5-Hydroxymethyluracil supplier

Name
5-Hydroxymethyluracil
EINECS 224-636-5
CAS No. 4433-40-3
Article Data62
CAS DataBase
Density 1.401 g/cm³
Solubility Soluble in water. (50 g/L ) at 20°C, DMSO, dimethyl formamide or 100% ethanol.
Melting Point >300 °C
Formula C₅H₆N₂O₃
Boiling Point 530.4 °C at 760 mmHg
Molecular Weight 142.114
Flash Point 274.6 °C
Transport Information
Appearance White Powder
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms Uracil,5-(hydroxymethyl)- (6CI,7CI,8CI);5-(Hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione;5-(Hydroxymethyl)-2,4(1H,3H)-pyrimidinedione;5-(Hydroxymethyl)uracil;NSC 20901;a-Hydroxythymine;
PSA 86.47000
LogP -0.61990

Synthetic route

: 50-00-0
formaldehyd

: 66-22-8
uracil

: 4433-40-3
5-hydroxymethyl uracil

Conditions

Conditions	Yield
With potassium hydroxide In water at 50 - 52℃; for 68h;	100%
With potassium hydroxide for 0.05h; microwave irradiation;	98%
With potassium hydroxide In water at 0 - 55℃; for 36h;	98%

: 3590-48-5
5-chloromethyluracil

: 107-21-1
ethylene glycol

A: 4433-40-3
5-hydroxymethyl uracil

B: 88459-62-5
5-<(2-hydroxyethoxy)methyl>uracil

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide for 24h; Title compound not separated from byproducts;	A n/a B 46%

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

B: 1195-08-0
2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

Conditions

Conditions	Yield
With sodium persulfate In water at 85 - 90℃; for 7h;	A 5% B 41%
With sodium thiosulfate In water at 85 - 90℃; for 7h;	A 5% B 41%
With sodium persulfate In water at 85℃; for 7h;	A 0.05 mmol B 0.41 mmol
With Na2S2O8 buffer pH=7.0 at 70℃; for 4h;	A 20 % Chromat. B 7 % Chromat.
With sodium persulfate In water at 85℃; for 7h; Product distribution; Mechanism; other N-methylated thymines and uracils;	A 0.05 mmol B 0.41 mmol

: 89179-86-2
5-(aminomethyl)-2,4(1H,3H)-pyrimidinedione

: 4433-40-3
5-hydroxymethyl uracil

Conditions

Conditions	Yield
With barium nitrite anschliessend mit wss.H2SO4;

: 94820-38-9
5-(1H-[1,2,4]Triazol-3-ylsulfanylmethyl)-1H-pyrimidine-2,4-dione

A: 4433-40-3
5-hydroxymethyl uracil

B: 1H-[1,2,4]Triazole-3-thiol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-71-1
5-(Benzooxazol-2-ylsulfanylmethyl)-1H-pyrimidine-2,4-dione

A: 4433-40-3
5-hydroxymethyl uracil

B: 75593-45-2
Benzooxazole-2-thiol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-81-3
5-(Benzooxazol-2-ylselanylmethyl)-1H-pyrimidine-2,4-dione

A: 4433-40-3
5-hydroxymethyl uracil

B: Benzooxazole-2-selenol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-70-0
5-(Benzothiazol-2-ylsulfanylmethyl)-1H-pyrimidine-2,4-dione

A: 4433-40-3
5-hydroxymethyl uracil

B: 45769-89-9
Benzothiazole-2-thiol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-75-5
5-(Benzothiazol-2-ylselanylmethyl)-1H-pyrimidine-2,4-dione

A: 4433-40-3
5-hydroxymethyl uracil

B: 111686-10-3
Benzothiazole-2-selenol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84389-05-9
5-(9H-Purin-6-ylsulfanylmethyl)-1H-pyrimidine-2,4-dione

A: 4433-40-3
5-hydroxymethyl uracil

B: 33426-51-6
6-Thiopurin Anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-64-2
5-(5-Phenyl-[1,3,4]oxadiazol-2-ylsulfanylmethyl)-1H-pyrimidine-2,4-dione

