Adenosine, 8-chloro- supplier

Name
8-CHLOROADENOSINE
EINECS
CAS No. 34408-14-5
Article Data9
CAS DataBase
Density 2.19 g/cm³
Solubility
Melting Point
Formula C₁₀H₁₂ClN₅O₄
Boiling Point 707.4 °C at 760 mmHg
Molecular Weight 301.689
Flash Point 381.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 8-Chloroadenosine;
PSA 139.54000
LogP -0.74540

Synthetic route

: 58-61-7
adenosine

: 34408-14-5
8-chloroadenosine

Conditions

Conditions	Yield
With N-chloro-succinimide; acetic acid In N,N-dimethyl-formamide at 20℃; for 48h; Concentration; Reagent/catalyst;	52%
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl acetamide for 3.5h; Ambient temperature;	50%
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl acetamide at 0 - 25℃; for 2.5h;	39%

: 3001-45-4
8-mercaptoadenosine

: 34408-14-5
8-chloroadenosine

Conditions

Conditions	Yield
With N-chloro-succinimide In methanol at 20℃; for 3h;	52%

: 4294-16-0
N6-Benzyladenosine

A: 34408-14-5
8-chloroadenosine

B: 1427459-38-8
6-benzylamino-8-chloro-9-(β-D-ribofuranosyl)purine

Conditions

Conditions	Yield
With N-chloro-succinimide In N,N-dimethyl-formamide at 45℃; for 18h;	A n/a B 20%

: N-chloro-succinamide

: 7732-18-5
water

: 58-61-7
adenosine

: 34408-14-5
8-chloroadenosine

Conditions

Conditions	Yield
With acetic acid In methanol; N,N-dimethyl-formamide	0.8 g (65%)

...Expand

: 2946-39-6
8-bromoadenosine

: 34408-14-5
8-chloroadenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thiourea / ethanol / 1 h / Reflux 2: N-chloro-succinimide / methanol / 3 h / 20 °C View Scheme

: 34408-14-5
8-chloroadenosine

: 74-89-5
methylamine

: 13389-13-4
8-Methylaminoadenosine

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 18.5h;	93%
With triethylamine at 20℃; for 20h;	93%

: 34408-14-5
8-chloroadenosine

: 108-24-7
acetic anhydride

: 64344-20-3
8-chloro-2',3',5'-tri-O-acetyladenosine

Conditions

Conditions	Yield
With pyridine for 16h; Ambient temperature;	88%

: 34408-14-5
8-chloroadenosine

: 67-64-1
acetone

: 2’,3’-O-isopropylidene-8-chloroadenosine

Conditions

Conditions	Yield
With perchloric acid at 20℃; for 0.5h;	79%

: 34408-14-5
8-chloroadenosine

: 701-99-5
Phenoxyacetyl chloride

: 508179-29-1
N6-phenoxyacetyl-8-chloroadenosine

Conditions

Conditions	Yield
With pyridine; 1,2,4-Triazole; chloro-trimethyl-silane In acetonitrile at 25 - 55℃; for 8h;	71%

: 926308-62-5
phenyl-1-yl-L-glycine benzyl ester phosphorochloridate

: 34408-14-5
8-chloroadenosine

: benzyl 2-(((((2R,3S,4R,5R)-5-(6-amino-8-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)acetate

Conditions

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;	28%

: 34408-14-5
8-chloroadenosine

: 2462-31-9
benzyl 2-aminoacetate hydrochloride

: 8-chloroadenosine 5’-O-bis(benzyloxyglycin-N-yl)phosphate

Conditions

Conditions	Yield
Stage #1: 8-chloroadenosine With phosphorous acid trimethyl ester; trichlorophosphate at -5 - 20℃; for 4h; Stage #2: benzyl 2-aminoacetate hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃; for 20h;	27%

: 34408-14-5
8-chloroadenosine

: naphth-1-yl-glycine pent-1-yl ester phosphorochloridate

: 5’-([(pent-1-yloxy-glycin-N-yl)naphth-1-yl]phosphatyl)-8-chloroadenosine

Conditions

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;	15%

: 34408-14-5
8-chloroadenosine

: phenyl-1-yl-L-glycine cyclohexyl ester phosphorochloridate

: cyclohexyl 2-(((((2R,3S,4R,5R)-5-(6-amino-8-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)acetate

