6-Chloropurine supplier | CasNO.87-42-3

Name
6-Chloropurine
EINECS 201-745-6
CAS No. 87-42-3
Article Data29
CAS DataBase
Density 1.653 g/cm³
Solubility 5 g/L in water
Melting Point >300 °C (dec.)(lit.)
Formula C₅H₃ClN₄
Boiling Point 449.6 °C at 760 mmHg
Molecular Weight 154.559
Flash Point 258.2 °C
Transport Information
Appearance light yellow crystalline powder
Safety 26-36-36/37/39
Risk Codes 22-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 1H-Purine, 6-chloro- (9CI);6-Chloro-1H-purine;1H-Purine, 6-chloro-;SK 6048;Purine, 6-chloro-;X 47;6-chloro-5H-purine;6-CP;6-Chloro purine 98%;NSC-744;PVC Pigment Dispersion Chips;Aquilaria sinensis (Lour.) Gilg 2-(2-Phenylethyl) chromone derivatives;
PSA 54.46000
LogP 1.00630

Synthetic route

: 1780-27-4
4,5,6-trichloropyrimidine

: formimidamide hydrochloride

: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
In ethanol at 15 - 25℃; for 12h;	97.1%

: 948037-39-6
6-[2-(ethoxycarbonyl)methyl]-9-(tetrahydropyran-2-yl)-9H-purine

: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
With Dowex 50 In ethanol at 70℃; for 3h;	93%

: 68-94-0
hypoxanthine

: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
With N,N-dimethyl-aniline; trichlorophosphate under 760.051 Torr; Heating;	92%
With trichlorophosphate In N,N-dimethyl acetamide at 120℃; for 2h;	86%
With trichlorophosphate In N,N-dimethyl-formamide at 80℃; for 8h;	76.7%
With trichlorophosphate In ethylbenzene; acetonitrile at 65℃; for 6h;	53%

: 68-94-0
Allopurinol

: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
With dmap; thionyl chloride; bis(trichloromethyl) carbonate Catalytic behavior; Reagent/catalyst; Reflux; Green chemistry;	90%
With trichlorophosphate In dichloromethane; N,N-dimethyl-formamide at 40℃; for 3h;	71.5%
With 2,3-Dimethylaniline; trichlorophosphate for 0.5h; Heating;	47%

: 917239-31-7
9-(3'-azido-2'-O-triflyl-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-6-chloro-9H-purine

A: benzoic acid 3-azido-furan-2-ylmethyl ester

B: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 20h;	A 84% B 82%

: 1062217-28-0
C20H30ClFN4O4Si

A: C14H16ClFN4O4

B: 1062217-43-9
C11H12ClFN4O4

C: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane for 7h;	A n/a B 41% C n/a

...Expand

: 1062217-31-5
C20H30ClFN4O4Si

A: 1062217-44-0
C11H12ClFN4O4

B: 1062217-36-0
C14H16ClFN4O4

C: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane for 7h;	A 37% B n/a C n/a

...Expand

: 33441-77-9
9-(1-Ethoxyethyl-1)-6-chloropurine

: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
In hydrogenchloride; water at 40.1℃; Kinetics; Mechanism;

: 4594-45-0
6-chloropurine-2'-deoxyriboside

: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
In hydrogenchloride; water at 50.1℃; Kinetics; Mechanism;

: 917239-30-6
9-(3'-azido-5'-O-benzoyl-3'-deoxy-β-D-ribofuranosyl)-6-chloro-9H-purine

: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / pyridine / CH2Cl2 / -40 °C 2: 82 percent / TBAF / tetrahydrofuran / 20 h / 20 °C View Scheme

: 69-89-6
xanthine

: 87-42-3
6-chloropurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / formamide / 0.5 h / 200 °C 2: 53 percent / POCl3 / ethylbenzene; acetonitrile / 6 h / 65 °C View Scheme

