Pentoxifylline supplier | CasNO.6493-05-6

Name
Pentoxifylline
EINECS 229-374-5
CAS No. 6493-05-6
Article Data17
CAS DataBase
Density 1.31 g/cm³
Solubility
Melting Point 98-100°C
Formula C₁₃H₁₈N₄O₃
Boiling Point 531.3 °C at 760 mmHg
Molecular Weight 278.311
Flash Point 275.1 °C
Transport Information
Appearance White to off-white solid
Safety 36
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms Theobromine,1-(5-oxohexyl)- (7CI,8CI);1-(5-Oxohexyl)-3,7-dimethylxanthine;1-(5-Oxohexyl)theobromine;3,7-Dihydro-3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6-dione;3,7-Dimethyl-1-(5-oxohexyl)-1H,3H-purin-2,6-dione;3,7-Dimethyl-1-(5-oxohexyl)xanthine;Agapurin;Agapurin Retard;Azupentat;BL191;Dimethyloxohexylxanthine;Durapental;EHT 0202;NSC 637086;Oxpentifylline;Pentoxifyllin;Pentoxifylline;Pentoxiphyllin;Pentoxiphylline;Pentoxyfilline;Pentoxyphyllin;Pexal;Rentylin;Torental;Trental;Vasotal;Vazofirin;
PSA 78.89000
LogP 0.19300

Synthetic route

: 83-67-0
theobromine /

: (5-oxohexyl) mesylate

: 6493-05-6
pentoxyphylline

Conditions

Conditions	Yield
With potassium carbonate In ethanol; water at 50℃; for 16h;	91.1%

: 83-67-0
theobromine /

: 10226-29-6
6-Bromo-2-hexanone

: 6493-05-6
pentoxyphylline

Conditions

Conditions	Yield
With sodium hydroxide In isopropyl alcohol at 120℃; for 24h; Yield given;

: 83-67-0
theobromine /

: 10226-30-9
6-chloro-2-hexanone

: 6493-05-6
pentoxyphylline

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 18h;

: 83-67-0
theobromine /

: 6493-05-6
pentoxyphylline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium methylate / methanol / Inert atmosphere; Reflux 2: sodium iodide / acetone / Reflux 3: (2-(dimethylamino)-N-(quinolin-8-yl)acetamido)nickel(II) chloride; manganese / N,N-dimethyl-formamide / 16 h / 20 °C / Sealed tube View Scheme

: 78449-22-6
1-(4-chlorobutyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

: 6493-05-6
pentoxyphylline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium iodide / acetone / Reflux 2: (2-(dimethylamino)-N-(quinolin-8-yl)acetamido)nickel(II) chloride; manganese / N,N-dimethyl-formamide / 16 h / 20 °C / Sealed tube View Scheme

: C15H17N3NiO2

: 1-(4-iodobutyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

: 6493-05-6
pentoxyphylline

Conditions

Conditions	Yield
With manganese; (2-(dimethylamino)-N-(quinolin-8-yl)acetamido)nickel(II) chloride In N,N-dimethyl-formamide at 20℃; for 16h; Sealed tube;	16.6 mg

: 6493-05-6
pentoxyphylline

: 1185879-03-1
3,7-dimethyl-1-(4,4,6,6,6-pentadeutero-5-oxohexyl)-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With water-d2; potassium carbonate In toluene at 55 - 87℃;	99.96%
Stage #1: pentoxyphylline With water-d2; potassium carbonate for 24h; Reflux; Stage #2: With water-d2 for 24h; Reflux;	93%
With water-d2; potassium carbonate for 48h; Reflux;	93%
With water-d2; potassium carbonate In toluene at 87℃;	90%
With water-d2; potassium carbonate In toluene at 85 - 87℃; for 4h;

: 6493-05-6
pentoxyphylline

: C13H17(2)HN4O3

Conditions

Conditions	Yield
With potassium tert-butylate; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 24h; regioselective reaction;	99%
With deuteromethanol; silver carbonate In tetrahydrofuran at 50℃; for 24h;	98%
With [(N,N’-bis(1R,2R,3R,5S)-(−)-isopinocampheyl-1,2-ethanediimine-radical)NiI(μ2-H)]2; deuterium In tetrahydrofuran at -196 - 45℃; under 760.051 Torr; for 24h; Sealed tube;	93%

: 6493-05-6
pentoxyphylline

: 6493-06-7, 100324-80-9, 100324-81-0
1-(5-hydroxyhexyl)theobromine

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate In acetonitrile at 0 - 20℃; for 3.33333h;	95%
With sodium tetrahydroborate In methanol at 20℃;	92%
With sodium tetrahydroborate In methanol for 1h;	80%

