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Chemical Structure| 50-01-1 Chemical Structure| 50-01-1
Chemical Structure| 50-01-1

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Guanidine HCl is a common used protein denaturant.

Synonyms: Guanidinium chloride; Aminoformamidine hydrochloride; Guanidine hydrochloride

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Product Details of Guanidine HCI

CAS No. :50-01-1
Formula : CH6ClN3
M.W : 95.53
SMILES Code : NC(N)=N.[H]Cl
Synonyms :
Guanidinium chloride; Aminoformamidine hydrochloride; Guanidine hydrochloride
MDL No. :MFCD00013026
InChI Key :PJJJBBJSCAKJQF-UHFFFAOYSA-N
Pubchem ID :5742

Safety of Guanidine HCI

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Guanidine HCI

* 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 [ 50-01-1 ]
  • Downstream synthetic route of [ 50-01-1 ]

[ 50-01-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 50-01-1 ]
  • [ 94-02-0 ]
  • [ 56741-94-7 ]
References: [1] RSC Advances, 2014, vol. 4, # 29, p. 15087 - 15090.
  • 2
  • [ 50-01-1 ]
  • [ 88-65-3 ]
  • [ 20198-19-0 ]
YieldReaction ConditionsOperation in experiment
52% With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24 h; 1.00 g (4.97mmol) of 2-bromobenzoic acid 44, 2.00 g (9.95 mmol) of guanidine hydrochloride, 6.48 g (19.9 mmol) of cesium carbonate and 95 mg (0.497mmol) of copper(I) iodide were dissolved in 20 ml of abs. DMF and stirred at 110 °C for 24 h. The solvent was distilled off in vacuo and the residue filtered through a short pad of silica gel using methanol as eluent. After recrystallization from ethanol 717 mg (52percent) of 2-aminoquinazolone 10 were obtained as a colorless solid. Mp.: >300°C. 1H-NMR(250 MHz, DMSO-d6): / ppm = 10.95 (s, 1H, NH); 7.87 (dd,J =7.9 Hz,J =1.5 Hz, 1H, Ar-H); 7.55 (ddd,J =8.5 Hz,J =7.2 Hz,J =1.6 Hz; 1H, Ar-H); 7.19 (d,J =8.2 Hz, 1H, Ar-H); 7.09 (t,J =7.5 Hz, 1H, Ar-H); 6.34 (br, 2H, NH2). 13C-NMR(75.4 MHz, DMSO-d6): / ppm = 163.2, 152.4, 150.2, 133.9, 125.9, 123.1, 121.4, 117.1. IR: ν = 3581 (w); 3399 (m); 3147 (m); 3063 (m); 2642 (m); 1801 (w); 1689 (m); 1657 (m); 1633 (m); 1608 (s); 1575 (m); 1558 (m); 1511 (m); 1473 (s); 1451 (m); 1402 (m); 1340 (m); 1248 (m); 1166 (m); 1153 (m); 1123 (m); 1041 (m); 1018 (m); 897 (m); 785 (m); 764 (s); 716 (w); 680 (m);623 (m); 591 (m); 537 (s); 491 (m); 465 (m). Anal. calcd. for C8H7N3O*1/3H2O(167,1): C 57.50; H 4.62; N 25.15; found: C 57.65; H 4.41; N 25.30.
References: [1] Applied Organometallic Chemistry, 2014, vol. 28, # 9, p. 661 - 665.
[2] Synthesis, 2009, # 16, p. 2679 - 2688.
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 24, p. 5576 - 5580.
  • 3
  • [ 50-01-1 ]
  • [ 134-20-3 ]
  • [ 20198-19-0 ]
YieldReaction ConditionsOperation in experiment
19% With sodium methylate In methanol; water; butan-1-ol A.
Preparation of 2-amino-4-(3H)-quinazolone
Guanidine hydrochloride (47.77 g, 0.5 mol) was added portionwise to a stirred suspension of sodium methoxide (32.42 g, 0.60 mol) in n-butanol (450 ml) at ambient temperature over 0.5 hour.
After a further 0.5 hour a solution of methyl anthranilate (15 g, 0.10 mol) in n-butanol (150 ml) was added dropwise and then slowly brought to reflux.
After distilling off ca.
100 ml of solvent the reaction mixture was heated under reflux at 116° for 117 hours.
The cooled suspension was filtered, excess solvent removed and the residue dissolved in water, acidified to pH 5 and extracted with diethyl ether.
The aqueous suspension was reacidified to pH 5, filtered off, washed with water and dried.
The solid was then triturated in methanol, filtered, washed with ether and dried to give 2-amino-4-(3H)-quinazolone (3.0 g, 19percent) m.p. >300°.
19% With sodium methylate In methanol; water; butan-1-ol A.
Preparation of 2-amino-4-(3H)-quinazolone
Guanidine hydrochloride (47.77 g, 0.5 mol) was added portionwise to a stirred suspension of sodium methoxide (32.42 g, 0.60 mol) in n-butanol (450 ml) at ambient temperature over 0.5 hour.
After a further 0.5 hour a solution of methyl anthranilate (15 g, 0.10 mol) in n-butanol (150 ml) was added dropwise and then slowly brought to reflux.
After distilling off ca.
100 ml of solvent the reaction mixture was heated under reflux at 116°C for 117 hours.
The cooled suspension was filtered, excess solvent removed and the residue dissolved in water, acidified to pH 5 and extracted with diethyl ether.
