6-O-Benzylguanine
- Product Name
- 6-O-Benzylguanine
- CAS No.
- 19916-73-5
- Chemical Name
- 6-O-Benzylguanine
- Synonyms
- 6-benzylguanine;O6-BENZYLGUANINE;O6-Benzylguanine ,98%;6-(benzyloxy)-7H-purin-2-aMine;O6-BenzyL;NSC 637037;6-O-BENZYLGUANINE;6-BENZYLOXY GUANINE;6-oxo -benzylguanine;4 6-Benzyloxyguanine
- CBNumber
- CB9263934
- Molecular Formula
- C12H11N5O
- Formula Weight
- 241.25
- MOL File
- 19916-73-5.mol
6-O-Benzylguanine Property
- Melting point:
- 193(dec.)
- Boiling point:
- 459.3±55.0 °C(Predicted)
- Density
- 1.48±0.1 g/cm3(Predicted)
- storage temp.
- room temp
- solubility
- methanol: 20 mg/mL
- form
- solid
- pka
- 7.47±0.20(Predicted)
- color
- Off-White to Light Yellow
- InChI
- InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)
- InChIKey
- KRWMERLEINMZFT-UHFFFAOYSA-N
- SMILES
- N1C2C(=NC(N)=NC=2OCC2=CC=CC=C2)NC=1
- CAS DataBase Reference
- 19916-73-5(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B2292
- Product name
- O6-Benzylguanine
- Purity
- ≥98% (TLC), solid
- Packaging
- 50mg
- Price
- $104.5
- Updated
- 2025/07/31
- Product number
- B4208
- Product name
- O6-Benzylguanine
- Packaging
- 5G
- Price
- $56
- Updated
- 2025/07/31
- Product number
- B4208
- Product name
- O6-Benzylguanine
- Packaging
- 25G
- Price
- $168
- Updated
- 2025/07/31
- Product number
- 16332
- Product name
- O6-Benzylguanine
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 16332
- Product name
- O6-Benzylguanine
- Purity
- ≥98%
- Packaging
- 1g
- Price
- $699
- Updated
- 2024/03/01
6-O-Benzylguanine Chemical Properties,Usage,Production
Chemical Properties
Light Yellow Solid
Uses
An irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. Assists in the protection against carcinogenic and therapeutic alkylating agents.
Uses
O6-Benzylguanine is an effective substrate and efficient inactivator of DNA alkyltransferase. O6-Benzylguanine is an inhibitor of MGMT. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.
Biochem/physiol Actions
O6-Benzylguanine (O6BG) inhibits methylguanine methyltransferase (MGMT) by blocking the active site through benzyl group transfer. The use of O6BG with bis-chloroethylnitrosourea (BCNU) or carmustine is effective in treating solid tumors including lymphomas, melanomas and sarcoma.
Synthesis
10310-21-1
100-51-6
19916-73-5
GENERAL STEPS: Benzyl alcohol (37.5 g, 0.347 mol) was mixed with sodium hydroxide (2.96 g, 0.074 mol) and heated until the sodium hydroxide was completely dissolved. After the reaction mixture was cooled, 2-amino-6-chloropurine (6.00 g, 0.035 mol) was added and the reaction was stirred at 80-90 °C for 5 hours. After completion of the reaction, methyl tert-butyl ether (120 mL) was added to the reaction mixture and extracted twice with sodium hydroxide solution (70 mL). The alkaline aqueous layers were combined, washed with toluene and subsequently evaporated to remove the toluene. The solution was neutralized to pH 6-8 with 35% hydrochloric acid and the precipitated crystals were collected by filtration. The resulting crude product 2-amino-6-(benzyloxy)purine (7.60 g, 0.032 mol, 92% yield) was dried under reduced pressure.
References
[1] Patent: WO2003/84957, 2003, A1. Location in patent: Page/Page column 9-10
[2] Nucleosides and Nucleotides, 1999, vol. 18, # 10, p. 2219 - 2231
[3] Helvetica Chimica Acta, 2012, vol. 95, # 12, p. 2621 - 2634
[4] Tetrahedron, 2007, vol. 63, # 24, p. 5323 - 5327
[5] Synthetic Communications, 2003, vol. 33, # 6, p. 941 - 952
6-O-Benzylguanine Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 6-O-Benzylguanine manufacturers
- Product
- 6-O-Benzylguanine 19916-73-5
- Price
- US $0.00-0.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 99%min
- Supply Ability
- 1000kgs
- Release date
- 2021-10-28
- Product
- 6-O-Benzylguanine 19916-73-5
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2024-10-24
- Product
- 6-O-Benzylguanine 19916-73-5
- Price
- US $150.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 5ton
- Release date
- 2024-04-22