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696-04-8

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696-04-8 Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 696-04-8 differently. You can refer to the following data:
1. 5,6-Dihydrothymine is a derivative of Thymine, a nucleobase in the nucleic acid of DNA . 5,6-Dihydrothymine is a radiolysis product of DNA.
2. 5,6-Dihydro-5-methyluracil, is used as an active pharmaceutical ingredient.

Definition

ChEBI: A pyrimidone obtained by formal addition of hydrogen across the 5,6-position of thymine.

Check Digit Verification of cas no

The CAS Registry Mumber 696-04-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,9 and 6 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 696-04:
(5*6)+(4*9)+(3*6)+(2*0)+(1*4)=88
88 % 10 = 8
So 696-04-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H8N2O2/c1-3-2-6-5(9)7-4(3)8/h3H,2H2,1H3,(H2,6,7,8,9)/t3-/m1/s1

696-04-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (L01996)  5,6-Dihydro-5-methyluracil, 98+%   

  • 696-04-8

  • 5g

  • 443.0CNY

  • Detail
  • Alfa Aesar

  • (L01996)  5,6-Dihydro-5-methyluracil, 98+%   

  • 696-04-8

  • 25g

  • 1574.0CNY

  • Detail

696-04-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 5,6-dihydrothymine

1.2 Other means of identification

Product number -
Other names 5,6-Dihydrothymine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:696-04-8 SDS

696-04-8Synthetic route

potassium cyanate
590-28-3

potassium cyanate

β-aminoisobutyric acid methyl ester hydrochloride
88512-06-5

β-aminoisobutyric acid methyl ester hydrochloride

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
Stage #1: potassium cyanate; β-aminoisobutyric acid methyl ester hydrochloride In water Milling; Green chemistry;
Stage #2: With caesium carbonate In water Green chemistry;
57%
thymin
65-71-4

thymin

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With hydrogen; 5% rhodium on alumina In water for 6h;56%
With sodium dihydrogenphosphate; water Irradiation;
With hydrogen
5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With Rh/Al2O3; acetic acid Hydrogenation;
methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

urea
57-13-6

urea

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With methanol at 135℃;
2,4-dihydroxy-5-methylpyrimidine
65-71-4

2,4-dihydroxy-5-methylpyrimidine

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With Rh/Al2O3; water Hydrogenation;
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

urea
57-13-6

urea

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
at 210 - 220℃;
3-ureido-2-methyl-propanoic acid
2905-86-4

3-ureido-2-methyl-propanoic acid

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With hydrogenchloride at 55 - 70℃; Kinetics;
5-bromo-6-hydroxy-5,6-dihydrothymine
1195-73-9

5-bromo-6-hydroxy-5,6-dihydrothymine

A

5-methylbarbituric acid
2417-22-3

5-methylbarbituric acid

B

thymin
65-71-4

thymin

C

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

D

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With sodium formate In water Mechanism; Irradiation; reaction in the presence of aromatic amine or inorganic reductant;A 15 % Turnov.
B 8 % Turnov.
C 19 % Turnov.
D n/a

A

5-methylbarbituric acid
2417-22-3

5-methylbarbituric acid

B

thymin
65-71-4

thymin

C

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

D

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With sodium formate; iron(II) sulfate In water Mechanism; Product distribution; Irradiation; different inorganic reductants, absence of reductants, adding aromatic amines; using alcohols as scavenger;A n/a
B n/a
C 14 % Turnov.
D n/a
thymin
65-71-4

thymin

A

2-imino-3-(indol-3-yl)propanoic acid
871023-09-5

2-imino-3-(indol-3-yl)propanoic acid

B

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
Irradiation;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

5-methylbarbituric acid
2417-22-3

5-methylbarbituric acid

C

6-hydroxy-5,6-dihydrothymine
1123-21-3

6-hydroxy-5,6-dihydrothymine

D

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

E

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
nickel(II) sulphate Product distribution; Irradiation; degradation in the presence and absence of different Ni(II) compounds; different atmospheres;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

