Cas no 86209-44-1 (2-Amino-4,6-bis(difluoromethoxy)pyrimidine)

2-Amino-4,6-bis(difluoromethoxy)pyrimidine is a versatile heterocyclic compound characterized by its difluoromethoxy substituents and amino group. Its unique structure endows it with significant advantages, including potent biological activity and tunable reactivity. This compound is highly sought after in drug discovery for its potential in inhibiting key enzymes, making it a valuable tool in medicinal chemistry research.
2-Amino-4,6-bis(difluoromethoxy)pyrimidine structure
86209-44-1 structure
Product Name:2-Amino-4,6-bis(difluoromethoxy)pyrimidine
CAS No:86209-44-1
MF:C6H5F4N3O2
MW:227.116414785385
MDL:MFCD08669334
CID:60959
PubChem ID:13491823
Update Time:2025-06-18

2-Amino-4,6-bis(difluoromethoxy)pyrimidine Chemical and Physical Properties

Names and Identifiers

    • 2-Amino-4,6-bis(difluoromethoxy)pyrimidine
    • 4,6-bis(difluoromethoxy)pyrimidin-2-amine
    • 2-AMINO-4,6-DIFLUOROMETHOXYPYRIMIDINE
    • 4,6-Bis(difluoromethoxy)-2-pyrimidinamine
    • 4,6-Bis(difluoromethoxy)-2-pyrimidinamine (ACI)
    • P9EM6J7W4U
    • MFCD08669334
    • 2-amino-4,6-bis-(difluoromethoxy)pyrimidine
    • DTXSID90542106
    • AKOS015891932
    • 2-Pyrimidinamine, 4,6-bis(difluoromethoxy)-
    • SCHEMBL1577067
    • 4,6-bis(difluoromethoxy)-2-aminopyrimidine
    • 86209-44-1
    • MDL: MFCD08669334
    • Inchi: 1S/C6H5F4N3O2/c7-4(8)14-2-1-3(15-5(9)10)13-6(11)12-2/h1,4-5H,(H2,11,12,13)
    • InChI Key: DARNJZBBTBLNCA-UHFFFAOYSA-N
    • SMILES: FC(OC1C=C(OC(F)F)N=C(N)N=1)F

Computed Properties

  • Exact Mass: 227.03200
  • Monoisotopic Mass: 227.03178906g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 4
  • Complexity: 179
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.4
  • Topological Polar Surface Area: 70.3?2

Experimental Properties

  • Density: 1.527
  • Boiling Point: 337 oC
  • Flash Point: 157 oC
  • Refractive Index: 1.428
  • PSA: 70.26000
  • LogP: 1.84280

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2-Amino-4,6-bis(difluoromethoxy)pyrimidine Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)
Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

Production Method 2

Reaction Conditions
1.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine
Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

Production Method 3

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  70 - 80 °C
1.2 4 h, 70 - 80 °C
Reference
Study on the synthesis of herbicide primisulfuron-methyl for corn farmland
Lu, Yang; et al, Jingxi Yu Zhuanyong Huaxuepin, 2006, 14(15), 13-14

Production Method 4

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water
Reference
Synthesis of ultrahigh effective herbicide primisulfuron-methyl
Xiao, Shenchu; et al, Huaxue Shijie, 2001, 42(7), 391-392

Production Method 5

Reaction Conditions
1.1 Reagents: Hydrogen peroxide Solvents: Acetic acid ,  Water
2.1 Reagents: Ammonia Solvents: Dichloromethane ,  Water
Reference
The synthesis of herbicide primisulfuron-methyl
Xiang, Dong; et al, Nongyao, 2000, 39(7),

Production Method 6

Reaction Conditions
1.1 Reagents: Sodium ethoxide Solvents: Toluene ;  rt → reflux
1.2 reflux; 4 - 5 h, reflux
1.3 Reagents: Hydrochloric acid Solvents: Water ;  neutralized
2.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  70 - 80 °C
2.2 4 h, 70 - 80 °C
Reference
Study on the synthesis of herbicide primisulfuron-methyl for corn farmland
Lu, Yang; et al, Jingxi Yu Zhuanyong Huaxuepin, 2006, 14(15), 13-14

Production Method 7

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  rt → 10 °C
1.2 0 - 10 °C; 4 h, 0 - 10 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, 0 - 10 °C; 1 h, 0 - 10 °C
2.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  rt → 65 °C; 4 h, 65 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6; 2 h, 65 °C
3.1 Reagents: Acetic acid ,  Hydrogen peroxide Solvents: Water ;  rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
4.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine
Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

Production Method 8

Reaction Conditions
1.1 Reagents: Sodium hydroxide
2.1 Catalysts: Tetrabutylammonium chloride Solvents: Acetonitrile
3.1 Reagents: Hydrogen peroxide Solvents: Acetic acid ,  Water
4.1 Reagents: Ammonia Solvents: Dichloromethane ,  Water
Reference
The synthesis of herbicide primisulfuron-methyl
Xiang, Dong; et al, Nongyao, 2000, 39(7),

