[ CAS No. 2240-25-7 ] {[proInfo.proName]}

Name: 2240-25-7|4-Amino-5-bromopyrimidin-2(1H)-one|95%
Brand: Ambeed
SKU: A140809
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Quality Control of [ 2240-25-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2240-25-7 ]

Product Details of [ 2240-25-7 ]

CAS No. :	2240-25-7	MDL No. :	MFCD00056025
Formula :	C₄H₄BrN₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QFVKLKDEXOWFSL-UHFFFAOYSA-N
M.W :	190.00	Pubchem ID :	75233
Synonyms :

Calculated chemistry of [ 2240-25-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	36.96
TPSA :	71.77 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.73
Log Po/w (XLOGP3) :	-0.4
Log Po/w (WLOGP) :	0.12
Log Po/w (MLOGP) :	-0.39
Log Po/w (SILICOS-IT) :	1.18
Consensus Log Po/w :	0.25

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.26
Solubility :	10.5 mg/ml ; 0.055 mol/l
Class :	Very soluble
Log S (Ali) :	-0.64
Solubility :	43.2 mg/ml ; 0.227 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.06
Solubility :	1.67 mg/ml ; 0.00881 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 2240-25-7 ]

Signal Word:	Danger	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H318-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2240-25-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 2240-25-7 ]
Downstream synthetic route of [ 2240-25-7 ]

[ 2240-25-7 ] Synthesis Path-Upstream 1~4

1
[ 71-30-7 ]
[ 2240-25-7 ]

Yield	Reaction Conditions	Operation in experiment
95.6%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 15℃; for 1 h; Sonication	The cytosine (55.6g, 0.5mol), N-bromosuccinimide (106.8g, 0 . 6mol) and DMF150mL in added in the reaction bottle, cooling to 15 °C ultrasonic reaction 1h, TLC raw material the reaction is complete, filtering, the filter cake is washed with water (20 ml × 2) washing, drying to obtain 5-bromocytosine (90.9g, 95.6percent).

Reference： [1] Patent: CN103819412, 2016, B, . Location in patent: Paragraph 0023-0025; 0031-0032; 0037; 0038
[2] Synthesis, 2005, # 7, p. 1103 - 1108
[3] Tetrahedron Letters, 1992, vol. 33, # 50, p. 7779 - 7782
[4] Chemistry Letters, 1987, p. 2311 - 2312
[5] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 11, p. 3750 - 3751
[6] Journal of Organic Chemistry, 1982, vol. 47, # 6, p. 1018 - 1023

2
[ 148214-56-6 ]
[ 2240-25-7 ]

Reference： [1] Journal of the American Chemical Society, 1934, vol. 56, p. 134,138

3
[ 71-30-7 ]
[ 51-20-7 ]
[ 2240-25-7 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 1994, vol. 34, # 7, p. 603 - 616

4
[ 71-30-7 ]
[ 2240-25-7 ]

Reference： [1] Journal of the American Chemical Society, 1934, vol. 56, p. 134,138

[ 2240-25-7 ] Synthesis Path-Downstream 1~44

1
[ 148214-56-6 ]
[ 2240-25-7 ]

Reference： [1]Journal of the American Chemical Society,1934,vol. 56,p. 134,138

2
2-ethylsulfanyl-5-bromo-pyrimidin-4-ylamine [ No CAS ]
[ 2240-25-7 ]

Reference： [1]American Chemical Journal,1904,vol. 31,p. 603
[2]American Chemical Journal,1906,vol. 36,p. 176

3
(2-ethylmercapto-5-bromo-pyrimidin-4-yl)-urea [ No CAS ]
[ 2240-25-7 ]

Reference： [1]American Chemical Journal,1905,vol. 33,p. 443

4
[ 71-30-7 ]
[ 2240-25-7 ]
4-amino-5,5-dibromo-6-hydroxy-5,6-dihydro-1<i>H</i>-pyrimidin-2-one; hydrobromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1934,vol. 56,p. 134,138

5
[ 2240-25-7 ]
[ 7081-78-9 ]
[ 83297-31-8 ]

Reference： [1]Tetrahedron,1982,vol. 38,p. 1517 - 1522

6
[ 2240-25-7 ]
[ 999-97-3 ]
[ 83966-86-3 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 152 - 156

7
[ 2240-25-7 ]
[ 89043-26-5 ]

Reference： [1]Journal of Physical Chemistry,1984,vol. 88,p. 1601 - 1605

8
[ 71-30-7 ]
[ 51-20-7 ]
[ 2240-25-7 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1994,vol. 34,p. 603 - 616

9
[ 71-30-7 ]
[ 2240-25-7 ]

Yield	Reaction Conditions	Operation in experiment
95.6%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 15℃; for 1h;Sonication;	The cytosine (55.6g, 0.5mol), N-bromosuccinimide (106.8g, 0 . 6mol) and DMF150mL in added in the reaction bottle, cooling to 15 C ultrasonic reaction 1h, TLC raw material the reaction is complete, filtering, the filter cake is washed with water (20 ml × 2) washing, drying to obtain 5-bromocytosine (90.9g, 95.6%).
93.6%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 25℃; for 10h;Large scale;	To a solution of cytosine (300 g, 2.70 mol, 1.00 equiv) in DMF (1.5 L) was added NBS (480 g, 2.70 mol, 1.00 equiv). The mixture was stirred at 25 C for 10 h at which time the crude 1H NMR spectrum indicated that the reaction was complete. The reaction mixture was filtered and the filter cake was washed with water (1 L x 4). The solid was collected and dried under reduced pressure to afford 5-bromocytosine (480 g, 2.53 mol, 93.6% yield) as a white solid. 1H NMR (400MHz, DMSO-d6) d 10.80 (br s, 1H), 11.36 - 10.16 (m, 1H), 7.74 (s, 1H), 6.83 (br s, 2H).
84.8%	With bromine; acetic acid; at 70℃; for 8h;	To a solution of 4-aminopyrimidin-2(1H)-one (2 g, 18 mmol) inacetic acid (10 mL) was added bromine (3.6 g, 22.5 mmol). The reactionmixture was stirred at 70 C for 8 h. The reaction mixture was dilutedwith H2O (30 mL) and the light yellow precipitate was filtered andwashed with water. The solid was then dried under reduced pressure togive the title compound (2.91 g, 84.8% yield). 1H NMR (300 MHz,DMSO-d6) delta 10.86 (s, 1H), 7.75 (s, 1H), 6.85 (s, 1H).

