Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate supplier

Name
Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate
EINECS 260-279-1
CAS No. 56602-33-6
Article Data2
CAS DataBase
Density
Solubility methanol: 25 mg/mL, clear
Melting Point >130 °C (dec.)(lit.)
Formula C₁₂H₂₂N₆OP^.PF₆
Boiling Point
Molecular Weight 442.284
Flash Point 138 °C
Transport Information UN 1325 4.1/PG 2
Appearance white to off-white powder
Safety 24/25-37/39-36-26
Risk Codes 37/38-44-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Btzo-tdmap;Phosphorus(1++), (1-hydroxy-1H-benzotriazolato-O)tris(N-methylmethanaminato)-, (beta-4)-, hexafluorophosphate(1-);Bop reagent;Tri(dimethylamino)benzotriazol-1-yloxyphosphonium hexafluorophosphate;Phosphorus(1+),(1-hydroxy-1Hbenzotriazolato- O)tris(N-methylmethanaminato)-,(T-4)-,hexafluorophosphate(1-);(1H-Benzotriazol-1-yloxy)-tris(dimethylamino)phosphonium hexafluorophosphate(1-);Phosphorus(1+), (1H-benzotriazol-1-olato-O)tris(N-methylmethanaminato)-, (T-4)-;BOP-Reagent;Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium;BOP hexafluorophosphate;Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate;
PSA 76.84000
LogP 4.60470

Synthetic route

: 2592-95-2
benzotriazol-1-ol

: chlorotris(dimethylamino)phosphonium hexafluorophosphate

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

Conditions

Conditions	Yield
With TEA In acetone for 1h;

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / potassium hexafluorophosphate; oxalyl chloride; DMF / acetonitrile / 4 h / 0 - 20 °C 2: TEA / acetone / 1 h View Scheme

: 957187-25-6
5-amino-4-chloro-2-fluorobenzoic acid

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 1386981-39-0
1H-benzo[d][1,2,3]triazol-1-yl 5-amino-4-chloro-2-fluorobenzoate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0℃; for 3h;	98.8%

: 300354-95-4
3-cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid

: 32955-21-8
2-amino-thiazole-5-carboxylic acid ethyl ester

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 588940-26-5
2-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionylamino]-thiazole-5-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane	98%

...Expand

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 4-((1H-benzo[d][1,2,3]triazol-1-yl)oxy)-2H-chromen-2-one

Conditions

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.166667h; Stage #2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In acetonitrile at 20℃; for 1h;	97%

: 96-50-4
2-thiazolylamine

: 300355-34-4
3-cyclopentyl-2-(3,4-dichlorophenyl)propionic acid

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 3-cyclopentyl-2-(3,4-dichlorophenyl)-N-thiazol-2-yl-propionamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane	96%
With triethylamine In dichloromethane	96%

...Expand

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 93778-57-5
9-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-1H-purin-6(9H)-one

: (2R,3S,5R)-5-(6-(1H-benzo[d][1,2,3]triazol-1-yloxy)-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-ol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	95%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 40h;	85%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 40h;	85%

: 96-50-4
2-thiazolylamine

: 2-(4-benzoylamino-phenyl)-3-cyclopentyl-propionic acid

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: N-{4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenyl}-benzamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane	95%

...Expand

: 934-32-7
1H-benzimidazol-2-amine

: 300355-34-4
3-cyclopentyl-2-(3,4-dichlorophenyl)propionic acid

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: N-(1H-benzoimidazol-2-yl)-3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane	95%

...Expand

: 934-32-7
1H-benzimidazol-2-amine

: 300355-72-0
2-(3-cyano-4-methanesulfonylphenyl)-3-cyclopentylpropionic acid

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: N-(1H-benzoimidazol-2-yl)-2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane	95%

...Expand

: 2-(4-methoxybenzenesulfonylamino)-2-methylpropionic acid

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: N-benzyloxy-2-(4-methoxybenzenesulfonylamino)-2-methyl-propionamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane; ethyl acetate	95%

...Expand

: 1195939-22-0
(3aS,4S,6R,6aR)-6-[2-amino-6-oxo-1H-purin-9(6H)-yl]-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 1195939-27-5
O6-(benzotriazol-1-yl)-2',3'-O-isopropylideneguanosine-5'-N-ethylcarboxamide

