium amide at 120℃;

...Expand

2402-78-0
2,6-dichloropyridine

141-86-6
2,6-Diaminopyridine

Conditions

Conditions Yield

With ammonia; copper In water at 240℃; under 56887.8 Torr; for 5h; Product distribution / selectivity; < 10 %Chromat.

2402-78-0
2,6-dichloropyridine

A

141-86-6
2,6-Diaminopyridine

B

45644-21-1
6-chloropyridin-2-amine

Conditions

Conditions Yield

With ammonium acetate; ammonia; copper(l) iodide In water at 150℃; under 7757.43 - 35167 Torr; for 8h; Product distribution / selectivity; A 91 %Chromat.
B 7 %Chromat.

With ammonia; copper(l) iodide In water at 150℃; under 7757.43 - 35167 Torr; for 8h; Product distribution / selectivity; A 72 %Chromat.
B n/a

phenazopyridine hydrochloride

ZnFe-SO4-LDH nanoplates modified with graphene oxide(GO), coated them on the glass substrate

ZnFe-SO4-LDH nanoplates modified with graphene oxide(GO), coated them on the glass substrate

A

79-16-3
N-methyl-acetamide

B

141-86-6
2,6-Diaminopyridine

C

107-10-8
propylamine

D

95-47-6
o-xylene

E

108-38-3
m-xylene

Conditions

Conditions Yield

With dipotassium peroxodisulfate In water for 3h; pH=8; Kinetics; Irradiation;

...Expand

141-86-6
2,6-Diaminopyridine

bis(2,6-diaminopyridinium) hexafluorosilicate

Conditions

Conditions Yield

With fluorosilicic acid In methanol 100%

141-86-6
2,6-Diaminopyridine

617-48-1
malic acid

1931-44-8
2-amino-8H-7-oxo-[1,8]-naphthyridine

Conditions

Conditions Yield

With sulfuric acid at 110℃; for 3h; Inert atmosphere; Cooling with ice; 100%

With sulfuric acid at 80 - 90℃; for 3h; 92%

Stage #1: 2.6-diaminopyridine; malic acid With sulfuric acid at 110℃; Inert atmosphere; Cooling with ice;
Stage #2: With ammonium hydroxide In water pH=8; Cooling with ice; 87%

141-86-6
2,6-Diaminopyridine

3282-30-2
pivaloyl chloride

101630-94-8
N,N'-2,6-pyridinediylbis<2,2-dimethylpropanamide>

Conditions

Conditions Yield

With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice; 99%

With triethylamine In tetrahydrofuran at 20℃; for 12h; Cooling with ice; 97%

With dmap; triethylamine In dichloromethane at 0 - 20℃; 96%

141-86-6
2,6-Diaminopyridine

75-24-1
trimethylaluminum

AlCH3[Al(CH3)2NHNHC5H3N]2

Conditions

Conditions Yield

In dichloromethane byproducts: CH4; (Ar), ligand in Ch2Cl2 added dropwise to AlMe3 in CH2Cl2 at 25°C,stirred for 1 h at room temp.; crystd. overnight at -20°C, elem. anal.; 99%

141-86-6
2,6-Diaminopyridine

34981-11-8
2,6-diamino-3,5-dinitropyridine

Conditions

Conditions Yield

With dinitrogen pentoxide In dichloromethane at 27 - 31℃; for 0.0166667h; Temperature; Cooling with ice; 99%

Stage #1: 2.6-diaminopyridine With sulfuric acid; sulfur trioxide at 0 - 20℃;
Stage #2: With nitric acid at 0 - 15℃; 95%

Multi-step reaction with 2 steps
1.1: sulfuric acid / isopropyl alcohol
2.1: sulfuric acid; sulfur trioxide / Cooling with ice
2.2: Cooling with ice
View Scheme

141-86-6
2,6-Diaminopyridine

16523-54-9
chlorodicyclohexylphosphane

N,N'-bis(dicyclohexyl)-2,6-diaminopyridine

Conditions

Conditions Yield

With triethylamine In toluene at 70℃; for 48h; 99%

141-86-6
2,6-Diaminopyridine

[D3]-2,6-2,6-diaminopyridine

Conditions

Conditions Yield

With palladium 10% on activated carbon; hydrogen; water-d2 at 180℃; under 750.075 Torr; for 24h; Autoclave; 99%

