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680-31-9

Basic Information
CAS No.: 680-31-9
Name: Hexamethylphosphoramide
Article Data: 81
Molecular Structure:
Molecular Structure of 680-31-9 (Hexamethylphosphoramide)
Formula: C6H18N3OP
Molecular Weight: 179.202
Synonyms: Phosphorictriamide, hexamethyl- (6CI,8CI,9CI);ENT 50,882;Eastman Inhibitor HPT;HMPA;HMPT;HMPTA;HPT;Hempa;Hexametapol;Hexamethylorthophosphoric triamide;
EINECS: 211-653-8
Density: 1.03 g/cm3
Melting Point: 7 °C(lit.)
Boiling Point: 233 °C at 760 mmHg
Flash Point: 94.7 °C
Solubility: miscible with water
Appearance: clear colorless to light amber liquid
Hazard Symbols: ToxicT
Risk Codes: 45-46
Safety: 53-45-9
PSA: 36.60000
LogP: 0.77930
Synthetic route
124-40-3

dimethyl amine

A

680-31-9

N,N,N,N,N,N-hexamethylphosphoric triamide

B

C11H30N6P(1+)

C

137334-99-7

1,1,1,3,3,3-hexakis(dimethylamino)-1λ5,3λ5-diphosphazenium fluoride

Conditions
ConditionsYield
Multistep reaction;A n/a
B n/a
C 93%
Yield given. Multistep reaction;
603-35-0

triphenylphosphine

680-31-9

N,N,N,N,N,N-hexamethylphosphoric triamide

Conditions
ConditionsYield
With Oxone In tetrahydrofuran; methanol Ambient temperature;93%
1608-26-0

Hexamethylphosphorous triamide

680-31-9

N,N,N,N,N,N-hexamethylphosphoric triamide

Conditions
ConditionsYield
With benzenesulfonyl chloride In diethyl ether92%
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

B

N,N,N',N',N'',N''-hexamethylphosphorimidic triamide cyanate

Conditions
ConditionsYield
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

B

N,N,N',N',N'',N''-hexamethylphosphorimidic triamide cyanate

Conditions
ConditionsYield
With carbon dioxide In benzene for 48h;A 91%
B 89%

CaCl2*3(N(CH3)2)3PO

A

680-31-9

N,N,N,N,N,N-hexamethylphosphoric triamide

B

CaCl2*2(N(CH3)2)3PO

Conditions
ConditionsYield
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
ConditionsYield
With dimethylselenuranylidene derivative of 1,3-indandione In dichloromethane for 12h; Product distribution; Ambient temperature; other reagent, other time;A n/a
B 89%

1,1'-azodicarbonyl-dipiperidine

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
ConditionsYield
at 20℃; for 0.25h;A n/a
B 85%
694-59-7

pyridine N-oxide

bromo-tris-dimethylamino-phosphonium hexafluorophosphate

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
ConditionsYield
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
ConditionsYield
With sodium hexaflorophosphate In various solvent(s) at 200℃; for 0.25h;A 2%
B 77%
C 15%
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Chemistry

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

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.

Production

 Hexamethylphosphoramide is producted by reacting of alkali chlorine and phosphorus.

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

   

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.

Safety Profile

Hazard Codes: ToxicT
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.

Standards and Recommendations

ACGIH TLV: Animal Carcinogen, Suspected Human Carcinogen
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen

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.