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163937

Sigma-Aldrich

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:
1605-65-8
Molecular Weight:
170.58
Beilstein:
471430
EC Number:
216-517-1
MDL number:
MFCD00008302
UNSPSC Code:
12352100
PubChem Substance ID:
24850043
NACRES:
NA.22

grade

technical grade

Assay

90%

form

liquid

refractive index

n20/D 1.466 (lit.)

density

1.152 g/mL at 25 °C (lit.)

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

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

Certificates of Analysis (COA)

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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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