6-Benzylaminopurine CAS 1214-39-7
Introduction：Basic information about 6-Benzylaminopurine CAS 1214-39-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
6-Benzylaminopurine Basic information
| Product Name: | 6-Benzylaminopurine |
| Synonyms: | 6-BENZYLAMINOPURINERESEARCH GRADE;6-Benzylaminopurine,BA, N6-Benzyladenine;6-BenzylaMinopurine, 99% 5GR;6-Benzyil AMinopurine;6-benzyl-6H-purin-6-aMine;6-BenzylaMino Purine Tech;6-(Benzylamino)-9H-purine;N-Benzyl-9H-purin-6-amine, N-(9H-Purin-6-yl)benzylamine |
| CAS: | 1214-39-7 |
| MF: | C12H11N5 |
| MW: | 225.25 |
| EINECS: | 214-927-5 |
| Product Categories: | Biochemistry;Cytokinins;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Plant Growth Regulators;Plant Hormones;Pharmaceutical Raw Materials;Miscellaneous;Purine;Amines;PLANT GROWTH REGULATOR;plantgrowth;1214-39-7;Elisa Kit-plant ELISA Kit |
| Mol File: | 1214-39-7.mol |
6-Benzylaminopurine Chemical Properties
| Melting point | 230-233 °C |
| Boiling point | 145 °C(lit.) |
| density | 0.899 g/mL at 20 °C |
| vapor density | >1 (vs air) |
| vapor pressure | 3.3 mm Hg ( 20 °C) |
| refractive index | n |
| Fp | 103 °F |
| storage temp. | 2-8°C |
| solubility | H2O: soluble |
| form | Liquid |
| pka | 9.36±0.20(Predicted) |
| color | White to very faint yellow |
| Odor | Characteristic acrylic. |
| Water Solubility | Soluble in water, methanol and acetone. Slightly soluble in ethyl acetate and dichloromethane and toluene. Insoluble in n-hexane. |
| BRN | 19406 |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| Major Application | food and beverages |
| Cosmetics Ingredients Functions | HAIR CONDITIONING |
| 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) |
| InChIKey | NWBJYWHLCVSVIJ-UHFFFAOYSA-N |
| SMILES | C(Nc1ncnc2nc[nH]c12)c3ccccc3 |
| LogP | 1.570 |
| CAS DataBase Reference | 1214-39-7(CAS DataBase Reference) |
| NIST Chemistry Reference | 1H-purin-6-amine, n-(phenylmethyl)-(1214-39-7) |
| EPA Substance Registry System | N-Benzyladenine (1214-39-7) |
Safety Information
| Hazard Codes | Xi,Xn |
| Risk Statements | 36/37/38-20/21/22-22 |
| Safety Statements | 9-24/25-37/39-26-36-23 |
| RIDADR | UN 2348 3/PG 3 |
| WGK Germany | 3 |
| RTECS | UD3150000 |
| F | 8 |
| TSCA | TSCA listed |
| HS Code | 29335995 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 2 Repr. 2 |
| Hazardous Substances Data | 1214-39-7(Hazardous Substances Data) |
| Toxicity | LD50 orl-rat: 2125 mg/kg TOIZAG 19,336,72 |
| Chemical Properties | Colorless to off-white or yellow powder. Corrosive. Insoluble in water, slightly soluble in ethanol, stable in acid and alkali. |
| Uses | 6-Benzylaminopurine is a plant growth regulator that belongs to the class of first generation synthetic cytokinin used in agriculture. 6-Benzylaminopurine has been used: to induce sprouting in plant materials. in seed germination medium for culturing of seeds. to modify Murashige and Skoog (MS) media for shoot initiation. inhibitor of respiratory kinase in plants. 6-Benzylaminopurine, benzyl adenine (BAP) is a synthetic cytokinin which together with auxins elicits plant growth and development responses. BAP is a widely use cytokinin supplement to plant growth media such as Murashige and Skoog medium, Gamborg’s medium, and Chu’s N6 medium. |
| Application | 6-Benzylaminopurine solution has been used as a component in the Murashige & Skoog medium (MS) for culturing mandarin explants and plantlets of Dendrocalamus asper (Schultes f.). It has also been used as a supplement in Nitsch and Nitsch medium (NN) of grapevine explants. |
| Preparation | synthesis of 6-benzylaminopurine: To 5g hypoxanthine, add 20mL SOCl2, 0.25g DMAP, 10gBTC dissolved in 20mL SOCl2. Heat and add BTC/SOCl2 dropwise. Reflux (refrigerant cooling) to complete dissolution, steam out SOCl2 (containing phosgene, which is used for recovery), evaporated (drained), cooled to room temperature to obtain a milky yellow solid (6-chloropurine and DMAP.Hcl). Directly add 4g benzylamine and 25g triethylamine to it, heat to 70～80 ℃, or microwave heating, until the 6-chloropurine reaction is complete (TLC monitoring), add ethanol, the solid filtered out is washed with ethanol, and dried to obtain 7 g of product 6-benzylaminopurine with a brown color. Preparation and biological activity of 6-benzylaminopurine derivatives in plants and human cancer cells |
| Definition | ChEBI: 6-Benzylaminopurine is a member of the class of 6-aminopurines that is adenine in which one of the hydrogens of the amino group is replaced by a benzyl group. It has a role as a plant metabolite and a cytokinin. It derives from an adenine. |
| General Description | 6-Benzylaminopurine is a plant growth regulator that belongs to the class of first generation synthetic cytokinin used in agriculture commodities. |
| Health Hazard | 6-benzylaminopurine (6-BA) is widely used in agriculture and horticulture as plant growth regulator. Its excessive use may pose a potential risk to both environment and human health, which is causing great concern. Vapor is irritating when breathed at high concentrations. Contact with liquid causes irritation of skin and burning of eyes; Vapors cause a slight smarting of the eyes or respiratory system if present in high concentrations; If spilled on clothing and allowed to remain, may cause smarting and reddening of the skin. |
