Basic information
- CAS
685-91-6- Standard SMILES
CCN(CC)C(C)=O- InChIKey
AJFDBNQQDYLMJN-UHFFFAOYSA-N- Molecular formula
- C6H13NO
- Average molar mass
- 115.17 g/mol
- Monoisotopic mass
- 115.09971404
Names & identifiers
- Preferred name
- N,N-Diethylacetamide
- IUPAC
- N,N-diethylacetamide
- English name
- Diethylacetamide
- Molecular formula
- C6H13NO
- Molecular weight
- 115.17
Names & synonyms
Show more names
Database identifiers
- CAS
685-91-6- PubChem CID
- 12703
- DTXSID
DTXSID9020459- ChEMBL
CHEMBL3184758- UNII
- 6YO81D7ST6
- EC Number
- 211-685-2
- Nikkaji
- J33.415D
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 20.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 76
Experimental & physicochemical properties
Vapor Pressure
0.89 [mmHg]
2 MM HG @ 35 °C
Physicochemical properties
- Melting point
- 20 °C · <20 °C
- Boiling point
- 182 · 182-186 °C (lit.)
- Density
- 0.925 g/mL · 0.925 g/mL at 25 °C (lit.)
- vapor pressure
- 1.2 hPa · 1.2 hPa (25 °C)
- refractive index
- 20 · n20/D 1.440(lit.)
- Flash point
- 159 °F · 159 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 53.5 g/l · 53.5g/l
- pka
- -0.41 · -0.41±0.70(Predicted)
- form
- clear liquid
- color
- Colorless to Almost colorless
- Water Solubility
- Soluble in water.
- BRN
- 1209428 · 1209428
- Dielectric constant
- 31.33 · 31.329999999999998
- InChI
- 1S/C6H13NO/c1-4-7(5-2)6(3)8/h4-5H2,1-3H3
- InChIKey
- AJFDBNQQDYLMJN-UHFFFAOYSA-N
- SMILES
- CCN(CC)C(C)=O
- CAS DataBase Reference
- 685 · 685-91-6(CAS DataBase Reference)
- FDA UNII
- 6 YO81D7ST6 · 6YO81D7ST6
- NIST Chemistry Reference
- Acetamide, N,N-diethyl-(685-91-6)
- EPA Substance Registry System
- N,N-Diethylacetamide (685-91-6)
- UNSPSC Code
- 12352111 · 12352111
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332-H315-H319-H335
- Precautionary statements
- 261 · P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn
- Risk Statements
- 20 · 20/21/22-36/37/38
- Safety Statements
- 26 · 26-27-36/37/39-45
- WGK Germany
- 3 · 3
- RTECS
- 7000000 · AB7000000
- TSCA
- TSCA listed
- HS Code
- 29241900 · 29241900
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 685 · 685-91-6(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 1500 mg/kg
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.2% (1 of 46) of reports.
Warning
H302 (97.8%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (87%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (97.8%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (97.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H332 (87%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (87%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 46 reports by companies.;There are 5 notifications provided by 45 of 46 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: Acetamide, N,N-diethyl-
N,N-Diethylacetamide: Does not have an individual approval but may be used under an appropriate group standard
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. N,N-Diethylacetamide is included on this list.
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Human Toxicity Excerpts
DIMETHYL ACETAMIDE HAS A RELATIVELY MODERATE HEPATOTOXIC ACTION IN OCCUPATIONALLY EXPOSED WORKERS. DUE TO SCANT KNOWLEDGE OF DIMETHYL ACETAMIDE TOXICITY, DATA RELATIVE TO SOME CMPDS WHICH PRESENT STRUCTURES & ACTION ANALOGUES TO DIMETHYL ACETAMIDE & WHOSE TOXICITY IS BETTER KNOWN ARE REPORTED AS AN APPENDIX.
Non-Human Toxicity Excerpts
THE CARCINOGENIC ACTIVITY OF DIETHYLACETAMIDE WAS STUDIED BECAUSE OF ITS ABILITY TO DENATURE PROTEINS & STRUCTURAL RESEMBLANCE TO NITROSAMINE DERIVATIVES. INGESTED, IT PRODUCED A TRANSITIONAL CELL CARCINOMA OF RAT KIDNEY & SEVERE RENAL DAMAGE. EVIDENCE DOES NOT SUPPORT THE VIEW THAT CYCLIC NITROSAMINES EXERT THEIR CARCINOGENIC ACTION VIA METAB TO DIAZOALKANES.
N,N-DIETHYLACETAMIDE 600 MG/KG GIVEN TO PREGNANT RATS ON THE 13TH OR 14TH DAYS OF GESTATION PRODUCED DIAPLACENTAL TERATOGENIC EFFECTS. THIS WAS 40% OF THE LD50 DOSE.
