1-beta-D-Arabinofuranosylcytosine hydrochloride supplier

Name
1-beta-D-Arabinofuranosylcytosine hydrochloride
EINECS 200-713-9
CAS No. 69-74-9
Article Data5
CAS DataBase
Density
Solubility soluble in water
Melting Point 197-198 °C(lit.)
Formula C₉H₁₃N₃O₅^.HCl
Boiling Point 545.7 °C at 760 mmHg
Molecular Weight 279.68
Flash Point 283.8 °C
Transport Information
Appearance fluffy white powder
Safety 26-36/37
Risk Codes 36-43-63
Molecular Structure
Hazard Symbols Xn
Synonyms 2(1H)-Pyrimidinone,4-amino-1-b-D-arabinofuranosyl-,monohydrochloride (9CI);Cytosine, 1-b-D-arabinofuranosyl-, monohydrochloride (8CI);1-b-D-Arabinofuranosylcytosinehydrochloride;1-b-D-Arabinofuranosylcytosinemonohydrochloride;Arabinofuranosylcytosine hydrochloride;Arabinosylcytosinehydrochloride;Aracytidine hydrochloride;Cytosinearabinoside hydrochloride;Spongocytidine-hydrochloride;U 19920A;Cytarabine HCl;
PSA 130.83000
LogP -1.17980

Synthetic route

: 147-94-4
arabinosyl cytosine

: 69-74-9
cytarabine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 2 - 25℃; for 4h;	96%
With hydrogenchloride In diethyl ether

: 10212-25-6
ancitabine hydrochloride

: 69-74-9
cytarabine hydrochloride

Conditions

Conditions	Yield
With ammonia In water at 80℃; for 0.5h; Temperature;	62.4%

: 69-74-9
cytarabine hydrochloride

: 219797-98-5
3-Acryloylamino-propionic acid pentafluorophenyl ester

: 186594-89-8
N-{2-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-ethyl}-acrylamide

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In pyridine at 80℃;	95%

: 69-74-9
cytarabine hydrochloride

: 17676-65-2
4-amino-5-chloro-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2(1H)-one

Conditions

Conditions	Yield
With hydrogenchloride; 3-chloro-benzenecarboperoxoic acid In N,N-dimethyl acetamide for 1h; Ambient temperature;	83.9%

: 69-74-9
cytarabine hydrochloride

: 219797-99-6
4-Acryloylamino-butyric acid pentafluorophenyl ester

: 186594-93-4
N-(3-(N4-carbamoyl-1-(β-D-arabinofuranosyl)cytosine)-propyl)acrylamide

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In pyridine at 80℃;	78%

: 112-77-6, 7378-94-1, 7459-35-0
elaidoyl chloride

: 69-74-9
cytarabine hydrochloride

: elacytarabine

Conditions

Conditions	Yield
In ISOPROPYLAMIDE at 30℃; for 22h;	72%

: 69-74-9
cytarabine hydrochloride

: gondoic acid chloride

: CP-4057

Conditions

Conditions	Yield
In ISOPROPYLAMIDE; N,N-dimethyl-formamide at 25℃; for 24h;	66%

: 1257411-82-7
N-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-8-yl)-6-oxo-6-(2-thioxothiazolidin-3-yl)hexanamide

: 69-74-9
cytarabine hydrochloride

: 1257411-83-8
N1-(2-(4-chlorophenyl)-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-8-yl)-N6-(1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)adipamide

Conditions

Conditions	Yield
With pyridine at 50℃;	66%

: 69-74-9
cytarabine hydrochloride

: 82626-74-2
2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid

: 1257411-86-1
2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N-(1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Conditions

Conditions	Yield
Stage #1: 2-(6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: cytarabine hydrochloride In N,N-dimethyl-formamide Inert atmosphere;	65%

: 2-(pyridin-2-yldisulfaneyl)ethyl 1H-1,2,4-triazole-1-carboxylate

: 69-74-9
cytarabine hydrochloride

: 2-(pyridin-2-yldisulfaneyl)ethyl (1-((3S,4S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	63%

: mono (2,2,2-trichloroethyl) azelaoyl chloride

: 69-74-9
cytarabine hydrochloride

: 879015-37-9
5'-O-[(2,2,2-trichloroethyl)-azelaoyl]-1-β-D-arabinofuranosyl-cytosine

