Thymine supplier | CasNO.65-71-4

Name
Thymine
EINECS 200-616-1
CAS No. 65-71-4
Article Data197
CAS DataBase
Density 1.227 g/cm³
Solubility Soluble in hot water. Slightly soluble in alcohol.
Melting Point 316 °C
Formula C₅H₆N₂O₂
Boiling Point 403.8°C at 760 mmHg
Molecular Weight 126.115
Flash Point 198oC
Transport Information
Appearance White crystalline powder
Safety 22-24/25-37/39-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Thymine(8CI);2,4-Dihydroxy-5-methylpyrimidine;4-Hydroxy-5-methylpyrimidin-2(1H)-one;5-Methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione;5-Methyl-2,4(1H,3H)-pyrimidinedione;5-Methyl-2,4-dihydroxypyrimidine;5-Methylpyrimidine-2,4-dione;5-Methyluracil;NSC 14705;NSC 168663;2,4(1H,3H)-Pyrimidinedione, 5-methyl-;2,4-pyrimidinediol, 5-methyl-;4-Hydroxy-5-methylpyrimidin-2(1H)-one;
PSA 65.72000
LogP -0.62840

Synthetic route

: 636-26-0
5-methyl-2-thiouracil

: 65-71-4
thymin

Conditions

Conditions	Yield
With sodium hydroxide; methyloxirane In water at 20℃;	100%
With iodosylbenzene In acetone for 15h; Ambient temperature;	65%

: 50-89-5
thymidine

A: α-D-2′-deoxyribofuranose-1-O-phosphate barium salt

B: 65-71-4
thymin

Conditions

Conditions	Yield
Stage #1: thymidine With magnesium(II) chloride hexahydrate; E. coli thymidine phosphorylase In aq. phosphate buffer at 40℃; for 120h; pH=7.0; Stage #2: With ammonium hydroxide; barium(II) acetate In aq. phosphate buffer at 4℃; pH=8.0;	A 93% B n/a

: 1195-73-9
5-bromo-6-hydroxy-5,6-dihydrothymine

: 65-71-4
thymin

Conditions

Conditions	Yield
With copper(II) sulfate; ascorbic acid In water for 0.0833333h; Ambient temperature;	92.9%
With sodium formate; iron(II) sulfate In water Irradiation;

: 80-43-3
bis(1-methyl-1-phenylethyl)peroxide

: 66-22-8
uracil

: 65-71-4
thymin

Conditions

Conditions	Yield
With acetic acid at 120℃;	87%

: 30516-87-1
3'-azido-2',3'-deoxythymidine

: 65-71-4
thymin

Conditions

Conditions	Yield
With iodine; hypophosphorous acid; acetic acid for 12h; Heating;	81%

: 15981-91-6
2-amino-5-methylpyrimidin-4-one

: 65-71-4
thymin

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 70℃; for 8h;	80%

: 554-01-8
5-methylcytosin

: 65-71-4
thymin

Conditions

Conditions	Yield
With 4-phenylnaphthalene-1,2-dione In water; dimethyl sulfoxide at 140℃; for 48h;	71%
With water at 95℃; Rate constant; pH 1.14; further pH (4.58);
With Escherichia coli K12 D314A cytosine deaminase In aq. buffer at 30℃; pH=7.5; Kinetics; Temperature; Reagent/catalyst; Concentration; Enzymatic reaction;

: 2,2'-anhydro-5-methyluridine

: 109-86-4
2-methoxy-ethanol

A: C23H32N4O12

B: 65-71-4
thymin

C: 163759-49-7
2'-O-(2-methoxyethyl)-5-methyluridine

Conditions

Conditions	Yield
Stage #1: 2,2'-anhydro-5-methyluridine; 2-methoxy-ethanol With tris(2-methoxyethyl)borate; sodium hydrogencarbonate at 130℃; under 760.051 Torr; for 21h; Argon atmosphere; Stage #2: With water for 0.5h; Heating / reflux;	A n/a B n/a C 69.4%