: 6493-05-6
pentoxyphylline

A: 100324-81-0
lisofylline

B: 100324-80-9
(+)-(S)-3,7-dimethyl-1-(5-hydroxyhexyl)-3,7-dihydropurine-2,6-dione

Conditions

Conditions	Yield
With Saccharomyces cerevisiae KKPU In phosphate buffer at 30℃; for 120h; Product distribution; Further Variations:; Solvents; Temperatures; Reagents; time;	A 95% B n/a
With potassium tert-butylate; hydrogen; C106H135ClIrNO2P2 In propan-1-ol at 20℃; under 6080.41 - 9120.61 Torr; Glovebox; Overall yield = 99 percent; Optical yield = 86 percent ee;
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol; dichloromethane / 0.67 h / 0 - 5 °C 2: immobilized Candida antarctica type B lipase Chirazyme L-2, C-3 / chloroform / 1 h / 60 °C / Sealed tube View Scheme

: 6493-05-6
pentoxyphylline

: 8-bromo-3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With N-Bromosuccinimide In dichloromethane; water for 120h;	95%
With N-Bromosuccinimide In dichloromethane; water for 120h;	95%

: 6493-05-6
pentoxyphylline

: 1185995-18-9
pentoxifylline-d5

Conditions

Conditions	Yield
With tris(pentafluorophenyl)borate; water-d2 In tetrahydrofuran at 100℃; for 12h; Solvent; Inert atmosphere; regioselective reaction;	95%
With water-d2; potassium carbonate at 80℃; for 12h; Reagent/catalyst;

: 6493-05-6
pentoxyphylline

: 1-(5-aminohexyl)-3,7-dimethylxanthine

Conditions

Conditions	Yield
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 120℃; for 24h; chemoselective reaction;	93%
With ammonia; hydrogen In tetrahydrofuran at 120℃; for 24h;	77%

: potassium cyanide

: 506-87-6
ammonium carbonate

: 6493-05-6
pentoxyphylline

: C15H20N6O4

Conditions

Conditions	Yield
In ethanol; water at 20℃; for 24h; Bucherer-Bergs Reaction; chemoselective reaction;	92%

...Expand

: 111-92-2
dibutylamine

: 6493-05-6
pentoxyphylline

1-(5-(dibutylamino)hexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione: 1-(5-(dibutylamino)hexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 130℃; under 3750.38 - 37503.8 Torr; Autoclave;	88%

: 6493-05-6
pentoxyphylline

: 149229-27-6
2-bromo-2,2-difluoro-1-morpholine-1-yl-ethanone

: 8-(1,1-difluoro-2-morpholino-2-oxoethyl)-3,7-dimethyl-1-(5-oxohexyl)-3,4,5,7-tetrahydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); potassium acetate In dichloromethane at 20℃; for 36h; Inert atmosphere; Schlenk technique; Irradiation;	82%

: 39971-65-8
bis(((trifluoromethyl)sulfinyl)oxy)zinc

: 6493-05-6
pentoxyphylline

: 1346252-46-7
3,7-dimethyl-1-(5-oxohexyl)-8-(trifluoromethyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With tert.-butylhydroperoxide In dichloromethane; water at 25℃;	79%
With tetraethylammonium perchlorate In dimethyl sulfoxide at 20℃; for 8h; Reagent/catalyst; Electrochemical reaction;	53%

: 6493-05-6
pentoxyphylline

: C26H34N8O5

Conditions

Conditions	Yield
With sodium ethanolate In isopropyl alcohol at 0 - 60℃; for 2h; Temperature; Reagent/catalyst; Solvent;	77.2%

: 2926-29-6
Langlois reagent

: 6493-05-6
pentoxyphylline

: 1346252-46-7
3,7-dimethyl-1-(5-oxohexyl)-8-(trifluoromethyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With mesoporous graphitic carbon nitride In dimethyl sulfoxide at 25℃; Irradiation;	76%
With lithium perchlorate; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 23℃; for 16h; Inert atmosphere; Irradiation; Electrochemical reaction;	72%

: 100-47-0
benzonitrile

: 6493-05-6
pentoxyphylline

: 1-(5-(benzylamino)hexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione hydrochloride

Conditions

Conditions	Yield
Stage #1: benzonitrile; pentoxyphylline With hydrogen In 2-methyltetrahydrofuran at 110℃; under 11251.1 Torr; for 20h; High pressure; Autoclave; Stage #2: With hydrogenchloride In diethyl ether	76%

: 6493-05-6
pentoxyphylline

: 74-88-4
methyl iodide

: 1-(5-oxohexyl)-3,7,9-trimethylxanthine iodide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 75℃; for 48h; Sealed tube;	75.2%

