2-Chloroadenine supplier | CasNO.1839-18-5

Name
2-Chloroadenine
EINECS 606-011-2
CAS No. 1839-18-5
Article Data30
CAS DataBase
Density 1.77 g/cm³
Solubility 8.3mg/L(25 oC)
Melting Point >300°C(dec)
Formula C₅H₄ClN₅
Boiling Point 315.2°C at 760 mmHg
Molecular Weight 169.573
Flash Point 144.4°C
Transport Information
Appearance
Safety 24/25
Risk Codes Xi:;
Molecular Structure
Hazard Symbols Xi
Synonyms 1H-Purin-6-amine,2-chloro- (9CI);Adenine, 2-chloro- (6CI,7CI,8CI);2-Chloro-6-aminopurine;6-Amino-2-chloropurine;NSC 7362;SQ 22982;2-chloro-7H-purin-6-amine;2-chloro-1H-purin-6-amine;7H-purin-6-amine, 2-chloro-;9H-purin-6-amine, 2-chloro-;
PSA 80.48000
LogP 1.16970

Synthetic route

: 5451-40-1
2,6 dichloropurine

: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
With ammonia In methanol at 100℃; for 12h;	100%
With ammonia In methanol at 100℃; for 16h;	97%
With ammonia In methanol at 160℃; for 24h;	95%

: 5451-40-1
2,6-dichloropurine

: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
With ammonia In isopropyl alcohol at 120℃;	100%

: 5451-40-1
2,6 dichloropurine

A: 85029-13-6
4-cyano-5-(cyanoamino)imidazole

B: 1839-18-5
2-chloroadenine

C: 1904-98-9
2,6-diaminopurine

Conditions

Conditions	Yield
With potassium amide In ammonia at -33℃; for 20h;	A 25% B 12% C 13%

...Expand

: 119530-58-4
2-Chloro-5'-O-(4,4'-dimethoxytrityl)-2',3'-O-thiocarbonyladenosine

A: 1839-18-5
2-chloroadenine

B: 115044-75-2
(2R,3R,5S)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol

C: 119530-61-9
9-{(3aR,4R,6R,6aR)-6-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-chloro-9H-purin-6-ylamine

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; acetic acid 1) toluene, 110-120 deg C, 3.5 h, 2) 50 deg C, 30 min; Yield given. Multistep reaction;

...Expand

: 244097-84-5
2-Chloro-9-(2-deoxy-β-L-erythro-pentofuranosyl)adenine

A: 1839-18-5
2-chloroadenine

B: Phosphoric acid mono-((2S,4R,5S)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl) ester

Conditions

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

: 244097-85-6
2-chloro-9-(2-deoxy-β-L-erythro-pentofuranosyl)adenine

A: 1839-18-5
2-chloroadenine

B: Phosphoric acid mono-((2R,4R,5S)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl) ester

Conditions

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

: 123318-82-1
clofarabine

A: 1839-18-5
2-chloroadenine

B: 850883-62-4
2-deoxy-2-fluoro-α-D-arabinofuranose 1-phosphate

Conditions

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

: 4291-63-8
2-chloro-2'-deoxyadenosine

A: 17039-17-7
2-deoxy–α-D-ribose 1-phosphate

B: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

: 4291-63-8
2-chloro-2'-deoxyadenosine

: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
With acetic acid In water pH=2.3; Hydrolysis;

: 2-chloro-9-(2-deoxy-2,2-difluoro-β-D-ribofuranosyl)adenine

A: 1839-18-5
2-chloroadenine

B: Phosphoric acid mono-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl) ester

Conditions

Conditions	Yield
With E. coli purine nucleoside phosphorylase Enzyme kinetics; Substitution;

: 146-77-0
2-Chloroadenosine

: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / pyridine / 24 h / Ambient temperature 2: 80 percent / acetonitrile / Ambient temperature 3: 1) AIBN, n-Bu3SnH, 2) aq.AcOH / 1) toluene, 110-120 deg C, 3.5 h, 2) 50 deg C, 30 min View Scheme
adenosine phosphorilase In water pH=7.4; Enzymatic reaction; Phosphate buffer;

: 883731-41-7
6-amino-2-chloro-9-(5'-deoxy-β-D-ribofuranosyl)-9H-purine

: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
adenosine phosphorilase In water pH=7.4; Enzymatic reaction; Phosphate buffer;