141-86-6
2,6-Diaminopyridine

98-88-4
benzoyl chloride

74305-33-2
N,N′-(pyridine-2,6-diyl)dibenzamide

Conditions

Conditions Yield

With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice; 98%

With triethylamine In dichloromethane at 20℃; for 15h; Inert atmosphere; 89%

With triethylamine In tetrahydrofuran at 20℃; for 20h; Cooling with ice; 77%

141-86-6
2,6-Diaminopyridine

617-48-1
malic acid

1931-44-8
2-amino-7-hydroxy-1,8-naphthyridine

Conditions

Conditions Yield

With sulfuric acid at 0 - 120℃; for 12h; 98%

With sulfuric acid at 110℃; for 3h; 97%

With sulfuric acid at 110℃; for 3h; Cooling with ice; 97%

141-86-6
2,6-Diaminopyridine

1079-66-9
chloro-diphenylphosphine

644988-94-3
N,N,N',N'-tetrakis(diphenylphosphino)pyridine-2,5-diamine

Conditions

Conditions Yield

With triethylamine In dichloromethane at 0 - 20℃; for 4h; 98%

With triethylamine In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; 95%

With triethylamine In tetrahydrofuran for 18h; Cooling with ice; Inert atmosphere; Reflux; 76%

141-86-6
2,6-Diaminopyridine

69674-00-6
diisopropoxythiophosphoryl isothiocyanate

H2NC5H3NNHC(S)NHP(S)(OC3H7)2

Conditions

Conditions Yield

98%

141-86-6
2,6-Diaminopyridine

2,6-diaminopyridine hemisulfate

Conditions

Conditions Yield

With sulfuric acid In water at 45 - 55℃; Product distribution / selectivity; 98%

141-86-6
2,6-Diaminopyridine

97480-49-4
difluoro(diethoxyphosphinyl)acetyl chloride

1217898-97-9
C17H25F4N3O8P2

Conditions

Conditions Yield

With pyridine; dmap In tetrahydrofuran at 0 - 20℃; Inert atmosphere; 98%

141-86-6
2,6-Diaminopyridine

26878-34-2
2,6-diaminopyridine monohydrochloride

Conditions

Conditions Yield

With hydrogenchloride In chloroform 98%

141-86-6
2,6-Diaminopyridine

cobalt pivalate

75-05-8
acetonitrile

721396-96-9
bis-trimethylacetato[N-(6-amino-κN-pyridin-2-yl)ethan-κN-imidamide]cobalt(II)

Conditions

Conditions Yield

In acetonitrile (Ar); a mixt. of Co compd. and 2,6-diaminopyridine in MeCN heated at 80°C; concd. at 0.1 Torr and 20°C, crystd. at 20°C for 12 h, decanted, washed with cold MeCN, dried (Ar); elem. anal.; 98%

...Expand

141-86-6
2,6-Diaminopyridine

617-48-1
malic acid

49655-93-8
2,7-dihydroxy-1,8-naphthyridine

Conditions

Conditions Yield

Stage #1: 2.6-diaminopyridine; malic acid With sulfuric acid at 110℃;
Stage #2: With sodium nitrite at 0 - 5℃; Cooling with ice; 98%

141-86-6
2,6-Diaminopyridine

41157-34-0
di-n-propylphosphinous chloride

N,N'-bis(n-propylphosphino)-2,6-diaminopyridine

Conditions

Conditions Yield

With triethylamine In toluene at 20℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; 98%

141-86-6
2,6-Diaminopyridine

623-27-8
terephthalaldehyde,

C18H16N6

Conditions

Conditions Yield

In methanol at 120℃; for 3h; 98%

141-86-6
2,6-Diaminopyridine

108-24-7
acetic anhydride

5441-02-1
N,N'-(2,6-pyridinediyl)bis(acetamide)

Conditions

Conditions Yield

In dichloromethane at 20℃; 97%

With acetic acid for 4h; Heating; 86%

In 1,4-dioxane for 24h; Heating; 72%

141-86-6
2,6-Diaminopyridine

3282-30-2
pivaloyl chloride

132784-74-8
2-amino-6-trimethylacetamidopyridine

Conditions

Conditions Yield

In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Cooling with ice; 97%

In 1,4-dioxane for 2h; 74%

In 1,4-dioxane 74%

In 1,4-dioxane at 25℃; for 2h; 46%

With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;

