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8-Bromotheophylline

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Name

8-Bromotheophylline

EINECS 233-846-6
CAS No. 10381-75-6 Density 1.862 g/cm3
PSA 72.68000 LogP -0.27720
Solubility N/A Melting Point 295-297 °C
Formula C7H7BrN4O2 Boiling Point 469.468 °C at 760 mmHg
Molecular Weight 259.062 Flash Point 237.726 °C
Transport Information UN 2811 Appearance White crystalline powder
Safety 24/25-36/37 Risk Codes 20/21/22
Molecular Structure Molecular Structure of 10381-75-6 (8-BROMOTHEOPHYLLINE) Hazard Symbols N/A
Synonyms

1H-Purine-2,6-dione,8-bromo-3,7-dihydro-1,3-dimethyl- (9CI);Theophylline, 8-bromo- (6CI,7CI,8CI);8-Bromotheophylline;Bromotheaminum;Bromotheophylline;NSC 164940;

Article Data 15

8-Bromotheophylline Synthetic route

86468-95-3

8-trifluoroacetoxymercuritheophylline

10381-75-6

8-bromotheophylline

Conditions
ConditionsYield
With bromine; sodium hydrogencarbonate; potassium bromide at 80℃; for 0.5h; pH 7;96%
58-55-9

theophylline

10381-75-6

8-bromotheophylline

Conditions
ConditionsYield
With bromine In water; acetic acid at 50℃; for 4h;94.5%
With bromine at 150℃; zuletzt auf 150grad;
With ethanol; bromine
208577-20-2

8-bromo-1,3-dimethyl-7-(1,1-dioxothietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione

A

82299-33-0

3-ethoxy-λ6-thietane 1,1-dioxide

B

10381-75-6

8-bromotheophylline

Conditions
ConditionsYield
With sodium In ethanol for 0.5h; Heating;A n/a
B 85%
2099-73-2

8-nitrotheophylline

10381-75-6

8-bromotheophylline

Conditions
ConditionsYield
With water; hydrogen bromide
2099-73-2

8-nitrotheophylline

10035-10-6, 12258-64-9

hydrogen bromide

10381-75-6

8-bromotheophylline

944-73-0

1,3-dimethyluric acid

A

10381-75-6

8-bromotheophylline

B

8-chloro-theophylline

8-chloro-theophylline

Conditions
ConditionsYield
With phosphorus pentabromide; trichlorophosphate at 145 - 150℃;
110-89-4

piperidine

10381-75-6

8-bromotheophylline

961-48-8

1,3-dimethyl-8-(1-piperidyl)-7H-purine-2,6-dione

Conditions
ConditionsYield
for 2h; Heating;98%
10381-75-6

8-bromotheophylline

2,4-dichloro-1-(cyclopropylmethoxy)benzene

8-bromo-7-[2-hydroxy-3-(2,4-dichlorophenoxy)prop-1-yl]theophylline

Conditions
ConditionsYield
Reflux;97.3%
10381-75-6

8-bromotheophylline

7-hex-5-enyl-1,3-dimethyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione

Conditions
ConditionsYield
With pyridine In butan-1-ol for 2h; Heating;97%
18800-34-5

1-bromo-2-(4'-methylphenoxy)ethane

10381-75-6

8-bromotheophylline

228247-62-9

7-(4'-methylphenoxy)ethyl-8-bromotheophylline

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 9h; Heating;96%

8-Bromotheophylline Specification

The IUPAC name of 1H-Purine-2,6-dione,8-bromo-3,9-dihydro-1,3-dimethyl- is 8-bromo-1,3-dimethyl-7H-purine-2,6-dione. With the CAS registry number 10381-75-6, it is also named as 8-Bromotheophylline. The product's categories are Pharmaceutical Raw Materials; Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides. It is white crystalline powder which is used as pharmaceutical intermediate.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.18; (4)ACD/LogD (pH 7.4): -1.52; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 14.58; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.651; (13)Molar Refractivity: 50.84 cm3; (14)Molar Volume: 139 cm3; (15)Polarizability: 20.15×10-24 cm3; (16)Surface Tension: 70.8 dyne/cm; (17)Enthalpy of Vaporization: 73.18 kJ/mol; (18)Vapour Pressure: 5.49E-09 mmHg at 25°C; (19)Tautomer Count: 4; (20)Exact Mass: 257.975238; (21)MonoIsotopic Mass: 257.975238; (22)Topological Polar Surface Area: 69.3; (23)Heavy Atom Count: 14; (24)Complexity: 297.

Preparation of 1H-Purine-2,6-dione,8-bromo-3,9-dihydro-1,3-dimethyl-: It can be obtained by 8-trifluoroacetoxymercuritheophylline. This reaction needs reagent Br2, aq. KBr, NaHCO3 at temperature of 80 °C. The reaction time is 30 min. The yield is 96%.

Uses of 1H-Purine-2,6-dione,8-bromo-3,9-dihydro-1,3-dimethyl-: It can react with chloromethyl-thiirane to get 8-bromo-1,3-dimethyl-7-(thietanyl-3)xanthine. This reaction needs reagent KOH and solvent H2O at temperature of 60 °C. The reaction time is 3 hours. The yield is 44%.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C2N(c1nc(Br)nc1C(=O)N2C)C
2. InChI:InChI=1/C7H7BrN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)
3. InChIKey:SKTFQHRVFFOHTQ-UHFFFAOYAW

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