Conditions

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;	14%

: phenyl (benzyloxy-D-alaninyl)phosphorochloridate

: 34408-14-5
8-chloroadenosine

: 5’-([(benzyloxy-D-alanin-N-yl)phenyl]phosphatyl)-8-chloroadenosine

Conditions

Conditions	Yield
Stage #1: 8-chloroadenosine With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: phenyl (benzyloxy-D-alaninyl)phosphorochloridate In tetrahydrofuran	11%

: 34408-14-5
8-chloroadenosine

: 1228377-60-3
naphth-1-yl-glycine benzyl ester phosphorochloridate

: 5’-([(benzyloxyglycin-N-yl)naphth-1-yl]phosphatyl)-8-chloroadenosine

Conditions

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;	4%

: 34408-14-5
8-chloroadenosine

: naphth-1-yl-glycine ethyl ester phosphorochloridate

: 5’-([(ethyloxy-glycin-N-yl)naphth-1-yl]phosphatyl)-8-chloroadenosine

Conditions

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;	4%

: 34408-14-5
8-chloroadenosine

: 183370-70-9
phenyl(benzyloxy-L-alaninyl)phosphorochloridate

: (2S)-benzyl 2-(((((2R,3S,4R,5R)-5-(6-amino-8-chloro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Conditions

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃;	2%

: 34408-14-5
8-chloroadenosine

: 220592-67-6
O-phenyl-N-(S)-1-(cyclohexoxycarbonyl)ethylphosphoramidic chloride

: 5’-([(cyclohexyloxy-L-alanin-N-yl)phenyl]phosphatyl)-8-chloroadenosine

Conditions

Conditions	Yield
Stage #1: 8-chloroadenosine With pyridine; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: O-phenyl-N-(S)-1-(cyclohexoxycarbonyl)ethylphosphoramidic chloride In tetrahydrofuran for 24h;	2%

: 34408-14-5
8-chloroadenosine

: C15H23ClNO4P

: 5’-([(neopentyloxy-2,2-dimethylglycin-N-yl)phenyl]phosphatyl)-8-chloroadenosine

Conditions

Conditions	Yield
Stage #1: 8-chloroadenosine With pyridine; tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: C15H23ClNO4P In tetrahydrofuran for 24h;	2%

: 74-83-9
methyl bromide

: 34408-14-5
8-chloroadenosine

: 6-Amino-8-chloro-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-methyl-9H-purin-1-ium; bromide

Conditions

Conditions	Yield
In N,N-dimethyl acetamide for 120h; Ambient temperature;

: 34408-14-5
8-chloroadenosine

A: 8chloroadenosine-5'-phosphate

B: 8-chloroadenosine-5'-diphosphate

C: 8-chloroadenosine-5'-triphosphate

Conditions

Conditions	Yield
With Tetraethyl pyrophosphate; phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 34408-14-5
8-chloroadenosine

: 508179-30-4
N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-8-chloro-9H-purin-6-yl)-2-phenoxy-acetamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C 2: 58 percent / DMAP / pyridine / 19 h View Scheme

: 34408-14-5
8-chloroadenosine

: 508179-32-6
N-{9-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-8-chloro-9H-purin-6-yl}-2-phenoxy-acetamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C 2: 58 percent / DMAP / pyridine / 19 h 3: 38 percent / pyridine; Et3N; AgNO3 / tetrahydrofuran / 2.83 h / 25 °C View Scheme

: 34408-14-5
8-chloroadenosine

: 508179-31-5
N-{9-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-8-chloro-9H-purin-6-yl}-2-phenoxy-acetamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C 2: 58 percent / DMAP / pyridine / 19 h 3: 16 percent / pyridine; Et3N; AgNO3 / tetrahydrofuran / 2.83 h / 25 °C View Scheme

: 34408-14-5
8-chloroadenosine

: Succinic acid mono-{(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-2-[8-chloro-6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl} ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C 2: 58 percent / DMAP / pyridine / 19 h 3: 38 percent / pyridine; Et3N; AgNO3 / tetrahydrofuran / 2.83 h / 25 °C 4: 71 percent / DMAP / pyridine / 12 h / 25 °C View Scheme

