imidazol-1-ylacetic acid
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: imidazol-1-ylacetic acid With phosphoric acid; phosphorus trichloride In 1,2-propylene cyclic carbonate; PEG 600 (polyethylene glycol) at 40 - 60℃; Stage #2: With water In 1,2-propylene cyclic carbonate; PEG 600 (polyethylene glycol) at 85℃; for 18h; Product distribution / selectivity; | 99% |
Stage #1: imidazol-1-ylacetic acid With phosphorous acid; phosphorus trichloride In 1,2-propylene cyclic carbonate; PEG 600 at 40 - 60℃; Stage #2: With water In 1,2-propylene cyclic carbonate; PEG 600 at 85℃; for 18h; Product distribution / selectivity; | 99% |
With sulfolane; phosphonic Acid; 1-butyl-3-methylimidazolium Tetrafluoroborate; phosphorus trichloride at 75℃; for 3h; Reagent/catalyst; Green chemistry; | 93% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: C8H8N4O2*ClH With phosphoric acid; phosphorus trichloride In toluene at 90℃; Stage #2: With hydrogenchloride In water; toluene at 20℃; Reagent/catalyst; Temperature; Solvent; Reflux; | 85.27% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 2-(1-imidazolyl)acetic acid hydrochloride With phosphorous acid; trichlorophosphate In silicon oil at 80℃; for 11 - 24h; Stage #2: With water In toluene; silicon oil at 80 - 100℃; for 16 - 19h; Product distribution / selectivity; | 74% |
Stage #1: 2-(1-imidazolyl)acetic acid hydrochloride With phosphorous acid; trichlorophosphate In toluene at 100℃; for 3h; Stage #2: With water In toluene at 80 - 100℃; for 16h; Product distribution / selectivity; | 69% |
Stage #1: 2-(1-imidazolyl)acetic acid hydrochloride With phosphonic Acid; trichlorophosphate In chlorobenzene at 85 - 95℃; for 4.5h; Stage #2: With water for 18h; Reflux; | 64% |
1H-imidazole
chloroacetic acid ethyl ester
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 1H-imidazole; chloroacetic acid ethyl ester With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In 1,4-dioxane at 20℃; for 0.5h; Reflux; Stage #2: With phosphoric acid; phosphorus trichloride In 1,4-dioxane at 20℃; for 1h; Stage #3: With hydrogenchloride In water for 6h; Reagent/catalyst; | 60.5% |
imidazol-1-yl-acetyl chloride
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: imidazol-1-yl-acetyl chloride With methanesulfonic acid; phosphorus trichloride at 26 - 80℃; for 16h; Stage #2: With water at 26 - 110℃; for 5h; Stage #3: With sodium hydroxide In water for 12h; pH=1.8; |
tetrakis(O-trimethylsilyl)hydroxyethylidenediphosphonic acid
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With water In ethanol for 0.5h; |
1-hydroxy-2-(1-imidazolyl)ethylidenebisphosphonic acid monosodium
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water at 89.84℃; for 0.25h; pH=1.5; |
imidazol-1-ylacetic acid
phosphorus trichloride
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: imidazol-1-ylacetic acid; phosphorus trichloride With methanesulfonic acid at 80℃; Green chemistry; Stage #2: In water Green chemistry; Stage #3: With sodium hydroxide In water Green chemistry; |
ethyl 2-(1H-imidazol-1-yl)acetate
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water / 7 h / 100 °C / pH 1.5 2.1: phosphoric acid / water / 0.5 h / 100 °C 2.2: 3 h / 65 - 100 °C 2.3: 5 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: water 2: water; phosphoric acid; phosphorus trichloride / chlorobenzene View Scheme |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / Reflux 2.1: phosphoric acid; phosphorus trichloride / toluene / 90 °C 2.2: 20 °C / Reflux View Scheme |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / Reflux 2.1: phosphoric acid; phosphorus trichloride / toluene / 90 °C 2.2: 20 °C / Reflux View Scheme |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / Reflux 2.1: phosphoric acid; phosphorus trichloride / toluene / 90 °C 2.2: 20 °C / Reflux View Scheme |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / Reflux 2.1: phosphoric acid; phosphorus trichloride / toluene / 90 °C 2.2: 20 °C / Reflux View Scheme |
