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D36550

Sigma-Aldrich

Dibenzyl phosphate

99%

Synonym(s):

DBzP

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About This Item

Linear Formula:
(C6H5CH2O)2P(O)(OH)
CAS Number:
1623-08-1
Molecular Weight:
278.24
Beilstein:
2055755
EC Number:
216-602-3
MDL number:
MFCD00004775
UNSPSC Code:
12352100
PubChem Substance ID:
24893773
NACRES:
NA.22

Quality Level

100

Assay

99%

form

powder

mp

78-80 °C (lit.)

storage temp.

2-8°C

SMILES string

OP(=O)(OCc1ccccc1)OCc2ccccc2

InChI

1S/C14H15O4P/c15-19(16,17-11-13-7-3-1-4-8-13)18-12-14-9-5-2-6-10-14/h1-10H,11-12H2,(H,15,16)

InChI key

HDFFVHSMHLDSLO-UHFFFAOYSA-N

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Application

Dibenzyl phosphate (DBzP) can be used:
  • To promote the monoselective ortho-C-H alkylation of N-quinolyl benzamides with primary and secondary alkyl iodides.
  • For the ring-opening reaction of epoxide such as benzylglycidol to synthesize dihydroxyacetone phosphate (DHAP).
  • As a reactant for the synthesis of stereospecific 1,2-trans glycosyl phosphates.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

D36550-25G:
D36550-VAR:
D36550-5G:
D36550-1G:
D36550-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBH8449
1418403
05430HT
S28972
05321LC

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An approach towards the synthesis of 1, 2-trans glycosyl phosphates via iodonium ion assisted activation of thioglycosides.
Veeneman GH, et al.
Tetrahedron Letters, 32(43), 6175-6178 (1991)
Lewis acid mediated regioselective ring opening of benzylglycidol with dibenzyl phosphate: short and attractive synthesis of dihydroxyacetone phosphate.
Meyer O, et al.
Organic Letters, 8(19), 4347-4350 (2006)
Syntheses of glycosyl phosphates by phase transfer catalysis.
Roy R, et al.
Canadian Journal of Chemistry, 69(9), 1462-1467 (1991)
Pd-Catalyzed Monoselective ortho-C-H Alkylation of N-Quinolyl Benzamides: Evidence for Stereoretentive Coupling of Secondary Alkyl Iodides.
Zhang SY, et al.
Journal of the American Chemical Society, 137(1), 531-539 (2014)
Biosynthetic studies on the ?-glucosidase inhibitor acarbose: the chemical synthesis of dTDP-4-amino-4, 6-dideoxy-?-d-glucose.
Bowers SG, et al.
Carbohydrate Research, 337(4), 297-304 (2002)
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Global Trade Item Number

SKUGTIN
D36550-1G
D36550-25G4061833427859
D36550-5G4061833563427

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