: 34408-14-5
8-chloroadenosine

: Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[8-chloro-6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 71 percent / pyridine; chlorotrimethylsilane; 1,2,4-triazole / acetonitrile / 8 h / 25 - 55 °C 2: 58 percent / DMAP / pyridine / 19 h 3: 16 percent / pyridine; Et3N; AgNO3 / tetrahydrofuran / 2.83 h / 25 °C 4: 50 percent / 2,4,6-collidine; N-methylimidazole / tetrahydrofuran / 4 h / 25 °C View Scheme

: 34408-14-5
8-chloroadenosine

: 8-Chloro-purine riboside

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / pyridine / 16 h / Ambient temperature 2: 39 percent / t-butyl nitrite / tetrahydrofuran / 1 h / Heating 3: 37 percent / aq. NH4HCO3 / 120 h / Ambient temperature; porcine liver esterase View Scheme

: 34408-14-5
8-chloroadenosine

: 157025-49-5
8-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / pyridine / 16 h / Ambient temperature 2: 39 percent / t-butyl nitrite / tetrahydrofuran / 1 h / Heating View Scheme

: 34408-14-5
8-chloroadenosine

: 92001-48-4
8-chloro-1-methyladenine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethyl-acetamide / 120 h / Ambient temperature 2: glacial acetic acid / 2.5 h / Heating 3: 232 mg / conc. aq. ammonia View Scheme

: 34408-14-5
8-chloroadenosine

: 6-Amino-8-chloro-1-methyl-9H-purin-1-ium; bromide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-acetamide / 120 h / Ambient temperature 2: glacial acetic acid / 2.5 h / Heating View Scheme

Adenosine, 8-chloro- Specification

The Adenosine, 8-chloro-, with the CAS registry number of 34408-14-5, is also known as 8-Chloroadenosine. This chemical's molecular formula is C₁₀H₁₂ClN₅O₄ and molecular weight is 301.69. What's more, its IUPAC name is 2-(6-Amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3, 4-diol. In addition, it must be stored in airtight containers and placed in a dry, cool place.

Physical properties about Adenosine, 8-chloro- are: (1)ACD/LogP: -0.46; (2)# of Rule of 5 Violations: 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 13.31; (6)ACD/KOC (pH 7.4): 13.33; (7)#H bond acceptors: 9; (8)#H bond donors: 5; (9)#Freely Rotating Bonds: 5; (10)Polar Surface Area: 83.76 Å²; (11)Index of Refraction: 1.912; (12)Molar Refractivity: 64.55 cm³; (13)Molar Volume: 137.4 cm³; (14)Surface Tension: 106.5 dyne/cm; (15)Density: 2.19 g/cm³; (16)Flash Point: 381.6 °C; (17)Enthalpy of Vaporization: 108.65 kJ/mol; (18)Boiling Point: 707.4 °C at 760 mmHg; (19)Vapour Pressure: 5.28E-21 mmHg at 25 °C.

Preparation: this chemical is prepared by Adenosine at ambient temperature. This reaction needs reagents HCl and m-Chloroperbenzoic acid. Meanwhile, it needs solvent N, N-Dimethyl-acetamide. The reaction time is 3.5 hours. The yield is about 50 %.

Uses: it is used to produce other chemicals. For example, it is used to produce N⁶-phenoxyacetyl-8-chloroadenosine. This reaction needs reagents Pyridine; Chlorotrimethylsilane; 1, 2, 4-Triazole. Meanwhile, it needs solvent Acetonitrile. The reaction time is 8 hours with reaction temperature of 25-55 °C. The yield is about 71 %.

You can still convert the following datas into molecular structure:
(1) SMILES: Clc2nc1c(ncnc1n2[C@@H]3O[C@@H]([C@@H](O)[C@H]3O)CO)N
(2) InChI: InChI=1/C10H12ClN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
(3) InChIKey: MHDPPLULTMGBSI-UUOKFMHZBR

Product Name

8-CHLOROADENOSINE

Synthetic route

Adenosine, 8-chloro- Specification

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