...Expand

: 22423-26-3
O-2,2'-cyclo-5-methyluridine

: 14983-42-7
tris(2-methoxyethyl)borate

A: C23H32N4O12

B: 65-71-4
thymin

C: 163759-49-7
2'-O-(2-methoxyethyl)-5-methyluridine

Conditions

Conditions	Yield
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate; sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	A n/a B n/a C 69.4%
Stage #1: O-2,2'-cyclo-5-methyluridine; tris(2-methoxyethyl)borate; sodium hydrogencarbonate In 2-methoxy-ethanol at 130℃; for 21h; Stage #2: With water for 0.5h; Heating / reflux;	A n/a B n/a C 69.4%

...Expand

: 56070-42-9
(2R,3S,5R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl acetate

: 100-51-6
benzyl alcohol

A: 53172-91-1
(benzyloxy)(tert-butyl)dimethylsilane

B: 21090-30-2
3'-O-acetylthymidine

C: 65-71-4
thymin

D: 50-89-5
thymidine

Conditions

Conditions	Yield
With copper(II) sulfate In xylene for 2h; Heating;	A n/a B 69% C n/a D n/a

...Expand

: 43179-29-9
(+)-trans-(5R,6R)-5-bromo-6-hydroxy-5,6-dihydrothymidine

A: 65-71-4
thymin

B: 13091-56-0
1-(2-Deoxy-β-D-erythro-pentopyranosyl)thymine

C: 50-89-5
thymidine

Conditions

Conditions	Yield
With copper(II) sulfate; ascorbic acid In water for 0.0833333h; Ambient temperature;	A 15.1% B 14% C 61.9%
With copper(II) sulfate; ascorbic acid In water for 0.0833333h; Ambient temperature;	A 15.1% B 14% C 61.9%

...Expand

: 87781-93-9
2-bromo-1,9-dihydro-6H-purin-6-one

: 50-89-5
thymidine

A: 123994-87-6
2-bromo-2'-deoxyinosine

B: 65-71-4
thymin

Conditions

Conditions	Yield
With purine nucleoside phosphorylase; thymidine phosphorylase In phosphate buffer at 37℃; for 20h; pH=7.4;	A 60% B n/a

...Expand

: 636-26-0
5-methyl-2-thiouracil

A: 17758-52-0
5-methyl-4(3H)-pyrimidinone

B: 65-71-4
thymin

C SO2, H2SO4: SO2, H2SO4

Conditions

Conditions	Yield
With oxygen; ozone In acetic acid for 0.166667h; Ambient temperature;	A 58% B 7% C n/a

...Expand

: 43179-28-8
(-)-trans-(5S,6S)-5-bromo-6-hydroxy-5,6-dihydrothymidine

A: 65-71-4
thymin

B: 13091-56-0
1-(2-Deoxy-β-D-erythro-pentopyranosyl)thymine

C: 50-89-5
thymidine

Conditions

Conditions	Yield
With copper(II) sulfate; ascorbic acid In water for 0.0833333h; Ambient temperature;	A 14.3% B 16.8% C 57.5%

...Expand

: 40733-26-4
3',5'-O-di(tert-butyldimethylsilyl)thymidine

: 100-51-6
benzyl alcohol

A: 53172-91-1
(benzyloxy)(tert-butyl)dimethylsilane

B: 65-71-4
thymin

C: 50-89-5
thymidine

Conditions

Conditions	Yield
With copper(II) sulfate In xylene Heating;	A 0.76 g B n/a C 55%

...Expand

: 64911-18-8
3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine

: 100-51-6
benzyl alcohol

A: 53172-91-1
(benzyloxy)(tert-butyl)dimethylsilane

B: 951-78-0
2'-deoxyuridine

C: 65-71-4
thymin

Conditions

Conditions	Yield
With copper(II) sulfate In xylene Heating;	A 0.92 g B 53% C n/a

...Expand

: 52417-07-9
3′,5′-di-O-trityl-thymidine

: 100-51-6
benzyl alcohol

A: 519-73-3
triphenylmethane

B: 5333-62-0
benzyl trityl ether

C: 65-71-4
thymin

D: 50-89-5
thymidine

Conditions

Conditions	Yield
With copper(II) sulfate In xylene for 5h; Heating;	A n/a B n/a C n/a D 51%

