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1214-39-7

Basic Information
CAS No.: 1214-39-7
Name: 1H-Purin-6-amine, N- (phenylmethyl)-
Molecular Structure:
Molecular Structure of 1214-39-7 (1H-Purin-6-amine, N- (phenylmethyl)-)
Formula: C12H11N5
Molecular Weight: 225.25
Synonyms: 6-Benzylamino Purine;6-Benzylaminopurine ( 6-BA);Benzylaminopurine;6-Benzylaminopurine (6BA);6-Benzyl Adenine(6-Benzyl Aminopurine);6-Benzylaminopurine;BA;6-Benzylaminopurine *;6-Benzylamino purine (6-BA);N-benzyl-7H-purin-6-amine;Paturyl;N-Benzyl-9H-purin-6-amine;N-(Phenylmethyl)-1H-purin-6-amine;BA (growth stimulator);6-(Benzylamino)purine;Prestwick_414;6-Benzylaminopurine (6-BA);N6-Benzyladenine;BAP (growth stimulant);N(6)-Benzylaminopurine;1H-Purin-6-amine,N-(phenylmethyl)-;Aminopurine, 6-benzyl;6-Benzyl Aminopurine;6-benzylaminopurine BA;6-(n-Benzyl) Aminopurin;N-6-Benzyladenine;benzyl(purin-6-yl)amine;9H-Purin-6-amine, N-(phenylmethyl)-;
EINECS: 214-927-5
Density: 1.393 g/cm3
Melting Point: 229-233 °C
Boiling Point: 529.388 °C at 760 mmHg
Flash Point: 273.964 °C
Solubility: soluble in water
Appearance: white to light yellow crystalline powder
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 36/37/38-20/21/22
Safety: 9-24/25-36/37/39-26-23
Transport Information: UN 2348 3/PG 3
PSA: 66.49000
LogP: 2.03800
Synthetic route
87-42-3

6-chloropurine

100-46-9

benzylamine

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
With triethylamine In ethanol for 5h; Reflux;96%
at 100℃; for 0.0833333h; microwave irradiation;95%
With indium(III) chloride In acetonitrile at 120℃; for 1h; Microwave irradiation; regioselective reaction;93%
4294-16-0

N6-Benzyladenosine

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 3h; Reagent/catalyst; Temperature;92%

phenylmagnesium bromide

111098-24-9

Benzotriazol-1-ylmethyl-(9H-purin-6-yl)-amine

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
In diethyl ether at 25℃; for 16h;80%
19769-32-5

6-methylsulfonylpurine

100-46-9

benzylamine

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
In butan-1-ol for 0.75h; Substitution;78.2%

7-benzyl-6-benzylamino-2-chloropurine

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
With potassium hydroxide; hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 15h; Hydrogenation;69%
7387-58-8, 80007-24-5

6-N-2',3',5'-tri-O-tetraacetyladenosine

A

1214-39-7

6-benzyladenine

B

18646-11-2

α-D-ribofuranosyl-1-phosphate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C
2: methanol; ammonia / 48 h / 20 °C
3: potassium dihydrogenphosphate; Escherichia coli purine nucleoside phosphorylase / 37 °C / pH 7.5 / aq. buffer; Enzymatic reaction
View Scheme
1338578-76-9

N6-acetyl-2',3',5'-tri-O-acetyl-N6-benzyladenosine

A

1214-39-7

6-benzyladenine

B

18646-11-2

α-D-ribofuranosyl-1-phosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; ammonia / 48 h / 20 °C
2: potassium dihydrogenphosphate; Escherichia coli purine nucleoside phosphorylase / 37 °C / pH 7.5 / aq. buffer; Enzymatic reaction
View Scheme
100-39-0

benzyl bromide

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C
2: methanol; ammonia / 48 h / 20 °C
3: potassium dihydrogenphosphate; Escherichia coli purine nucleoside phosphorylase / 37 °C / pH 7.5 / aq. buffer; Enzymatic reaction
View Scheme
4294-16-0

