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1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate

Product Name
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate
CAS No.
56602-33-6
Chemical Name
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate
Synonyms
BOP;BOP REAGENT;BENZOTRIAZOL-1-YLOXYTRIS(DIMETHYLAMINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE;1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate [Coupling Reagent for Peptide];cas:56602-33-6;BOP-reaagent;CASTROS REAGENT;CASTRO'S REAGENT;BOP Reagent(BOP);Benzotriazole-1-yl-o
CBNumber
CB9434718
Molecular Formula
C12H22F6N6OP2
Formula Weight
442.29
MOL File
56602-33-6.mol
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1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Property

Melting point:
>130 °C (dec.)(lit.)
Flash point:
138°C
storage temp. 
2-8°C
solubility 
methanol: 25 mg/mL, clear
form 
Powder
color 
White to off-white
Water Solubility 
Soluble in methanol, acetone and dichloromethane. Insoluble in water.
Decomposition 
138 ºC
Sensitive 
Moisture & Light Sensitive
BRN 
4287025
CAS DataBase Reference
56602-33-6(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi,E,F
Risk Statements 
37/38-44-36/37/38-11-2
Safety Statements 
24/25-37/39-36-26-35-36/37/39
RIDADR 
UN 1325 4.1/PG 2
WGK Germany 
3
8-10-21
Hazard Note 
Irritant
HazardClass 
4.1
PackingGroup 
HS Code 
29339980
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H228Flammable solid

H315Causes skin irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.51004
Product name
BOP
Purity
Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate Novabiochem?
Packaging
25g
Price
$101
Updated
2024/03/01
Sigma-Aldrich
Product number
8.51004
Product name
BOP
Purity
Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate Novabiochem?
Packaging
100g
Price
$312
Updated
2024/03/01
Sigma-Aldrich
Product number
226084
Product name
(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate
Purity
97%
Packaging
1g
Price
$23.12
Updated
2024/03/01
Sigma-Aldrich
Product number
226084
Product name
(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate
Purity
97%
Packaging
5g
Price
$90.4
Updated
2024/03/01
TCI Chemical
Product number
B1651
Product name
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate [Coupling Reagent for Peptide]
Purity
>98.0%(HPLC)
Packaging
5g
Price
$42
Updated
2024/03/01
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1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Chemical Properties,Usage,Production

Chemical Properties

white to off-white powder

Uses

Peptide coupling reagent which suppresses racemization.

Uses

1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate is used as a reagent for peptide coupling, lactonization, selective esterification, amidation of alfa amino acids without racemization and synthesis of magnolamide for antioxidative activity and catalyst for 9-acridinecaroboxamide derivative. It is also used as a precursor for the synthesis of phenyl esters of amino acids. It acts as a substitute for (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) reagent.

Uses

1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate is a peptide coupling reagent. Can be used 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.

Preparation

To vigorously stirred HMPA (15.0 g, 83.7 mmol) at 0 C°, a solution of triphosgene (11.28 g, 38.01 mmol) in dichloromethane (15 mL) was added over a period of 40 min. The ice bath was then removed and the mixture was stirred at room temperature. At various intervals, small aliquots were removed in order to follow the disappearance of the HMPA spectroscopically. After 3 h, the solvent was removed under reduced pressure to leave a residue. This residue was redissolved in dry dichloromethane (40 mL) and solid hydroxybenzotriazole monohydrate (12.76 g, 94.4 mmol) was added with stirring. The resulting solution was cooled to about 5 C° with an acetone/ice bath, whereupon triethylamine (8.42 g, 83.4 mmol) was added over a period of 15 min and stirring was continued at -5 C for 4 h. The residue was dissolved in water (50 mL) and mixed with a filtered solution of potassium hexafluorophosphate (16.68 g, 90.6 mmol) in water (120 mL) to give benzotriazolyl-N-oxytris(dimethylamino)phosphonium hexafluorophosphate 1317 (BOP) as a crystalline solid (28.91 g, 78%).
Chloroformates 1319 and chlorides 1320 are also formed when secondary benzyl alcohols 1318 are treated with trichloromethyl chloroformate (diphosgene) in the presence of triethylamine. The distribution of products can be controlled.

Reactions of tetrahydropyranylated alcohols 1321 with N,N-dimethylphosgeniminium chloride (‘‘Viehe salt’’) 1322 give the corresponding alkyl chloride 1300 in good yields [997]. This conversion can be conveniently accomplished by adding the ‘‘Viehe salt’’ (1.05 equiv.) as a solid to a solution of the THP-protected alcohol (1 equiv.) in anhydrous dichloromethane (0.3 m) under argon at 0 C°. After completion of the reaction and aqueous work-up, the crude alkyl chlorides are purified by column chromatography.

Purification Methods

Dissolve it in CH2Cl2, dry (MgSO4), filter, concentrate it under a vacuum, then add dry Et2O and filter off the first crop. Add CH2Cl2 to the filtrate and concentrate again to obtain a second crop. The solid is washed with dry Et2O and dried in a vacuum. Also recrystallise it from dry Me2CO/Et2O and check the purity by NMR. Store it in the dark. [Castro et al. Synthesis 751 1976, Nguyen et al J Chem Soc, Perkin Trans I 1915 1987, Coste et al. Tetrahedron Lett 36 4253 1995.]

1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Preparation Products And Raw materials

Raw materials

Preparation Products

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1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate Suppliers

Suzhou Highfine Biotech Co., Ltd
Tel
0512-68311833 13962195826
Fax
0512-68417696
Email
wuhao@highfine.com
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China
ProdList
499
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Shanghai Jizhi Biochemical Technology Co. Ltd.
Tel
4009004166/18616739031 18616739031
Email
3007523370@qq.com
Country
China
ProdList
52693
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58
Fuxin Kaituo Fine Chemical Technology Co., Ltd
Tel
15714082442
Email
3757845877@qq.com
Country
China
ProdList
346
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58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
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China
ProdList
94657
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
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China
ProdList
40228
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future industrial shanghai co., ltd
Tel
400-0066400 13621662912
Fax
021-55660885
Email
sales@jonln.com
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China
ProdList
1995
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Alfa Aesar
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400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
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TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
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81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8418
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Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
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View Lastest Price from 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
BOP hexafluorophosphate 56602-33-6
Price
US $0.00/g
Min. Order
100g
Purity
98.0%
Supply Ability
100kg/month
Release date
2021-12-13
Hebei Weibang Biotechnology Co., Ltd
Product
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate 56602-33-6
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2023-02-24
Hebei Mojin Biotechnology Co., Ltd
Product
1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate 56602-33-6
Price
US $50.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20tons
Release date
2023-08-16

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