Alendronic acid supplier | CasNO.66376-36-1

Name
Alendronic Acid
EINECS 204-352-8
CAS No. 66376-36-1
Article Data46
CAS DataBase
Density 1.857 g/cm³
Solubility soluble in water, easily soluble in ethanol, and almost insoluble in chloroform
Melting Point 230-235 °C
Formula C₄H₁₃NO₇P₂
Boiling Point 616.7 °C at 760 mmHg
Molecular Weight 249.097
Flash Point 326.7 °C
Transport Information
Appearance white fine powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Phosphonicacid, (4-amino-1-hydroxybutylidene)bis- (9CI);4-Amino-1-hydroxybutane-1,1-diphosphonate;4-Amino-1-hydroxybutane-1,1-diphosphonicacid;4-Amino-1-hydroxybutane-1,1-diyldiphosphonic acid;4-Amino-1-hydroxybutylidene-1,1-bis(phosphonic acid);ABDP;BPH 1;Alendronate;
PSA 180.93000
LogP -0.57290

Synthetic route

: 56-12-2
4-amino-n-butyric acid

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
Stage #1: 4-amino-n-butyric acid With phosphonic Acid; phosphorus trichloride In methoxybenzene at 60 - 105℃; for 5.66667 - 5.75h; Stage #2: With water In methoxybenzene at 110 - 115℃; for 5 - 6h; Reflux;	90%
Stage #1: 4-amino-n-butyric acid With phosphorus trichloride In methanesulfonic acid at 80 - 85℃; Stage #2: With water In methanesulfonic acid at 105℃; for 4h;	88%
Stage #1: 4-amino-n-butyric acid With phosphonic Acid; phosphorus trichloride In methanesulfonic acid at 65 - 70℃; for 18h; Stage #2: With water In methanesulfonic acid for 5h; Reflux;	85%

: 948317-79-1
[4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-1-hydroxy-1-phosphonobutyl]phosphonic acid

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
With hydrazine hydrate In water at 20℃; for 0.5h;	82%
With hydrogenchloride In water for 5.5h; Reflux;

: 616-45-5
2-pyrrolidinon

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
Stage #1: 2-pyrrolidinon With methanesulfonic acid at 100 - 105℃; for 6h; Stage #2: With phosphorus trichloride at 75℃; for 8h; Stage #3: In water for 5h; Heating;	72%

: 952615-43-9
1-hydroxy-4-pent-4-ynamidobutane-1,1-diyldiphosphonic acid

: copper sulfide pentahydrate

: 146-75-8, 6381-77-7, 6866-66-6, 7317-67-1, 7378-23-6, 21547-69-3, 58657-35-5, 134-03-2
sodium L-ascorbate

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
	70%

...Expand

: 69038-04-6
N-hydroxysuccinimide ester of 4-(tert-butoxycarbonylamino)butyric acid

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
With tris(trimethylsilyl) phosphite In tetrahydrofuran at 50℃; for 72h;	61%

: 125040-13-3
tetramethyl (4-phthalimido-1-hydroxybutylidene)bisphosphonate

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
With hydrogenchloride for 10h; Heating;

: 10314-06-4
4-phthalimidobutyryl chloride

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
With hydrogenchloride; methyl phosphite; phosphorous acid trimethyl ester 1.) 80 deg C, 8 h, 2.) reflux, 20 h; Yield given. Multistep reaction;

: 121268-17-5
sodium alendronate

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
With hydrogenchloride; ethanol; water at 20 - 50℃; for 2h;

: 56-12-2
4-amino-n-butyric acid

A 4-amino-1-hydroxybutylidene-1,1-biphosphonic Acid Monosodium Salt Trihydrate: 4-amino-1-hydroxybutylidene-1,1-biphosphonic Acid Monosodium Salt Trihydrate

B: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: C17H39NO8P2Si

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
With hydrogen bromide In water for 17h; Reflux;