N6-Benzyladenosine

A

1214-39-7

6-benzyladenine

B

18646-11-2

α-D-ribofuranosyl-1-phosphate

Conditions
ConditionsYield
With Escherichia coli purine nucleoside phosphorylase at 25℃; pH=7.5; Kinetics; aq. phosphate buffer; Enzymatic reaction;
With potassium dihydrogenphosphate; Escherichia coli purine nucleoside phosphorylase at 37℃; pH=7.5; Equilibrium constant; aq. buffer; Enzymatic reaction;
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: magnesium methanolate / methanol / 3 h / 55 °C
2: sodium tetrahydroborate / methanol / 20 °C
View Scheme
1214-39-7

6-benzyladenine

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃;

C16H15N5O2

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
With propylamine In methanol at 20℃;
68-94-0

Allopurinol

100-46-9

benzylamine

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 75℃; for 4h; Temperature; Reagent/catalyst;18.2 g
68-94-0

Allopurinol

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bis(trichloromethyl) carbonate; dmap; thionyl chloride / Reflux; Green chemistry
2: triethylamine / ethanol / Reflux; Inert atmosphere
View Scheme
68-94-0

hypoxanthine

1214-39-7

6-benzyladenine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trichlorophosphate; N,N-dimethyl-aniline / 760.05 Torr / Heating
2: water / 0.75 h / 100 °C / Green chemistry
View Scheme
59278-00-1

2-acetoxyethyl acetoxymethyl ether

1214-39-7

6-benzyladenine

173205-63-5

9-<(2-acetoxyethoxy)methyl>-6-benzylaminopurine

Conditions
ConditionsYield
With aluminum oxide; silica gel for 0.0666667h; microwave irradiation;95%
78-94-4

methyl vinyl ketone

1214-39-7

6-benzyladenine

1-(butan-3-one-1-yl)-6-benzylaminopurine

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In dimethyl sulfoxide at 70℃; for 2h; Michael addition;94%
107-04-0

1-Bromo-2-chloroethane

1214-39-7

6-benzyladenine

120593-22-8

6-benzylamino-9-(2-chloroethyl)purine

Conditions
ConditionsYield
With sodium hydroxide; (C8H17)4NBr In water; benzene at 80℃; for 0.5h; Product distribution; other catalyst, other solvent, other reaction time, other temperature;90%
With sodium hydroxide; (C8H17)4NBr In water; benzene at 80℃; for 0.5h;90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;82%
292638-85-8

acrylic acid methyl ester

1214-39-7

6-benzyladenine

3-(6-benzylamino-purin-9-yl)-propionic acid methyl ester

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium hydroxide at 25℃; for 2h; Michael addition;90%
With 1-methyl-1H-imidazole In dimethyl sulfoxide at 70℃; for 2h; Michael addition;84%
141-32-2

acrylic acid n-butyl ester

1214-39-7

6-benzyladenine

1033400-03-1

3-(6-benzylamino-purin-9-yl)-propionic acid butyl ester

Conditions
ConditionsYield
With tetrabutylammomium bromide; zinc(II) oxide at 120℃; for 0.333333h; Michael addition; microwave irradiation;89%
109-70-6

1,3-chlorobromopropane

1214-39-7

6-benzyladenine

120593-24-0

6-benzylamino-9-(3-chloropropyl)purine

Conditions
ConditionsYield
With sodium hydroxide; (C8H17)4NBr In water; benzene at 80℃; for 1h;85%
105-36-2

ethyl bromoacetate

1214-39-7

6-benzyladenine

N6-benzyl-9-(ethoxycarbonylmethyl)adenine

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile for 0.0833333h; microwave irradiation;85%
106-93-4

ethylene dibromide

1214-39-7

6-benzyladenine

120593-27-3

6-benzylamino-9-(2-bromoethyl)purine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;82%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 40℃; for 1h; Product distribution; other reaction time, other temperature;50%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 40℃; for 1h;50%
107-04-0