: 6493-05-6
pentoxyphylline

: 1185995-43-0
1-(5-hydroxyhexyl-5-d)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With samarium diiodide; water-d2 In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; regioselective reaction;	75%
With samarium diiodide; water-d2 In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; chemoselective reaction;	75%

: bis(((difluoromethyl)sulfinyl)oxy)zinc

: 6493-05-6
pentoxyphylline

: 1355729-57-5
8-(difluoromethyl)-3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; trifluoroacetic acid In dichloromethane; water at 23℃; for 22h; regioselective reaction;	72%
With tert.-butylhydroperoxide In dichloromethane; water at 25℃;	72%
With tert.-butylhydroperoxide; trifluoroacetic acid In dichloromethane; water for 22h;	72%
With tert.-butylhydroperoxide In water; dimethyl sulfoxide at 60℃; for 8h; Reagent/catalyst;	49%
With tert.-butylhydroperoxide; trifluoroacetic acid In nonane; dimethyl sulfoxide at 20℃;	6.8%

: 110-59-8
pentanonitrile

: 6493-05-6
pentoxyphylline

: 3,7-dimethyl-1-(5-(pentylamino)hexyl)-3,7-dihydro-1H-purine-2,6-dione hydrochloride

Conditions

Conditions	Yield
Stage #1: pentanonitrile; pentoxyphylline With hydrogen In 2-methyltetrahydrofuran at 110℃; under 11251.1 Torr; for 20h; High pressure; Autoclave; Stage #2: With hydrogenchloride In diethyl ether	72%

: 59647-77-7
bis(3-methoxyphenyl)acetylene

: 6493-05-6
pentoxyphylline

A: (E)-1-(5-oxohexyl)-3,7-dimethyl-8-[1,2-di(3-methoxyphenyl)ethenyl]-3,7-dihydro-1H-purine-2,6-dione

B: (Z)-1-(5-oxohexyl)-3,7-dimethyl-8-[1,2-di(3-methoxyphenyl)ethenyl]-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With 2,2-dimethylbutyric acid; Pd{dba(OMe)}2; tricyclohexylphosphine In 1,4-dioxane at 120℃; for 24h; Inert atmosphere; Overall yield = 78 %;	A 70% B n/a

...Expand

: 1336-21-6
ammonium hydroxide

: ammonium chloride

: 6493-05-6
pentoxyphylline

: 1-(5-aminohexyl)-3,7-dimethylxanthine

Conditions

Conditions	Yield
With ammonium acetate; sodium cyanoborohydride In methanol; dichloromethane; water	68%

...Expand

: 1336-21-6
ammonium hydroxide

: ammonium chloride

: 6493-05-6
pentoxyphylline

A: 1-(5-aminohexyl)-3,7-dimethylxanthine

B: 1-(9'-acetoxy-10'-bromodecyl)-3,7-dimethylxanthine

Conditions

Conditions	Yield
With ammonium acetate; sodium cyanoborohydride In methanol; dichloromethane; water	A 68% B n/a

...Expand

: 64-17-5
ethanol

: 6493-05-6
pentoxyphylline

: 1016900-98-3
8-(1-hydroxyethyl)-3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With di-tert-butyl peroxide for 24h; Irradiation;	66%

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 6493-05-6
pentoxyphylline

: 3,7-dimethyl-1-(6,6,6-trifluoro-5-methyl-5-(trimethylsilyloxy)hexyl)-1H-purine-2,6(3H,7H)dione

Conditions

Conditions	Yield
With cesium fluoride In tetrahydrofuran at 0 - 20℃; for 2h;	66%

: 7521-41-7
2-Aminonicotinaldehyde

: 6493-05-6
pentoxyphylline

A: 3,7-dimethyl-1-[4-(1,8-naphthyridin-2-yl)butyl]-3,7-dihydro-1H-purine-2,6-dione

B: 3,7-dimethyl-1-[3-(2-methyl-[1,8]naphthyridin-3-yl)-propyl]-3,7-dihydro-purine-2,6-dione

Conditions

Conditions	Yield
With 1,3,3-trimethyl-6-azabicyclo[3.2.1]octane; sulfuric acid In methanol; ethanol at 60℃; for 2.75h; Friedlaender reaction;	A 65% B n/a
With sodium hydroxide; sulfuric acid In methanol at 65 - 70℃; Friedlaender reaction; Title compound not separated from byproducts;

...Expand

: 76-84-6
triphenylmethyl alcohol

: 6493-05-6
pentoxyphylline

: 1-(5-hydroxy-5-phenylhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium tert-butylate; C69H57N2O2(1+)BF4(1-)H(1+) In toluene at 125℃; for 24h; Sealed tube;	64%

