N,N-Diethylacetamide

HCID 12703

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

N,N-DIETHYLACETAMIDE685-91-6Acetamide, N,N-diethyl-DTXSID9020459Acetic acid, amide, N,N-diethyl6YO81D7ST6NSC-101DTXCID10459RefChem:161180211-685-2DiethylacetamideN-Acetyldiethylamine
Show more names
CH3CON(C2H5)2ACETYL DIETHYLAMINEn,n-diethyl-acetamidN,N-Diethylethanamideacetamine,n,n-diethyl-
MFCD00009047N,N-diethyl-acetamideN,N-DiaethylacetamidN,N-Diaethylacetamid [German]HSDB 5513NSC 101Acetic acid diethylamideAcetamide,N,N-Diethyl-

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

Experimental & physicochemical properties

LogPlog Kow = 0.34
OdorFaint odor
Density0.9130 @ 17 °C
Color/FormColorless liquid
SolubilitySol in water, alcohol; sol in all proportions in ether, acetone, benzene
Flash Point170 °F

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 2 items

Chemical: Acetamide, N,N-diethyl-

N,N-Diethylacetamide: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialFlammable when exposed to heat or flame.
Hazards SummaryOral LD50 (rat) = 1500 mg/kg; [HSDB] An irritant; [MSDSonline] See Dimethyl acetamide.
TSCA Requirements · 1 item

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.

Toxic Combustion ProductsWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Hazard Classes and CategoriesAcute Tox. 4 (97.8%);Acute Tox. 4 (87%);Skin Irrit. 2 (97.8%);Eye Irrit. 2 (97.8%);Acute Tox. 4 (87%);STOT SE 3 (87%)

Safety & protection

Fire Fighting ProceduresTo fight fire, use foam, mist, /carbon dioxide/, dry chemical.
Disposal Methods · 1 item

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

InteractionsCMPDS INCLUDING N,N-DIETHYLACETAMIDE SHOWED NONSPECIFIC SPASMOLYTIC PROPERTIES AGAINST HISTAMINE-, CARBACHOL-, & BARIUM CHLORIDE-INDUCED SPASMS IN ISOLATED GUINEA PIG ILEUM.
Adverse EffectsNeurotoxin - Acute solvent syndrome;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Human Toxicity Excerpts · 1 item

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 · 5 items

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 · 2 items

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 · 4 items

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 · 2 items

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 · 1 item

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

Chemistry & industry

Pharmacology

Metabolism/MetabolitesIN MICE, THE DISCREPANCY BETWEEN IN VITRO & IN VIVO LIVER ENZYME INHIBITION ACTIVITY MAY BE DUE TO OXIDATIVE N-DEALKYLATION OF N,N-DIETHYLACETAMIDE OCCURRING IN VIVO, FACILITATING THE INHIBITION.

Uses & manufacturing

General Manufacturing Information · 3 items

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 · 1 item

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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
武汉欣扬瑞和化学科技有限公司13720274133 · [email protected]

Related reactions

28 records

Compound notes

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