: C19H31NO9P2Si

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

Conditions

Conditions	Yield
With hydrogenchloride In water for 17h; Reflux;

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 2052-49-5
tetra(n-butyl)ammonium hydroxide

: tetrabutylammonium alendronate

Conditions

Conditions	Yield
In water at 40℃; for 0.5h;	100%
In water at 20℃; for 2h;	100%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

1-(2-hydroxyethyl)-3-methylimidazolium halide: 1-(2-hydroxyethyl)-3-methylimidazolium halide

: [C2OHMIM]2[ALN]

Conditions

Conditions	Yield
With anion-exchange column Amberlyst A26-OH In methanol; water at 20℃; for 1h;	100%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

1-(2-hydroxyethyl)-3-methylimidazolium halide: 1-(2-hydroxyethyl)-3-methylimidazolium halide

: [C2OHMIM][ALN]

Conditions

Conditions	Yield
With anion-exchange column Amberlyst A26-OH In methanol; water at 20℃; for 1h;	100%

: 108-78-1
2,4,6-triamino-s-triazine

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 1,3,5-triazine-2,4,6-triamine

Conditions

Conditions	Yield
With water pH=Ca. 6 - 8; Heating;	99%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: C29H23N5O6

: (1-hydroxy-4-(((2-((4-(2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-yl)oxy)ethoxy)carbonyl)amino)butane-1,1-diyl)bis(phosphonic acid)

Conditions

Conditions	Yield
Stage #1: 4-amino-1-hydroxybutylidenebisphosphonic acid; C29H23N5O6 With triethylamine In 1,4-dioxane; water at 25℃; Inert atmosphere; Stage #2: With sodium acetate; acetic acid In methanol at 80℃; for 1h;	93.1%

: 64987-85-5
4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: {4‐[({4‐[(2,5‐dioxo‐2,5‐dihydro‐1H‐pyrrol‐1‐yl)methyl]cyclohexyl}carbonyl)amino]‐1‐hydroxybutane‐1,1‐diyl}bis(phosphonic acid)

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃; pH=8 - 9;	93%

: 132178-37-1
2,5-dioxopyrrolidin-1-yl pent-4-ynoate

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 952615-43-9
1-hydroxy-4-pent-4-ynamidobutane-1,1-diyldiphosphonic acid

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; for 12h; pH=7.0;	90%
With sodium hydroxide In water; acetonitrile at 0℃; for 18h; pH=7.2 - 7.4; Inert atmosphere;	277 mg

: pentynoic acid 2,5-dioxo-pyrrolidin-1-yl ester

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 952615-43-9
1-hydroxy-4-pent-4-ynamidobutane-1,1-diyldiphosphonic acid

Conditions

Conditions	Yield
	90%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 4-amino-1-hydroxybutylidene-1,1-biphosphonato hexaccordinated octahedral sodium monoaquo complex dihydrate

Conditions

Conditions	Yield
In water for 4 - 5h; pH=4.2 - 4.8; Na+ Exchange resin AMBERLITE SR1L; Product distribution / selectivity;	89.2%
In water for 4 - 5h; pH=4.2 - 4.8; Na+ Exchange resin AMBERJET 1200; Product distribution / selectivity;	89.9%

: 1353016-71-3
4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanoic acid

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: C23H26N2O9P2

Conditions

Conditions	Yield
In water; dimethyl sulfoxide pH=8.1;	89%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: lithium alendronate dihydrate

Conditions

Conditions	Yield
With lithium carbonate In water	87%

K(2-x)(NMe4)(x)[I2Mo10O10S10(OH)10(H2O)5*20H2O: K(2-x)(NMe4)(x)[I2Mo10O10S10(OH)10(H2O)5*20H2O

