Hexamethylphosphoramide

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Names

[ CAS No. ]:
680-31-9

[ Name ]:
Hexamethylphosphoramide

[Synonym ]:
hexamethyl
HMPTA
hexamethylphosphoric triamide
HPT
hexamethylphosphoric acid triamide
HEXAMETAPOL
Hexamethylphosphoramide
ENT 50,882
MFCD00008303
EINECS 211-653-8
HEMPA
HMPA
tris(dimethylamino)phosphine oxide
hexamethyl-phosphoric triamide
PO(NMe2)3 (hexamethylphosphorous triamide)
N,N,N',N',N'',N''-hexamethyl-phosphoric triamide

Chemical & Physical Properties

[ Density]:
1.03 g/mL at 25 °C(lit.)

[ Boiling Point ]:
230-232 °C740 mm Hg(lit.)

[ Melting Point ]:
7 °C(lit.)

[ Molecular Formula ]:
C₆H₁₈N₃OP

[ Molecular Weight ]:
179.20000

[ Flash Point ]:
222 °F

[ Exact Mass ]:
179.11900

[ PSA ]:
36.60000

[ LogP ]:
0.77930

[ Vapour density ]:
6.18 (vs air)

[ Vapour Pressure ]:
0.07 mm Hg ( 25 °C)

[ Index of Refraction ]:
n20/D 1.459(lit.)

[ Stability ]:
Stable. Incompatible with strong acids, strong oxidizing agents.

[ Water Solubility ]:
Miscible

[ Freezing Point ]:
7℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TD0875000

CHEMICAL NAME :: Phosphoric triamide, hexamethyl-

CAS REGISTRY NUMBER :: 680-31-9

LAST UPDATED :: 199712

DATA ITEMS CITED :: 101

MOLECULAR FORMULA :: C6-H18-N3-O-P

MOLECULAR WEIGHT :: 179.24

WISWESSER LINE NOTATION :: 1N1&PO&N1&1&N1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2650 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Kidney, Ureter, Bladder - hematuria Kidney, Ureter, Bladder - incontinence

TYPE OF TEST :: LCLo - Lowest published lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2920 mg/m3/4H

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea Blood - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3500 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - fasciculations Behavioral - convulsions or effect on seizure threshold Kidney, Ureter, Bladder - hematuria

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2600 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1175 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 835 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6 gm/kg/60D-C

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 8640 mg/kg/72D-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - bronchiectasis Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis)

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 400 ppb/6H/32W-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4600 mg/kg/92D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis) Endocrine - changes in thymus weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1500 mg/kg/21D-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in ovarian weight

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 ppb/52W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TC - Toxic concentration (other than lowest)

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 400 ppb/35W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TC - Toxic concentration (other than lowest)

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 ppb/26W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TC - Toxic concentration (other than lowest)

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 ppb/6H/1Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TC - Toxic concentration (other than lowest)

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4000 ppb/39W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TC - Toxic concentration (other than lowest)

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 ppb/6H/26W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TC - Toxic concentration (other than lowest)

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 400 ppb/6H/43W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TC - Toxic concentration (other than lowest)

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 ppb/6H/52W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TC - Toxic concentration (other than lowest)

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 ppb/6H/26W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TC - Toxic concentration (other than lowest)

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 ppb/6H/52W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2430 mg/kg

SEX/DURATION :: multigenerations

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2 gm/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Dominant lethal test

TYPE OF TEST :: Heritable translocation test

TYPE OF TEST :: Heritable translocation test

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Dominant lethal test

TYPE OF TEST :: Dominant lethal test

TYPE OF TEST :: Sperm Morphology

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Dominant lethal test

MUTATION DATA

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TEST SYSTEM :: Rodent - hamster Liver

