Product Name

  • Name

    Emtricitabine

  • EINECS 604-363-1
  • CAS No. 143491-57-0
  • Article Data28
  • CAS DataBase
  • Density 1.82 g/cm3
  • Solubility
  • Melting Point 136-140 °C
  • Formula C8H10FN3O3S
  • Boiling Point 443.3 °C at 760 mmHg
  • Molecular Weight 247.25
  • Flash Point 221.9 °C
  • Transport Information
  • Appearance white to off-white crystalline solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 143491-57-0 (Emtricitabine)
  • Hazard Symbols
  • Synonyms 2(1H)-Pyrimidinone,4-amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2R-cis)-;(-)-2',3'-Dideoxy-5-fluoro-3'-thiacytidine;(-)-2'-Deoxy-5-fluoro-3'-thiacytidine;(-)-FTC;524W91;BW 1592;BW 524W91;Coviracil;Emtriva;FTC, (-)-;
  • PSA 115.67000
  • LogP 0.12620

Synthetic route

2',3'-dideoxy-5-fluoro-3'-thiacytidine hydrochloride
258832-61-0

2',3'-dideoxy-5-fluoro-3'-thiacytidine hydrochloride

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With triethylamine In methanol at 15 - 60℃;93.2%
With triethylamine In methanol at 25 - 65℃; for 0.25h; Heating / reflux;82%
With tributyl-amine In dichloromethane at 25 - 35℃; for 5.5h;
Amberlite LA2 liquid ion-exchange resin;25 g
(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine salicylate

(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine salicylate

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With triethylamine In ethanol at 50℃; for 1h;91.88%
4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one; benzoic acid

4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one; benzoic acid

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With Isopropyl acetate; triethylamine at 15 - 30℃; for 4h; Reagent/catalyst;90%
In acetone for 2h; Reflux;87%
C8H10FN3O3S*BrH

C8H10FN3O3S*BrH

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In methanol at 15 - 60℃;88.9%
(+/-)-cis-2',3'-dideoxy-5-fluoro-3'-thiacytidine

(+/-)-cis-2',3'-dideoxy-5-fluoro-3'-thiacytidine

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
Stage #1: (+/-)-cis-2',3'-dideoxy-5-fluoro-3'-thiacytidine With 1,1'-bi-2-naphthol In methanol Reflux;
Stage #2: With hydrogenchloride In water; ethyl acetate for 0.5h; pH=2 - 3;		88.9%
C23H20FN3O6S

C23H20FN3O6S

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With methanol; potassium carbonate at 0 - 25℃; for 3h;87.34%
5S-(5'-fluorocytosinyl)-1,3-oxathiolane-2R-methyl-L-menthol carbonate

5S-(5'-fluorocytosinyl)-1,3-oxathiolane-2R-methyl-L-menthol carbonate

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With potassium carbonate In methanol at 0 - 25℃; for 3h;86%
With potassium carbonate In methanol at 0 - 25℃; for 3.5h;82%
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[5-fluoro-2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[5-fluoro-2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[5-fluoro-2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate With methanol at 40℃; Inert atmosphere;
Stage #2: With sodium tetrahydroborate; dipotassium hydrogenphosphate; water; sodium hydroxide In methanol at 20℃; for 1h; diastereoselective reaction;		75%
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With sodium tetrahydroborate; dipotassium hydrogenphosphate; water; sodium hydroxide In ethanol at 20℃; Temperature;70%
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate With sodium tetrahydroborate In methanol at -5℃; for 5h; Inert atmosphere;
Stage #2: With isopropyl alcohol In water at 60℃; for 1h;
Stage #3: With methanol In water Product distribution / selectivity;		65%
With methanol; sodium tetrahydroborate at -7 - -5℃; for 6h; Product distribution / selectivity; Inert atmosphere;65%
N-[5-Fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

N-[5-Fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With ammonia Ambient temperature; Yield given;
(-)-(2R,5S)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine
145913-69-5

(-)-(2R,5S)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature
2: methanolic NH3 / Ambient temperature
View Scheme
4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-[1,3]-oxathiolan-5-yl]-(1H)-pyrimidin-2-one monosuccinate
1313482-37-9

4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-[1,3]-oxathiolan-5-yl]-(1H)-pyrimidin-2-one monosuccinate

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol at 20℃; for 5h;
5-(4-acetylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester
1321928-75-9