choline chloride
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: choline chloride With anion-exchange column A-26 (OH) In methanol Stage #2: 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid In methanol; water for 1h; | 100% |
choline chloride
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: choline chloride With anion-exchange column A-26 (OH) In methanol Stage #2: 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid In methanol; water for 1h; | 100% |
3-ethyl-1-methyl-1H-imidazol-3-ium bromide
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 3-ethyl-1-methyl-1H-imidazol-3-ium bromide With anion-exchange column A-26 (OH) In methanol Stage #2: 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid In methanol; water for 1h; | 100% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 3-(2-hydroxyethyl)-1-methyl-1H-imidazol-3-ium chloride With anion-exchange column A-26 (OH) In methanol Stage #2: 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid In methanol; water for 1h; | 100% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 3-(2-hydroxyethyl)-1-methyl-1H-imidazol-3-ium chloride With anion-exchange column A-26 (OH) In methanol Stage #2: 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid In methanol; water for 1h; | 100% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 1-methyl-3-(2-methoxyethyl)-1H-imidazol-3-ium chloride With anion-exchange column A-26 (OH) In methanol Stage #2: 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid In methanol; water for 1h; | 100% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 1-methyl-3-(2-methoxyethyl)-1H-imidazol-3-ium chloride With anion-exchange column A-26 (OH) In methanol Stage #2: 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid In methanol; water for 1h; | 100% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
N,N,N',N'-tetramethylguanidine
Conditions | Yield |
---|---|
In methanol; water for 1h; | 100% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
N,N,N',N'-tetramethylguanidine
Conditions | Yield |
---|---|
In methanol; water for 1h; | 100% |
DBN
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
In methanol; water for 1h; | 100% |
DBN
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
In methanol; water for 1h; | 100% |
1-ethyl-3-methyl-1H-imidazol-3-ium chloride
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 1-ethyl-3-methyl-1H-imidazol-3-ium chloride With anion-exchange column A-26 (OH) In methanol Stage #2: 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid In methanol; water for 1h; | 100% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
1-hydroxy-2-(1-imidazolyl)ethylidenebisphosphonic acid monosodium
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 16h; Product distribution / selectivity; Heating / reflux; | 99% |
With sodium hydroxide In ethanol; water for 16h; Product distribution / selectivity; Heating / reflux; | 98% |
With sodium hydroxide In ethanol for 16h; Product distribution / selectivity; Heating / reflux; | 96% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water for 19h; Heating / reflux; | 99% |
With sodium hydroxide In ethanol; water for 18.5h; Product distribution / selectivity; Heating / reflux; | 98% |
With sodium hydroxide In methanol; water for 17h; Product distribution / selectivity; Heating / reflux; | 97% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
zoledronic acid monohydrate
Conditions | Yield |
---|---|
With water at 70 - 80℃; Heating / reflux; | 89% |
With water In ethanol at 60℃; for 2h; |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 20h; Product distribution / selectivity; Heating / reflux; | 84% |
With sodium hydroxide In water; isopropyl alcohol for 16h; Product distribution / selectivity; Heating / reflux; | 79% |
With sodium hydroxide In methanol; water for 16h; Product distribution / selectivity; Heating / reflux; | 64% |