Reference： [1]Patent: CN103819412,2016,B .Location in patent: Paragraph 0023-0025; 0031-0032; 0037; 0038
[2]Patent: WO2019/152419,2019,A1 .Location in patent: Paragraph 0145; 0148-0150
[3]Synthesis,2005,p. 1103 - 1108
[4]Bioorganic Chemistry,2019,vol. 90
[5]Tetrahedron Letters,1992,vol. 33,p. 7779 - 7782
[6]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 180 - 185
[7]Chemistry Letters,1987,p. 2311 - 2312
[8]Chemistry - A European Journal,2019,vol. 25,p. 1773 - 1780
[9]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3750 - 3751
[10]Journal of Organic Chemistry,1982,vol. 47,p. 1018 - 1023

10
[ 2240-25-7 ]
[ 870-63-3 ]
4-amino-5-bromo-1-(3-methyl-2-buten-1-yl)pyrimidin-2(1H)-one [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1513 - 1515

11
[ 2240-25-7 ]
[ 7348-78-9 ]
4-amino-5-bromo-1-<(Z)-2-penten-1-yl>pyrimidin-2(1H)-one [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1513 - 1515

12
[ 2240-25-7 ]
[ 171866-29-8 ]
[ 178687-99-5 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2835 - 2843

13
[ 2240-25-7 ]
[ 197452-17-8 ]
[ 197452-35-0 ]
[ 197452-36-1 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3635 - 3644

14
[ 2240-25-7 ]
[ 98-59-9 ]
[ 199486-81-2 ]
5-bromo-1-p-toluenesulfonylcytosine [ No CAS ]

Reference： [1]Croatica Chemica Acta,1999,vol. 72,p. 957 - 966
[2]Nucleosides and Nucleotides,1997,vol. 16,p. 1067 - 1071

15
[ 2240-25-7 ]
[ 98-59-9 ]
5-bromo-1-p-toluenesulfonylcytosine [ No CAS ]

Reference： [1]Nucleosides and Nucleotides,1997,vol. 16,p. 1067 - 1071

16
[ 67-56-1 ]
[ 2240-25-7 ]
[ 71-30-7 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 3243 - 3246

17
[ 2240-25-7 ]
[ 999-97-3 ]
5-bromo-1-trimethylsilanyl-4-(trimethylsilanyl-amino)-1<i>H</i>-pyrimidin-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 859 - 867

Yield	Reaction Conditions	Operation in experiment
		The remainder of the transformations are carried out substantially as described to produce first the corresponding 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)pyrimidine derivative and thereafter the 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)pyrimidine derivative....5-fluorouracil,6-azathymine,5-bromocytosine,5-chlorocytosine,...

20
[ 2240-25-7 ]
[ 166411-46-7 ]
[ 255818-55-4 ]

Reference： [1]Nucleosides and Nucleotides,1999,vol. 18,p. 2233 - 2252

21
[ 2240-25-7 ]
[ 169736-20-3 ]
5-bromo-1-(4-thio-β-D-arabinofuranosyl)cytosine [ No CAS ]
5-bromo-1-(4-thio-α-D-arabinofuranosyl)cytosine [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2000,vol. 19,p. 2005 - 2017

22
[ 2240-25-7 ]
[ 169736-20-3 ]
5-bromo-1-(2,3,5-tri-O-benzyl-4-thio-α-D-arabinofuranosyl)cytosine [ No CAS ]
5-bromo-1-(2,3,5-tri-O-benzyl-4-thio-αbD-arabinofuranosyl)cytosine [ No CAS ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2000,vol. 19,p. 2005 - 2017

23
[ 2240-25-7 ]
[ 108-24-7 ]
[ 945548-37-8 ]

Yield	Reaction Conditions	Operation in experiment
98.5%	at 70℃; for 4h;	<strong>[2240-25-7]5-<strong>[2240-25-7]bromocytosine</strong></strong> (95g, 0.5 mol), acetic anhydride (306.3g, 3mol) added to the reaction flask, the reaction was warmed to 70 °C 4h, the solvent was distilled off under reduced pressure, was added 200mL of methanol was heated to reflux for 30min, cooled to room temperature, filtered, the filter cake was washed with 30mL of methanol, and drying to give N-acetyl-<strong>[2240-25-7]5-<strong>[2240-25-7]bromocytosine</strong></strong> (114.3g, 98.5percent).

Reference： [1]Patent: CN103819412,2016,B .Location in patent: Paragraph 0026; 0027; 0039; 0040
[2]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. S976 - S978

24
[ 2240-25-7 ]
[ 267421-93-2 ]
5-[(3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl]cytosine [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 9163 - 9168

25
[ 2240-25-7 ]
[ 107-13-1 ]
C₇H₇BrN₄O [ No CAS ]

Reference： [1]Synlett,2007,p. 721 - 724

26
[ 2240-25-7 ]
[ 930-69-8 ]
5-(phenylthio)cytosine [ No CAS ]