Conditions

Conditions	Yield
In DMA at 20℃;	56.7%

: 69-74-9
cytarabine hydrochloride

: 142-61-0
Hexanoyl chloride

: C15H23N3O6

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	55%

: 69-74-9
cytarabine hydrochloride

: 111-64-8
n-octanoic acid chloride

: 31088-08-1
4-amino-1-(O5-octanoyl-β-D-arabinofuranosyl)-1H-pyrimidin-2-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	55%

: 69-74-9
cytarabine hydrochloride

: 685111-92-6
(4S)-5'-O-cis-[4-(pyridin-4yl)-2-oxido-1,3,2-dioxaphosphorinan-2yl]-cytosine-β-D-arabinofuranoside

Conditions

Conditions	Yield
Stage #1: (-)-(S)-1-(pyridin-4-yl)-1,3-propanediol With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; trichlorophosphate In pyridine; acetonitrile at -17 - 42℃; for 3.6h; Stage #2: cytarabine hydrochloride In pyridine; acetonitrile at 4 - 6℃; for 88h;	48%

: 24424-99-5
di-tert-butyl dicarbonate

: 69-74-9
cytarabine hydrochloride

A: tert-butyl 1-((2R,3S,4R,5R)-3,4-bis(tert-butoxycarbonyloxy)-5-((tert-butoxycarbonyloxy)-methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-ylcarbamate

B: 1257411-75-8
C24H37N3O11

Conditions

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water at 20℃; for 17h;	A 15% B 48%

...Expand

: 69-74-9
cytarabine hydrochloride

: 141-75-3
butyryl chloride

: 917898-23-8
C13H19N3O6

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	42%

: 79-03-8
propionyl chloride

: 69-74-9
cytarabine hydrochloride

: 881848-60-8
5'-O-propionyl ara-C

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	39%

: 69-74-9
cytarabine hydrochloride

: 112-13-0
n-decanoyl chloride

: 58611-44-2
4-amino-1-(O5-decanoyl-β-D-arabinofuranosyl)-1H-pyrimidin-2-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	31%

: 69-74-9
cytarabine hydrochloride

: 75-36-5
acetyl chloride

: 31088-09-2
4-amino-1-(O5-acetyl-β-D-arabinofuranosyl)-1H-pyrimidin-2-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	27%

: (4S)-(-)-trans-(4-pyridyl)-2-chloro-2-oxo-1,3,2-dioxaphosphorinane

: 69-74-9
cytarabine hydrochloride

: 685111-92-6
(4S)-5'-O-cis-[4-(pyridin-4yl)-2-oxido-1,3,2-dioxaphosphorinan-2yl]-cytosine-β-D-arabinofuranoside

Conditions

Conditions	Yield
Stage #1: (4S)-(-)-trans-(4-pyridyl)-2-chloro-2-oxo-1,3,2-dioxaphosphorinane; cytarabine hydrochloride With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In acetonitrile at 20 - 35℃; for 48h; Stage #2: With methanol In acetonitrile at 20℃; for 2h;	26%

: 69-74-9
cytarabine hydrochloride

: 362512-44-5
[2-(4-chlorophenyl)-6,8-dichloroimidazo[1,2-a]pyridin-3-yl]acetic acid

: 1257411-84-9
2-(6,8-dichloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N-(1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Conditions

Conditions	Yield
Stage #1: [2-(4-chlorophenyl)-6,8-dichloroimidazo[1,2-a]pyridin-3-yl]acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: cytarabine hydrochloride In N,N-dimethyl-formamide Inert atmosphere;	25%

: 69-74-9
cytarabine hydrochloride

: 573704-25-3
(6,8-Dichloro-2-phenyl-imidazo[1,2-a]pyridin-3-yl)-acetic acid

: 1257411-85-0
2-(6,8-dichloro-2-(phenyl)imidazo[1,2-a]pyridin-3-yl)-N-(1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

Conditions

Conditions	Yield
Stage #1: (6,8-Dichloro-2-phenyl-imidazo[1,2-a]pyridin-3-yl)-acetic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: cytarabine hydrochloride In N,N-dimethyl-formamide Inert atmosphere;	23%

: 56555-02-3
methyl 9-chloro-9-oxononanoate

: 69-74-9
cytarabine hydrochloride

: 848046-38-8
1-(5-O-azelayl-β-D-arabinofuranosyl)cytosine methyl ester

Conditions

Conditions	Yield
Stage #1: methyl 9-chloro-9-oxononanoate; cytarabine hydrochloride In 2,4-dichlorophenoxyacetic acid dimethylamine at 20℃; Stage #2: With triethylamine	21.6%