| Agricultural Uses | 6-Benzylaminopurine is a plant growth promoter, is the first applied synthetic cytokinin, mainlyused as a broad- spectrum plant growth regulator. It can be used inagriculture, horticulture, for plants at different stages, from germination to harvest. It enhance the shape of apples and to increase the fruit set in pears. It increases the yield of pistachios and tomatoes. Not listed for use in EU countries. Registered for use in the U.S. |
| Trade name | ABG® 3034; ACCEL®; AGTROL®;6-BA®; BA® (growth stimulant); CHRYSAL BVB®;EXILIS®; PERLAN®; PROMALIN®; SD® 4901; SQ®4609 |
| Biological Activity | Cell permeable: no', 'Km = 1 nM in stimulating Ca2+ influx', 'Primary Target P2-purinergic receptors', 'Product does not compete with ATP.', 'Reversible: no |
| Safety Profile | Moderately toxic by ingestion andskin contact. Human mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx. |
| Synthesis | 87-42-3 100-46-9 1214-39-7 The general procedure for the synthesis of 6-benzylaminopurine from 6-chloropurine and benzylamine was as follows: 154.5 g (1 mol) of 6-chloropurine was dissolved in 200 mL of ethanol, triethylamine (1.2 mol) was added, followed by the slow dropwise addition of 118 g (1.1 mol) of benzylamine. The reaction mixture was heated to reflux for 5 hours. Upon completion of the reaction, ethanol was removed by rotary evaporation, water was added to the residue and extracted three times with ethyl acetate. The organic layers were combined and dried by rotary evaporation to give 216 g of white needle-like solid 6-benzylaminopurine in 96.0% yield. |
| Potential Exposure | A polyamine plant growth regulatorused to lengthen and enhance the shape of apples and toincrease the fruit set in pears. It increases the yield of pistachiosand tomatoes. Not listed for use in the EU countries. |
| Shipping | UN3259 Amines, solid, corrosive, n.o.s, orPolyamines, solid, corrosive, n.o.s., Hazard class: 8;Labels: 8—Corrosive material, Technical Name Required. |
| Purification Methods | It is purified by recrystallisation from aqueous EtOH. It has at 207 and 270nm (H2O), 268 nm max (pH 6), 274nm (0.1 N HCl) and 275nm (0.1 N NaOH). [Daly J Org Chem 21 1553 1956, Bullock et al. J Am Chem Soc 78 3693 1956, Beilstein 26 III/IV 3575.] |
| Incompatibilities | May react with strong oxidizers such aschlorates, peroxides, nitrates, etc. May release heat on contactwith water. Solid and corrosive amines are chemicalbases. Neutralize acids to form salts plus water in exothermicreactions. May be incompatible with isocyanates, halogenatedorganics, peroxides, phenols (acidic), epoxides,anhydrides, and acid halides. May generate flammable gaseoushydrogen in combination with strong reducing agents,such as hydrides. |
| Waste Disposal | Dissolve or mix the materialwith a combustible solvent and burn in a chemical incineratorequipped with an afterburner and scrubber. All federal,state, and local environmental regulations must beobserved. |
| References | [1] Patent: CN106883233, 2017, A. Location in patent: Paragraph 0051; 0052 [2] Tetrahedron, 2007, vol. 63, # 24, p. 5323 - 5327 [3] Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 185 - 195 [4] Patent: WO2016/11394, 2016, A1. Location in patent: Page/Page column 125; 126 [5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 21, p. 4728 - 4732 |
6-Benzylaminopurine Preparation Products And Raw materials
| Raw materials | Methanol-->Acrylic acid-->Poly(acrylic acid)-->6-Hydroxypurine-->6-Chloropurine-->Benzylamine-->Ethanol-->Triethylamine |
| Preparation Products | Poly(acrylic acid)-->Butyl acrylate-->Ethyl pyruvate-->Pyruvic acid-->PAINT-->acrylate ternary copolymer bound disulfide platinum complex catalyst-->Sodium polyacrylate-->Styrene-acrylic latex-->EAM resin adhesive modified with diisocyanate for orthodontias-->Lorcainide-->Atracurium besylate-->polyurethane photosensitive prepolymer-->sheeting sensitized glue-->acrylic resin coating finish-->Acrylic latex-->Adhesive for nonwoven fabric-->6-benzylaminopurine hydrochloride-->1-Isopropyl-4-piperidone-->N-(4-chlorophenyl)-1-isopropylpiperidin-4-amine-->coupling agent NBC-1-->Pressure sensitive adhesive-->THERMOPLASTIC ACRYLIC RESIN-->4-(4-(Chlorophenyl)imino)-1-isopropyl piperidine-->butadiene resin emulsion LHYJ-DS50-->Ethyl α-cyanoacrylate instantaneous adhesive-->2-Pentyl-3-methyl-2-cyclopenten-1-one-->methyl 2-(2′-hydroxy phenyl)-3-methoxy acrylate-->acrylic resin emulsion FX-1-->Silicone acrylic emulsion-->Water-soluble electrophoretic paint-->Construction emulsion BC-01-->modified acrylic resin emulsion SB-->sizing agent NBJ for jet loom-->flocculant TS-614-->nonformaldehyde resin finishing agent CN-NF^{3^}-->leather binder CAF-->WPT-S silicone modified water proof. fatliquoring and retanning agent-->HMP muti-functional retanning agent HMP |