A: 4433-40-3
5-hydroxymethyl uracil

B: 5-Phenyl-[1,3,4]oxadiazole-2-thiol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-68-6
5-<<<5-(2-thienyl)-1,3,4-oxadiazol-2-yl>thio>methyl>uracil

A: 4433-40-3
5-hydroxymethyl uracil

B: 5-Thiophen-2-yl-[1,3,4]oxadiazole-2-thiol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-69-7
5-(5-Thiophen-2-yl-2-thioxo-[1,3,4]oxadiazol-3-ylmethyl)-1H-pyrimidine-2,4-dione

A: 4433-40-3
5-hydroxymethyl uracil

B: 5-Thiophen-2-yl-[1,3,4]oxadiazole-2-thiol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-65-3
5-(5-Phenyl-2-thioxo-[1,3,4]oxadiazol-3-ylmethyl)-1H-pyrimidine-2,4-dione

A: 4433-40-3
5-hydroxymethyl uracil

B: 5-Phenyl-[1,3,4]oxadiazole-2-thiol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-62-0
5-<(1-phenyl-5-thioxo-2-tetrazolin-4-yl)methyl>uracil

A: 4433-40-3
5-hydroxymethyl uracil

B: 53079-79-1
1-Phenyl-1H-tetrazole-5-thiol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-57-3
5-<<(1-phenyl-1,2,3,4-tetrazol-5-yl)thio>methyl>uracil

A: 4433-40-3
5-hydroxymethyl uracil

B: 53079-79-1
1-Phenyl-1H-tetrazole-5-thiol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant; Mechanism; Thermodynamic data; other α-substituted thymines; ΔH(excit.), ΔS(excit.), var. pH;

: 84345-76-6
5-<<(1-phenyl-1,2,3,4-tetrazol-5-yl)seleno>methyl>uracil

A: 4433-40-3
5-hydroxymethyl uracil

B: 1-Phenyl-1H-tetrazole-5-selenol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 84345-73-3
5-<<<5-(p-toluidino)-1,3,4-selenadiazolo-2-yl>seleno>methyl>uracil

A: 4433-40-3
5-hydroxymethyl uracil

B: 5-p-Tolylamino-[1,3,4]selenadiazole-2-selenol anion

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 22℃; Rate constant;

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

B: 2417-22-3
5-methylbarbituric acid

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

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

E: 13514-92-6
6-Hydroxydihydrothymine

Conditions

Conditions	Yield
With air; water Quantum yield; Irradiation; var. irradiation: γ-radiolysis;

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

B: 2417-22-3
5-methylbarbituric acid

C: 13514-92-6
6-Hydroxydihydrothymine

D: 20433-38-9
5,6-dihydroxyuracil

Conditions

Conditions	Yield
With Saline; dinitrogen monoxide In water Ambient temperature; Irradiation; Further byproducts given;

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

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

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

D: 13514-92-6
6-Hydroxydihydrothymine

Conditions

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

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

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

C: 20433-38-9
5,6-dihydroxyuracil

Conditions

Conditions	Yield
With tempol; Saline; dinitrogen monoxide In water Ambient temperature; Irradiation;

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

B: 2417-22-3
5-methylbarbituric acid

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

D: 13514-92-6
6-Hydroxydihydrothymine

E: 696-04-8
5,6-dihydrothymine

Conditions

Conditions	Yield
nickel(II) sulphate Product distribution; Irradiation; degradation in the presence and absence of different Ni(II) compounds; different atmospheres;

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

B: 2417-22-3
5-methylbarbituric acid

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

: 1124-84-1, 1431-06-7, 2943-56-8, 57908-05-1, 57908-06-2, 57968-48-6, 57968-49-7, 57968-50-0, 58000-49-0
cis-5,6-dihydroxy-5,6-dehydrothymine

E: 13514-92-6
6-Hydroxydihydrothymine

F: 696-04-8
5,6-dihydrothymine

Conditions

Conditions	Yield
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;

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

B: 2417-22-3
5-methylbarbituric acid

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

D: 13514-92-6
6-Hydroxydihydrothymine

E: 20433-38-9
5,6-dihydroxyuracil

F: 696-04-8
5,6-dihydrothymine

Conditions

Conditions	Yield
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;