1-Bromo-2-chloroethane

1214-39-7

6-benzyladenine

120593-26-2

Benzyl-(9-vinyl-9H-purin-6-yl)-amine

Conditions
ConditionsYield
With sodium hydroxide; (C8H17)4NBr In water; benzene at 80℃; for 2.5h; Product distribution; other catalyst, other solvent, other reaction time, other temperature;80%
With sodium hydroxide; (C8H17)4NBr In water; benzene at 80℃; for 2.5h;80%
1214-39-7

6-benzyladenine

2032-35-1

Bromoacetaldehyde diethyl acetal

1527480-25-6

N-benzyl-9-(2,2-diethoxyethyl)-9H-purin-6-amine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 8h; Inert atmosphere;80%
96-34-4

methyl chloroacetate

1214-39-7

6-benzyladenine

6-benzylamino-9-((methoxycarbonyl)methyl)-9H-purine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 0.133333h; microwave irradiation;78%
108-05-4

vinyl acetate

1214-39-7

6-benzyladenine

1-(6-benzylaminoallopurin-9-yl)ethyl acetate

Conditions
ConditionsYield
With D-aminoacylase from Escherichia coli (EC 3.5.1.81) In dimethyl sulfoxide at 50℃; for 96h;77%
With [bmIm]OH at 50℃; for 24h; Markovnikov addition;70%
5396-24-7

n-propyl chloracetate

1214-39-7

6-benzyladenine

6-benzylamino-9-((n-propoxycarbonyl)methyl)-9H-purine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 0.133333h; microwave irradiation;76%
3874-54-2

4-(4-fluorophenyl)-4-oxo-n-butyl chloride

1214-39-7

6-benzyladenine

cyclopropyl-{4-(6-(benzylamino)-9H-purin-9-yl)phenyl}methanone

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 140℃;76%
1214-39-7

6-benzyladenine

75-26-3

isopropyl bromide

111853-20-4

6-benzylamino-9-isopropylpurine

Conditions
ConditionsYield
With sodium hydroxide; (C8H17)4NBr In benzene for 3h; Heating;75%
With potassium carbonate In dimethyl sulfoxide Alkylation;
68673-84-7

methyl 1,2,3-tri-O-acetyl-β-D-ribofuronate

1214-39-7

6-benzyladenine

1012864-67-3

methyl 1-[N6-(benzyl)adenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate

Conditions
ConditionsYield
Stage #1: 6-benzyladenine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane 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.;
75%

copper (II) carbonate hydroxide

166826-77-3

(carboxymethyl(4-methylbenzyl)amino)acetic acid

1214-39-7

6-benzyladenine

[Cu(MEBIDA)(HBAP)(H2O)]·H2O

Conditions
ConditionsYield
In isopropyl alcohol at 25 - 50℃; for 1h;75%
107-13-1

acrylonitrile

1214-39-7

6-benzyladenine

3-(6-benzylamino-purin-9-yl)-propionitrile

Conditions
ConditionsYield
With triethylamine In water at 100℃; for 0.0833333h; Michael addition; microwave irradiation;74%
110-87-2

3,4-dihydro-2H-pyran

1214-39-7

6-benzyladenine

2312-73-4

6-benzylamino-9-(2-tetrahydropyranyl)purine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In various solvent(s) for 2h; Addition; Heating;71.4%
110-80-5

2-ethoxy-ethanol

1214-39-7

6-benzyladenine

1013022-32-6

benzyl-[9-(2-ethoxy-ethyl)-9H-purin-6-yl]-amine

Conditions
ConditionsYield
With iodine; potassium carbonate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide for 9h; Reflux;71%
With potassium carbonate; 1-n-butyl-3-methylimidazolim bromide; triethylamine; p-toluenesulfonyl chloride at 80℃; for 7h; Green chemistry; regioselective reaction;64%
With potassium carbonate; triethylamine In N,N-dimethyl-formamide for 4h; Heating;58%
With tetrachloromethane; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide for 5h; Reflux;58%

copper (II) carbonate hydroxide

57362-11-5

2,2'-((furan-2-ylmethyl)azanediyl)diacetic acid

1214-39-7

6-benzyladenine

[Cu(FurIDA)(HBAP)]

