| Identification | More | [Name]
2,4-Diamino-6-hydroxypyrimidine | [CAS]
56-06-4 | [Synonyms]
2,4-DIAMINO-6(1H)-PYRIMIDINONE
2,4-DIAMINO-6-HYDROXYPYRIMIDINE
2,4-DIAMINO-6-PYRIMIDINOL
2,4-DIAMINOPYRIMIDIN-6-OL
2,6-DIAMINO-4(1H)-PYRIMIDINONE
2,6-DIAMINO-4-HYDROXYPYRIMIDINE
2,6-DIAMINO-4-PYRIMIDINOL
2,6-DIAMINO-4-PYRIMIDINONE
2,6-DIAMINOPYRIMIDIN-4-OL
AKOS MSC-0109
AURORA KA-376
DAHP
TIMTEC-BB SBB004252
2,6-Diamino-4-Hydroxyprimidine
2,6-diamino-1H-pyrimidin-4-one
2,4-Diamino-6.-Hydroxypyimidine
2,6-DIAMINO-3H-PYRIMIDIN-4-ONE
2,4-Diamino-6-hydroxypyrimidiine
4(1H)-Pyrimidinone, 2,6-diamino-(8CI,9CI)
2,6-Diaminopyrimidin-4-one | [EINECS(EC#)]
200-254-4 | [Molecular Formula]
C4H6N4O | [MDL Number]
MFCD00006098 | [Molecular Weight]
126.12 | [MOL File]
56-06-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
285-286 °C (dec.) (lit.) | [Boiling point ]
234.22°C (rough estimate) | [density ]
1.3659 (rough estimate) | [refractive index ]
1.7990 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Fine Crystalline Powder | [pka]
10.61±0.50(Predicted) | [color ]
White to cream | [Sensitive ]
Light Sensitive | [Usage]
It stands at the beginning of the enzyme-catalyzed cascade that starts with this seven-carbon carbohydrate and ends with the aromatic amino acids phenylalanine, tyrosine, and tryptophan | [Detection Methods]
HPLC,NMR | [Merck ]
14,2981 | [BRN ]
125006 | [InChIKey]
SWELIMKTDYHAOY-UHFFFAOYSA-N | [CAS DataBase Reference]
56-06-4(CAS DataBase Reference) | [NIST Chemistry Reference]
4(1H)-pyrimidinone, 2,6-diamino-(56-06-4) | [EPA Substance Registry System]
56-06-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29335995 |
| Hazard Information | Back Directory | [Description]
2,4-Diamino-6-hydroxypyrimidine (DAHP) is a selective, specific inhibitor of GTP cyclohydrolase I, the rate limiting step for de novo pterin synthesis. In HUVEC cells, the IC50 for inhibition of BH4 biosynthesis is about 0.3 mM. DAHP can be used to effectively block NO production in several cell types.1,2,3 | [Chemical Properties]
White Solid | [Uses]
2,4-Diamino-6-hydroxypyrimidine (DAHP) is a selective, specific inhibitor of GTP cyclohydrolase I, the rate limiting step for de novo pterin synthesis. In HUVEC cells, the IC50 for inhibition of BH4 biosynthesis is about 0.3 mM. DAHP can be used to effectively block NO production in several cell types.[Cayman Chemical] | [Uses]
It stands at the beginning of the enzyme-catalyzed cascade that starts with this seven-carbon carbohydrate and ends with the aromatic amino acids phenylalanine, tyrosine, and tryptophan | [Synthesis]
A solution of sodium ethoxide is prepared from 23 g. (1 g. atom) of sodium and 250 ml of anhydrous ethanol in a 1-l round-bottomed flask fitted with a reflux condenser carrying a calcium chloride drying tube. After the sodium has dissolved, the solution is cooled and 113 g. (1 mole) of ethyl cyanoacetate is added. This mixture is allowed to stand while a second solution of sodium ethoxide of the same volume and concentration is prepared. To this solution is added 97 g. (1.02 moles) of guanidine hydrochloride. The sodium chloride is separated by filtration, and the clear filtrate containing guanidine is added to the solution of ethyl sodiocyanoacetate. This mixture is heated for 2 hours under reflux and is then evaporated to dryness at atmospheric pressure. The solid product is dissolved in 325 ml. of boiling water and acidified with 67 ml. of glacial acetic acid. Upon cooling of the solution, 101–103 g. (80–82%) of yellow needles separates; m.p. 260–270° (dec.)
| [storage]
4°C, protect from light | [Purification Methods]
It recrystallises from H2O. [Beilstein 25 III/IV 3642.] | [References]
[1] Patent: CN107857734, 2018, A. Location in patent: Paragraph 0032; 0033; 0034; 0035 |
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