141-86-6
2,6-Diaminopyridine

105-13-5
4-Methoxybenzyl alcohol

70826-09-4
N2,N6-bis(4-methoxybenzyl)pyridine-2,6-diamine

Conditions

Conditions Yield

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Py2NPiPr2; potassium tert-butylate In tetrahydrofuran; diethylene glycol dimethyl ether at 70℃; for 48h; Inert atmosphere; 97%

With potassium hydroxide; 4-methoxy-benzaldehyde at 195 - 245℃; for 1h; 91.1%

With C55H43ClN5P2Ru(1+)*Cl(1-); potassium hydroxide In toluene at 140℃; for 12h; Sealed tube; 85%

With [RuCl(CO)(PPh3)(PNS-Me)]; potassium hydroxide In toluene at 100℃; for 12h; 76%

107-20-0
2-chloroethanal

141-86-6
2,6-Diaminopyridine

5-aminoimidazo[1,2-a]pyridine hydrochloride

Conditions

Conditions Yield

In water; acetone 97%

In water; acetone Cyclization; Heating;

141-86-6
2,6-Diaminopyridine

100-51-6
benzyl alcohol

51505-08-9
N2-benzylpyridine-2,6-diamine

Conditions

Conditions Yield

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Py2NPiPr2; potassium tert-butylate In tetrahydrofuran; diethylene glycol dimethyl ether at 70℃; for 24h; Inert atmosphere; 97%

With C55H43ClN5P2Ru(1+)*Cl(1-); potassium hydroxide In toluene at 140℃; for 12h; Sealed tube; 68%

141-86-6
2,6-Diaminopyridine

368-66-1
2,4,6-tris(trifluoromethyl)-1,3,5-triazine

1431426-32-2
2,4-bis(trifluoromethyl)pyrido[2,3-d]pyrimidin-7-amine

Conditions

Conditions Yield

With acetic acid at 0 - 80℃; 97%

141-86-6
2,6-Diaminopyridine

372-31-6
ethyl 4,4,4-trifluoroacetoacetate

57980-08-2
7-amino-4-(trifluoromethyl)-1,8-naphthyridin-2(1H)-one

Conditions

Conditions Yield

In diphenylether at 130 - 190℃; for 20h; 97%

141-86-6
2,6-Diaminopyridine

75-36-5
acetyl chloride

5441-02-1
N,N'-(2,6-pyridinediyl)bis(acetamide)

Conditions

Conditions Yield

With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice; 96%

With triethylamine In tetrahydrofuran Ambient temperature; 86%

With triethylamine In dichloromethane at 20℃; Condensation; 82%

141-86-6
2,6-Diaminopyridine

105-53-3
diethyl malonate

76541-91-8
7-amino-1,8-naphthyridine-2,4-diol

Conditions

Conditions Yield

In diphenylether at 150 - 180℃; 96%

In diphenylether for 2.5h; Reflux; 55%

Microwave irradiation;

141-86-6
2,6-Diaminopyridine

79-04-9
chloroacetyl chloride

N,N'-bis(2-chloroacetamido)-2,6-diaminopyridine

Conditions

Conditions Yield

With triethylamine In acetone at 20℃; for 2h; 96%

With triethylamine In acetone at 20℃; for 2h; 80%

With triethylamine In tetrahydrofuran at 0 - 20℃; for 10h; 69%

141-86-6
2,6-Diaminopyridine

16537-27-2, 32276-73-6, 35389-37-8
copper(II) dipivaloate

71-43-2
benzene

1135444-61-9
bis(2,6-diaminopyridine)tetra(μ-O,O'-trimethylacetato)dicopper(II)*benzene

Conditions

Conditions Yield

In benzene (Ar); addn. of benzene to copper compd. and pyridine deriv., stirring at80°C for 20 min; concg. at 20°C in vac., keeping at 20°C for 24 h, decantation, washing with cold benzene, drying in air, elem. anal.; 96%