With sodium hydroxide In ethanol; water for 16h; Product distribution / selectivity; Heating / reflux; | 58% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid With barium hydroxide octahydrate In water at 0℃; for 0.166667h; Stage #2: [Pt(ethylenediamine)(H2O)(OSO3)] In water at 0 - 4℃; pH=5; | 84% |
4,4'-bipyridine
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: nickel(II) sulfate hexahydrate; 1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid In ethanol; water for 0.166667h; Stage #2: 4,4'-bipyridine In ethanol; water at 180℃; for 72h; pH=6.08; Autoclave; | 83% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With triethylamine In water ligand added to aq. soln. of NaVO3*H2O, stirred for 1 h, triethylamine added dropwise to pH 5, stirred for 1 h at 80°C; evapd. at room temp. for 5 d; elem. anal.; | 79% |
[Re(2,2′-bipyridine)(CO)3(H2O)](CF3SO3)
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water pH=7; Reflux; | 77% |
water
copper(II) sulfate
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
In water High Pressure; hydrothermal treatment of a mixt. of a ligand (0.10 mmol), CuSO4 (0.15 mmol) in H2O (pH=2.14) at 140°C for 24 h; elem. anal.; powder XRD; | 70.6% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water; N,N-dimethyl-formamide at 100℃; for 0.333333h; Sealed tube; Microwave irradiation; | 70% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With CH3CO2NH4/CH3CO2H In water High Pressure; ligand and (NH4)6Mo7O24*4H2O dissolved in CH3CO2NH4/CH3CO2H, placed in autoclave, heated to 130°C for 4 h, kept for 20 h, cooled to room temp. over 36 h; filtered; elem. anal.; | 68% |
ammonia
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With ammonium acetate In aq. acetate buffer at 20 - 130℃; for 60h; pH=6; Autoclave; | 67% |
[2,2]bipyridinyl
water
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 140℃; for 72h; pH=2.52; Autoclave; High pressure; | 67% |
1-hydroxy-2-(imidazol-1-yl)ethylidene-1,1-bisphosphonic acid
Conditions | Yield |
---|---|
With ammonium hydroxide In aq. acetate buffer at 130℃; for 24h; pH=6; Autoclave; | 67% |
IUPAC Name: (1-Hydroxy-2-imidazol-1-yl-1-phosphonoethyl)phosphonic acid
Molecular Formula: C5H10N2O7P2
Molecular Weight: 272.09 g/mol
Canonical SMILES: c1cncn1CC(O)(P(O)(=O)O)P(O)(=O)O
InChI: InChI=1/C5H10N2O7P2/c8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7/h1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14)
Classification Code: Bone Density Conservation Agents
Product Categories: Pharmaceutical material and intermeidates; Bone resorption inhibitor; Antiosteoporotic; Zoledronate;All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Zoledronic
Density: 2.13 g/cm3
Flash Point: 415.8 °C
Enthalpy of Vaporization: 116.73 kJ/mol
Boiling Point: 764 °C at 760 mmHg
Melting Point: 193-2040 °C
Vapour Pressure of Zoledronic acid (CAS NO.118072-93-8): 1.53E-24 mmHg at 25 °C
Zoledronic Acid is a single 5 mg infusion for the treatment of Paget's disease of bone. In 2007, the U.S. Food and Drug Administration (FDA) also approved Zoledronic Acid for the treatment of postmenopausal osteoporosis.
Zoledronic acid (CAS NO.118072-93-8) is used to prevent skeletal fractures in patients with cancers such as multiple myeloma and prostate cancer, as well as for treating osteoporosis. It can also be used to treat hypercalcemia of malignancy and can be helpful for treating pain from bone metastases.
Hazard Codes: Xi
Risk Statements: 21/22-36/37/38
R21/22: Harmful in contact with skin and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements of Zoledronic acid (CAS NO.118072-93-8): 24/25-36/37/39
S24/25: Avoid contact with skin and eyes.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
Zoledronic acid (CAS NO.118072-93-8), its Synonyms are (1-Hydroxy-2-imidazol-1-ylethylidene)diphosphonic acid ; Phosphonic acid, (1-hydroxy-2-(1H-imidazol-1-yl)ethylidene)bis- ; Zoledronate ; Zometa ; Reclast ; Aclasta . It is white solid.
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