: 2,2’-bis(benzo[d]isothiazol-3(2H)-one-1,1’-dioxide)-iodobenzene

: 6493-05-6
pentoxyphylline

: 8-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)-3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With iodine In chloroform at 20℃; for 16h; Irradiation; regioselective reaction;	63%

: 88192-19-2
3-azidopropylamine

: 6493-05-6
pentoxyphylline

: 1-(5-((3-azidopropyl)amino)hexyl)-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
Stage #1: 3-azidopropylamine; pentoxyphylline With acetic acid In methanol at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride at 20℃; for 2h;	60%

: 6493-05-6
pentoxyphylline

: 67-63-0
isopropyl alcohol

: (RS,RS)-1-{[2-hydroxy-2-methylcyclobutyl]methyl}-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

B: 1016900-95-0
8-(1-hydroxy-1-methylethyl)-3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione

C: 2530-99-6
N-allyltheobromine

D: 6493-06-7, 100324-80-9, 100324-81-0
1-(5-hydroxyhexyl)theobromine

Conditions

Conditions	Yield
With acetone for 24h; Irradiation;	A 5% B 55% C 17% D 4%

...Expand

: 6493-05-6
pentoxyphylline

difluoromethanesulfinate salt: difluoromethanesulfinate salt

: 1355729-57-5
8-(difluoromethyl)-3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With mesoporous graphitic carbon nitride In dimethyl sulfoxide at 25℃; Irradiation;	54%

Pentoxifylline Chemical Properties

IUPAC Name:3,7-Dimethyl-1-(5-oxohexyl)purine-2,6-dione
Synonyms 3,7-Dimethyl-1-(5-oxohexyl)purine-2,6-dione ; 3,9-Dimethyl-1-(5-oxohexyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione
Product Categories: All Inhibitors;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Cyclic Nucleotide related;pentoxifylline
Molecular Structure of Pentoxifylline (CAS NO. 6493-05-6) :
Molecular Formula of Pentoxifylline (CAS NO. 6493-05-6) : C₁₃H₁₈N₄O₃
Molecular Weight of Pentoxifylline (CAS NO. 6493-05-6) : 278.31
CAS NO: 6493-05-6
EINECS: 229-374-5
Mol File: 6493-05-6.mol
Index of Refraction: 1.62
Surface Tension: 50.5 dyne/cm
Density: 1.31 g/cm³
Flash Point: 275.1 °C
Enthalpy of Vaporization: 80.68 kJ/mol
Boiling Point: 531.3 °C at 760 mmHg
Vapour Pressure: 2.27E-11 mmHg at 25°C
Melting point: 98-100°C
Solubility: H₂O: ≥43 mg/mL
Appearance: Pentoxifylline (CAS NO. 6493-05-6)color white solid

Pentoxifylline Uses

A metabolite of Pentoxifylline (CAS NO. 6493-05-6). Methylxanthine derivative that improves blood flow by decreasing blood viscosity. Phosphodiesterase inhibitor. Inhibits the synthesis of tumor necrosis factor a (TNF-a)

Pentoxifylline Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	239mg/kg (239mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 1446, 1971.
mouse	LD50	intravenous	108mg/kg (108mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 267, 1977.
mouse	LD50	oral	1225mg/kg (1225mg/kg)		Drugs in Japan Vol. 6, Pg. 779, 1982.
mouse	LD50	subcutaneous	480mg/kg (480mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 267, 1977.
rabbit	LD50	intravenous	100mg/kg (100mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 8, Pg. 267, 1977.
rat	LD50	intraperitoneal	230mg/kg (230mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 13, 1981.
rat	LD50	intravenous	231mg/kg (231mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 1446, 1971.
rat	LD50	oral	1170mg/kg (1170mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 9, Pg. 13, 1981.
rat	LD50	subcutaneous	375mg/kg (375mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 15, Pg. 153, 1978.
women	TDLo	oral	80mg/kg (80mg/kg)	CARDIAC: PULSE RATE	British Medical Journal. Vol. 288, Pg. 26, 1984.

Pentoxifylline Safety Profile

Hazard Codes Harmful Xn
Risk Statements 22
R22:Harmful if swallowed.
Safety Statements 36
S36:Wear suitable protective clothing.
WGK Germany 3
RTECS XH2475000

Product Name

Pentoxifylline

Synthetic route

Pentoxifylline Chemical Properties

Pentoxifylline Uses

Pentoxifylline Toxicity Data With Reference

Pentoxifylline Safety Profile

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