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; for 16h;	95%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃;	95%

: 106568-79-0
9-(3',5'-di-O-acetyl-2'-deoxy-β-D-erythro-pentofuranosyl)-1H-purine-6(9H)-one

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 1220116-25-5
3',5'-di-O-acetyl-O(6)-(benzotriazol-1-yl)-2'-deoxyinosine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 22h;	94%

: 73579-08-5
Methyl-(1-methyl-[4]piperidyl)-amin

: 39968-33-7
1-hydroxy-7-aza-benzotriazole

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 7087-68-5
N-ethyl-N,N-diisopropylamine

: 4-(5-Cyclohexylimino-4-methyl-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-N-methyl-N-(1-methyl-piperidin-4-yl)-benzamide

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; N,N-dimethyl-formamide	93.5%

...Expand

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 14080-50-3
thieno[2,3-d]pyrimidin-4(3H)one

: 4-(benzotriazol-1-yloxy)thieno[2,3-d]pyrimidine

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 12h;	93%

: C13H10F2N4O2

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 4-((1H-benzo[d][1,2,3]triazol-1-yl)oxy)-2-amino-6-(2,6-difluorophenyl)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-one

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 48h; Inert atmosphere;	93%

: 123215-04-3
potassium trifluorotris(pentafluoroethyl)phosphate

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium tris(pentafluoroethyl)trifluorophosphate

Conditions

Conditions	Yield
In acetonitrile at 20℃;	93%

: 123-75-1
pyrrolidine

: 4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 1-(4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carbonyl)pyrrolidine

Conditions

Conditions	Yield
With triethylamine In dichloromethane; ethyl acetate	92%

...Expand

: 565237-17-4
2',3'-O-isopropylideneguanosine-5'-N-methylcarboxamide

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 1277176-19-8
O6-(benzotriazol-1-yl)-2-amino-2',3'-O-isopropylideneinosine-5'-N-methylcarboxamide

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃;	92%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; for 16h;	92%

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 3181-38-2
2',3',5'-tri-O-acetylinosine

: acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-[6-(benzotriazol-1-yloxy)purin-9-yl]tetrahydrofuran-2-ylmethyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 0 - 20℃; for 1.3h;	91%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 22h;	91%

: 110-91-8
morpholine

: 51549-35-0
3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 2-amino-6-morpholino-9-[2-deoxy-3,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pento-furanosyl]purine

Conditions

Conditions	Yield
Stage #1: 3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 1h; Inert atmosphere; Stage #2: morpholine In acetonitrile at 20℃; for 2h; Inert atmosphere;	91%

...Expand

(+-)-2,6-Di-tert-butyl-4-methoxyphenyl-4-[N-{(3RS,4SR)-N,3-dimethyl-4-piperidinyl}-phenylamino]benzoate: (+-)-2,6-Di-tert-butyl-4-methoxyphenyl-4-[N-{(3RS,4SR)-N,3-dimethyl-4-piperidinyl}-phenylamino]benzoate

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 109-89-7
diethylamine

: (+/-)-4-[N-{(3RS,4SR)-N,3-Dimethyl-4-piperidinyl}phenylamino]-N,N-diethylbenzamide

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; sodium methylate; triethylamine In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; toluene	90%

...Expand

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 6979-94-8
2',3',5'-tri-O-acetyl-guanosine

: 1277176-16-5
2',3',5'-tri-O-acetyl-O6-(benzotriazol-1-yl)guanosine

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃;	90%

: 2-morpholinopyrimidin-4(3H)-one

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 1332525-41-3
1-(2-morpholinopyrimidin-4yloxy)-1H-benzo[d]-[1,2,3] triazole

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 5h;	90%

: 865710-41-4
O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyxanthosine

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-O2-tris(dimethylamino)phosphonium-2'-deoxyxanthosine hexafluorophosphate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 5h; Inert atmosphere;	88%

: 6-(4-fluorophenyl)-2-(phenylamino)-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 4-((1H-benzo[d][1,2,3]triazol-1-yl)oxy)-6-(4-fluorophenyl)-2-(phenylamino)-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-7(8H)-one

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 48h; Inert atmosphere;	88%

: 491-36-1
4-Hydroxyquinazoline

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 897930-10-8
4-(1H-benzo[d][1,2,3]triazol-1-yloxy)quinazoline

