7355-55-7

Basic information

• Product Name: 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine
• Synonyms: deazaguanine;2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine 7-Deazaguanine;2-amino-1H-pyrrolo[2,3-d]pyrimidin-4-ol;2-Amino-1H-pyrrolo[2,3-d]pyrimidin-4(7H)-one;2-AMINO-3,7-DIHYDRO-PYRROLO[2,3-D]PYRIMIDIN-4-ONE;2-AMINO-4-HYDROXY-7H-PYRROLO[2,3-DPYRIMIDINE];2-AMINO-4-HYDROXYPYRROLO-[2,3-D]PYRIMIDINE;2-AMINO-7H-PYRROLO[2,3-D]PYRIMIDIN-4-OL
• CAS NO: 7355-55-7
• Molecular Formula: C₆H₆N₄O
• Molecular Weight: 150.14
• EINECS: 948-371-6
• Product Categories: PYRIMIDINE;AMINEPRIMARY;Heterocyclic Series;Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Intermediates;Nucleotides
• Mol File: 7355-55-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: >230°C (dec.)
• Boiling Point: 452.7oC at 760 mmHg
• Flash Point: 227.6oC
• Appearance: tan/crystalline
• Density: 1.87g/cm3
• Vapor Pressure: 2.2E-08mmHg at 25°C
• Refractive Index: 1.89
• Storage Temp.: -20°C Freezer
• Solubility: Soluble in N,N-Dimethylformamide, Dimethyl sulfoxide.
• PKA: 10.83±0.20(Predicted)
• CAS DataBase Reference: 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine(7355-55-7)
• EPA Substance Registry System: 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine(7355-55-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37-60
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 7355-55-7(Hazardous Substances Data)

Usage

Chemical Properties

Pink solid

Uses

Ethidium bromide efficiently intercalates into synthetic duplex DNAs with 7-deazaguanine in place of guanine, but shows none of the fluorescence enhancement usually observed upon intercalation. 7-Deazaadenine-duplexes show about 70% of the expected fluorescence enhancement.

InChI:InChI=1/C6H6N4O/c7-6-9-4-3(1-2-8-4)5(11)10-6/h1-2H,(H4,7,8,9,10,11)

Upstream product

• 626-46-0 2,6-diamino-4-pyrimidinone 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 

Downstream Products

• 137281-08-4 N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide 
• 1369493-16-2 7-benzyl-N⁽⁴⁾-(3-bromophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine 
• 1417521-00-6 C₂₂H₂₈N₆O₂ 
• 1417521-04-0 C₁₇H₂₀N₆ 
• 1417521-21-1 C₁₂H₁₈N₆ 
• 934524-13-7 4-chloro-7-[(4-methylbenzene)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 88523-20-0 N-(5-((dibenzylamino)methyl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)octanamide 
• 99044-54-9 2-amino-7-benzyl-4-chloropyrrolo<2,3-d>pyrimidine 
• 914496-81-4 4-(2-amino-7-benzyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3,5-dimethyl-benzonitrile 
• 914496-82-5 4-(7-benzyl-2-fluoro-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3,5-dimethyl-benzonitrile 

Relevant articles and documents

Synthesis of Galactosyl-Queuosine and Distribution of Hypermodified Q-Nucleosides in Mouse Tissues

Queuosine (Q) is a hypermodified RNA nucleoside that is found in tRNAHis, tRNAAsn, tRNATyr, and tRNAAsp. It is located at the wobble position of the tRNA anticodon loop, where it can interact with U as well as C bases located at the respective position of the corresponding mRNA codons. In tRNATyr and tRNAAsp of higher eukaryotes, including humans, the Q base is for yet unknown reasons further modified by the addition of a galactose and a mannose sugar, respectively. The reason for this additional modification, and how the sugar modification is orchestrated with Q formation and insertion, is unknown. Here, we report a total synthesis of the hypermodified nucleoside galactosyl-queuosine (galQ). The availability of the compound enabled us to study the absolute levels of the Q-family nucleosides in six different organs of newborn and adult mice, and also in human cytosolic tRNA. Our synthesis now paves the way to a more detailed analysis of the biological function of the Q-nucleoside family.