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5-Fluoroorotic acid

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Name

5-Fluoroorotic acid

EINECS 211-876-0
CAS No. 703-95-7 Density 1.81 g/cm3
PSA 103.02000 LogP -1.09950
Solubility NH4OH 4 M: 50 mg/mL, clear, faintly yellow Melting Point 278 °C (dec.)(lit.)
Formula C5H3FN2O4 Boiling Point 143°C (rough estimate)
Molecular Weight 174.088 Flash Point N/A
Transport Information N/A Appearance white to off-white crystalline solid
Safety 26-36 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 703-95-7 (5-Fluoroorotic acid) Hazard Symbols HarmfulXn
Synonyms

Oroticacid, 5-fluoro- (6CI,8CI);5-Fluoroorotate;ENT 26398;Fluoroorotic acid;NSC 143130;NSC 31712;WR 152520;5-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid;4-pyrimidinecarboxylic acid, 5-fluoro-1,2,3,6-tetrahydro-2,6-dioxo-;5-Fluoro orotic acid;5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid;

Article Data 10

5-Fluoroorotic acid Synthetic route

C7H7FN2O4

703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 50℃; for 3h;83%

C8H9FN2O4

703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 60℃; for 4h;79%
717-48-6

ethyl 2-(methylmercapto)-4-hydroxy-5-fluoro-6-pyrimidinecarboxylate

703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride for 4h; Heating;48.4%
721-33-5

2-ethylsulfanyl-5-fluoro-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
703-95-7

5-fluoroorotic acid

74-88-4

methyl iodide

1996-54-9

methyl 5-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

Conditions
ConditionsYield
Stage #1: 5-fluoroorotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-d6-formamide at 20℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 60℃; for 4h;
70%
703-95-7

5-fluoroorotic acid

75-03-6

ethyl iodide

132214-26-7

ethyl 5-fluoroorotic acid

Conditions
ConditionsYield
Stage #1: 5-fluoroorotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.5h;
Stage #2: ethyl iodide In N,N-dimethyl-formamide at 60℃; for 2h;
66%
Stage #1: 5-fluoroorotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.5h;
Stage #2: ethyl iodide In N,N-dimethyl-formamide at 60℃; for 2h;
Stage #1: 5-fluoroorotic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.5h;
Stage #2: ethyl iodide at 60℃; for 2h;
703-95-7

5-fluoroorotic acid

7797-34-4

benzylglycylglycinate hydrochloride

5-FOrt-Gly-Gly-O-Bzl

Conditions
ConditionsYield
With 4-methyl-morpholine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In N,N-dimethyl-formamide at 50 - 55℃;53%
703-95-7

5-fluoroorotic acid

68858-20-8

Fmoc-Val-OH

35661-60-0

Fmoc-Leu-OH

131570-56-4, 122235-70-5

Boc-Dap(Fmoc)-OH

N-Fmoc-3-aminobenzoic acid(2R,3S)-N-Fmoc-3-amino-2-hydroxy-4-phenylbutyric acid

N-Fmoc-3-aminobenzoic acid(2R,3S)-N-Fmoc-3-amino-2-hydroxy-4-phenylbutyric acid

KMI-446

Conditions
ConditionsYield
Multistep reaction;
703-95-7

5-fluoroorotic acid

5-fluoroorotyl-L-leucyl-L-leucine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-(ethoxycarbonyl)-2-ethoxy-1,2-dihydroquinoline, N-methylmorpholine / dimethylformamide / 36 h / 50 - 55 °C
2: 95 percent / 1N HCl in acetic acid / 2 h / Ambient temperature
View Scheme

{(S)-2-Amino-1-[(S)-1-((S)-1-{(1S,2R)-1-benzyl-2-hydroxy-2-[3-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenylcarbamoyl]-ethylcarbamoyl}-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

703-95-7

5-fluoroorotic acid

C42H53FN10O12

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;

5-Fluoroorotic acid Specification

The 5-Fluoroorotic acid, with the CAS registry number 703-95-7 and EINECS registry number 211-876-0, has the IUPAC name of 5-fluoro-2,4-dioxo-1H-pyrimidine-6-carboxylic acid. It is a kind of white to off-white crystalline solid, and the molecular formula of this chemical is C5H3FN2O4. What's more, it inhibits the dietary induction of serine dehydratase, and often used as a research reagents in genetic engineering. Besides, it should be stored at -20°C.

The physical properties of 5-Fluoroorotic acid are as following: (1)ACD/LogP: -1.00; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.29; (4)ACD/LogD (pH 7.4): -4.84; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 66.92 Å2; (13)Index of Refraction: 1.58; (14)Molar Refractivity: 31.9 cm3; (15)Molar Volume: 95.8 cm3; (16)Polarizability: 12.64×10-24cm3; (17)Surface Tension: 71.8 dyne/cm; (18)Density: 1.81 g/cm3.

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin, and it is also harmful if swallowed. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)\C1=C(/F)C(=O)NC(=O)N1
(2)InChI: InChI=1/C5H3FN2O4/c6-1-2(4(10)11)7-5(12)8-3(1)9/h(H,10,11)(H2,7,8,9,12)
(3)InChIKey: SEHFUALWMUWDKS-UHFFFAOYAV

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 981mg/kg (981mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat LD50 intraperitoneal 300mg/kg (300mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.

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