5-methylbarbituric acid
2417-22-3

5-methylbarbituric acid

C

6-hydroxy-5,6-dihydrothymine
1123-21-3

6-hydroxy-5,6-dihydrothymine

E

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

F

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With ammonium ferric sulfate In water Product distribution; γ-radiolysis, absence of NH4Fe(SO4)2, in presence of NH4Fe(SO4)2 and t-butyl alcohol;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

5-methylbarbituric acid
2417-22-3

5-methylbarbituric acid

C

N1-formyl-N2-pyruvylurea
27284-91-9

N1-formyl-N2-pyruvylurea

D

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

E

5,6-dihydroxyuracil
20433-38-9

5,6-dihydroxyuracil

F

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With Saline In water Product distribution; Mechanism; Ambient temperature; Irradiation; promotion effect of addition of 2,2,6,6-tetramethylpiperidine-1-oxyls, influence of various saturation gases;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

6-hydroxy-5,6-dihydrothymine
1123-21-3

6-hydroxy-5,6-dihydrothymine

C

5,6-dihydro-5,6-dihydroxythymine
2943-56-8

5,6-dihydro-5,6-dihydroxythymine

D

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

E

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With (60)Co γ-ray irradiation; 1H-4(5)-nitroimidazole In water Mechanism; Irradiation; var. nitro compounds, pH=7.0+/-0.1;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

6-hydroxy-5,6-dihydrothymine
1123-21-3

6-hydroxy-5,6-dihydrothymine

C

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

D

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With 1H-4(5)-nitroimidazole In water Irradiation; pH=7.0+/-0.1; Further byproducts given;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

5,6-dihydro-5,6-dihydroxythymine
2943-56-8

5,6-dihydro-5,6-dihydroxythymine

C

N1-formyl-N2-pyruvylurea
27284-91-9

N1-formyl-N2-pyruvylurea

D

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

E

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With water Quantum yield; Irradiation; var. irradiation: γ-radiolysis;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

1-(6'-hydroxy-5',6'-dihydrothymin-5'-yl)thymine (5a) and 1-(5'-hydroxy-5',6'-dihydrothymin-6'-yl)thymine
94705-75-6, 95180-99-7, 142237-27-2

1-(6'-hydroxy-5',6'-dihydrothymin-5'-yl)thymine (5a) and 1-(5'-hydroxy-5',6'-dihydrothymin-6'-yl)thymine

C

1-(5'-hydroxy-5',6'-dihydrothymin-6'-yl)thymine

1-(5'-hydroxy-5',6'-dihydrothymin-6'-yl)thymine

D

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With sodium chloride In water for 5h; galvanostatic electrolysis, Pt electrodes; Further byproducts given;A 4.0 % Chromat.
B 66.0 % Chromat.
C 15.8 % Chromat.
D 9.1 % Chromat.
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

C

5,6-dihydroxyuracil
20433-38-9

5,6-dihydroxyuracil

D

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With Saline In water Ambient temperature; Irradiation; Further byproducts given;
thymin
65-71-4

thymin

A

6-hydroxy-5,6-dihydrothymine
1123-21-3

6-hydroxy-5,6-dihydrothymine

B

5,6-dihydro-5,6-dihydroxythymine
2943-56-8

5,6-dihydro-5,6-dihydroxythymine

C

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

D

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With 1H-4(5)-nitroimidazole In water Irradiation; pH=7.0+/-0.1; Further byproducts given;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

C

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

D

2,6-Diamino-4-(5-hydroxy-5-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl)-hexanoic acid

2,6-Diamino-4-(5-hydroxy-5-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl)-hexanoic acid

E

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With Nitrogen dioxide Mechanism; Irradiation;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

C

2,6-Diamino-4-(5-hydroxy-5-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl)-hexanoic acid

2,6-Diamino-4-(5-hydroxy-5-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl)-hexanoic acid

D

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With dinitrogen monoxide Irradiation; Further byproducts given. Title compound not separated from byproducts;
thymin
65-71-4

thymin

A

2,6-Diamino-4-(5-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-hexanoic acid

2,6-Diamino-4-(5-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-hexanoic acid

B

2,6-Diamino-4-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl)-hexanoic acid

2,6-Diamino-4-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl)-hexanoic acid

