Hexamethylphosphoramide
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
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
Precursor & DownStream
Precursor
DownStream
Articles
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Cationic naked nanocrystals (NCs) are useful building units for assembling hierarchical mesostructured materials. Until now, their preparation required strongly electrophilic reagents that irreversibl...
Modified in vivo comet assay detects the genotoxic potential of 14-hydroxycodeinone, an α,β-unsaturated ketone in oxycodone.Environ. Mol. Mutagen. 56 , 777-87, (2015)
14-Hydroxycodeinone (14-HC) is an α,β-unsaturated ketone impurity found in oxycodone drug substance and has a structural alert for genotoxicity. 14-HC was tested in a combined Modified and Standard Co...
Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane.Chem. Commun. (Camb.) (36) , 4309-11, (2008)
Lewis bases such as Ph3P=O and HMPA catalyze the 1,4-reduction of alpha,beta-unsaturated ketones with trichlorosilane, and because the 1,2-reduction of aldehydes scarcely proceeded under the condition...