...Expand

2,6-Diaminopyridine Chemical Properties

IUPAC Name: Pyridine-2,6-diamine
Molecular Formula: C₅H₇N₃
Molecular Weight: 109.13 g/mol
Canonical SMILES: n1c(cccc1N)N
InChI: InChI=1/C5H7N3/c6-4-2-1-3-5(7)8-4/h1-3H,(H4,6,7,8)
EINECS: 205-507-2
Classification Code: Mutation data
Product Categories: compounds of pyridine; Pyridine; Pyridines derivates; C5; Heterocyclic Building Blocks; Pyridines
XLogP3-AA: 0.2
H-Bond Donor: 2
H-Bond Acceptor: 3
Surface Tension: 70.9 dyne/cm
Density: 1.251 g/cm³
Flash Point: 161.3 °C
Enthalpy of Vaporization: 52.4 kJ/mol
Boiling Point: 285 °C at 760 mmHg
Melting Point: 117-122 °C(lit.)
Water Solubility: 9.9 g/100 mL (20 °C)
Vapour Pressure of 2,6-Diaminopyridine (CAS NO.141-86-6): 0.00288 mmHg at 25 °C

2,6-Diaminopyridine Uses

2,6-Diaminopyridine (CAS NO.141-86-6) is used as an intermediate for the synthesis of analgesic drugs. At abroad, it is mainly used for production of a painkiller-phenazopyridine.

2,6-Diaminopyridine Production

2,6-Diaminopyridine (CAS NO.141-86-6) is synthesized from pyridine or 2-aminopyridine by amination under the more intensity condition.

2,6-Diaminopyridine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source

mouse LD50 intraperitoneal 100mg/kg (100mg/kg) Journal of Medicinal Chemistry. Vol. 8, Pg. 296, 1965.

mouse LD50 intravenous 56mg/kg (56mg/kg) U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00146,

2,6-Diaminopyridine Consensus Reports

Reported in EPA TSCA Inventory.

2,6-Diaminopyridine Safety Profile

Poison by intravenous and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x .
Hazard Codes: Xn,T,Xi
Risk Statements: 22-36/37/38-25
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
R25: Toxic if swallowed.
Safety Statements: 26-45-37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S37/39: Wear suitable gloves and eye/face protection.
S36: Wear suitable protective clothing.
RIDADR: 2811
WGK Germany: 3
RTECS: US7570000
HazardClass: 6.1
PackingGroup of 2,6-Diaminopyridine (CAS NO.141-86-6): II

2,6-Diaminopyridine Standards and Recommendations

PURITY: 99.0% min
WATER: 0.3% max
ASH: 0.1% max

2,6-Diaminopyridine Specification

2,6-Diaminopyridine (CAS NO.141-86-6), its Synonyms are 2,6-Pyridinediamine ; Pyridine, 2,6-diamino- ; Pyridine-2,6-diyldiamine ; DAP (amine) . It is off-white crystal powder/granuale.

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Conditions	Yield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water; ethylene glycol at 110 - 140℃; for 16h;	96%
With copper(I) oxide; potassium carbonate; ammonium hydroxide; N,N-dimethylethylenediamine In ethylene glycol at 60℃; for 16h; Inert atmosphere;	68%
With ammonia; water at 200℃;

Conditions	Yield
With ammonia In water at 190℃; under 18751.9 Torr; for 6h;	A n/a B 88.9%
With ammonium hydroxide at 180℃;
With copper(I) oxide; potassium carbonate; ammonium hydroxide; N,N-dimethylethylenediamine In ethylene glycol at 60℃; for 16h; Inert atmosphere;

Conditions	Yield
With p-toluidine; sodium amide; decalin In water under 2250.23 Torr; for 0.00555556h; Pressure; Microwave irradiation;	78%
With vaseline oil; sodium amide at 125 - 180℃;
With sodium amide

Conditions	Yield
With ammonia; copper(l) iodide In water at 150℃; under 6050.79 - 21875.9 Torr; for 8h; Product distribution / selectivity;	69%
With ammonium acetate; ammonia; copper(l) iodide In water at 150℃; under 6050.79 - 21875.9 Torr; for 8h; Product distribution / selectivity;	81 %Chromat.

