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Merck
CN

T67806

Triisopropyl phosphite

95%

Synonym(s):

Isopropyl phosphite, Tri-2-propyl phosphite, Triisopropoxyphosphine, Tris(isopropyl) phosphite

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About This Item

Linear Formula:
[(CH3)2CHO]3P
CAS Number:
116-17-6
Molecular Weight:
208.24
Beilstein:
1701528
EC Number:
204-130-0
MDL number:
MFCD00008874
UNSPSC Code:
12352100
PubChem Substance ID:
24900404
NACRES:
NA.22

Key Documents

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vapor pressure

<2 mmHg ( 20 °C)

Quality Level

200

Assay

95%

refractive index

n20/D 1.411 (lit.)

bp

63-64 °C/11 mmHg (lit.)

density

0.844 g/mL at 25 °C (lit.)

SMILES string

CC(C)OP(OC(C)C)OC(C)C

InChI

1S/C9H21O3P/c1-7(2)10-13(11-8(3)4)12-9(5)6/h7-9H,1-6H3

InChI key

SJHCUXCOGGKFAI-UHFFFAOYSA-N

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Application

Triisopropyl phosphite can be used as a reactant:
  • With Ru-based indenylidene complexes to form 1st generation complexes for metathesis reactions.
  • In Perkow-type reaction to synthesize compounds containing polarized carbon-carbon double bonds.
  • For the synthesis of phosphonohydrazines by reacting with arylamines and isoamyl nitrite.

It can also be used as an alternative to triphenylphosphine in Mitsunobu reaction to facilitate the isolation of products.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315

Precautionary Statements

P301 + P310 + P330 - P302 + P352

Hazard Classifications

Acute Tox. 3 Oral - Skin Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

154.4 °F - closed cup

Flash Point(C)

68 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ3901
MKCV3265
MKCM4475
MKCK2664
MKCG5204

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Nef-isocyanide-Perkow synthesis of new polarized olefins containing 2-dicyanomethylene-2, 3-dihydrothiazole and 2-dicyanomethylene-1, 3-dithiole moieties
Yavari I, et al.
Tetrahedron, 69(11), 2462-2467 (2013)
Ruthenium indenylidene ?1st generation? olefin metathesis catalysts containing triisopropyl phosphite
Guidone S, et al.
Beilstein Journal of Organic Chemistry, 11, 1520-1520 (2015)
Mitsunobu reactions of nucleoside analogs using triisopropyl phosphite-DIAD
Veliz EA and Beal PA
Tetrahedron Letters, 47(18), 3153-3156 (2006)
Convenient synthesis of phosphonohydrazines from arylamines
Kent GT, et al.
Tetrahedron Letters, 57(19), 2097-2099 (2016)
Su Mei Liu et al.
Marine pollution bulletin, 60(9), 1591-1599 (2010-04-30)
Inorganic or bulk organic chemical indicators, including organic carbon (OC), total nitrogen, organic nitrogen (ON), fixed ammonium (N(fix)), exchangeable ammonium, exchangeable nitrate, organic phosphorus (OP), inorganic phosphorus (IP), and biogenic silica (BSi), were examined in a 3-m core collected in
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