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H11602

Sigma-Aldrich

Hexamethylphosphoramide

99%

Synonym(s):

HMPA, Hexamethylphosphoric acid triamide, Tris(dimethylamino)phosphine oxide

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About This Item

Linear Formula:
[(CH3)2N]3PO
CAS Number:
680-31-9
Molecular Weight:
179.20
Beilstein:
1099903
EC Number:
211-653-8
MDL number:
MFCD00008303
UNSPSC Code:
12352111
PubChem Substance ID:
24895433
NACRES:
NA.22
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vapor density

6.18 (vs air)

Quality Level

200

vapor pressure

0.07 mmHg ( 25 °C)

Assay

99%

refractive index

n20/D 1.459 (lit.)

bp

230-232 °C/740 mmHg (lit.)

mp

7 °C (lit.)

density

1.03 g/mL at 25 °C (lit.)

SMILES string

CN(C)P(=O)(N(C)C)N(C)C

InChI

1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3

InChI key

GNOIPBMMFNIUFM-UHFFFAOYSA-N

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General description

Hexamethylphosphoramide is a polar aprotic solvent.[1]

Application

Hexamethylphosphoramide can be used as a solvent:
  • For the conversion of carboxylate salt into esters by reacting with alkyl halides.[2]
  • To synthesize aryl thioethers via nucleophilic displacement of unactivated aryl halides by thiolate ions.[3]
  • To synthesize polyazomethines (PAZs) from dialdehyde and diamine via high-temperature solution polycondensation.[4]

Pictograms

Health hazardCorrosion
GHS08,GHS05

Signal Word

Danger

Hazard Statements

H314,H340,H350

Hazard Classifications

Carc. 1B - Eye Dam. 1 - Muta. 1B - Skin Corr. 1C

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

291.2 °F - closed cup

Flash Point(C)

144 °C - closed cup

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.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF2939V
WXBF3238V
WXBF3674V
WXBF2401V
WXBD7028V

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Hexamethylphosphoramide
Normant H.
Angewandte Chemie (International Edition in English), 6(12), 1046-1067 (1967)
Optical and structural study of thin film of polyazomethine with triphenylamine unit prepared via spin-coating method.
Palewicz M, et al.
Polymer Bull., 66(1), 65-76 (2011)
Controlled/?Living? Reverse Atom Transfer Radical Polymerization of a Monocyclic Olefin, Methyl 1-Cyclobutenecarboxylate.
Chen X P, et al.
Macromolecules, 35(11), 4277-4281 (2002)
Nucleophilic aromatic substitution reactions of unactivated aryl halides with thiolate ions in hexamethylphosphoramide.
Cogolli P, et al.
The Journal of Organic Chemistry, 44(15), 2642-2646 (1979)
Ge Gao et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(15), 5417-5420 (2004-03-18)
It is found that the addition of hexamethylphosphoramide to the solution of an alkyne, Et(2)Zn, and (S)-1,1'-bi-2-naphthol in methylene chloride allows the generation of an alkynylzinc at room temperature and shows highly enantioselective additions to aldehydes. The mild condition for
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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