C

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With hydrogenchloride; dinitrogen monoxide 1.) irradiation, 2.) 120 deg C, 6 h; Multistep reaction;
thymin
65-71-4

thymin

A

5-hydroxymethyl uracil
4433-40-3

5-hydroxymethyl uracil

B

6-Hydroxydihydrothymine
13514-92-6

6-Hydroxydihydrothymine

C

2,6-Diamino-4-(5-hydroxy-5-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl)-hexanoic acid

2,6-Diamino-4-(5-hydroxy-5-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl)-hexanoic acid

D

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Conditions
ConditionsYield
With 2,6-diaminocaproic acid; dinitrogen monoxide Irradiation; Further byproducts given. Title compound not separated from byproducts;
With 2,6-diaminocaproic acid; dinitrogen monoxide Irradiation; Further byproducts given;
2-methyl-1,4-butanediamide
77928-77-9

2-methyl-1,4-butanediamide

potassium hypobromite

potassium hypobromite

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

sodium N,N-diethyldithiocarbamate
148-18-5

sodium N,N-diethyldithiocarbamate

A

N-methyl-acetamide
79-16-3

N-methyl-acetamide

B

N-formyldiethylamine
617-84-5

N-formyldiethylamine

C

N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

D

N-formyl-N-methylformamide
18197-25-6

N-formyl-N-methylformamide

E

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

F

N-ethylacetamide
625-50-3

N-ethylacetamide

Conditions
ConditionsYield
With ozone In water at 25℃; for 0.333333h; Kinetics; UV-irradiation;
p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

1,3-Bis-(4-methoxy-benzyl)-5-methyl-dihydro-pyrimidine-2,4-dione
188057-17-2

1,3-Bis-(4-methoxy-benzyl)-5-methyl-dihydro-pyrimidine-2,4-dione

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 8h; Ambient temperature;63%
acetal dimethylique du 3,4-di-O-acetyl-2,5-anhydro-6-O-p-tolylsulfonyl-D-mannose
73080-40-7

acetal dimethylique du 3,4-di-O-acetyl-2,5-anhydro-6-O-p-tolylsulfonyl-D-mannose

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

A

acetal dimethylique du 3,4-di-O-acetyl-2,5-anhydro-6-desoxy-6-(thymin-1yl)-D-mannose
73080-42-9

acetal dimethylique du 3,4-di-O-acetyl-2,5-anhydro-6-desoxy-6-(thymin-1yl)-D-mannose

B

Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[3-((2R,3R,4S,5S)-3,4-diacetoxy-5-dimethoxymethyl-tetrahydro-furan-2-ylmethyl)-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl]-5-dimethoxymethyl-tetrahydro-furan-3-yl ester

Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[3-((2R,3R,4S,5S)-3,4-diacetoxy-5-dimethoxymethyl-tetrahydro-furan-2-ylmethyl)-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl]-5-dimethoxymethyl-tetrahydro-furan-3-yl ester

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 24h;A 62%
B 8%
acetic anhydride
108-24-7

acetic anhydride

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

1-acetyl-5-methyl-dihydro-pyrimidine-2,4-dione
65179-44-4

1-acetyl-5-methyl-dihydro-pyrimidine-2,4-dione

5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

ethyl 3-amino-2-methylpropanoate
22560-81-2

ethyl 3-amino-2-methylpropanoate

Conditions
ConditionsYield
With hydrogenchloride at 120℃; Kochen der entstandenen Carbonsaeure mit aethanol.HCl;
5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

thymin
65-71-4

thymin

Conditions
ConditionsYield
In water at 40 - 50℃; for 0.666667h; Rate constant; Irradiation; irradiation by argon arch plasma; by hydrogen-oxygen flame;1.0 % Chromat.
With disodium tetrasulfide
5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

3-ureido-2-methyl-propanoic acid
2905-86-4

3-ureido-2-methyl-propanoic acid

Conditions
ConditionsYield
With sodium hydroxide
5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

A

5-methylbarbituric acid
2417-22-3

5-methylbarbituric acid

B

thymin
65-71-4

thymin

Conditions
ConditionsYield
With oxygen; dinitrogen monoxide In water Product distribution; Irradiation; pH dependence of the yield of products in the radiolysis;
5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

