Product Name

  • Name

    5-Fluoroorotic acid

  • EINECS 211-876-0
  • CAS No. 703-95-7
  • Article Data10
  • CAS DataBase
  • Density 1.81 g/cm3
  • 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
  • Transport Information
  • 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;
  • PSA 103.02000
  • LogP -1.09950

Synthetic route

C7H7FN2O4

C7H7FN2O4

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 50℃; for 3h;83%
C8H9FN2O4

C8H9FN2O4

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 60℃; for 4h;79%
ethyl 2-(methylmercapto)-4-hydroxy-5-fluoro-6-pyrimidinecarboxylate
717-48-6

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

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride for 4h; Heating;48.4%
2-ethylsulfanyl-5-fluoro-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester
721-33-5

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

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

methyl iodide
74-88-4

methyl iodide

methyl 5-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate
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%
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

ethyl iodide
75-03-6

ethyl iodide

ethyl 5-fluoroorotic acid
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;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

benzylglycylglycinate hydrochloride
7797-34-4

benzylglycylglycinate hydrochloride

5-FOrt-Gly-Gly-O-Bzl

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%
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

Boc-Dap(Fmoc)-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

KMI-446

Conditions
ConditionsYield
Multistep reaction;
...Expand
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

5-fluoroorotyl-L-leucyl-L-leucine

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

{(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

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C42H53FN10O12

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

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

5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C42H53FN10O11S

C42H53FN10O11S

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
703-95-7

5-fluoroorotic acid

C36H52N10O7

C36H52N10O7

C41H53FN12O10

C41H53FN12O10

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
703-95-7

5-fluoroorotic acid

C37H52N8O8S

C37H52N8O8S

C42H53FN10O11S

C42H53FN10O11S

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
703-95-7

5-fluoroorotic acid

C37H52N8O8S

C37H52N8O8S

C42H53FN10O11S

C42H53FN10O11S

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
703-95-7

5-fluoroorotic acid

C38H55N9O7S

C38H55N9O7S

C43H56FN11O10S

C43H56FN11O10S

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
703-95-7

5-fluoroorotic acid

5-phospho-α-D-ribosyl 1-pyrophosphate

5-phospho-α-D-ribosyl 1-pyrophosphate

5-fluoroorotidine 5′-monophosphate
70629-37-7

5-fluoroorotidine 5′-monophosphate

Conditions
ConditionsYield
With orotate phosphoribosyl transferase Enzymatic reaction;
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C36H53N5O8
1258505-53-1

C36H53N5O8

C41H54FN7O11

C41H54FN7O11

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C36H53N5O8
1258505-53-1

C36H53N5O8

C35H50FN7O11

C35H50FN7O11

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C39H57N5O8

C39H57N5O8

C44H58FN7O11

C44H58FN7O11

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C33H53N5O8

C33H53N5O8

C38H54FN7O11

C38H54FN7O11

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C29H48N6O7

C29H48N6O7

C34H49FN8O10

C34H49FN8O10

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide
5-fluoroorotic acid
703-95-7

5-fluoroorotic acid

C32H52N6O7

C32H52N6O7

C37H53FN8O10

C37H53FN8O10

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide

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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