: C6H6Cl2N4

: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
With ammonia In methanol

: 5451-40-1
2,6-dichloro-7H-purine

: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
With ammonia In methanol

: 146-77-0
2-Chloroadenosine

A: C5H9O8P(2-)*2K(1+)

B: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; E-purine nucleoside phosphorylase-0002 In aq. buffer at 40℃; for 0.3h; pH=9; Equilibrium constant; Thermodynamic data; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction;

: 4291-63-8
2-chloro-2'-deoxyadenosine

A: C5H9O7P(2-)*2K(1+)

B: 1839-18-5
2-chloroadenine

Conditions

Conditions	Yield
With potassium dihydrogenphosphate; E-purine nucleoside phosphorylase-0002 In aq. buffer at 40℃; for 0.3h; pH=9; Equilibrium constant; Thermodynamic data; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction;

: 1839-18-5
2-chloroadenine

: 17201-43-3
4-cyanobenzyl bromide

: 927822-40-0
4-((6-amino-2-chloro-9H-purin-9-yl)methyl)benzonitrile

Conditions

Conditions	Yield
Stage #1: 2-chloroadenine With potassium carbonate In dimethyl sulfoxide for 0.0833333h; Stage #2: 4-cyanobenzyl bromide In dimethyl sulfoxide at 20℃; for 22h;	96%

: 16004-15-2
1-bromomethyl-4-iodobenzene

: 1839-18-5
2-chloroadenine

: 2-chloro-9-(4-iodobenzyl)adenine

Conditions

Conditions	Yield
Stage #1: 2-chloroadenine With potassium carbonate In dimethyl sulfoxide for 0.0333333h; Stage #2: 1-bromomethyl-4-iodobenzene In dimethyl sulfoxide at 20℃; for 19h;	95%

: 100-39-0
benzyl bromide

: 1839-18-5
2-chloroadenine

: 56046-25-4
6-amino-9-benzyl-2-chloropurine

Conditions

Conditions	Yield
Stage #1: 2-chloroadenine With potassium carbonate In dimethyl sulfoxide for 0.0333333h; Stage #2: benzyl bromide In dimethyl sulfoxide at 20℃; for 30h;	94%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; Inert atmosphere;	67%
With potassium carbonate In N,N-dimethyl-formamide	58%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;	44%

: 109-73-9
N-butylamine

: 1839-18-5
2-chloroadenine

: 5463-09-2
6-amino-2-butylamino-9H-purine

Conditions

Conditions	Yield
In water at 180℃; for 1h;	92%
at 18℃; for 18h; Autoclave;	86%
In water at 180℃; for 18h; Autoclave;	86%

: 1839-18-5
2-chloroadenine

: 4152-90-3
m-chlorobenzylamine

: 2-(3-chlorobenzylamino)-6-aminopurine

Conditions

Conditions	Yield
With triethylamine In butan-1-ol at 90℃; for 4h;	92%

: 5720-07-0
4-methoxyphenylboronic acid

: 1839-18-5
2-chloroadenine

: 2-(4-methoxyphenyl)adenine

Conditions

Conditions	Yield
With caesium carbonate; palladium diacetate In water; acetonitrile at 150℃; for 0.0833333h; Suzuki-Miyaura cross-coupling reaction; microwave irradiation;	90%

: 68673-84-7
methyl 1,2,3-tri-O-acetyl-β-D-ribofuronate

: 1839-18-5
2-chloroadenine

: 1012864-69-5
methyl 1-[2-chloroadenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate

Conditions

Conditions	Yield
Stage #1: 2-chloroadenine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 16h; Heating; Stage #2: methyl 1,2,3-tri-O-acetyl-β-D-ribofuronate With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 90℃; for 0.333333h; microwave irradiation; Further stages.;	89%

: 2'-deoxyribose 1-phosphate diammonium salt

: 1839-18-5
2-chloroadenine

: 4291-63-8
2-chloro-2'-deoxyadenosine

Conditions

Conditions	Yield
With magnesium hydroxide; purine nucleoside phosphorylase In water at 45℃;	88%

: 1839-18-5
2-chloroadenine

: 1129-28-8
3-methoxycarbonylbenzyl bromide

: 1001253-33-3
Methyl 3-((6-amino-2-chloro-9H-purin-9-yl)methyl)benzoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h;	86%

: 611-19-8
1-chloro-2-(chloromethyl)benzene

: 1839-18-5
2-chloroadenine

: 914220-98-7
2-chloro-9-(2-chlorobenzyl)adenine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 4h;	85%