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: rubidium chloride

: 7732-18-5
water

: Rb4.75K3.25[(Mo2O2S2(H2O))4(Alendronic acid-4H)4]*25H2O

Conditions

Conditions	Yield
With NaOH In water to an aq. soln. of I2Mo10-contg. compd. (0.417 mmol) was added a ligand (2.09 mmol); pH=5 (NaOH); stirring at 80°C for 30 min; cooling toroom temp.; powder was eliminated by centrifugation; addn. of RbCl (8.1 0 mmol); stirring for 1 h; the powder was filtered off, the soln. was left to evap. at room temp.; crystals were collected by filtration; elem. anal.;	86%

...Expand

: 5190-68-1
4-chloroquinazoline

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: [1-hydroxy-4-(quinazolin-4-ylamino)butane-1,1-diyl]bis(phosphonic acid)

Conditions

Conditions	Yield
Stage #1: 4-chloroquinazoline; 4-amino-1-hydroxybutylidenebisphosphonic acid With potassium carbonate In water at 95℃; for 20h; Reflux; Stage #2: With hydrogenchloride In water at 5℃; for 24h; pH=1;	83%

: 498-62-4
3-thiophene carboxaldehyde

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: C9H15NO7P2S(2-)*2Na(1+)

Conditions

Conditions	Yield
Stage #1: 3-thiophene carboxaldehyde; 4-amino-1-hydroxybutylidenebisphosphonic acid With triethylamine In methanol at 65℃; for 1.5h; Stage #2: With tetramethylammonium borohydride In methanol at 65℃; Stage #3: With sodium hexaflorophosphate In methanol at 20℃;	82%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 2,5-dioxopyrrolidin-1-yl 4-(2-(((R,E)-4-((R)-1-(7-ethoxy-7-oxoheptyl)-5-oxopyrrolidin-2-yl)-1,1-difluoro-1-phenylbut-3-en-2-yl)oxy)-2-oxoethyl)benzoate

: sodium (4-(4-(2-(((R,E)-4-((R)-1-(7-ethoxy-7-oxoheptyl)-5-oxopyrrolidin-2-yl)-1,1-difluoro-1-phenylbut-3-en-2-yl)oxy)-2-oxoethyl)benzamido)-1-hydroxybutane-1,1-diyl)bis(hydrogenphosphonate)

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 0.166667h;	80%

: 6141-13-5
2-chloroquinazoline

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: [1-hydroxy-4-(quinazolin-2-ylamino)butane-1,1-diyl]bis(phosphonic acid)

Conditions

Conditions	Yield
Stage #1: 2-chloroquinazoline; 4-amino-1-hydroxybutylidenebisphosphonic acid With potassium carbonate In water at 90 - 180℃; for 25h; Reflux; Stage #2: With hydrogenchloride In water at 5℃; for 24h; pH=1;	80%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 121268-17-5
sodium alendronate

Conditions

Conditions	Yield
With sodium carbonate In water for 3h; Heating;	79%
With sodium hydroxide In water at 0 - 5℃; for 3h; pH=4.3;
With sodium hydroxide In water at 30 - 70℃;

: 55750-63-5
6-maleimidohexanoic acid N-hydroxylsuccinimide ester

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: (4‐{[6‐(2,5‐dioxo‐2,5‐dihydro‐1H‐pyrrol‐1‐yl)hexanoyl]amino}‐1‐hydroxybutane‐1,1‐diyl)bis(phosphonic acid)

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃; pH=8 - 9;	79%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 107-15-3
ethylenediamine

: C2H8N2*C4H13NO7P2*2H2O

Conditions

Conditions	Yield
With water pH=Ca. 6 - 8; Heating;	77%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 109-81-9
N-methyl-ethane-1,2-diamine

: C3H10N2*C4H13NO7P2*3H2O

Conditions

Conditions	Yield
With water pH=Ca. 6 - 8; Heating;	76%

: 1722-12-9
2-chloropyrimidine

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: [1-hydroxy-4-(pyrimidin-2-ylamino)butane-1,1-diyl]bis(phosphonic acid)