Production Method 9

Reaction Conditions
1.1 Reagents: Sodium methoxide Solvents: Methanol
2.1 Reagents: Sodium hydroxide
3.1 Catalysts: Tetrabutylammonium chloride Solvents: Acetonitrile
4.1 Reagents: Hydrogen peroxide Solvents: Acetic acid ,  Water
5.1 Reagents: Ammonia Solvents: Dichloromethane ,  Water
Reference
The synthesis of herbicide primisulfuron-methyl
Xiang, Dong; et al, Nongyao, 2000, 39(7),

Production Method 10

Reaction Conditions
1.1 Reagents: Ammonia Solvents: Dichloromethane ,  Water
Reference
The synthesis of herbicide primisulfuron-methyl
Xiang, Dong; et al, Nongyao, 2000, 39(7),

Production Method 11

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  1 h, 60 - 70 °C
Reference
Synthesis and herbicidal activity of Primisulfuron-methyl
Huang, Mingzhi, Nongyao, 2003, 42(10), 15-16

Production Method 12

Reaction Conditions
1.1 Solvents: Acetonitrile ;  3 h, 50 °C
Reference
Process for preparation of fluorine-containing herbicides
, China, , ,

Production Method 13

Reaction Conditions
1.1 Reagents: Hydrogen peroxide Solvents: Acetic acid ,  Water ;  rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
1.2 Reagents: Water
2.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)
Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

Production Method 14

Reaction Conditions
1.1 Reagents: Acetic acid ,  Hydrogen peroxide Solvents: Water ;  rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
2.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine
Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

Production Method 15

Reaction Conditions
1.1 Reagents: Sodium ethoxide Solvents: Ethanol
2.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water
Reference
Synthesis of ultrahigh effective herbicide primisulfuron-methyl
Xiao, Shenchu; et al, Huaxue Shijie, 2001, 42(7), 391-392

Production Method 16

Reaction Conditions
1.1 Catalysts: Tetrabutylammonium chloride Solvents: Acetonitrile
2.1 Reagents: Hydrogen peroxide Solvents: Acetic acid ,  Water
3.1 Reagents: Ammonia Solvents: Dichloromethane ,  Water
Reference
The synthesis of herbicide primisulfuron-methyl
Xiang, Dong; et al, Nongyao, 2000, 39(7),

Production Method 17

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  4 h, rt → 65 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6, rt
1.3 2 h, rt → 65 °C
2.1 Reagents: Hydrogen peroxide Solvents: Acetic acid ,  Water ;  rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
2.2 Reagents: Water
3.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)
Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

Production Method 18

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  rt → 65 °C; 4 h, 65 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6; 2 h, 65 °C
2.1 Reagents: Acetic acid ,  Hydrogen peroxide Solvents: Water ;  rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
3.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine
Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

Production Method 19

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  rt → 10 °C; 0 - 10 °C; 4 h, 0 - 10 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, 0 - 10 °C; 1 h, 0 - 10 °C
2.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  4 h, rt → 65 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6, rt
2.3 2 h, rt → 65 °C
3.1 Reagents: Hydrogen peroxide Solvents: Acetic acid ,  Water ;  rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
3.2 Reagents: Water
4.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)
Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

Production Method 20

Reaction Conditions
1.1 Reagents: Sodium methoxide Solvents: Methanol ,  Water ;  30 min, rt; 5 h, rt → 70 °C; 70 °C → rt
2.1 Reagents: Sodium hydroxide Solvents: Water ;  rt → 10 °C; 0 - 10 °C; 4 h, 0 - 10 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, 0 - 10 °C; 1 h, 0 - 10 °C
3.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  4 h, rt → 65 °C
3.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6, rt
3.3 2 h, rt → 65 °C
4.1 Reagents: Hydrogen peroxide Solvents: Acetic acid ,  Water ;  rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
4.2 Reagents: Water
5.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino]carbonyl]amino]sulfonyl]benzoic acid methyl ester (primisulfuron)
Wang, Jin-Ling; et al, Yingyong Huaxue, 2009, 26(4), 486-488

Production Method 21

Reaction Conditions
1.1 Reagents: Sodium methoxide Solvents: Methanol ;  30 min, rt; rt → 70 °C; 5 h, 70 °C
2.1 Reagents: Sodium hydroxide Solvents: Water ;  rt → 10 °C
2.2 0 - 10 °C; 4 h, 0 - 10 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, 0 - 10 °C; 1 h, 0 - 10 °C
3.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  rt → 65 °C; 4 h, 65 °C
3.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6; 2 h, 65 °C
4.1 Reagents: Acetic acid ,  Hydrogen peroxide Solvents: Water ;  rt → 85 °C; 80 - 85 °C; 2 h, 80 - 85 °C
5.1 Reagents: Ammonium hydroxide Solvents: Dichloromethane ,  Water ;  rt; 3 h, rt
Reference
Synthesis of 4,6-bis(difluoromethoxy)-2-aminopyridine
Wang, Jinling; et al, Nongyao, 2008, 47(5), 346-347

2-Amino-4,6-bis(difluoromethoxy)pyrimidine Raw materials

2-Amino-4,6-bis(difluoromethoxy)pyrimidine Preparation Products

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