PyBOP (HCID 2724699)

Names & identifiers

Preferred name: PyBOP
IUPAC: benzotriazol-1-yloxy(tripyrrolidin-1-yl)phosphanium hexafluorophosphate
English name: PyBOP
Molecular formula: C18H28F6N6OP2
Molecular weight: 520.39

Names & synonyms

PyBOP128625-52-5DTXSID40369209RefChem:177361DTXCID50320245(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate((1H-Benzo[d][1,2,3]triazol-1-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V)MFCD00077411Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphatebopp1H-Benzotriazol-1-yloxytripyrrolidinophosphonium HexafluorophosphateBenzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate

Show more names

N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphateBOP REAGENTBYPOPBENZOTRIAZOLE-1-YL-OXY-TRIS-PYRROLIDINO-PHOSPHONIUM HEXAFLUOROPHOSPHATEBENZOTRIAZOL-1-YLOXYTRIS(PYRROLIDINO)PHOSPHONIUM HEXAFLUOROPHOSPHATE

benzotriazol-1-yl-oxytripyrrolidinphosphonium hexafluorophosphate1-Benzotriazolyloxytripyrrolidinylphosphonium hexafluorophosphateBenzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate(Benzotriazol-1-yloxy)tripyrrolidinophosphonium (hexafluorophosphate)benzotriazol-1-yloxy(tripyrrolidin-1-yl)phosphanium;hexafluorophosphate132701-58-7Benzotriazole-1-yl-Y6KQR4GY6T

Database identifiers

CAS: 128625-52-5
PubChem CID: 2724699
DTXSID: DTXSID40369209
UNII: Y6KQR4GY6T
EC Number: 603-290-2

Properties

Computed structural properties

Topological polar surface area: 49.7 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 13
Rotatable bonds: 5
Heavy atoms: 33
Formal charge: 0
Complexity: 500

Physicochemical properties

Melting point: 154 · 154-156 °C (dec.)(lit.)
Density: 1.438 at · 1.438 at 20℃
vapor pressure: 0 · 0-0Pa at 20-50℃
storage temp.: 2 · 2-8°C
solubility: 25 mg/mL, · methanol: 25 mg/mL, clear
form: Fine Crystalline Powder
color: White to off-white
Sensitive: Moisture Sensitive
BRN: 3584612 · 3584612
Major Application: peptide synthesis
InChI: InChI=1S/C18H28N6OP.F6P/c1-2-10-18-17(9-1)19-20-24(18)25-26(21-11-3-4-12-21,22-13-5-6-14-22)23-15-7-8-16-23;1-7(2,3,4,5)6/h1-2,9-10H,3-8,11-16H2;/q+1;-1
InChIKey: BYCLGHOAELJLOF-UHFFFAOYSA-M
SMILES: [P+](ON1N=NC2C=CC=CC1=2)(N1CCCC1)(N1CCCC1)N1CCCC1.[P-](F)(F)(F)(F)(F)F
LogP: -0.3 at · -0.3 at 26℃ and pH3.5-3.7
CAS DataBase Reference: 128625 · 128625-52-5(CAS DataBase Reference)
UNSPSC Code: 12352107 · 12352107
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07,GHS09
Signal word: Warning
Hazard statements: 302 · H302-H317-H410
Precautionary statements: 261 · P261-P264-P273-P280-P301+P312-P302+P352
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 37 · 37/38-44-36/37/38
Safety Statements: 26 · 26-36-24/25-37/39
RIDADR: 1325 · UN 1325 4.1/PG 2
WGK Germany: 3 · 3
F: 8 · 8-10-21
Hazard Note: Irritant
HS Code: 29339980 · 29339980
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (14.9%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (87.8%): Causes skin irritation [Warning Skin corrosion/irritation]；H317 (12.2%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H319 (87.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (86.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H410 (12.2%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 74 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationStatus: Active Update: 24-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/30080；Status: Active Update: 07-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/27481

Hazard Classes and CategoriesAcute Tox. 4 (14.9%)；Skin Irrit. 2 (87.8%)；Skin Sens. 1 (12.2%)；Eye Irrit. 2 (87.8%)；STOT SE 3 (86.5%)；Aquatic Chronic 1 (12.2%)

Regulatory information

Regulatory InformationStatus: Active Update: 24-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/30080；Status: Active Update: 07-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/27481

Safety data

F: 8-10-21
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
ridadr: UN 1325 4.1/PG 2
hs_code: 29339980
risk_code: 37/38-44-36/37/38
Signal word: Warning
Symbol(GHS): GHS07,GHS09
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-36-24/25-37/39
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H317-H410
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1
Precautionary statements: P261-P264-P273-P280-P301+P312-P302+P352

Chemistry & industry

Applications · 4 items

UsesOne of the most convenient coupling reagents for peptide synthesis without carcinogenic by-products. It replaces BOP reagent. This is especially suitable for solid-phase peptide synthesis, avoids racemization.

Uses1H-Benzotriazol-1-yloxytri(1-pyrrolidinyl) phosphonium hexafluorophosphate (PyBOP) is a peptide coupling reagent utilized in solid phase peptide synthesis. It is also used as a substitute for the (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) reagent.

UsesPyBOP is a reagent for: Synthesis of single labeled oligonucleotides that fluoresce upon matched hybridization Generation of endocrine disruptor chemical binders Cycloaddition to template-assembled multivalent peptide conjugates

General Description(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) is an activator of carboxyl group commonly used in peptide synthesis. It also participates in the carboxylic acid esterification. It shows characteristics similar to benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and can be utilized as an alternative to BOP in peptide bond formation.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

江苏吉泰肽业科技有限公司051580855088 18762539991 · [email protected]

Additional notes · 1 item

DefinitionPyBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate) coupling reagent was selected for the peptidic bond formation. This selection was because PyBOP is efficient and could generate less toxic byproducts. PyBOP is an efficient coupling reagent utilized in solid-phase peptide synthesis. It reacts similarly to BOP, but its byproduct is not highly carcinogenic. PyBOP was utilized in the solid-phase synthesis of the tetrapeptide H-Ile-Ala-Leu-Pro-OH on 2-chlorotrityl resin. In contrast to uronium-based coupling reagents, PyBOP does not form guanidinated byproducts when used in excess. This makes it useful in fragment condensation reactions and head-to-tail cyclizations[1].