Conditions	Yield
With ammonia; palladium 10% on activated carbon at 200℃; under 87917.5 Torr; for 45h; Product distribution / selectivity; Autoclave;	17.3%
With ammonia; 0.5% Pd on alumina In ethanol at 309℃; Product distribution / selectivity; Gas phase;
With ammonia In ethanol at 160℃; Product distribution / selectivity;

Conditions	Yield
With ammonia; palladium 10% on activated carbon at 200℃; for 45h; Product distribution / selectivity;	10%
With ammonia; 5%-palladium/activated carbon at 200℃; for 45h; Product distribution / selectivity;	0.7%

Conditions	Yield
With ammonium acetate; ammonia; copper(l) iodide In water at 150℃; under 7757.43 - 35167 Torr; for 8h; Product distribution / selectivity;	A 91 %Chromat. B 7 %Chromat.
With ammonia; copper(l) iodide In water at 150℃; under 7757.43 - 35167 Torr; for 8h; Product distribution / selectivity;	A 72 %Chromat. B n/a

Conditions	Yield
With sulfuric acid at 110℃; for 3h; Inert atmosphere; Cooling with ice;	100%
With sulfuric acid at 80 - 90℃; for 3h;	92%
Stage #1: 2.6-diaminopyridine; malic acid With sulfuric acid at 110℃; Inert atmosphere; Cooling with ice; Stage #2: With ammonium hydroxide In water pH=8; Cooling with ice;	87%

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice;	99%
With triethylamine In tetrahydrofuran at 20℃; for 12h; Cooling with ice;	97%
With dmap; triethylamine In dichloromethane at 0 - 20℃;	96%

Conditions	Yield
With dinitrogen pentoxide In dichloromethane at 27 - 31℃; for 0.0166667h; Temperature; Cooling with ice;	99%
Stage #1: 2.6-diaminopyridine With sulfuric acid; sulfur trioxide at 0 - 20℃; Stage #2: With nitric acid at 0 - 15℃;	95%
Multi-step reaction with 2 steps 1.1: sulfuric acid / isopropyl alcohol 2.1: sulfuric acid; sulfur trioxide / Cooling with ice 2.2: Cooling with ice View Scheme

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice;	98%
With triethylamine In dichloromethane at 20℃; for 15h; Inert atmosphere;	89%
With triethylamine In tetrahydrofuran at 20℃; for 20h; Cooling with ice;	77%

Conditions	Yield
With sulfuric acid at 0 - 120℃; for 12h;	98%
With sulfuric acid at 110℃; for 3h;	97%
With sulfuric acid at 110℃; for 3h; Cooling with ice;	97%

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 4h;	98%
With triethylamine In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	95%
With triethylamine In tetrahydrofuran for 18h; Cooling with ice; Inert atmosphere; Reflux;	76%

Conditions	Yield
In dichloromethane at 20℃;	97%
With acetic acid for 4h; Heating;	86%
In 1,4-dioxane for 24h; Heating;	72%

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Cooling with ice;	97%
In 1,4-dioxane for 2h;	74%
In 1,4-dioxane	74%
In 1,4-dioxane at 25℃; for 2h;	46%
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Py2NPiPr2; potassium tert-butylate In tetrahydrofuran; diethylene glycol dimethyl ether at 70℃; for 48h; Inert atmosphere;	97%
With potassium hydroxide; 4-methoxy-benzaldehyde at 195 - 245℃; for 1h;	91.1%
With C55H43ClN5P2Ru(1+)*Cl(1-); potassium hydroxide In toluene at 140℃; for 12h; Sealed tube;	85%
With [RuCl(CO)(PPh3)(PNS-Me)]; potassium hydroxide In toluene at 100℃; for 12h;	76%

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice;	96%
With triethylamine In tetrahydrofuran Ambient temperature;	86%
With triethylamine In dichloromethane at 20℃; Condensation;	82%

Conditions	Yield
In diphenylether at 150 - 180℃;	96%
In diphenylether for 2.5h; Reflux;	55%
Microwave irradiation;

Conditions	Yield
With triethylamine In acetone at 20℃; for 2h;	96%
With triethylamine In acetone at 20℃; for 2h;	80%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 10h;	69%

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	100mg/kg (100mg/kg)		Journal of Medicinal Chemistry. Vol. 8, Pg. 296, 1965.
mouse	LD50	intravenous	56mg/kg (56mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00146,

Product Name

2,6-Diaminopyridine

Synthetic route

2,6-Diaminopyridine Chemical Properties

2,6-Diaminopyridine Uses

2,6-Diaminopyridine Production

2,6-Diaminopyridine Toxicity Data With Reference

2,6-Diaminopyridine Consensus Reports

2,6-Diaminopyridine Safety Profile

2,6-Diaminopyridine Standards and Recommendations

2,6-Diaminopyridine Specification

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