Bis(2-oxo-3-oxazolidinyl)phosphinic chloride (HCID 152842)

Overview

responsible for racemization in peptide synthesis

Names & identifiers

Preferred name: Bis(2-oxo-3-oxazolidinyl)phosphinic chloride
IUPAC: 3-[chloro-(2-oxo-1,3-oxazolidin-3-yl)phosphoryl]-1,3-oxazolidin-2-one
English name: Bis(2-oxo-3-oxazolidinyl)phosphinic chloride
Molecular formula: C6H8ClN2O5P
Molecular weight: 254.56

Names & synonyms

68641-49-6Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideBOP-ClPhosphinic chloride, bis(2-oxo-3-oxazolidinyl)-V974K6W8Y7NSC-377647DTXSID30218732RefChem:120101DTXCID80141223629-561-5MFCD00010077Bis(2-oxooxazolidin-3-yl)phosphinic chloride

Show more names

BOP-CIBOP-CBOPDCidinyLBIS(2-OXO-3-OXPhosphoric acid biBis(2-oxo-3-oxazoL

Phosphoric acid bis(2-oxooxazolidide) chloride3-[chloro-(2-oxo-1,3-oxazolidin-3-yl)phosphoryl]-1,3-oxazolidin-2-onen,n-bis(2-oxo-3-oxazolidinyl)phosphinic chlorideBis(2-oxo-3-oxazolidinyl)phosphonic chloridebis-(2-oxo-3-oxazolidinyl)phosphinic chloridebis(2-oxo-1,3-oxazolidin-3-yl)phosphinic chloride3-[chloro-(2-oxooxazolidin-3-yl)phosphoryl]oxazolidin-2-onen,n-bis(2-oxo-3-oxazolidinyl)phosphonic chloride

Database identifiers

CAS: 68641-49-6
PubChem CID: 152842
DTXSID: DTXSID30218732
UNII: V974K6W8Y7
EC Number: 629-561-5
Nikkaji: J236.612F

Properties

Computed structural properties

XLogP: -0.1
Topological polar surface area: 76.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 15
Formal charge: 0
Complexity: 331

Physicochemical properties

Melting point: 191 °C · 191 °C (dec.)(lit.)
Boiling point: 332.8 · 332.8±25.0 °C(Predicted)
Density: 1.71 · 1.71±0.1 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
solubility: 2 Cl2, · slightly sol CH2Cl2, MeCN, THF, DMF; dec H2O
pka: -2.47 · -2.47±0.20(Predicted)
form: Crystalline Powder
color: White to off-white
Water Solubility: Hydrolyzes with water.
Sensitive: Moisture Sensitive
BRN: 3654596 · 3654596
InChI: InChI=1S/C6H8ClN2O5P/c7-15(12,8-1-3-13-5(8)10)9-2-4-14-6(9)11/h1-4H2
InChIKey: KLDLRDSRCMJKGM-UHFFFAOYSA-N
SMILES: P(N1CCOC1=O)(N1CCOC1=O)(Cl)=O
CAS DataBase Reference: 68641 · 68641-49-6(CAS DataBase Reference)
FDA UNII: 974 K6W8Y7 · V974K6W8Y7
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 314 · H314
Precautionary statements: 260 · P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363
PPE: 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: C
Risk Statements: 34 · 34
Safety Statements: 26 · 26-36/37/39-45-27
RIDADR: 3261 · UN 3261 8/PG 2
WGK Germany: 3 · 3
RTECS: 5871000 · SZ5871000
F: 10 · 10-21
HazardClass: 8 · 8
PackingGroup: II
HS Code: 29349990 · 29349990
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 B · Skin Corr. 1B
Limited Quantities: 1 Kg · 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Corr. 1B (100%)

Safety data

F: 10-21
PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
rtecs: SZ5871000
ridadr: UN 3261 8/PG 2
hs_code: 29349990
risk_code: 34
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: C
safety_code: 26-36/37/39-45-27
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: II
Hazard statements: H314
Limited Quantities: 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Hazard Classifications: Skin Corr. 1B
Precautionary statements: P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363

Chemistry & industry

Applications · 2 items

DescriptionBis(2-oxo-3-oxazolidinyl)phosphinic chloride is a reagent for activating carboxyl groups, converting acids to esters (including thioesters and phosphoesters), amides (including peptides and β-lactams), and anhydrides; reagent for kinetic resolution of racemic carboxylic acids and alcohols.

UsesBis(2-oxo-3-oxazolidinyl)phosphinic chloride was used in the preparation of hexadepsipeptide.