...Expand

: 76223-04-6
1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxy-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

: 100-51-6
benzyl alcohol

A: 53172-91-1
(benzyloxy)(tert-butyl)dimethylsilane

B: 951-78-0
2'-deoxyuridine

C: 65-71-4
thymin

Conditions

Conditions	Yield
With copper(II) sulfate In xylene Heating;	A n/a B 49% C n/a

...Expand

: 7791-71-1
5'-O-tritylthymidine

: 100-51-6
benzyl alcohol

A: 519-73-3
triphenylmethane

B: 5333-62-0
benzyl trityl ether

C: 65-71-4
thymin

D: 50-89-5
thymidine

Conditions

Conditions	Yield
With copper(II) sulfate In xylene for 5h; Heating;	A n/a B n/a C n/a D 49%

...Expand

: 40733-28-6
5'-tert-butyldimethylsilyloxy-2'-deoxythymidine

: 100-51-6
benzyl alcohol

A: 53172-91-1
(benzyloxy)(tert-butyl)dimethylsilane

B: 65-71-4
thymin

C: 50-89-5
thymidine

Conditions

Conditions	Yield
With copper(II) sulfate In xylene Heating;	A 0.76 g B n/a C 49%

...Expand

: 82949-83-5
5,10-bis(uracil-5-ylmethyl)tetrahydropteroylglutamic acid

: 65-71-4
thymin

Conditions

Conditions	Yield
at 250 - 275℃; for 5h; in vacuo;	39%
at 255℃; Product distribution; i. vac.;	39%
With other (uracil-5-ylmethyl)tetrahydropteroylglutamic acid at 250 - 275℃; for 5h; Mechanism;

: 65-71-4
thymin

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

Conditions

Conditions	Yield
With ammonium bisulphate In 1,2-dichloro-ethane Reflux; Inert atmosphere; Schlenk technique;	100%
With ammonium sulfate at 160℃; for 4h;	97.95%
With ammonium sulfate In toluene at 120℃; for 0.5h; Inert atmosphere;	96.6%

: 922-67-8
propynoic acid methyl ester

: 65-71-4
thymin

: 287727-77-9
(E)-3-[3-((E)-2-Methoxycarbonyl-vinyl)-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-acrylic acid methyl ester

Conditions

Conditions	Yield
With dmap In acetonitrile at 20℃; for 2h; hetero-Michael addition;	100%

: 1148114-29-7
C19H29FO4Si

: 65-71-4
thymin

: 1148114-32-2
C22H31FN2O4Si

Conditions

Conditions	Yield
Stage #1: C19H29FO4Si; thymin With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 2h;	100%

: 1374576-25-6
(1S,2R,4S,6S)-2-[(tert-butyldimethylsilyl)oxy]-4-[(ethoxycarbonyl)methyl]-6-trimethylsilyloxy-9-oxatricyclo-[4.3.0(1,6).0(2,4)]non-7-ene

: 65-71-4
thymin

: 1374576-26-7
1-[(3'R,5'R,6'S)-3'-O-trimethylsilyl-5'-O-(tert-butyldimethylsilyl)-6'-[(ethoxycarbonyl)methyl]-2'-deoxy-2'-iodo-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine

Conditions

Conditions	Yield
With N-iodo-succinimide; N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane at 0℃;	100%
With N-iodo-succinimide; N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0℃;	100%
Stage #1: thymin With BSA In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: (1S,2R,4S,6S)-2-[(tert-butyldimethylsilyl)oxy]-4-[(ethoxycarbonyl)methyl]-6-trimethylsilyloxy-9-oxatricyclo-[4.3.0(1,6).0(2,4)]non-7-ene With N-iodo-succinimide In dichloromethane at 0 - 20℃; Inert atmosphere;