Conditions

Conditions	Yield
Stage #1: 2-chloropyrimidine; 4-amino-1-hydroxybutylidenebisphosphonic acid With potassium carbonate In water at 90 - 180℃; for 5h; Reflux; Stage #2: With hydrogenchloride In water at 5℃; pH=1;	76%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 91425-31-9
2-(triphenylmethylthio)ethanoic acid-N-hydroxysuccinimido ester

: (1-hydroxy-4-(2-(tritylthio)acetamido)butane-1,1-diyl)diphosphonic acid

Conditions

Conditions	Yield
Stage #1: 4-amino-1-hydroxybutylidenebisphosphonic acid With triethylamine In water for 0.0833333h; Stage #2: 2-(triphenylmethylthio)ethanoic acid-N-hydroxysuccinimido ester In water; N,N-dimethyl-formamide at 20℃; for 1h;	76%
Stage #1: 4-amino-1-hydroxybutylidenebisphosphonic acid With triethylamine In water for 0.0833333h; Stage #2: 2-(triphenylmethylthio)ethanoic acid-N-hydroxysuccinimido ester In water; N,N-dimethyl-formamide at 20℃; for 1h;	76%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 100-36-7
N,N-diethylethylenediamine

: C6H16N2*C4H13NO7P2*2H2O

Conditions

Conditions	Yield
With water pH=Ca. 6 - 8; Heating;	67%

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: 1121-22-8, 1436-59-5, 20439-47-8, 21436-03-3, 41013-43-8, 694-83-7
trans-1,2-Diaminocyclohexane

: C6H14N2*C4H13NO7P2*3H2O

Conditions

Conditions	Yield
With water pH=Ca. 6 - 8; Heating;	66%

: 1477-55-0
1,3-di(aminomethyl)benzene

: 66376-36-1
4-amino-1-hydroxybutylidenebisphosphonic acid

: benzene-1,3-dimethylamine

Conditions

Conditions	Yield
With water pH=Ca. 6 - 8; Heating;	62%

Alendronic acid Specification

The IUPAC name of Alendronate is (4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid. With the CAS registry number 66376-36-1, it is also named as Acide alendronique. The classification codes are Bone Density Conservation Agents; Reproductive Effect. It is white fine powder which is soluble in water, easily soluble in ethanol, and almost insoluble in chloroform. When heated to decomposition it emits toxic vapors of NO_x and PO_x. Besides, this chemical is DBPA resorption inhibitors which is mainly used for the treatment of osteoporosis. Additionally, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -3.52; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -7.15; (4)ACD/LogD (pH 7.4): -7.92; (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: 8; (10)#H bond donors: 7; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 103.15 Å²; (13)Index of Refraction: 1.593; (14)Molar Refractivity: 45.5 cm³; (15)Molar Volume: 134.1 cm³; (16)Surface Tension: 119.3 dyne/cm; (17)Enthalpy of Vaporization: 104.87 kJ/mol; (18)Vapour Pressure: 8.72E-18 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Exact Mass: 249.016725; (21)MonoIsotopic Mass: 249.016725; (22)Topological Polar Surface Area: 161; (23)Heavy Atom Count: 14; (24)Complexity: 257.

Preparation of Alendronate: Adding 1mol 4-aminobutyric acid to 95 °C melting 1.5mol phosphoric acid. And then dropping 2mol phosphorus trihalides in 60min. When the reactants is hardening, heat 3h more. Then adding 300ml water to hydrolysis. After cooling, pouring into 1500ml methanol. Collecting the precipitate to get the product.

People can use the following data to convert to the molecule structure.
1. SMILES:O=P(O)(O)C(O)(CCCN)P(=O)(O)O
2. InChI:InChI=1/C4H13NO7P2/c5-3-1-2-4(6,13(7,8)9)14(10,11)12/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12)
3. InChIKey:OGSPWJRAVKPPFI-UHFFFAOYAU

Product Name

Alendronic Acid

Synthetic route

Alendronic acid Specification

Related Products

Hot Products