: 87990-00-9
Acetic acid (3S,4R)-4-acetoxy-2-chloro-tetrahydro-pyran-3-yl ester

: 87-42-3
6-chloropurine

: 87990-01-0
Acetic acid (2R,3R,4S)-4-acetoxy-2-(6-chloro-purin-9-yl)-tetrahydro-pyran-3-yl ester

Conditions

Conditions	Yield
With 3 A molecular sieve; Quecksilber(I)-cyanid In nitromethane for 3h; Heating;	100%

: 87-42-3
6-chloropurine

: 15397-15-6
1,2,3,5-tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose

: 205171-04-6
(2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(6-chloro-9H-purin-9-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

Conditions

Conditions	Yield
	100%
With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60℃; for 4h;	83%
With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 60℃; for 3h;
With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 18h;

: 87-42-3
6-chloropurine

: 765-30-0
Cyclopropylamine

: 117761-02-1
6-(cyclopropylamino)-9H-purine

Conditions

Conditions	Yield
In ethanol for 6h; Heating;	100%
In isopropyl alcohol at 120℃; for 2h;	90%
In methanol	81.4%
In ethanol Heating;
In ethanol for 16h; Heating;

: 110-91-8
morpholine

: 87-42-3
6-chloropurine

: 2846-96-0
6-morpholinopurine

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 0.5h; Microwave irradiation; regioselective reaction;	100%
at 80℃;	96%
at 80℃; for 0.0166667h; microwave irradiation;	94%

: 2524-67-6
4-morpholino-4-yl-phenylamine

: 87-42-3
6-chloropurine

: 6-(4-morpholinophenylamino)-9H-purin-3-ium chloride

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 1h; Microwave irradiation; regioselective reaction;	100%

: 55075-31-5
2-(hydroxy(phenyl)methyl)-4-methylphenol

: 87-42-3
6-chloropurine

: C19H15ClN4O

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 6h;	100%

: 110-87-2
3,4-dihydro-2H-pyran

: 87-42-3
6-chloropurine

: 7306-68-5
6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethyl acetate at 90℃; for 1h;	99%
With toluene-4-sulfonic acid In ethyl acetate at 90℃; for 1h;	99.3%
With toluene-4-sulfonic acid In ethyl acetate at 90℃; for 0.1h;	97%

: 536-74-3
phenylacetylene

: 87-42-3
6-chloropurine

: 85110-23-2
6-(phenylethynyl)-9H-purine

Conditions

Conditions	Yield
With sodium tetrachloropalladate(II); dicyclohexyl {2-sulfo-9-[3-(4-sulfophenyl)propyl]-9H-fluoren-9-yl}phosphonium hydrogen sulfate; potassium carbonate In water at 95℃; for 16h; Sonogashira coupling; Inert atmosphere;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In dimethyl sulfoxide at 90℃; for 1.5h;	65%

: 930-69-8
sodium thiophenolate

: 87-42-3
6-chloropurine

: 5450-35-1
6-(phenylsulfanyl)purine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.0166667h; microwave irradiation;	99%

: 141-52-6
sodium ethanolate

: 87-42-3
6-chloropurine

: 17861-06-2
6-ethoxy-9H-purine

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 100℃; for 0.0333333h; microwave irradiation;	99%

: 87-42-3
6-chloropurine

: 5188-07-8
sodium thiomethoxide

: 50-66-8
6-methylthiopurine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.0166667h; microwave irradiation;	99%

: 645-96-5
Benzeneselenol

: 87-42-3
6-chloropurine

: 6-(phenylselanyl)-9H-purine

Conditions

Conditions	Yield
With barium dihydroxide In water at 90℃; for 0.0333333h; microwave irradiation;	99%

: 124-41-4
sodium methylate

: 87-42-3
6-chloropurine

: 1074-89-1
6-methoxypurine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 0.0166667h; microwave irradiation;	99%
In methanol for 18h; Reflux;	72%
In methanol for 12h; Reflux; Inert atmosphere;	43%