: 1458-98-6
2-methyl-3-bromo-1-propene

: 65-71-4
thymin

: N1-2′-methylallyl-thymine

Conditions

Conditions	Yield
Stage #1: thymin In acetonitrile for 0.0833333h; Inert atmosphere; Reflux; Stage #2: 2-methyl-3-bromo-1-propene With chloro-trimethyl-silane; sodium iodide In acetonitrile for 16h; Inert atmosphere; Reflux;	100%

: 5-O-(o-toluoyl)-1,2-diacetyl-3-deoxyxylofuranose

: 65-71-4
thymin

: 5'-O-(o-toluoyl)-2'-O-acetyl-3'-deoxythymidine

Conditions

Conditions	Yield
Stage #1: thymin With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20℃; for 0.333333h; Vorbrueggen Nucleoside Synthesis; Stage #2: 5-O-(o-toluoyl)-1,2-diacetyl-3-deoxyxylofuranose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -20 - 70℃; for 2h; Vorbrueggen Nucleoside Synthesis; stereoselective reaction;	100%

: 100-39-0
benzyl bromide

: 65-71-4
thymin

: 78450-19-8
N,N'-dibenzylthymine

Conditions

Conditions	Yield
Stage #1: thymin With potassium carbonate for 1h; Milling; Stage #2: benzyl bromide In N,N-dimethyl-formamide for 1h; Milling;	99%
With potassium hydroxide; tetrabutylammomium bromide 1.) 80 deg C, 2 h, 2.) 1 h; Yield given. Multistep reaction;

: 75-77-4
chloro-trimethyl-silane

: 65-71-4
thymin

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane Ambient temperature;	99%
With triethylamine In benzene for 2h; Inert atmosphere; Reflux;	93%
With triethylamine In benzene Inert atmosphere;	89%

: 65-71-4
thymin

: 140-88-5
ethyl acrylate

: 101852-97-5
3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidine-1-yl)propionic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; Aza-Micheal reaction;	99%
With tetrabutylammomium bromide; zinc(II) oxide at 100℃; for 0.416667h; Michael addition; microwave irradiation;	89%
With ethanol; sodium In benzene for 24h; Michael Addition; Reflux;	86%

: 65-71-4
thymin

: 293751-03-8
1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose

: 293751-04-9
1-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)thymine

Conditions

Conditions	Yield
Stage #1: thymin; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 80℃; Large scale; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 80℃; for 1.33333h; Vorbrueggen Nucleoside Synthesis; Large scale;	99%
Stage #1: thymin; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 1h; Heating; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 4h; Heating; Further stages.;	88%
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile	88%
Stage #1: thymin; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 1h; Heating / reflux; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 2h; Heating / reflux;	85%
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 60℃; Vorbrueggen Nucleoside Synthesis; Inert atmosphere;

: 65-71-4
thymin

: 92283-88-0
1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol

: 401906-49-8
1,5-anhydro-4,6-O-benzylidene-2-deoxy-2-(thymin-1-yl)-D-altro-hexitol

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 85℃; for 36h;	99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80 - 90℃; for 3h;	75%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 85℃; for 12h;	65.6%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 85℃; for 7h;

: 1352230-42-2
C40H46O9Si

: 65-71-4
thymin

: 1352230-43-3
C43H48N2O9Si

Conditions

Conditions	Yield
Stage #1: C40H46O9Si; thymin With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 55℃; for 1.5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 0 - 60℃;	99%
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile

: 65-71-4
thymin

: 35455-79-9
5-methyl-4-thiouracil

Conditions

Conditions	Yield
With diphosphorus pentasulfide; sodium hydrogencarbonate In diethylene glycol dimethyl ether at 110℃; for 2h;	98%
With Lawessons reagent In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 2h;	74%