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

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

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

D: 13514-92-6
6-Hydroxydihydrothymine

E: 696-04-8
5,6-dihydrothymine

Conditions

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

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

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

C: 13514-92-6
6-Hydroxydihydrothymine

D: 696-04-8
5,6-dihydrothymine

Conditions

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

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

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

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

D: 13514-92-6
6-Hydroxydihydrothymine

E: 696-04-8
5,6-dihydrothymine

Conditions

Conditions	Yield
With water Quantum yield; Irradiation; var. irradiation: γ-radiolysis;

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

B: 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

D: 696-04-8
5,6-dihydrothymine

Conditions

Conditions	Yield
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.

...Expand

: 65-71-4
thymin

A: 4433-40-3
5-hydroxymethyl uracil

B: 13514-92-6
6-Hydroxydihydrothymine

C: 20433-38-9
5,6-dihydroxyuracil

D: 696-04-8
5,6-dihydrothymine

Conditions

Conditions	Yield
With Saline In water Ambient temperature; Irradiation; Further byproducts given;

...Expand

: 4433-40-3
5-hydroxymethyl uracil

: 3590-48-5
5-chloromethyluracil

Conditions

Conditions	Yield
With thionyl chloride In 1,4-dioxane for 4h; Heating / reflux;	100%
With hydrogenchloride at 20 - 35℃;	99%
With hydrogenchloride at 20℃; for 2h;	71%

: 4433-40-3
5-hydroxymethyl uracil

: 52-89-1
l-cysteine hydrochloride

: S-[(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]-L-cysteine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride at 50℃; for 48h;	94%

: 4433-40-3
5-hydroxymethyl uracil

: 67-63-0
isopropyl alcohol

: 143424-32-2
5-isopropoxymethyluracil

Conditions

Conditions	Yield
With hydrogenchloride for 4h; Heating;	93.5%

: 4433-40-3
5-hydroxymethyl uracil

: 1195-08-0
2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate In water at 40℃; for 0.583333h;	93%
With dipotassium peroxodisulfate; silver nitrate In water	84%
With dipotassium peroxodisulfate; silver nitrate In water at 40 - 45℃;	83%

: 4433-40-3
5-hydroxymethyl uracil

: 76-83-5
trityl chloride

: 53910-86-4
5-(triphenylmethoxymethyl)uracil

Conditions

Conditions	Yield
With pyridine at 95 - 100℃; for 3h;	93%

: 4433-40-3
5-hydroxymethyl uracil

: 71-43-2
benzene

: 18493-83-9
5-benzyluracil

Conditions

Conditions	Yield
With trifluoroacetic acid at 130℃; for 0.333333h; Sealed tube;	84%
With trifluoroacetic acid at 140℃; for 14h;	82%

: 4433-40-3
5-hydroxymethyl uracil

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1234711-50-2
5-(tert-butyldiphenylsiloxy)methyl-1H,3H-pyrimidine-2,4-dione

Conditions

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 20℃;	84%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	81%

: 4433-40-3
5-hydroxymethyl uracil

: 123-51-3
i-Amyl alcohol

: 5-isopentoxymethyluracil

Conditions

Conditions	Yield
With hydrogenchloride at 100℃; for 3h;	83%

: 4433-40-3
5-hydroxymethyl uracil

: 1006-59-3
2,6-diethylphenol

: 84876-24-4
5-(3,5-diethyl-4-hydroxybenzyl)uracil

Conditions

Conditions	Yield
With hydrogenchloride for 5h; Heating;	82%

: 4433-40-3
5-hydroxymethyl uracil

: 98-88-4
benzoyl chloride

: 378750-51-7
bis-N,O-benzoyl-5-(hydroxymethyl)uracil

Conditions

Conditions	Yield
In pyridine; acetonitrile	82%

: 4433-40-3
5-hydroxymethyl uracil

: 105-36-2
ethyl bromoacetate

: 944249-69-8
ethyl 2-(5-hydroxymethyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	82%
Stage #1: 5-hydroxymethyl uracil With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide Inert atmosphere;	30%