Conditions
ConditionsYield
In methanol; water at 25℃; for 0.5h;70%

O,O‐diethyl 2-iodoethoxymethylphosphonate

1214-39-7

6-benzyladenine

A

O,O-diethyl((2-(6-(benzylamino)-7H-purin-7-yl)ethoxy)methyl)phosphonate

B

O,O-diethyl((2-(6-(benzylamino)-9H-purin-9-yl)ethoxy)methyl)phosphonate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; regioselective reaction;A 3%
B 70%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Benzyladenine, with the CAS registry number 1214-39-7, is also known as Benzyl(purin-6-yl)amine. It belongs to the product categories of Pharmaceutical Raw Materials; Miscellaneous; Purine; Amines; Biochemistry; Cytokinins; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Plant Growth Regulators; Plant Hormones. Its EINECS number is 214-927-5. This chemical's molecular formula is C12H11N5 and molecular weight is 225.25. What's more, its systematic name is N-Benzyl-7H-purin-6-amine. Its classification codes are: (1)Agricultural Chemical; (2)Growth Substances; (3)Growth regulator / Fertilizer; (4)Mutation data; (5)Plant growth regulators. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides. This substance is a first-generation synthetic cytokinin that elicits plant growth and development responses, setting blossoms and stimulating fruit richness by stimulating cell division. It is an inhibitor of respiratory kinase in plants, and increases post-harvest life of green vegetables.

Physical properties of Benzyladenine are: (1)ACD/LogP: 2.164; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.15; (4)ACD/LogD (pH 7.4): 2.16; (5)ACD/BCF (pH 5.5): 25.36; (6)ACD/BCF (pH 7.4): 25.92; (7)ACD/KOC (pH 5.5): 349.77; (8)ACD/KOC (pH 7.4): 357.43; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 66.49 Å2; (13)Index of Refraction: 1.766; (14)Molar Refractivity: 66.899 cm3; (15)Molar Volume: 161.701 cm3; (16)Polarizability: 26.521×10-24cm3; (17)Surface Tension: 80.4 dyne/cm; (18)Density: 1.393 g/cm3; (19)Flash Point: 273.964 °C; (20)Enthalpy of Vaporization: 80.442 kJ/mol; (21)Boiling Point: 529.388 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 7(9)H-purin-6-ylamine and phenylmethanol; sodium salt at the temperature of 130 °C. The reaction time is 17 hours. The yield is about 55%.

Benzyladenine can be prepared by 7(9)H-purin-6-ylamine and phenylmethanol; sodium salt at the temperature of 130 °C

Uses of Benzyladenine: it can be used to produce by benzyl-(1-oxy-9H-purin-6-yl)-amine at the temperature of 30 °C. It will need regent MCPBA and solvent methanol with the reaction time of 20 hours. The yield is about 35%.

Benzyladenine can be used to produce by benzyl-(1-oxy-9H-purin-6-yl)-amine at the temperature of 30 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. You must avoid contact with skin and eyes. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should keep the container in a well-ventilated place. You must not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: n1c(c2c(nc1)ncn2)NCc3ccccc3
(2)Std. InChI: InChI=1S/C12H11N5/c1-2-4-9(5-3-1)6-13-11-10-12(15-7-14-10)17-8-16-11/h1-5,7-8H,6H2,(H2,13,14,15,16,17)
(3)Std. InChIKey: NWBJYWHLCVSVIJ-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 1300mg/kg (1300mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 19, Pg. 336, 1972.
mouse LD50 skin > 5gm/kg (5000mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 19, Pg. 336, 1972.
mouse LD50 subcutaneous > 2300mg/kg (2300mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 19, Pg. 336, 1972.
rat LD50 oral 2125mg/kg (2125mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 19, Pg. 336, 1972.