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Cas Database |
| Name |
Hexamethylphosphoramide |
EINECS | 211-653-8 |
| CAS No. | 680-31-9 | Density | 1.03 g/cm3 |
| PSA | 36.60000 | LogP | 0.77930 |
| Solubility | miscible with water | Melting Point |
7 °C(lit.) |
| Formula | C6H18N3OP | Boiling Point | 233 °C at 760 mmHg |
| Molecular Weight | 179.202 | Flash Point | 94.7 °C |
| Transport Information | N/A | Appearance | clear colorless to light amber liquid |
| Safety | 53-45-9 | Risk Codes | 45-46 |
| Molecular Structure |
|
Hazard Symbols |
 T
|
| Synonyms |
Phosphorictriamide, hexamethyl- (6CI,8CI,9CI);ENT 50,882;Eastman Inhibitor HPT;HMPA;HMPT;HMPTA;HPT;Hempa;Hexametapol;Hexamethylorthophosphoric triamide; |
Article Data | 81 |
Hexamethylphosphoramide Synthetic route
- 124-40-3
dimethyl amine
A
- 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide
C
- 137334-99-7
1,1,1,3,3,3-hexakis(dimethylamino)-1λ5,3λ5-diphosphazenium fluoride
| Conditions | Yield |
|---|---|
| Multistep reaction; | A n/a B n/a C 93% |
| Yield given. Multistep reaction; |
| Conditions | Yield |
|---|---|
| With Oxone In tetrahydrofuran; methanol Ambient temperature; | 93% |
| Conditions | Yield |
|---|---|
| With benzenesulfonyl chloride In diethyl ether | 92% |
| With substituted 3-hydroperoxy-1,2-benzisothiazole 1,1-dioxide In dichloromethane at 0℃; for 0.75h; | 98 % Spectr. |
| With oxygen; fullerene-C60 In 1,2-dichloro-benzene at 20℃; |
- 124-38-9
carbon dioxide
- 49778-01-0
iminotris(dimethylamino)phosphorane
A
- 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide
| Conditions | Yield |
|---|---|
| In benzene for 48h; | A 91% B 89% |
- 49778-01-0
iminotris(dimethylamino)phosphorane
A
- 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide
| Conditions | Yield |
|---|---|
| With carbon dioxide In benzene for 48h; | A 91% B 89% |
| Conditions | Yield |
|---|---|
| In neat (no solvent) heated (vac., 200°C); residue dissolved in C6H6; hexane added; vac. (100°C); elem.anal.; | A n/a B 89.1% |
- 1608-26-0
Hexamethylphosphorous triamide
A
- 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide
B
- 61904-00-5
tris(dimethylamino)methylphosphonium tetraphenylborate
| Conditions | Yield |
|---|---|
| With dimethylselenuranylidene derivative of 1,3-indandione In dichloromethane for 12h; Product distribution; Ambient temperature; other reagent, other time; | A n/a B 89% |
- 1608-26-0
Hexamethylphosphorous triamide
A
- 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide
B
- 1355083-83-8
2,5-di(piperidin-1-yl)-1,3,4-oxadiazole
| Conditions | Yield |
|---|---|
| at 20℃; for 0.25h; | A n/a B 85% |
- 694-59-7
pyridine N-oxide
- 108-91-8
cyclohexylamine
A
- 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide
B
- 15513-16-3
N-cyclohexylpyridin-2-amine
| Conditions | Yield |
|---|---|
| With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; | A n/a B 83% |
- 1605-65-8
N,N,N',N'-Tetramethylphosphorodiamidic chloride
A
- 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide
B
- 115-26-4
dimefox
C
- 354-43-8
N,N-dimethylphosphoramidic difluoride
| Conditions | Yield |
|---|---|
| With sodium hexaflorophosphate In various solvent(s) at 200℃; for 0.25h; | A 2% B 77% C 15% |
Hexamethylphosphoramide Chemical Properties
Molecule structure of Hexamethylphosphoramide (CAS NO.680-31-9):
IUPAC Name: N-[Bis(dimethylamino)phosphoryl]-N-methylmethanamine
Molecular Weight: 179.200381 g/mol
Molecular Formula: C6H18N3OP
Density: 1.032 g/cm3
Melting Point: 7 °C(lit.)