The aqueous suspension was reacidified to pH 5, filtered off, washed with water and dried.
The solid was then triturated in methanol, filtered, washed with ether and dried to give 2-amino-4-(3H)-quinazolone (3.0 g, 19percent) m.p. >300°C.
References: [1] Patent: US5064833, 1991, A, .
[2] Patent: EP322133, 1989, A1, .
  • 4
  • [ 50-01-1 ]
  • [ 118-91-2 ]
  • [ 20198-19-0 ]
References: [1] Synthesis, 2009, # 16, p. 2679 - 2688.
  • 5
  • [ 88-67-5 ]
  • [ 50-01-1 ]
  • [ 20198-19-0 ]
References: [1] Green Chemistry, 2009, vol. 11, # 11, p. 1881 - 1888.
  • 6
  • [ 50-01-1 ]
  • [ 133-13-1 ]
  • [ 30201-72-0 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With sodium In ethanol at 20℃; for 4 h; Inert atmosphere
Stage #2: for 1 h; Inert atmosphere; Reflux
General procedure: Metallic sodium (12.9 g, 0.56 mol) was dissolved in absolute ethanol (300 mL) under argon while being intensively stirred with a mechanical stirrer. The reaction flask was equipped with a reflux condenser with a chlorocalcium tube. After all the sodium was dissolved and the reaction mixture was cooled to room temperature; guanidine hydrochloride(21.02 g, 0.22 mol) was added under intensive stirring, followed by the corresponding monosubstituted malonic acid diester (0.2 mol). The reaction mixture was further intensively stirred due to the production of the solid product,which is so massive that after 2 h it already practically precludes stirring. After another 2 h, absolute ethanol (200 mL) was added and the reaction mixture was refluxed for 1 h while being stirred. Afterward, ethanol (ca200–300 mL) was evaporated on a vacuum rotary evaporatorand water (500 mL) was added to the reaction mixture. After stirring, the product (in the form of sodium salt) was almost dissolved. The obtained mixture was subsequently neutralized by dropwise addition of acetic acid, resulting in immediate and quantitative precipitation of the desired product in the form of a fine solid. This mixture was subsequently heated under reflux for 10 min and then cooled to laboratory temperature. This heating and cooling was repeated twice to get a well-filterable solid product. The solid product was filtered off, washed with water (2 x 50 mL),ethanol (2 x 50 mL), and acetone (2 x 50 mL). The product was dried under high vacuum at 60 °C for 2 days. The obtained purity of the product prepared in this manner is sufficient for the following reaction and based on analyses contains only crystalline water.
88% With sodium In ethanolInert atmosphere General procedure: Metallic sodium (12.9 g, 0.56 mol) was dissolved in absolute ethanol (300 mL) under argon while being intensively stirred with a mechanical stirrer. The reaction flask was equipped with a reflux condenser with a chlorocalcium tube. After all the sodium was dissolved and the reaction mixture was cooled to room temperature; guanidine hydrochloride (21.02 g, 0.22 mol) was added under intensive stirring, followed by the corresponding monosubstituted malonicacid diester (0.2 mol). The reaction mixture was further intensively stirred due to the production of the solid product, which is so massive that after 2 h it already practically precludes stirring. After another 2 h, absolute ethanol (200 mL) was added and the reaction mixture was refluxed for 1 h while being stirred. Afterward, ethanol (ca 200–300 mL) was evaporated on a vacuum rotary evaporator and water (500 mL) was added to the reaction mixture. After stirring, the product (in the form of sodium salt) was almost dissolved. The obtained mixture was subsequently neutralized by dropwise addition of acetic acid, resulting in immediate and quantitative precipitation of the desired product in the form of a fine solid. This mixture was subsequently heated under reflux for 10 min and then cooled to laboratory temperature. This heating and cooling was repeated twice to get a well-filterable solid product. The solid product was filtered off, washed with water (2 9 50 mL), ethanol (2 9 50 mL), and acetone (2 9 50 mL). The product was dried under high vacuum at 60 °C for 2 days. The obtained purity of the product prepared in this manner is sufficient for the following reaction and based on analyses contains only crystalline water.
References: [1] Medicinal Chemistry Research, 2014, vol. 23, # 10, p. 4482 - 4490.
[2] Medicinal Chemistry Research, 2014, vol. 23, # 10, p. 4482 - 4490.
 

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