: 1839-18-5
2-chloroadenine

: 212970-74-6
Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

: 1341075-05-5
(2R,3R,4S,5S)-2-(6-amino-2-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((tert-butyldiphenylsilyloxy)methyl)-5-(tosyloxymethyl)tetrahydrofuran-3-yl acetate

Conditions

Conditions	Yield
Stage #1: 2-chloroadenine; Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 65℃; for 1.5h; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 65℃; for 3h; Vorbrüggen coupling; Inert atmosphere; Stage #3: With sodium hydrogencarbonate In water; acetonitrile Inert atmosphere;	85%

Yield

Stage #1: 2-chloroadenine; Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 65℃; for 1.5h; Inert atmosphere;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 65℃; for 3h; Vorbrüggen coupling; Inert atmosphere;
Stage #3: With sodium hydrogencarbonate In water; acetonitrile Inert atmosphere;

85%

: 1839-18-5
2-chloroadenine

: 58-96-8
uridine

: 146-77-0
2-Chloroadenosine

Conditions

Conditions	Yield
With hydrogenchloride; potassium dihydrogenphosphate; potassium hydroxide In water; dimethyl sulfoxide at 58 - 61℃; for 4h; pH=7.1-7.2; Enzymatic reaction;	85%
With potassium phosphate; Geobacillus thermoglucosidasius purine nucleoside phosphorylase; Thermus thermophilus pyrimidine nucleoside phosphorylase In water at 70℃; for 1h; pH=7; Enzymatic reaction;
With dipotassium hydrogenphosphate; purine nucleoside phosphorylase; pyrimidine nucleoside phosphorylase; glycine In aq. buffer at 60℃; pH=9; Equilibrium constant; Enzymatic reaction;

: 961-07-9
2'-Deoxyguanosine

: 1839-18-5
2-chloroadenine

: 4291-63-8
2-chloro-2'-deoxyadenosine

Conditions

Conditions	Yield
With 1A cells; E. coli BMT 4D In phosphate buffer at 65℃; for 4h; pH=7.5;	81%
With purine nucleoside 2’-deoxyribosyltransferase from Trypanosoma brucei immobilized on glutaraldehyde-activated MagReSynAmine microspheres In aq. phosphate buffer at 50℃; for 0.333333h; pH=6; Enzymatic reaction;

: 65024-85-3
1-β-D-ribofuranosyl-1H-benzotriazole

: 1839-18-5
2-chloroadenine

: 79999-39-6, 24638-99-1
2',3',5'-tri-O-acetyl-2-chloroadenosine

Conditions

Conditions	Yield
With tin(IV) chloride In nitromethane at 20℃; for 3h; Solvent; Cooling with ice;	81%

: 16473-35-1
4-(hydroxymethyl)benzyl chloride

: 1839-18-5
2-chloroadenine

: 930785-53-8
2-chloro-9-(4-hydroxymethylbenzyl)adenine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	80%

: C14H18BrNO

: 1839-18-5
2-chloroadenine

: C19H21ClN6O

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 70℃;	80%

: 106-95-6
allyl bromide

: 1839-18-5
2-chloroadenine

: 111430-12-7
C8H8ClN5

Conditions

Conditions	Yield
With sodium hydroxide In water at 100℃; for 0.166667h; Microwave irradiation; regioselective reaction;	79%

: 107-13-1
acrylonitrile

: 1839-18-5
2-chloroadenine

: C8H7ClN6

Conditions

Conditions	Yield
With triethylamine In water at 100℃; for 0.0833333h; Michael addition; microwave irradiation;	77%

: 1839-18-5
2-chloroadenine

: 3958-60-9
2-nitrophenylmethyl bromide

: 1261602-05-4
2-chloro-9-(2-nitrobenzyl)-9H-purin-6-ylamine

Conditions

Conditions	Yield
Stage #1: 2-chloroadenine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Stage #2: 2-nitrophenylmethyl bromide In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere;	77%

: 1839-18-5
2-chloroadenine

: 151965-56-9
diisopropyl 2-(chloroethoxy)methylphosphonate

: 228874-51-9
6-amino-2-chloro-9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}-9H-purine