Boiling Point: 233 °C at 760 mmHg
Flash Point: 94.7 °C
Index of Refraction: 1.464
Molar Refractivity: 47.88 cm3
Molar Volume: 173.4 cm3
Surface Tension: 34.3 dyne/cm
Enthalpy of Vaporization: 46.97 kJ/mol
Vapour Pressure: 0.0572 mmHg at 25 °C
Water Solubility: miscible
Freezing Point: 7 °C
XLogP3: 0.3
H-Bond Acceptor: 4
Rotatable Bond Count: 3
Exact Mass: 179.118749
MonoIsotopic Mass: 179.118749
Topological Polar Surface Area: 26.8
Heavy Atom Count: 11
Canonical SMILES: CN(C)P(=O)(N(C)C)N(C)C
InChI: InChI=1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3
InChIKey: GNOIPBMMFNIUFM-UHFFFAOYSA-N
EINECS: 211-653-8
Classification Code: Agricultural Chemical ; Chemosterilants; Insect attractant, repellent and chemosterilant; Insecticide;
Mutation data; Pesticides; Reproductive Effect; Skin / Eye Irritant; TSCA Flag S [Substance is identified in a proposed or final SNUR (Significant New Use Rule) under TSCA]; Tumor data
Hexamethylphosphoramide Uses
Hexamethylphosphoramide (CAS NO.680-31-9) is a useful polar aprotic solvent and additive in organic synthesis.
Hexamethylphosphoramide is used as a solvent for polymers, gases, and organometallic compounds. It usefully improves the selectivity of lithiation reactions, because it breaks up the oligomers of lithium bases such as butyllithium. Hexamethylphosphoramide also used gas chromatography stationary phase, violet inhibitors, rocket fuel additives to reduce the freezing point, chemical sterilization agent.
Hexamethylphosphoramide Production
Hexamethylphosphoramide is producted by reacting of alkali chlorine and phosphorus.
Hexamethylphosphoramide Toxicity Data With Reference
| 1. | dns-hmn:hla 125 mg/L | PMRSDJ Progress in Mutation Research. 5 (1985),375. | ||
| 2. | cyt-hmn:lym 500 mg/L | MUREAV Mutation Research. 156 (1985),19. | ||
| 3. | sce-rat:lvr 2 g/L | PMRSDJ Progress in Mutation Research. 5 (1985),287. | ||
| 4. | ihl-rat TCLo:50 ppb/52W-C:CAR | AJPAA4 American Journal of Pathology. 106 (1982),8. | ||
| 5. | orl-rat LD50:2650 mg/kg | NATUAS Nature. 211 (1966),146. | ||
| 6. | skn-rat LDLo:3500 mg/kg | NATUAS Nature. 211 (1966),146. | ||
| 7. | orl-mus LD50:2400 mg/kg | NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. 70 (1974),114P. | ||
| 8. | ipr-mus LD50:1600 mg/kg | PMRSDJ Progress in Mutation Research. 1 (1981),682. | ||
| 9. | ivn-mus LD50:800 mg/kg | CHINAG Chemistry and Industry.(36),(1966),1529. | ||
| 10. | orl-rbt LDLo:1500 mg/kg | JEENAI Journal of Economic Entomology. 48 (1955),139. | ||
| 11. | skn-rbt LD50:2600 mg/kg |
Hexamethylphosphoramide Consensus Reports
NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 15 , 1977,p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Hexamethylphosphoramide Safety Profile
Hazard Codes: 
T
Risk Statements: 45-46
R45:May cause cancer.
R46:May cause heritable genetic damage.
Safety Statements: 53-45-9
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S9:Keep container in a well-ventilated place.
RIDADR: 2810
WGK Germany: 3
RTECS: TD0875000
F: 8
HazardClass: 6.1(b)
PackingGroup: III
Hazardous Substances Data: 680-31-9(Hazardous Substances Data)
Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Moderately toxic by ingestion, skin contact, intraperitoneal, and intravenous routes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of phosphine, POx, and NOx.
Hexamethylphosphoramide Standards and Recommendations
ACGIH TLV: Animal Carcinogen, Suspected Human Carcinogen
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen
Hexamethylphosphoramide Specification
Hexamethylphosphoramide (CAS NO.680-31-9) is also named as AI3-50882 ; CCRIS 332 ; ENT 50882 ; Eastman ; Inhibitor HPT ; HSDB 2031 ; Hempa ; Hexametapol ; Hexamethyl phosphoramide ; Hexamethylfosforamid ; Hexamethylfosforamid [Czech] ; Hexamethylorthophosphoric triamide ; Hexamethylphosphoric acid triamide ; Hexamethylphosphoric triamide ; N,N,N,N,N,N-Hexamethylphosphoric triamide ; NSC 113131 ; NSC 7967 ; Phosphoric acid hexamethyltriamide ; Phosphoric hexamethyltriamide ; Phosphoric triamide, hexamethyl- ; Phosphoric tris(dimethylamide) ; Phosphoryl hexamethyltriamide ; Tris(dimethylamino)phosphine oxide ; Tris(dimethylamino)phosphorus oxide ; Tris-(dimethylamid) kyseliny fosforecne ; Tris-(dimethylamid) kyseliny fosforecne [Czech] . Hexamethylphosphoramide (CAS NO.680-31-9) is clear colorless to light amber liquid with a spicy odor. It is soluble in water. Hexamethylphosphoramide may react with strong oxidizing agents and strong acids. It is susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Hexamethylphosphoramide is combustible.
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