CMPDS INCLUDING N,N-DIETHYLACETAMIDE SHOWED NONSPECIFIC SPASMOLYTIC PROPERTIES AGAINST HISTAMINE-, CARBACHOL-, & BARIUM CHLORIDE-INDUCED SPASMS IN ISOLATED GUINEA PIG ILEUM, & AT LOW IV DOSES AFFECTED THE HEART RATE & BLOOD PRESSURE IN RATS, CATS, & DOGS.
IN MOUSE LIVER HOMOGENATES, N,N-DIETHYLACETAMIDE HAD NO EFFECT ON A SERIES OF LIVER MIXED-FUNCTION OXIDASE & CYTOCHROME C REDUCTASE ACTIVITIES, BUT IN VIVO (150 MG/KG, IP) IT INHIBITED THESE ACTIVITIES WITHIN 45 MIN & INCREASED HEXOBARBITAL SLEEPING TIME.
INJECTIONS OF N,N-DIETHYLACETAMIDE INDUCED SOME JUMPS OF CONVULSIONS IN MICE. IT INDUCED TESTICULAR ATROPHY IN RATS. RATS GIVEN 1/20 LD50 DOSES DAILY FOR 6 WK DID NOT EXHIBIT TOXIC EFFECTS BUT DID EXHIBIT DECREASED PONDERAL GROWTH.
Antidote and Emergency Treatment
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/
Non-Human Toxicity Values
LD50 Rat oral 1500 mg/kg
LD50 Rat iv 1 g/kg
LD50 Mouse ip 1690 mg/kg
LD50 Dog iv 1 g/kg
Regulatory information
Regulatory Information
Chemical: Acetamide, N,N-diethyl-
N,N-Diethylacetamide: Does not have an individual approval but may be used under an appropriate group standard
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. N,N-Diethylacetamide is included on this list.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AB7000000
- hs_code
- 29241900
- Toxicity
- LD50 orally in Rabbit: 1500 mg/kg
- risk_code
- 20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-27-36/37/39-45
- Storage Class
- 10 - Combustible liquids
- target organs
- Respiratory system
- Hazard statements
- H302+H312+H332-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
- Hazardous Substances Data
- 685-91-6(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
General Manufacturing Information
Acetamide, N,N-diethyl-: ACTIVE
DIETHYLACETAMIDE- AN EXAMPLE OF DRUG ABUSE.
SOLVENTS WERE TESTED IN MICE FOR THEIR TOXICITY, CENTRAL NERVOUS SYSTEM PROFILE, AND ACTIVITY IN THE INCLINED SCREEN AND BALANCE ROD TESTS AFTER INTRAPERITONEAL ADMINISTRATION, PLUS THEIR INFLUENCE ON THE HEXABARBITONE SLEEPING TIME AND MUSCLE RELAXANT PROPERTIES ON THE ROTA-ROD AFTER ORAL ADMINISTRATION. N,N-DIETHYLACETAMIDE WAS RECOMMENDED NOT TO EXCEED A CONCENTRATION OF 0.3 IN DRUG SOLUTIONS AS SOLVENT FOR SCREENING PURPOSES.
Applications
UsesN,N-Diethylacetamide was used to investigate the spectroscopic properties ofN,N-diethyl-2-[(4-substituted)phenylsulfinyl] acetamides. It is commonly used as drug solvent.
General DescriptionN,N-Diethylacetamide is commonly used as drug solvent.
Preparation methods
PreparationThe industrial synthesis route for N,N-diethylacetamide is as follows: 3 tons of acetic acid are pumped into the bottom of a 10 m³ packed column. Diethylamine is pumped into the bottom of the column at a rate of 200 kg/h. The temperature is raised to 60°C to establish reflux. Once the column temperature stabilizes, diethylamine is collected from the top of the column at a rate of 200 kg/h and returned directly to the bottom of the distillation column. Process wastewater is collected from the second section of the distillation column at a rate of 36 kg/h and treated in a wastewater treatment system. When the purity of the product in the bottom of the column exceeds 98.0%, the ethylenediamine flow is stopped, and distillation is performed to obtain 5.31 tons of crude N,N-diethylacetamide, with a yield of 94.3% and a purity of 98.6%. Then, 100 kg of calcium oxide (118% excess) is added to the crude product, and the mixture is stirred at 60°C for 1 hour. Distillation yields 5.08 tons of refined N,N-diethylacetamide. This method uses ethylenediamine and acetic acid as raw materials. It promotes the forward reaction by removing water and recycled diethylamine produced in the reaction through reactive distillation. Compared to existing processes, this method is simpler, as the reaction and distillation sections share a single set of equipment, requiring less floor space and lower equipment investment. Furthermore, it eliminates the need for catalysts, making it more economical and efficient than previous methods.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
Compound notes
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