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 16h;	76.5%

: 1839-18-5
2-chloroadenine

: 2372-45-4
sodium butanolate

: 473930-51-7
2-butoxyadenine

Conditions

Conditions	Yield
for 9h; Heating / reflux;	76%

: 1839-18-5
2-chloroadenine

: 4909-78-8
N,N-dimethylformamide dineopentyl acetal

: 2-chloro-N6-dimethylaminomethyleneadenine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Ambient temperature;	75%

: 1839-18-5
2-chloroadenine

: 71-36-3
butan-1-ol

: 473930-51-7
2-butoxy-9H-purin-6-amine

Conditions

Conditions	Yield
With sodium at 140℃; for 10h;	75%
With potassium tert-butylate In tetrahydrofuran at 170℃; for 0.666667h; Microwave irradiation;	70%
With potassium tert-butylate In tetrahydrofuran at 170℃; for 0.666667h; Microwave irradiation;	70%

: 97614-44-3
2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

: 1839-18-5
2-chloroadenine

: 355138-50-0
6-amino-2-chloro-9-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine

Conditions

Conditions	Yield
Stage #1: 2-chloroadenine With calcium hydride In acetonitrile; tert-butyl alcohol at 53℃; for 2.5h; Stage #2: 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide In dichloromethane; acetonitrile; tert-butyl alcohol at 50℃; for 3h; Solvent; Temperature; Reagent/catalyst;	75%
With potassium tert-butylate In tert-Amyl alcohol; 1,2-dichloro-ethane; acetonitrile at 50℃; for 19h; Inert atmosphere;	50%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In CHCl3/MeOH; chloroform; acetonitrile	16 mg (28%)

: 124-41-4
sodium methylate

: 1839-18-5
2-chloroadenine

: 28128-30-5
2-methoxy-9H-purin-6-amine

Conditions

Conditions	Yield
Stage #1: sodium methylate; 2-chloroadenine In methanol at 100℃; for 24h; Stage #2: With hydrogenchloride In methanol; water at 20 - 60℃; for 17h; pH=9.5;	73%
In methanol at 100℃; for 24h; Sealed vessel;	70%

: 98693-55-1, 102783-28-8
α-D-2′-deoxyribofuranose-1-O-phosphate bis(cyclohexylammonium) salt

: 1839-18-5
2-chloroadenine

: 4291-63-8
2-chloro-2'-deoxyadenosine

Conditions

Conditions	Yield
With purine nucleoside phosphorylase; calcium hydroxide at 45℃; for 48h; pH=9.3; Enzymatic reaction;	72%

: 1839-18-5
2-chloroadenine

: 100-46-9
benzylamine

: 1001253-97-9
2-benzylamino-6-aminopurine

Conditions

Conditions	Yield
In dimethyl sulfoxide; butan-1-ol at 170℃; for 1.5h; Microwave irradiation;	71%

: 100-44-7
benzyl chloride

: 1839-18-5
2-chloroadenine

: 56046-25-4
6-amino-9-benzyl-2-chloropurine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	70%
With sodium hydroxide; Aliquat 336 In hexane for 8h; Heating;	27%
Stage #1: 2-chloroadenine With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 1h; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 90℃; for 18h;	25%

2-Chloroadenine Specification

The 2-Chloroadenine, with the CAS registry number 1839-18-5, has the systematic name of 2-chloro-7H-purin-6-amine. And the molecular formula of this chemical is C₅H₄ClN₅. It is a kind of irritant chemical, and belongs to the following product categories: Pharmacetical; Amines; Purine; Purines; Bases & Related Reagents; Heterocycles; Nucleotides; Fused Ring Systems.

The physical properties of 2-Chloroadenine are as following: (1)ACD/LogP: 0.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.35; (4)ACD/LogD (pH 7.4): 0.34; (5)ACD/BCF (pH 5.5): 1.09; (6)ACD/BCF (pH 7.4): 1.07; (7)ACD/KOC (pH 5.5): 36.89; (8)ACD/KOC (pH 7.4): 36.47; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 46.84 Å²; (13)Index of Refraction: 1.826; (14)Molar Refractivity: 41.93 cm³; (15)Molar Volume: 95.7 cm³; (16)Polarizability: 16.62×10^-24cm³; (17)Surface Tension: 116.8 dyne/cm; (18)Density: 1.77 g/cm³.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1nc(c2c(n1)ncn2)N
(2)InChI: InChI=1/C5H4ClN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)
(3)InChIKey: HBJGQJWNMZDFKL-UHFFFAOYAY

Product Name

2-Chloroadenine

Synthetic route

2-Chloroadenine Specification

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