CAS 767-69-1 Purine, 6-bromo- (HCID 5287830)

Substructure search Find similar structures

Basic information

CAS: 767-69-1
Standard SMILES: Brc1ncnc2nc[nH]c12
InChIKey: CTGFGRDVWBZYNB-UHFFFAOYSA-N
Molecular formula: C5H3BrN4
Average molar mass: 199.01 g/mol
Monoisotopic mass: 197.9541082

Names & identifiers

Preferred name: Purine, 6-bromo-
IUPAC: 6-bromo-7H-purine
English name: 6-Bromopurine
Molecular formula: C5H3BrN4
Molecular weight: 199.01

Names & synonyms

6-Bromopurine6-BROMO-7H-PURINE767-69-16-bromo-9H-purine6-Bromo-1H-purinePurine, 6-bromo-1H-Purine, 6-bromo-BB-127EEINECS 212-187-8NSC 45150DTXSID20227499RefChem:870374

Show more names

6-bromo-purin6-Bromopurine ,98%

1H-Purine, 6-bromo-(9CI)DTXCID70149990212-187-8MFCD000226486-Bromo purine6-Bromo-1H-purine; 6-Bromo-9H-purine; 6-Bromopurine; NSC 451506-Bromopurine, 97%6-Bromopurine, 98%

Database identifiers

CAS: 767-69-1
PubChem CID: 5287830
DTXSID: DTXSID20227499
EC Number: 212-187-8
Nikkaji: J193.144J

Properties

Computed structural properties

XLogP: 1.3
Topological polar surface area: 54.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 0
Heavy atoms: 10
Formal charge: 0
Complexity: 131

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Melting Point>300 °C

Physicochemical properties

Melting point: 300 °C · >300 °C (lit.)
Boiling point: 240.9 · 240.9±50.0 °C(Predicted)
Density: 2.28 · 2.28±0.1 g/cm3(Predicted)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 7.39 · 7.39±0.20(Predicted)
color: Pale Beige
InChI: InChI=1S/C5H3BrN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H,7,8,9,10)
InChIKey: CTGFGRDVWBZYNB-UHFFFAOYSA-N
SMILES: N1C2C(=NC=NC=2Br)NC=1
EWG's Food Scores

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
rtecs: UO7513000
hs_code: 29339900
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 3 items

Description6-Bromopurine is a 6-halogenated purine nucleoside analogue. Studies have shown that 6-halogenopurine inhibits tumour growth when combined with azaserine, which may be related to the blockage of guanine nucleotide biosynthesis. The inhibitory effect of bromopurine occurs between inosine 5‘-phosphate and guanosine 5’-phosphate. 6-Bromopurine also enhances the carcinostatic activity of azaserine. In addition, 6-Bromopurine is also used as an intermediate in the synthesis of Idelalisib.

Uses6-Bromopurine was used in the synthesis of 6-halopurine alkynes and corresponding triazole derivatives. 6-Bromopurine was used in the synthesis and chemical characterization of 2,3,4,5-tetrahydro-1,5-benzoxazepines-3-ol.

General Description6-Bromopurine enhances the carcinostatic activity of azaserine in a test system employing ascites cell forms of sarcoma 180 and Ehrlich carcinoma in vivo. 6-bromopurine nucleosides are excellent substrates for substitution reactions with N-, O-, and S-containing nucleophiles in polar solvents.