REFERENCE :: PMRSDJ Progress in Mutation Research. (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.1- 1981- Volume(issue)/page/year: 5,397,1985 *** REVIEWS *** ACGIH TLV-Animal carcinogen (skin) DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 15,211,1977 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 15,211,1977 IARC Cancer Review:Group 2B IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-AUSTRALIA;Skin;Carcinogen JAN 1993 OEL-BELGIUM;Skin;Carcinogen JAN 1993 OEL-FINLAND;Carcinogen JAN 1993 OEL-FRANCE;Carcinogen JAN 1993 OEL-GERMANY;Carcinogen JAN 1993 OEL-SWEDEN;Carcinogen JAN 1993 OEL-SWITZERLAND:.;Skin;Carcinogen JAN 1993 OEL-SWITZERLAND;Skin;Carcinogen JAN 1993 OEL IN BULGARIA, COLOMBIA, JORDAN, KOREA check ACGIH TLV OEL IN NEW ZEALAND, SINGAPORE, VIETNAM check ACGIH TLV *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH RECOMMENDED EXPOSURE LEVEL (REL) : NIOSH REL TO THE CHEMICAL-air:CA lowest feasible concentration REFERENCE : NIOSH* National Institute for Occupational Safety and Health, U.S. Dept. of Health, Education, and Welfare, Reports and Memoranda. Volume(issue)/page/year: DHHS #92-100,1992 NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4066 No. of Facilities: 92 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 700 (estimated) No. of Female Employees: 51 (estimated)

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H340-H350

[ Precautionary Statements ]:
P201-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R45;R46

[ Safety Phrases ]:
S53-S45

[ RIDADR ]:
2810

[ WGK Germany ]:
3

[ RTECS ]:
TD0875000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

Hexamethylphosphorous triamide
phosphorodiamidic chloride, tetramethyl-
Triphenylphosphine
4-Nitrobenzaldehyde
tris(dimethylamino)[(ethoxycarbonyl)methylene]phosphorane
Tris-dimethylamino-phosphin-boran-Komplex
Dimethylamine
BOP reagent
stearic acid
4-Nitrobenzoic acid

DownStream

Methyl 4,4-dimethyl-3-oxopentanoate
Imino-tris(dimethylamino)phosphorane
2-picoline
2-(Dimethylaminomethyl)pyridine
bis(dimethylamino)chlorophosphine
Benzamide,N,N,4-trimethyl-
1,1'-(Trimethylene)dinaphthalene
5-Cyano-5H-dibenz[b,f]azepine
1,2-Benzisothiazol-3-amine,N,N-dimethyl-, 1,1-dioxide
N,N-dimethyl-2-nitrobenzamide

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Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane.

Chem. Commun. (Camb.) (36) , 4309-11, (2008)

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Hexamethylphosphoramide-d18
.(hexamethylphosphoramide)oxodiperoxomolybdenum
benzyltriphenylphosphonium (Mo(O)O2(CN)3) hexamethylphosphoramide
dioxo-(pyridine-2,6-dicarboxylato)(hexamethylphosphoramide)molybdenum(VI)
O-{[1-(4-chloro-1-ethyl-1H-imidazol-5-yl)cyclopropyl]methyl}hydroxylamine
1-methyl-3-(oxan-4-yl)-1H-pyrazole-4-thiol
2-[1-(2-Methyl-6-nitrophenyl)cyclopropyl]propan-2-amine
tert-butyl N-[3-amino-2-(2-methyloxolan-3-yl)propyl]carbamate
rac-(1R,2R)-2-(2-fluoro-4-hydroxyphenyl)cyclopropane-1-carboxylic acid
3-(6-Fluoropyridin-3-yl)azetidin-3-ol
3-(1-ethyl-1H-imidazol-2-yl)-2,2-dimethylpropan-1-ol
rac-(1R,3S)-2,2-dimethyl-3-(thiolan-3-yl)cyclopropane-1-carboxylic acid
5-(5-methyl-1,2-oxazol-3-yl)-1H-imidazol-2-amine
2-Methoxy-3-[(3-methylazetidin-3-yl)oxy]quinoline

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