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.333333h;	87%

: 264272-67-5
3-(tert-butyldimethylsilyloxy)benzylamine

: 4919-37-3
3,5-dimethyl-4-hydroxybenzoic acid

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: N-[3-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]methyl]-3,5-dimethyl-4-hydroxybenzamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate; Petroleum ether	87%

...Expand

: 31167-21-2
2-(benzylsulfanyl)pyrimidin-4(3H)-one

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 1332525-29-7
1-[2-(benzylsulfanyl)pyrimidin-4-yloxy]-1H-[b]-[1,2,3]-benzotriazole

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; for 3h;	87%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.25h;	60%

: 2,3,4,9-tetrahydro-10H-[1,4]oxazino[2,3-f]quinazolin-10-one

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 10-((1H-benzo[d][1,2,3]triazol-1-yl)oxy)-3,4-dihydro-2H-[1,4 ]oxazino[2,3-f]quinazoline

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;	87%

: 220441-14-5
1-[(4'-fluorobiphenyl-4-sulfonyl)-(2-methoxycarbonylethyl)amino]-cyclopentane-1-carboxylic acid

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 3-[(1-benzyloxycarbamoylcyclopentyl)-(4'-fluorobiphenyl-4-sulfonyl)amino]propionic acid methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide	86%
With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide	86%

...Expand

: 56602-33-6
(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

: 110526-62-0
2',3',5'-tris-O-(tert-butyldimethylsilyl)-2'-deoxyinosine

: 927818-51-7
O6-(1H-benzo[d][1,2,3]triazol-1-yl)-2',3',5'-tris-O-(tert-butyldimethylsilyl)inosine

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.25h;	85%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 43h;	80%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 23h; Product distribution / selectivity;	80%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
With caesium carbonate In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;

Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate Standards and Recommendations

Purity: 99%min
Loss on dryging: 0.5%max
Heavy metals: 20 ppm max

Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate Specification

BOP , with the CAS register number 56602-33-6 , is also known to us as (1-hydroxy-1h-benzotriazolato-o)tris(n-methylmethanaminato)-phosphorus(1++;benzotriazol-1-yl-oxytris(dimethylamino)phosphoniumhexa-fluorophosphate(bop) , BENZOTRIAZOLYL-N-OXYTRIS-(DIMETHYLAMINO-PHOSPHONIUM HEXAFLUOROPHOSPHATE) , BENZOTRIAZOLE-1-YL-OXY-TRIS-DIMETHYLAMINOPHOPHONIUM ,etc.

Some characteristics of this chemical are as below: (1)Melting point 136-140°C ; (2)Decomposition 138°C. It is a kind of white to off-white powder and it is soluble in the methanol 25 mg/mL. And it is sensitive to the moisture and light. As for its usage, it could be used as peptide coupling reagent and it is also applied in the preparation of phenyl esters of amino acids which have been shown to be valuable as blocked derivatives of amino acids in the field of peptide synthesis. While storing, it should be put in a 2-8 °C environment.

Being a kind of irritant chemical, it may cause inflammation to the skin or other mucous membranes. For one thing, it is irritant to eyes, respiratory system and skin, and for another, it has the risk of explosion if heated under confinement. So while using this chemical, you should wear suitable gloves and eye/face protection. And avoid contact with skin and eyes, but if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, if you need more safety information, you could refer to WGK Germany 3.

This kind of chemical belongs to the product categories which are as the following: Pharmaceutical Intermediates, Peptide Coupling Reagents & Miscellaneous Reagents, Biochemistry, Condensation & Active Esterification, Coupling Reactions (Peptide Synthesis), Phosphonium Compounds, Synthetic Organic Chemistry.

And you could also obtain the molecular structure by converting the following data information:
SMILES: F[P-](F)(F)(F)(F)F.n1nn(O[P+](N(C)C)(N(C)C)N(C)C)c2ccccc12
InChI: InChI=1/C12H22N6OP.F6P/c1-15(2)20(16(3)4,17(5)6)19-18-12-10-8-7-9-11(12)13-14-18;1-7(2,3,4,5)6/h7-10H,1-6H3;/q+1;-1
InChIKey: MGEVGECQZUIPSV-UHFFFAOYAP

Product Name

Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate

Synthetic route

Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate Standards and Recommendations

Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate Specification

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