Sodium; 2-methyl-3-ureido-propionate
84796-57-6

Sodium; 2-methyl-3-ureido-propionate

Conditions
ConditionsYield
With sodium hydroxide Heating;
5,6-dihydrothymine
696-04-8

5,6-dihydrothymine

trans-6-Hydroperoxy 5,6-dihydro thymine
33599-51-8, 33599-52-9

trans-6-Hydroperoxy 5,6-dihydro thymine

cis-6-Hydroperoxy 5,6-dihydro thymine
33599-51-8, 33599-52-9

cis-6-Hydroperoxy 5,6-dihydro thymine

D

thymin
65-71-4

thymin

E

5-hydroperoxy-5,6-dihydrothymine

5-hydroperoxy-5,6-dihydrothymine

trans-5,6-dihydroxy-5,6-dehydrothymine

trans-5,6-dihydroxy-5,6-dehydrothymine

Conditions
ConditionsYield
With oxygen; dinitrogen monoxide In water under 760 Torr; Product distribution; Rate constant; Quantum yield; Irradiation; pH=6; also without N2O; with <14C-2> labelled compounds; G-values of degradation products;

696-04-8Relevant articles and documents

Ozone and ozone/vacuum-UV degradation of diethyl dithiocarbamate collector: Kinetics, mineralization, byproducts and pathways

Fu, Pingfeng,Ma, Yanhong,Yang, Huifen,Li, Gen,Lin, Xiaofeng

, p. 23579 - 23588 (2019/08/12)

The diethyl dithiocarbamate (DDC) collector, a precursor of toxic N-nitrosamines, is detected in flotation wastewaters usually at the ppm level. In this study, the O3 and O3/Vacuum-UV (O3/VUV) processes were compared to investigate the efficient removal of DDC with a low risk of N-nitrosamine formation. The results showed that 99.55% of DDC was removed at 20 min by O3/VUV, and the degradation rate constant was 3.99 times higher than that using O3-alone. The C, S and N mineralization extents of DDC using O3/VUV reached 36.36%, 62.69% and 79.76% at 90 min, respectively. O3/VUV achieved a much higher mineralization extent of DDC than O3-alone. After 90 min of degradation, O3/VUV achieved lower residual concentrations of CS2 and H2S, and released lower amounts of gaseous sulfur byproducts compared to O3-alone. The solid phase extraction and gas chromatography-mass spectrometry (SPE/GC-MS) analysis indicated that the main byproducts in O3/VUV degradation of DDC were amide compounds without the detection of N-nitrosamines. The avoidance of N-nitrosamine formation might be attributed to exposure of UV irradiation and enhanced formation of OH radicals in the O3/VUV system. The degradation pathways of DDC were proposed. This work indicated that O3/VUV was an efficient alternative treatment technique for the removal of DDC flotation collector with low risk of N-nitrosamine formation.

Mechanochemical preparation of hydantoins from amino esters: Application to the synthesis of the antiepileptic drug phenytoin

Konnert, Laure,Reneaud, Benjamin,De Figueiredo, Renata Marcia,Campagne, Jean-Marc,Lamaty, Frdric,Martinez, Jean,Colacino, Evelina

, p. 10132 - 10142 (2015/02/19)

The eco-friendly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and potassium cyanate in a planetary ball-mill is described. The one-pot/two-step protocol consisted in the formation of ureido ester intermediates, followed by a base-catalyzed cyclization to hydantoins. This easy-handling mechanochemical methodology was applied to a large variety of α- and β-amino esters, in smooth conditions, leading to hydantoins in good yields and with no need of purification steps. As an example, the methodology was applied to the "green" synthesis of the antiepileptic drug Phenytoin, with no use of any harmful organic solvent.

DIHYDROURACIL COMPOUNDS AS ANTI-ICTOGENIC OR ANTI-EPILEPTOGENIC AGENTS

-

Page 34, (2010/11/30)

Methods and compounds useful for the inhibition of convulsive disorders, including epilepsy, are disclosed. The methods and compounds of the invention inhibit or prevent or treat ictogenesis, epileptogenesis, or epileptogenesis-associated conditions. Methods for preparing the compounds of the invention are also described. Particularly preferred compounds of the invention include Formula 1 as described herein.

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