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6-Thioguanosine
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Name

6-Thioguanosine

 EINECS 201-597-2
CAS No. 85-31-4 Density 2.18 g/cm3
PSA 174.53000 LogP -0.73620
Solubility Soluble in Ammonium Hydroxide and water Melting Point 230-231°C
Formula C10H13 N5 O4 S Boiling Point 756.9 °C at 760 mmHg
Molecular Weight 299.31 Flash Point 411.6 °C
Transport Information N/A Appearance Yellow-Green Powder
Safety Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS. Risk Codes N/A
Molecular Structure Molecular Structure of 85-31-4 (6-THIOGUANOSINE) Hazard Symbols N/A
Synonyms

6H-Purine-6-thione,2-amino-1,9-dihydro-9-b-D-ribofuranosyl- (8CI); 9H-Purine-6(1H)-thione, 2-amino-9-b-D-ribofuranosyl- (6CI,7CI);2-Amino-6-mercaptopurine ribonucleoside; 2-Amino-6-mercaptopurine riboside;2-Amino-9-(b-D-ribofuranosyl)purine-6-thiol;2-Amino-9-b-D-ribofuranosyl-9H-purine-6-thiol;2-Amino-9-b-D-ribofuranosylpurine-6-thione;6-Mercaptoguanine riboside; 6-Mercaptoguanosine; 6-Thioguanine ribonucleoside;6-Thioguanine riboside; 6-Thioguanosine; 9-b-D-Ribofuranosylthioguanine; NSC-29422; Thioguanosine

Article Data 10

6-Thioguanosine Synthetic route

88010-92-8

O2',O3',O5'-tribenzoyl-6-thio-guanosine

85-31-4

6-thioguanosine

Conditions
ConditionsYield
With sodium ethanolate
118-00-3

G

85-31-4

6-thioguanosine

Conditions
ConditionsYield
With pyridine; sodium hydrogensulfide; trifluoroacetic anhydride 1) 40 min, ice-bath, 2) DMF, 24 h; Multistep reaction;
66048-53-1

2',3',5'-tri-O-benzoylguanosine

85-31-4

6-thioguanosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous pyridine; P2S5
2: ethanolic sodium ethylate
View Scheme
70-34-8

2,4-Dinitrofluorobenzene

85-31-4

6-thioguanosine

74418-21-6

(2R,3R,4S,5R)-2-[2-Amino-6-(2,4-dinitro-phenylsulfanyl)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Conditions
ConditionsYield
With triethylamine80%
With triethylamine
85-31-4

6-thioguanosine

123002-38-0

6-amino-1-β-D-ribofuranosylimidazo<4,5-c>pyridine-4-sulfenamide

Conditions
ConditionsYield
With potassium hydroxide; chloroamine for 0.75h; from 0 deg C to RT;74%
With potassium hydroxide; chloroamine at 0℃; for 1.5h;73.7%
15715-58-9

triethylamine carbonate

85-31-4

6-thioguanosine

6-thioguanosine 5'-O-monophosphate triethylammonium salt

Conditions
ConditionsYield
Stage #1: 6-thioguanosine With trimethyl phosphite; trichlorophosphate at 0℃; for 48h;
Stage #2: triethylamine carbonate In water		68%

cobalt(II) nitrate hexahydrate

85-31-4

6-thioguanosine

[Co(6-thioGuo)3] sesquihydrate

Conditions
ConditionsYield
In methanol; water at 86℃; for 3h;48%

cobalt(II) sulphate heptahydrate

85-31-4

6-thioguanosine

[bis(6-thioguanosine-k2N,S)(6-thioguanosinato-k2N,S)cobalt(III)] sulphate trihydrate

Conditions
ConditionsYield
With sodium hydroxide In water for 3h; pH=8; Reflux;15%
85-31-4

6-thioguanosine

A

154-42-7

thioguanine

B

18646-11-2

α-D-ribofuranosyl-1-phosphate

Conditions
ConditionsYield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;
85-31-4

6-thioguanosine

623164-06-7

N2-phenoxyacetyl-S6-(2,4-dinitrophenyl)-6-thioguanosine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / triethylamine
2: NH3 / H2O
View Scheme
Multi-step reaction with 4 steps
1: Et3N
2: pyridine
3: pyridine
4: aq. NH3
View Scheme

6-Thioguanosine Chemical Properties

Molecular Formula: C10H13N5O4S
Molar mass: 299.31 g/mol
EINECS: 201-597-2
Density: 2.18 g/cm3
Flash Point: 411.6 °C
Index of Refraction: 1.975
Boiling Point: 756.9 °C at 760 mmHg
Vapour Pressure: 4.44E-24 mmHg at 25°C
Melting point: 230-231°C
Appearance: Tan powder
Product categories of 6-Thioguanosine (85-31-4): Nucleotides and Nucleosides;Sulfur & Selenium Compounds;Bases & Related Reagents;Nucleotides
Structure of 6-Thioguanosine (85-31-4):

XLogP3-AA: -1.2
H-Bond Donor: 5
H-Bond Acceptor: 7
Systematic Name: 2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3H-purine-6-thione 
SMILES: S=C3/N=C(/N)Nc1c3ncn1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO 
InChI: InChI=1/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1 
InChIKey: OTDJAMXESTUWLO-UUOKFMHZBV 
Std. InChI: InChI=1S/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1 
Std. InChIKey: OTDJAMXESTUWLO-UUOKFMHZSA-N

6-Thioguanosine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD10 unreported 1700mg/kg (1700mg/kg)   Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970.
mouse LD50 intraperitoneal 156mg/kg (156mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat LD50 intraperitoneal 200mg/kg (200mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.

6-Thioguanosine Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS.

6-Thioguanosine Specification

 6-Thioguanosine (85-31-4) also can be called 2-Amino-6-mercapto-9-b-D-ribofuranosylpurinee ; 6H-Purine-6-thione, 2-amino-1,9-dihydro-9-.beta.-D-ribofuranosyl- ; 2-Amino-9-(.beta.-D-ribofuranosyl)purine-6-thiol ; 9H-Purine-6-thiol, 2-amino-9-.beta.-D-ribofuranosyl- ; 2-Amino-6-mercapto-9-(.beta.-D-ribofuranosyl)purine ; and ; 6-Mercaptoguanosine .

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