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Product Details of Formimidamide acetate

CAS No. :3473-63-0
Formula : C3H8N2O2
M.W : 104.11
SMILES Code : N=CN.CC(O)=O
MDL No. :MFCD00012866
InChI Key :XPOLVIIHTDKJRY-UHFFFAOYSA-N
Pubchem ID :160693

Safety of Formimidamide acetate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317
Precautionary Statements:P261-P280

Application In Synthesis of Formimidamide acetate

* 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 [ 3473-63-0 ]
  • Downstream synthetic route of [ 3473-63-0 ]

[ 3473-63-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 3473-63-0 ]
  • [ 6705-03-9 ]
  • [ 19181-64-7 ]
YieldReaction ConditionsOperation in experiment
87% at 125℃; for 18 h; [0144] A mixture of 2-amino-5-methoxybenzoic acid (10.0 g, 59.9 mmol), formamidine acetate (12.3 g, 119 mmol) in 80 mL of 2-methoxyethanol was heated at 125 °C for 18 hours. After being cooled to room temperature, the precipitate was collected by filtration, washed twice with 2-methoxyethanol and dried in the vacuum to provide 6-methoxyquinazolin- 4(3H)-one (9.1 g, 87percent yield).
References: [1] Patent: WO2019/60611, 2019, A1, . Location in patent: Paragraph 0144.
[2] Patent: US2014/336182, 2014, A1, . Location in patent: Paragraph 0502.
  • 2
  • [ 3473-63-0 ]
  • [ 619-17-0 ]
  • [ 20872-93-9 ]
YieldReaction ConditionsOperation in experiment
84% at 130℃; for 18 h; A mixture of 2-amino-4-nitrobenzoic acid (10.0 g, 54.93 mmol) was refluxed at 130° C. for 18 h in methoxyethanol (50 mL) and formamidine acetate (11.43 g, 109.81 mmol).
The clear reaction mixture was cooled to room-temperature to form a yellowish precipitant.
The solvent was removed under vacuum, and the precipitant was washed several times with aqueous ammonia (0.01 M).
The solid was dried in vacuo to yield 8.9 g (84percent) of a light yellow powder. 1H NMR Data: dmso-d6-ppm (δ); 12.68 (1H), 8.37 (d, 1H), 8.33 (d, 1H), 8.26 (1H) and 8.23 (dd, 1H).
References: [1] Patent: US2016/376298, 2016, A1, . Location in patent: Paragraph 0220.
[2] Spectroscopy Letters, 2012, vol. 45, # 7, p. 530 - 540,11.
[3] Patent: CN103360382, 2016, B, . Location in patent: Paragraph 0228; 0244; 0245.
  • 3
  • [ 5922-60-1 ]
  • [ 3473-63-0 ]
  • [ 19808-35-6 ]
References: [1] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 6, p. 1407 - 1413.
  • 4
  • [ 62009-47-6 ]
  • [ 3473-63-0 ]
  • [ 56973-26-3 ]
References: [1] Patent: EP2196460, 2010, A1, . Location in patent: Page/Page column 6.
  • 5
  • [ 33884-41-2 ]
  • [ 3473-63-0 ]
  • [ 87379-42-8 ]
References: [1] Bulletin de la Societe Chimique de France, 1987, # 2, p. 318 - 324.
  • 6
  • [ 18856-72-9 ]
  • [ 3473-63-0 ]
  • [ 87379-55-3 ]
  • [ 87379-42-8 ]
References: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, # 3, p. 649 - 654.
  • 7
  • [ 3473-63-0 ]
  • [ 5794-88-7 ]
  • [ 155690-79-2 ]
YieldReaction ConditionsOperation in experiment
91% for 16 h; Heating / reflux To a 1.2 M solution of 5-bromoanthranilic acid (1 equiv) in N,N-dimethylformamide was added formamidine acetate (1 equiv). The mixture was heated to reflux and stirred at this temperature for 16 hours. After this time, the reaction was cooled and NaHCO3 solution (5 percent in H2O) (3 volumes) were carefully added and the mixture stirred vigorously. The resulting <n="113"/>precipitate was collected by filtration and then washed with water (2 X 1 volume) and then t- butyl methylether (2 X 1 volume) before being dried in a vacuum oven to give the desired product which required no further purification.6-Bromo-3H-pyrido[2,3-d]pyriniidin-4-one: (91 percent yield, insert) m/z (LC-MS,ESP):225 [M- H]- R/T = 2.31 minutes)
References: [1] Patent: WO2008/23161, 2008, A1, . Location in patent: Page/Page column 111-112.
  • 8
  • [ 3473-63-0 ]
  • [ 52833-94-0 ]
  • [ 155690-79-2 ]
YieldReaction ConditionsOperation in experiment
1.7 g at 120℃; for 36 h; Inert atmosphere 2-Amino-S -bromonictoinic acid (2 g) and formamidine acetate (3.0 g) were heated at 120 °C in2-methoxyethanol (15 ml) for 36 h under argon. The heterogeneous reaction mixture was diluted with water and filtered. The solid was suction dried to obtain 1.7 g of 6-bromopyrido[2,3- d]pyrimidin-4(3H)-one. ‘H NMR (300 MHz, DMSO-d6) ö 12.70 (s, 1H), 9.01 (d, J= 2.6 Hz, 1H), 8.59 (d, J= 2.6 Hz, 1H), 8.33 (s, 1H).
References: [1] Patent: WO2015/157093, 2015, A1, . Location in patent: Paragraph 1314; 1315.
 

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