: 4433-40-3
5-hydroxymethyl uracil

: 57-13-6
urea

: 89533-46-0
N-[(uracil-5-yl)methyl]urea

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 4h;	82%

: 4433-40-3
5-hydroxymethyl uracil

: 71-41-0
pentan-1-ol

: 133635-46-8
5-pentoxymethyluracil

Conditions

Conditions	Yield
With hydrogenchloride a) r.t., 15 min, b) 100 deg C, 3h;	81%

: 4433-40-3
5-hydroxymethyl uracil

: 107-21-1
ethylene glycol

: 88459-62-5
5-<(2-hydroxyethoxy)methyl>uracil

Conditions

Conditions	Yield
With hydrogenchloride for 0.0833333h; Heating;	81%

: 4433-40-3
5-hydroxymethyl uracil

: (propa-1,2-dien-1-yloxy)cyclohexane

: (S)-1-(1-(cyclohexyloxy)allyl)-5-(hydroxymethyl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With pyridine; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); (1R,2R)-diamino-(1N,2N)-bis(1'-diphenylphosphino-2-naphthoyl)cyclohexane at 0℃; for 7h; Inert atmosphere; enantioselective reaction;	79.6%

: 4433-40-3
5-hydroxymethyl uracil

: 100-51-6
benzyl alcohol

: 7295-02-5
benzyl hydroxymethyl uridine

Conditions

Conditions	Yield
With hydrogenchloride for 1h; Heating;	79%
With acid
With hydrogenchloride Reflux;

: 4433-40-3
5-hydroxymethyl uracil

: 13035-61-5
1,2,3,5-tetraacetylribose

: 285549-57-7
2′,3′,5′-tri-O-acetyl-5-hydroxymethyluridine

Conditions

Conditions	Yield
With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 75℃; for 2h; Substitution;	79%

5-Hydroxymethyluracil Chemical Properties

IUPAC Name: 5-(Hydroxymethyl)-1H-pyrimidine-2,4-dione
Following is the structure of 2,4(1H,3H)-Pyrimidinedione,5-(hydroxymethyl)- (CAS NO.4433-40-3):

Empirical Formula: C₅H₆N₂O₃
Molecular Weight: 142.1127 g/mol
EINECS: 224-636-5
Index of Refraction: 1.528
Molar Refractivity: 31.23 cm³
Molar Volume: 101.3 cm³
Density: 1.401 g/cm³
Flash Point: 274.6 °C
Melting point: >300 °C
Surface Tension: 49.1 dyne/cm
Enthalpy of Vaporization: 84.8 kJ/mol
Boiling Point: 530.4 °C at 760 mmHg
Vapour Pressure: 4.44E-12 mmHg at 25°C
Product Categories of 2,4(1H,3H)-Pyrimidinedione,5-(hydroxymethyl)- (CAS NO.4433-40-3): PYRIMIDINE; Nucleotides and Nucleosides; Nucleic acids; 5-FOA; Bases & Related Reagents; Nucleotides; Building Blocks; Heterocyclic Building Blocks; Pyrimidines
Appearance of 2,4(1H,3H)-Pyrimidinedione,5-(hydroxymethyl)- (CAS NO.4433-40-3): White powder
Canonical SMILES: C1=C(C(=O)NC(=O)N1)CO
InChI: InChI=1S/C5H6N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1,8H,2H2,(H2,6,7,9,10)
InChIKey: JDBGXEHEIRGOBU-UHFFFAOYSA-N

5-Hydroxymethyluracil Safety Profile

Hazard Codes: Xi
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: YR0513000
Hazard Note: Irritant
HazardClass: IRRITANT

5-Hydroxymethyluracil Specification

2,4(1H,3H)-Pyrimidinedione,5-(hydroxymethyl)- , its cas register number is 4433-40-3. It also can be called 4-Methyl-5-oxyuracil ; 5-(Hydroxymethyl)uracil ; 5-Oxymethyluracil ; 5-Hydroxymethyluracil ; and Thymine, alpha-hydroxy- .

Product Name

5-Hydroxymethyluracil

Synthetic route

5-Hydroxymethyluracil Chemical Properties

5-Hydroxymethyluracil Safety Profile

5-Hydroxymethyluracil Specification

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