5-(4-acetylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanesulfonic acid / methanol / 4 h
1.2: 0.17 h
2.1: sodium hydroxide; dipotassium hydrogenphosphate; sodium tetrahydroborate / water; industrially methylated spirit / 4 h / 18 - 22 °C
2.2: 22 - 42 °C
3.1: triethylamine / isopropyl alcohol; water / 6 h / 6 - 20 °C
View Scheme
4-amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolane-5-yl)-1H-pyrimidin-2-one 2-fluorobenzoic acid salt
1321928-76-0

4-amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolane-5-yl)-1H-pyrimidin-2-one 2-fluorobenzoic acid salt

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
With triethylamine In water; isopropyl alcohol at 6 - 20℃; for 6h;
C15H14FN3O4S

C15H14FN3O4S

emtricitabine
143491-57-0

emtricitabine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: (S)-2-phenylglycine / methanol / Reflux
1.2: 8 h / 20 °C
2.1: 1,1'-bi-2-naphthol / methanol / Reflux
2.2: 0.5 h / pH 2 - 3
View Scheme
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

emtricitabine
143491-57-0

emtricitabine

(Z)-N’-(5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-N,N-dimethylformimidamide

(Z)-N’-(5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-N,N-dimethylformimidamide

Conditions
ConditionsYield
In methanol at 20℃; for 21h;100%
emtricitabine
143491-57-0

emtricitabine

C18H26FN3O4S*ClH

C18H26FN3O4S*ClH

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol at 10 - 20℃; for 2h; Solvent; Temperature;93.6%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

emtricitabine
143491-57-0

emtricitabine

4-amino-1-((2R,5S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoropyrimidin-2(1H)-one
1365246-84-9

4-amino-1-((2R,5S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoropyrimidin-2(1H)-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h;90%
With 1H-imidazole In tetrahydrofuran at 20℃; for 2h; Concentration; Inert atmosphere; Cooling;
emtricitabine
143491-57-0

emtricitabine

isobutyl chloroformate
543-27-1

isobutyl chloroformate

isobutyl (5-fluoro-1-((2S,5R)-2-(((isobutoxycarbonyl)oxy)methyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

isobutyl (5-fluoro-1-((2S,5R)-2-(((isobutoxycarbonyl)oxy)methyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere;83%
emtricitabine
143491-57-0

emtricitabine

methyl chloroformate
79-22-1

methyl chloroformate

methyl (5-fluoro-1-((2R,5S)-2-(((methoxycarbonyl)oxy)methyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

methyl (5-fluoro-1-((2R,5S)-2-(((methoxycarbonyl)oxy)methyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;68%
dodecyl 1H-imidazole-1-carboxylate
148204-50-6

dodecyl 1H-imidazole-1-carboxylate

emtricitabine
143491-57-0

emtricitabine

dodecyl (1-((2S,5R)-2-((((dodecyloxy)carbonyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

dodecyl (1-((2S,5R)-2-((((dodecyloxy)carbonyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

Conditions
ConditionsYield
With pyridine; potassium hydroxide In dichloromethane at 20℃; for 18h; Inert atmosphere;67%
emtricitabine
143491-57-0

emtricitabine

carbonochloridic acid, butyl ester
592-34-7

carbonochloridic acid, butyl ester

butyl (5-fluoro-1-((2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

butyl (5-fluoro-1-((2S,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere;60%
C17H21F5NO8P

C17H21F5NO8P

emtricitabine
143491-57-0

emtricitabine

isopropyl (2S)‐2‐{[(R)‐[(2R,5S)‐5‐(4‐amino‐5‐fluoro‐2‐oxopyrimidin‐1‐yl)‐1,3‐oxathiolan‐2‐yl]methoxy([(isopropoxycarbonyl)oxy]methoxy)phosphoryl]amino}propanoate

isopropyl (2S)‐2‐{[(R)‐[(2R,5S)‐5‐(4‐amino‐5‐fluoro‐2‐oxopyrimidin‐1‐yl)‐1,3‐oxathiolan‐2‐yl]methoxy([(isopropoxycarbonyl)oxy]methoxy)phosphoryl]amino}propanoate

