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Chemical Structure| 3512-18-3 Chemical Structure| 3512-18-3

Structure of 3512-18-3

Chemical Structure| 3512-18-3

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Product Details of [ 3512-18-3 ]

CAS No. :3512-18-3
Formula : C5H2F3N
M.W : 133.07
SMILES Code : FC1=CC=C(F)C(F)=N1
MDL No. :MFCD03001158
InChI Key :HRLIANGJWPJFKW-UHFFFAOYSA-N
Pubchem ID :2783288

Safety of [ 3512-18-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 3512-18-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 3512-18-3 ]
  • Downstream synthetic route of [ 3512-18-3 ]

[ 3512-18-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 3512-18-3 ]
  • [ 944799-22-8 ]
YieldReaction ConditionsOperation in experiment
74% With ammonia In water at 100℃; for 3 h; A mixture of 2,3,6-trifluoropyridine (8.18 g, 61.5 mmol) and concentrated NH4OH (40 ml_) was heated at 100° in a steel bomb for 3 h. The vessel was chilled in an ice bath and the resulting precipitate collected by filtration. After washing with cold water, the solid was dried to afford 3,6-difluoro-2-pyridinamine (5.95 g ,74percent) as fine white needles. 1H NMR (CDCI3): δ.7.25 (m, 1H), 6.18 (d, 1H). MS m/z 131 (M+1).
62% With ammonia In 1,4-dioxane; water at 100℃; for 16 h; Inert atmosphere To a stirred solution of 2,3,6-trifluoropyridine (5 g, 37.59 mmol) in 1, 4-dioxane (20 mL) under an argon atmosphere was added aq. ammonia (20 mL) at room temperature. The reaction mixture was stirred at 100 oC for 16 h. After consumption of the starting material (monitored by TLC), the reaction was quenched with cold water (500 mL) and extracted with CH2Cl2 (2 x 500 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain 3,6-difluoropyridin-2-amine (3 g, 62percent) as an off-white solid used in the next step without further purification. TLC: 10percent EtOAc:hexanes (Rf: 0.5).
62% With ammonia In 1,4-dioxane; water at 100℃; for 16 h; Inert atmosphere Synthesis of 3, 6-difluoropyridin-2-amine
To a stirred solution of 2,3,6-trifluoropyridine (5 g, 37.59 mmol) in 1,4-dioxane (20 mL) under an argon atmosphere was added aq. ammonia (20 mL) at room temperature.
The reaction mixture was stirred at 100° C. for 16 h.
After consumption of the starting material (monitored by TLC), the reaction was quenched with cold water (500 mL) and extracted with CH2Cl2 (2*500 mL).
The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain 3,6-difluoropyridin-2-amine (3 g, 62percent) as an off-white solid used in the next step without further purification. TLC: 10percent EtOAc:hexanes (Rf: 0.5).
References: [1] Patent: WO2007/87549, 2007, A2, . Location in patent: Page/Page column 117.
[2] Patent: WO2015/109109, 2015, A1, . Location in patent: Paragraph 0742.
[3] Patent: US2017/44182, 2017, A1, . Location in patent: Paragraph 1026.
 

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