: 854141-63-2
1-(hydroxymethyl)-4-propylpyrrolidin-2-one

: 87-42-3
6-chloropurine

: 916257-23-3
1-[(6-chloro-9H-purin-9-yl)methyl]-4-propylpyrrolidin-2-one

Conditions

Conditions	Yield
N,N-diethylcarbamyl chloride In acetonitrile at 100℃; for 5h; Microwave;	99%

: 1483-72-3
diphenyliodonium chloride

: 87-42-3
6-chloropurine

: 5470-24-6
6-Chloro-9-phenyl-9H-purine

Conditions

Conditions	Yield
With potassium carbonate; copper(I) bromide In dichloromethane for 2.5h; Reflux; Inert atmosphere; regioselective reaction;	99%

: 111-26-2
hexan-1-amine

: 87-42-3
6-chloropurine

: 14333-96-1
N6-n-hexyladenine

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 1.5h; Microwave irradiation; regioselective reaction;	99%

: 2-[hydroxy(4-methylphenyl)methyl]phenol

: 87-42-3
6-chloropurine

: C19H15ClN4O

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 5h;	99%

: 106-45-6
para-thiocresol

: 87-42-3
6-chloropurine

: 6-(p-tolylthio)purine

Conditions

Conditions	Yield
With potassium tert-butylate In isopropyl alcohol at 50℃;	98%

: 13515-76-9, 116457-91-1, 4465-44-5
methyl N-trityl-L-serinate

: 87-42-3
6-chloropurine

: 1228040-59-2
methyl 3-(6-chloro-9H-purin-9-yl)-2-(tritylamino)propanoate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 25℃; for 1h; Mitsunobu reaction;	98%

: 2-(hydroxymethyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

: 87-42-3
6-chloropurine

: C11H11BClN5O4

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 23℃; for 0.5h; Mitsunobu Displacement;	98%

: 39546-32-2
4-carboxamidopiperidine

: 87-42-3
6-chloropurine

: 1-(9H-purin-6-yl)piperidine-4-carboxylic acid amide

Conditions

Conditions	Yield
With triethylamine In butan-1-ol at 100℃;	97%
With triethylamine In butan-1-ol at 100℃; for 0.666667h;

: 76-83-5
trityl chloride

: 87-42-3
6-chloropurine

: 1008361-76-9
6-chloro-9-trityl-9H-purine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	97%

: 62-53-3
aniline

: 87-42-3
6-chloropurine

: 6-(phenylamino)-9H-purin-3-ium chloride

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 120℃; for 0.5h; Microwave irradiation; regioselective reaction;	97%

: 3-((trimethylsilyl)oxy)propan-1-amine hydrochloride

: 87-42-3
6-chloropurine

: 15500-81-9
N6-(3-hydroxypropyl)adenine

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 70℃; for 72h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	97%

: 1795-76-2, 26806-03-1, 35042-70-7
4-hydroxy-3-methyl-trans-but-2-enylamine

: 87-42-3
6-chloropurine

: 1637-39-4
trans-zeatin

Conditions

Conditions	Yield
With triethylamine In ethanol for 5h; Reflux;	96.8%
With triethylamine In butan-1-ol for 3h; Heating;	80%

: 4479-75-8
3-methyl-2-butenamide

: 87-42-3
6-chloropurine

: 21589-34-4
3-methyl-but-2-enoic acid 7(9)H-purin-6-ylamide

Conditions

Conditions	Yield
With triethylamine In ethanol for 5h; Reflux;	96.8%

: 617-89-0
furan-2-ylmethanamine

: 87-42-3
6-chloropurine

: 525-79-1
kinetin

Conditions

Conditions	Yield
With triethylamine In ethanol for 5h; Reflux;	96.7%
In ethanol Reflux; Inert atmosphere;	88%
With triethylamine In butan-1-ol at 110℃; for 5h;	76.4%
With triethylamine In butan-1-ol at 110℃;	73.9%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 100℃; for 16h;