Conditions
ConditionsYield
Stage #1: emtricitabine With tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: C17H21F5NO8P In tetrahydrofuran at 0 - 20℃; for 20h;		53%
tetra(n-butyl)ammonium hydroxide
2052-49-5

tetra(n-butyl)ammonium hydroxide

emtricitabine
143491-57-0

emtricitabine

emtricitabine monophosphate 1.6*nBu4N+ salt

emtricitabine monophosphate 1.6*nBu4N+ salt

Conditions
ConditionsYield
Stage #1: emtricitabine With trichlorophosphate at 0℃; for 1h; Inert atmosphere;
Stage #2: With water for 1h; Cooling with ice;
Stage #3: tetra(n-butyl)ammonium hydroxide In water pH=7.0;		36%
3-Phenylpropan-1-amine
2038-57-5

3-Phenylpropan-1-amine

emtricitabine
143491-57-0

emtricitabine

C17H19FN4O3S

C17H19FN4O3S

Conditions
ConditionsYield
With copper(l) iodide; 9-azabicyclo<3.3.1>nonane-N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 4h; Sealed tube;35%
emtricitabine
143491-57-0

emtricitabine

Allyl chloroformate
2937-50-0

Allyl chloroformate

allyl (5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

allyl (5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 15h; Inert atmosphere;23%
emtricitabine
143491-57-0

emtricitabine

β-L-2',3'-dideoxy-3'-thia-5-fluoro-N4-hydroxycytidine

β-L-2',3'-dideoxy-3'-thia-5-fluoro-N4-hydroxycytidine

Conditions
ConditionsYield
With hydroxylamine hydrochloride In water for 24h; pH=6.0;16%
emtricitabine
143491-57-0

emtricitabine

salicylic acid
69-72-7

salicylic acid

(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine salicylate

(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine salicylate

Conditions
ConditionsYield
In water at 80℃;13%
emtricitabine
143491-57-0

emtricitabine

(-)-5'-O-(t-butyldimethylsilyl)-N4-(4,4'-dimethoxytrityl)-5-fluoro-2',3'-dideoxy-3'-thiacytidine
1365246-85-0

(-)-5'-O-(t-butyldimethylsilyl)-N4-(4,4'-dimethoxytrityl)-5-fluoro-2',3'-dideoxy-3'-thiacytidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C
2: pyridine / 0 - 20 °C
View Scheme

Emtricitabine Chemical Properties

Molecular Structure:
Molecular Formula: C8H10FN3O3S
Molecular Weight: 247.2467
IUPAC Name: 4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
Synonyms of Emtricitabine (CAS NO.143491-57-0): Truvada ; (-)-2'-Deoxy-5-fluoro-3'-thiacytidine ; (-)-FTC ; (2R-cis)-4-Amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone ; 2'-Deoxy-5-fluoro-3'-oxa-4'-thiocytidine ; 2'-Deoxy-5-fluoro-3'-thiacytidine ; 2-FTC ; 5-Fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine ; 524W91 ; BW 1592 ; BW 524W91 ; BW524W91 ; Coviracil ; DRG-0208 ; Emtriva ; FTC ; FTC, (-)- ; HSDB 7337 ; UNII-G70B4ETF4S ; dOTFC ; 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-cis)-
CAS NO: 143491-57-0
Classification Code: Anti-Infective Agents ; Antiretroviral ; Antiviral Agents ; Antiviral [treatment of HIV-1 and hepatitis B infections]
Melting point: 136-140°C 
Polar Surface Area: 79.67 Å2
Index of Refraction: 1.731
Molar Refractivity: 54.01 cm3
Molar Volume: 135.1 cm3
Surface Tension: 72.8 dyne/cm
Density: 1.82 g/cm3
Flash Point: 221.9 °C
Enthalpy of Vaporization: 80.89 kJ/mol
Boiling Point: 443.3 °C at 760 mmHg
Vapour Pressure: 1.01E-09 mmHg at 25°C

Emtricitabine History

Dr. Dennis C. Liotta, Dr. Raymond Schinazi and Dr. Woo-Baeg Choi of Emory University and licensed to Triangle Pharmaceuticals discovered Emtricitabine (CAS NO.143491-57-0) by Emory in 1996. Triangle Pharmaceuticals was acquired in 2003 by Gilead Sciences, who completed development and now market the product with the brand name Emtriva.

Emtricitabine Uses

 Emtricitabine (CAS NO.143491-57-0) is used as an anti-AIDS drug. It is also used as an antiviral drug.

Emtricitabine Safety Profile

Hazardous Substances Data Emtricitabine (CAS NO.143491-57-0): 143491-57-0(Hazardous Substances Data)

Emtricitabine Specification

 Emtricitabine (CAS NO.143491-57-0) works by inhibiting reverse transcriptase which can help to lower the amount of HIV and increase the number of immune system cells.

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