: 3080-30-6, 6974-32-9, 14215-97-5, 16162-35-9, 20822-87-1, 21138-42-1, 22249-15-6, 22249-17-8, 26287-72-9, 53403-35-3, 53403-36-4, 57236-69-8, 70832-64-3, 99395-04-7, 100101-51-7, 109668-83-9, 120019-54-7
1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose

: 65-71-4
thymin

: 237060-98-9
2',3',5'-tri-O-benzoyl-5-methyl-L-uridine

Conditions

Conditions	Yield
With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 65℃; Condensation;	98%
Substitution;	92%
With ammonium sulfate; N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 80℃; for 3.5h; Reflux; stereoselective reaction;	60%

: 6674-22-2
1,8-diazabicyclo[5.4.0]undec-7-ene

: 65-71-4
thymin

: 2,3,4,6,7,8,9,10-octahydro-pyrimido[1,2-a]azepine; compound with 5-methyl-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
In acetonitrile at 20℃;	98%

: 65-71-4
thymin

: 364335-62-6
Acetic acid (3aR,5R,6R,7S,7aS)-6,7-bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-yl ester

: 1-((3aR,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-hexahydro-furo[3,2-b]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With chloro-trimethyl-silane; potassium nonaflate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 20℃; for 0.5h;	98%

: 65-71-4
thymin

: 426836-31-9
(S)-[2-(acetoxymethoxy)-2-phenyl]ethyl benzoate

: 426836-32-0
(S)-1-[(2-benzoyloxy-1-phenylethoxy)methyl]thymine

Conditions

Conditions	Yield
Stage #1: thymin With NH4(SO4)2; 1,1,1,3,3,3-hexamethyl-disilazane Heating; Stage #2: (S)-[2-(acetoxymethoxy)-2-phenyl]ethyl benzoate With dibenzo-18-crown-6; potassium iodide In toluene; acetonitrile	98%

: 65-71-4
thymin

: 871118-07-9
(R)-[2-(acetoxymethoxy)-2-phenyl]ethyl benzoate

: 499203-31-5
(R)-1-[(2-benzoyloxy-1-phenylethoxy)methyl]thymine

Conditions

Conditions	Yield
Stage #1: thymin With NH4(SO4)2; 1,1,1,3,3,3-hexamethyl-disilazane Heating; Stage #2: (R)-[2-(acetoxymethoxy)-2-phenyl]ethyl benzoate With dibenzo-18-crown-6; potassium iodide In toluene; acetonitrile	98%

: 942428-83-3
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

: 65-71-4
thymin

: 3180-74-3
(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions

Conditions	Yield
Stage #1: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate; thymin With N,O-Bis(trimethylsilyl)trifluoroacetamide In nitromethane at 20℃; for 0.5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In nitromethane at 20℃;	98%
Stage #1: thymin With N,O-Bis(trimethylsilyl)trifluoroacetamide In acetonitrile at 20℃; for 0.5h; Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; Further stages.;	91%

: 1055317-41-3
2,3,5-tri-O-benzoyl-D-ribofuranosyl(N-phenyl)trifluoroacetimidate

: 65-71-4
thymin

: 3180-76-5
2',3',5'-tri-O-benzoyluridine

Conditions

Conditions	Yield
Stage #1: 2,3,5-tri-O-benzoyl-D-ribofuranosyl(N-phenyl)trifluoroacetimidate; thymin With N,O-Bis(trimethylsilyl)trifluoroacetamide In acetonitrile at 20℃; for 0.5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃;	98%
Stage #1: thymin With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20℃; for 0.5h; Stage #2: 2,3,5-tri-O-benzoyl-D-ribofuranosyl(N-phenyl)trifluoroacetimidate With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; Further stages.;	88%

: 100-44-7
benzyl chloride

: 65-71-4
thymin

: 78450-19-8
N,N'-dibenzylthymine

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride for 8h;	97%
With sodium hydroxide; tetrabutylammomium bromide In benzene at 80℃; for 14h;	73%

