163937
N,N,N′,N′-Tetramethylphosphorodiamidic chloride
technical grade, 90%
Synonym(s):
Bis(dimethylamido)phosphoric chloride
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About This Item
Linear Formula:
[(CH3)2N]2P(O)Cl
CAS Number:
Molecular Weight:
170.58
Beilstein:
471430
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
grade
technical grade
Quality Level
Assay
90%
form
liquid
refractive index
n20/D 1.466 (lit.)
density
1.152 g/mL at 25 °C (lit.)
functional group
phosphoramide
SMILES string
CN(C)P(Cl)(=O)N(C)C
InChI
1S/C4H12ClN2OP/c1-6(2)9(5,8)7(3)4/h1-4H3
InChI key
WYLQARGYFXBZMD-UHFFFAOYSA-N
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Application
N,N,N′,N′-Tetramethylphosphorodiamidic chloride was used in the synthesis of (-)-allohedycaryol and C2-symmetric binaphthyl phosphortriamide. It was also used in total synthesis of neohedycaryol.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
235.4 °F - closed cup
Flash Point(C)
113 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Total Synthesis of Neohedycaryol. Its Possible Role in the Biosynthesis of Eudesmane Sesquiterpenes.
Adriaan J. Minnaard et al.
The Journal of organic chemistry, 62(8), 2344-2349 (1997-04-18)
The total synthesis of neohedycaryol (4), the C(9)-C(10) double bond regioisomer of the germacrane sesquiterpene hedycaryol, was accomplished in 10 steps from the known dione 6. A Marshall fragmentation of the intermediate mesylate 14 was used to prepare the trans,trans-cyclodeca-1,6-diene
Vladimir N. Zhabinskii et al.
The Journal of organic chemistry, 61(12), 4022-4027 (1996-06-14)
The enantiomer of (+)-allohedycaryol, a germacrane alcohol isolated from giant fennel (Ferula communis L.), has been synthesized, thereby elucidating the relative and absolute stereochemistry of the natural product. The synthesis of (-)-allohedycaryol started from (+)-alpha-cyperone (5) which was available in
A I Meyers et al.
Chirality, 9(5-6), 431-434 (1997-01-01)
By use of an asymmetric Ullmann coupling involving chiral naphthalene oxazolines 1, the title compounds were prepared in good yields and with high diastereoselectivity. Hydrolysis of the binaphthyl oxazolines 2 led to the di-aldehydes 5, which were transformed into the
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