: 13822-06-5, 108963-90-2
3,3-dimethylallylamine

: 87-42-3
6-chloropurine

: 2365-40-4
N6-(2-isopentenyl)adenine

Conditions

Conditions	Yield
With triethylamine In ethanol for 5h; Reflux;	96.6%

: 87-42-3
6-chloropurine

: 66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9
adenine

Conditions

Conditions	Yield
With ammonium hydroxide; triethylamine In ethanol for 5h; Reflux;	96.3%
With potassium amide In ammonia at -33℃; for 20h; Yield given;
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 17 h / 20 °C / Inert atmosphere 2: ammonia / tert-butyl alcohol / 21 h / 120 °C 3: potassium carbonate / 7 h / 200 °C / Microwave irradiation View Scheme

6-Chloropurine Specification

The IUPAC name of 6-Chloropurine is 6-chloro-7H-purine. With the CAS registry number 87-42-3, it is also named as 1H-Purine, 6-chloro- (9CI). The product's categories are Fine Chemical & Intermediates; Heterocyclic Compounds; Nucleotides and Nucleosides; Purines; Biochemistry; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents; Nucleotides; Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Biochemicals and Reagents; Nucleosides, Nucleotides, Oligonucleotides. It is light yellow crystalline powder which is soluble in water, ether and dimethyl formamide. Additioanlly, this chemical should be sealed in the container and stored at the temperature of 4 °C.

Physical properties about 6-Chloropurine are: (1)ACD/LogP: -0.061; (2)ACD/LogD (pH 5.5): -0.06; (3)ACD/LogD (pH 7.4): -0.06; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 22.06; (7)ACD/KOC (pH 7.4): 22.06; (8)#H bond acceptors: 4; (9)Index of Refraction: 1.843 ; (10)Molar Refractivity: 37.302 cm³; (11)Molar Volume: 83.984 cm³; (12)Polarizability: 14.788 10-24cm³; (13)Surface Tension: 73.2460021972656 dyne/cm; (14)Density: 1.84 g/cm³; (15)Flash Point: 109.146 °C; (16) Enthalpy of Vaporization: 47.442 kJ/mol; (17)Boiling Point: 256.862 °C at 760 mmHg; (18)Vapour Pressure: 0.0240000002086163 mmHg at 25°C

Preparation of 6-Chloropurine: It can be obtained by 1,7(9)-dihydro-purin-6-one. This reaction needs reagent POCl₃, dimethylaniline by heating. The reaction time is 0.5 hours. The yield is 47%.

Preparation of 6-Chloropurine

Uses of 6-Chloropurine: It is used as intermediate of purine products. It also can react with 3-methyl-oxazolidine to get 8-methyl-7,8-dihydro-6H-[1,3,6]oxdiazocino[3,4,5-g,h]purine. This reaction needs solvent N,N-dimethyl-acetamide at temperature of 110 °C. The reaction time is 30 min. The yield is 60%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H3ClN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H,7,8,9,10);
(2)InChIKey=ZKBQDFAWXLTYKS-UHFFFAOYSA-N;
(3)Smilesc12c(ncnc1Cl)nc[nH]2

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD10	unreported	230mg/kg (230mg/kg)	BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE	Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970.
mouse	LD50	intraperitoneal	132mg/kg (132mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse	LD50	oral	720mg/kg (720mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse	LD50	subcutaneous	514mg/kg (514mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
quail	LD50	oral	> 316mg/kg (316mg/kg)		Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rat	LD50	intraperitoneal	400mg/kg (400mg/kg)		Advances in Teratology. Vol. 3, Pg. 181, 1968.

Product Name

6-Chloropurine

Synthetic route

6-Chloropurine Specification

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