: 74-83-9
methyl bromide

: 65-71-4
thymin

: 4401-71-2
1,3-dimethylthymine

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 40℃; for 3h;	97%

: 65-71-4
thymin

: 77-78-1
dimethyl sulfate

: 4401-71-2
1,3-dimethylthymine

Conditions

Conditions	Yield
With sodium hydroxide; water for 1h; Methylation;	97%
With sodium hydroxide In water at 20 - 50℃; for 20.5h;	94%
With potassium hydroxide Heating;	85%
With sodium hydroxide
With sodium hydroxide In water at 20 - 40℃; for 20h;

: 65-71-4
thymin

: {[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-difluoro-methyl}-phosphonothioic acid O,O-diethyl ester

: O,O-diethyl (2S,3S)-[2-{[tert-butyl(diphenyl)siloxy]methyl}-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl](difluoro)methylphosphonothioate

Conditions

Conditions	Yield
Stage #1: thymin; {[2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-difluoro-methyl}-phosphonothioic acid O,O-diethyl ester With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane for 4h; Heating; Stage #2: With titanium tetrachloride In dichloromethane at 0℃; for 3h;	97%

: 65-71-4
thymin

: 339276-10-7
2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)-2,2,2-trifluoroacetimidate

: 31506-00-0
1-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)thymine

Conditions

Conditions	Yield
Stage #1: thymin; 2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)-2,2,2-trifluoroacetimidate With N,O-Bis(trimethylsilyl)trifluoroacetamide In nitromethane at 20℃; for 0.5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In nitromethane at 20℃;	97%

: 65-71-4
thymin

: thymine-potassium

Conditions

Conditions	Yield
With potassium hydroxide In water for 0.166667h;	97%

: 3,5-di-O-benzoyl-α-D-ribofuranose-1,2-(pent-4-enyl orthobenzoate)

: 65-71-4
thymin

: 3180-76-5
2',3',5'-tri-O-benzoyluridine

Conditions

Conditions	Yield
Stage #1: thymin With trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane at 85℃; Inert atmosphere; Stage #2: 3,5-di-O-benzoyl-α-D-ribofuranose-1,2-(pent-4-enyl orthobenzoate) With N-iodo-succinimide; ytterbium(III) triflate In acetonitrile at 0 - 20℃; for 4h;	97%

: 65-71-4
thymin

: 233266-81-4
1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-ethynyl-D-ribo-pentofuranose

: 233266-83-6
1-(2-O-acetyl-3,5-di-O-benzyl-4-C-ethynyl-β-D-ribo-pentofuranosyl)thymine

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 13h; Heating;	96.1%

: 65-71-4
thymin

: 23945-44-0
2,4-dihydroxypyrimidine-5-carboxylic acid

Conditions

Conditions	Yield
With dihydrogen peroxide; 1-hydroxy-1,2,3-benzotriazine-4(3H)-one In water at 130℃; for 3h; Temperature; Autoclave;	96.1%
Multi-step reaction with 2 steps 1: ascorbic acid; iron(II) ammonium sulfate; magnesium chloride; ATP; coenzyme A; NADH; succinyl-CoA synthetase, His6-tag fused protein; pyruvate kinase; lactate dehydrogenase; Neurospora crassa thymine-7-hydroxylase, wild-type, full-length, residues 1–333 / aq. buffer / 25 °C / pH 7.5 / Enzymatic reaction 2: ascorbic acid; iron(II) ammonium sulfate; magnesium chloride; ATP; coenzyme A; NADH; succinyl-CoA synthetase, His6-tag fused protein; pyruvate kinase; lactate dehydrogenase; Neurospora crassa thymine-7-hydroxylase, wild-type, full-length, residues 1–333 / aq. buffer / 25 °C / pH 7.5 / Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1: ascorbic acid; iron(II) ammonium sulfate; magnesium chloride; ATP; coenzyme A; NADH; succinyl-CoA synthetase, His6-tag fused protein; pyruvate kinase; lactate dehydrogenase; Neurospora crassa thymine-7-hydroxylase, wild-type, full-length, residues 1–333 / aq. buffer / 25 °C / pH 7.5 / Enzymatic reaction 2: ascorbic acid; iron(II) ammonium sulfate; magnesium chloride; ATP; coenzyme A; NADH; succinyl-CoA synthetase, His6-tag fused protein; pyruvate kinase; lactate dehydrogenase; Neurospora crassa thymine-7-hydroxylase, wild-type, full-length, residues 1–333 / aq. buffer / 25 °C / pH 7.5 / Enzymatic reaction 3: ascorbic acid; iron(II) ammonium sulfate; magnesium chloride; ATP; coenzyme A; NADH; succinyl-CoA synthetase, His6-tag fused protein; pyruvate kinase; lactate dehydrogenase; Neurospora crassa thymine-7-hydroxylase, wild-type, full-length, residues 1–333 / aq. buffer / 25 °C / pH 7.5 / Enzymatic reaction View Scheme