: 69-74-9
cytarabine hydrochloride

: 501-53-1
benzyl chloroformate

: 170935-63-4
benzyl 1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-ylcarbamate

Conditions

Conditions	Yield
With potassium hydrogencarbonate In water; ethyl acetate at 80℃; for 16h;	15%

: 108-24-7
acetic anhydride

: 69-74-9
cytarabine hydrochloride

: 6742-08-1
N4-acetyl-1-<2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl>cytosine

Conditions

Conditions	Yield
With pyridine at 45℃; for 18h;	129 g

: 75-77-4
chloro-trimethyl-silane

: 69-74-9
cytarabine hydrochloride

: 51432-43-0
4-Amino-1-((2R,3S,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one

Conditions

Conditions	Yield
With pyridine at 20℃; for 1h;

: 69-74-9
cytarabine hydrochloride

: 16640-05-4
1-(β-D-arabinofuranosyl)-N4-benzoylcytosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 1 h / 20 °C 2: pyridine / 4 h / 20 °C 3: aq. NH4OH / 0.25 h / 20 °C View Scheme

: 69-74-9
cytarabine hydrochloride

: N-[1-((2R,3S,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 1 h / 20 °C 2: pyridine / 4 h / 20 °C View Scheme

: 69-74-9
cytarabine hydrochloride

: 6742-07-0
1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 129 g / pyridine / 18 h / 45 °C 2: ZnBr2 / CHCl3; methanol / Ambient temperature View Scheme

1-beta-D-Arabinofuranosylcytosine hydrochloride Specification

The IUPAC name of 1-beta-D-Arabinofuranosylcytosine hydrochloride is 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one hydrochloride. With the CAS registry number 69-74-9, it is also named as Cytarabine hydrochloride. The product's categories are Pyridines, Pyrimidines, Purines and Pteredines. Besides, it is fluffy white powder, which should be stored at 2-8 °C. It undergoes decomposition in acidic solutions. In addition, its molecular formula is C₉H₁₃N₃O₅^.HCl and molecular weight is 279.68.

The other characteristics of this product can be summarized as: (1)EINECS: 200-713-9; (2)ACD/LogP: -1.94; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): -1.94; (5)ACD/LogD (pH 7.4): -1.94; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 2.1; (9)ACD/KOC (pH 7.4): 2.11; (10)#H bond acceptors: 8; (11)#H bond donors: 5; (12)#Freely Rotating Bonds: 5; (13)Polar Surface Area: 72.83 Å²; (14)Melting Point: 180-182 °C; (15)Flash Point: 283.8 °C; (16)Enthalpy of Vaporization: 94.8 kJ/mol; (17)Boiling Point: 545.7 °C at 760 mmHg; (18)Vapour Pressure: 3.5E-14 mmHg at 25 °C.

Preparation and Uses of 1-beta-D-Arabinofuranosylcytosine hydrochloride: this chemical can be prepared by 5'-CMP or Calcium Gluconate. Additionally, it is ntineoplastic agent that inhibits the synthesis of DNA. It is mainly used for the treatment of acute leukemia and gastrointestinal cancer. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties.

When you are using this chemical, please be cautious about it as the following: it irritates to eyes, and may cause sensitization by skin contact. It is also possible risk of harm to the unborn child. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing and gloves.

People can use the following data to convert to the molecule structure.
(1)SMILES: Cl.O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@@H]2O)CO
(2)InChI: InChI=1/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/m1./s1
(3)InChIKey: KCURWTAZOZXKSJ-JBMRGDGGBO

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	172mg/kg (172mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 353, 1974.
monkey	LD50	intravenous	396mg/kg (396mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS GASTROINTESTINAL: NAUSEA OR VOMITING	Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 353, 1974.
mouse	LD50	intraperitoneal	825mg/kg (825mg/kg)	BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1255, 1972.
mouse	LD50	oral	826mg/kg (826mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse	LD50	subcutaneous	2262mg/kg (2262mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat	LD50	intraperitoneal	5500mg/kg (5500mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1255, 1972.
rat	LD50	oral	> 3200mg/kg (3200mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1255, 1972.

Product Name

1-beta-D-Arabinofuranosylcytosine hydrochloride

Synthetic route

1-beta-D-Arabinofuranosylcytosine hydrochloride Specification

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