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65-71-4

Basic Information
CAS No.: 65-71-4
Name: Thymine
Article Data: 197
Molecular Structure:
Molecular Structure of 65-71-4 (Thymine)
Formula: C5H6N2O2
Molecular Weight: 126.115
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;
EINECS: 200-616-1
Density: 1.227 g/cm3
Melting Point: 316 °C
Boiling Point: 403.8°C at 760 mmHg
Flash Point: 198oC
Solubility: Soluble in hot water. Slightly soluble in alcohol.
Appearance: White crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-37/39-26
PSA: 65.72000
LogP: -0.62840
Synthetic route
636-26-0

5-methyl-2-thiouracil

65-71-4

thymin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With acetic acid at 120℃;87%
30516-87-1

3'-azido-2',3'-deoxythymidine

65-71-4

thymin

Conditions
ConditionsYield
With iodine; hypophosphorous acid; acetic acid for 12h; Heating;81%
15981-91-6

2-amino-5-methylpyrimidin-4-one

65-71-4

thymin

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 70℃; for 8h;80%
554-01-8

5-methylcytosin

65-71-4

thymin

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