Thymine Specification

The Thymine, with the CAS registry number 65-71-4 and EINECS registry number 200-616-1, has the systematic name of 5-methylpyrimidine-2,4(1H,3H)-dione. The molecular formula of this chemical is C₅H₆N₂O₂. It is a kind of white crystalline powder, and belongs to the following product categories: Pyridines, Pyrimidines, Purines and Pteredines; Pyridine; Heterocyclic Compounds;Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic acids.

The Thymine is one of the four nucleobases in the nucleic acid of DNA. In RNA, thymine is replaced with uracil in most cases. In DNA, thymine (T) binds to adenine (A) via two hydrogen bonds, thus stabilizing the nucleic acid structures. And it is often used as immunopotentiator to treat immunodeficiency disorder, such as thymic hypoplasia and ataxia telangiectasia.

The physical properties of Thymine are as following: (1)# of Rule of 5 Violations: 0 ; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 10.93; (5)ACD/KOC (pH 7.4): 10.419; (6)#H bond acceptors: 4; (7)#H bond donors: 2; (8)#Freely Rotating Bonds: 0; (9)Polar Surface Area: 58.2 Å²; (10)Index of Refraction: 1.49; (11)Molar Refractivity: 29.712 cm³; (12)Molar Volume: 102.793 cm³; (13)Polarizability: 11.779×10^-24cm³; (14)Surface Tension: 35.741 dyne/cm; (15)Density: 1.227 g/cm³.

Preparation of Thymine: This chemical can be prepared by 5-bromo-6-hydroxy-5-methyl-dihydro-pyrimidine-2,4-dione. The reaction will need reagents CuSO₄ and ascorbic acid, and the solvent H₂O. The reaction time is 5 minutes with ambient temperature, and the yield is about 92.9%.

Thymine can be prepared by 5-bromo-6-hydroxy-5-methyl-dihydro-pyrimidine-2,4-dione

Uses of Thymine: It can react with piperidine and formaldehyde to produce 5-methyl-1,3-bis-piperidin-1-ylmethyl-1H-pyrimidine-2,4-dione. This reaction will need solvent ethanol. The reaction time is 2 hours with heating, and the yield is about 90%.

Thymine can react with piperidine and formaldehyde to produce 5-methyl-1,3-bis-piperidin-1-ylmethyl-1H-pyrimidine-2,4-dione

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Do not breathe dust and then try to avoid contacting with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1c[nH]c(=O)[nH]c1=O
(2)InChI: InChI=1/C5H6N2O2/c1-3-2-6-5(9)7-4(3)8/h2H,1H3,(H2,6,7,8,9)
(3)InChIKey: RWQNBRDOKXIBIV-UHFFFAOYAL

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	3500mg/kg (3500mg/kg)		Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 44, Pg. 56, 1955.
mouse	LDLo	intraperitoneal	1gm/kg (1000mg/kg)		Annals of the New York Academy of Sciences. Vol. 60, Pg. 251, 1954.

Product Name

Thymine

Synthetic route

Thymine Specification

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