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CAS No.: | 2315-36-8 |
---|---|
Name: | N,N-Diethylchloroacetamide |
Article Data: | 53 |
Molecular Structure: | |
Formula: | C6H12ClNO |
Molecular Weight: | 149.62 |
Synonyms: | 2-(Diethylamino)-2-oxoethylchloride;2-Chloro-N,N-diethylacetamide;CDEA;Chloro-N,N-diethylacetamide;N,N-Diethyl-2-chloroacetamide;N-(2-Chloroacetyl)diethylamine;N-(Chloroacetyl)diethylamine;NSC 1726;a-Chloro-N,N-diethylacetamide; |
EINECS: | 219-019-2 |
Density: | 1.043 g/cm3 |
Melting Point: | 58 °C |
Boiling Point: | 236.8 °C at 760 mmHg |
Flash Point: | 77 °C |
Solubility: | soluble in water |
Appearance: | clear brown liquid |
Hazard Symbols: | T+, Xn |
Risk Codes: | 36/37/38-26-21/22-20/21/22 |
Safety: | 45-38-36/37/39-28A-26-28-36 |
Transport Information: | UN 2810 |
PSA: | 20.31000 |
LogP: | 1.09360 |
Conditions | Yield |
---|---|
In dichloromethane; water at 5℃; Temperature; Solvent; | 100% |
With triethylamine In dichloromethane at 0℃; | 99% |
With triethylamine In 1,2-dichloro-ethane at 10 - 20℃; for 3h; Cooling with ice; | 95% |
Conditions | Yield |
---|---|
With benzene |
Conditions | Yield |
---|---|
(i) nBuLi, (ii) H2O; Multistep reaction; |
2-diethylamino-4,5-dimethyl-2,2-dipropoxy-2λ5-[1,3,2]dioxaphosphole
Chloroacetic anhydride
2-Chloro-N,N-diethylacetamide
Conditions | Yield |
---|---|
Stage #1: chloroacetic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; Stage #2: diethylamine With dmap In dichloromethane at 20℃; |
Conditions | Yield |
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With N-ethyl-N,N-diisopropylamine |
2-bromoacetyl chloride
diethylamine
A
2-bromo-N,N-diethylacetamide
B
2-Chloro-N,N-diethylacetamide
Conditions | Yield |
---|---|
In dichloromethane at -25 - 20℃; for 3.5h; |
2-Chloro-N,N-diethylacetamide
N,N-diethyl-2-iodoacetamide
Conditions | Yield |
---|---|
With sodium iodide In acetone for 48h; | 100% |
With sodium iodide In acetone for 0.25h; Heating; | |
With sodium iodide In tetrahydrofuran; N,N-dimethyl-formamide for 1h; Substitution; Heating; | |
Multi-step reaction with 2 steps 1: 4 h / 0 - 20 °C 2: iodine View Scheme |
2-Chloro-N,N-diethylacetamide
Conditions | Yield |
---|---|
Stage #1: 2-Chloro-N,N-diethylacetamide With lithium diisopropyl amide In tetrahydrofuran at -80℃; for 0.333333h; Stage #2: ethyl 2-methylene-6-(tert-butyldimethylsilyl)-5,6-epoxy-(Z)-3-hexenoate In tetrahydrofuran at -80℃; for 0.25h; | 100% |
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The IUPAC name of N,N-Diethylchloroacetamide is 2-chloro-N,N-diethylacetamide. With the CAS registry number 2315-36-8, it is also named as Diethylamid kyseliny chloroctove. The product's categories are Industrial / Fine Chemicals; Amide; Amide Organic Building Blocks; Carbonyl Compounds; Herbicides; Pesticides & Metabolites. It is clear brown liquid which is highly toxic. When heated to decomposition it emits very toxic fumes of Cl− and NOx. So the storage environment should be well-ventilated, low-temperature and dry. Keep N,N-Diethylchloroacetamide separate from raw materials of food.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.55; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.55; (4)ACD/LogD (pH 7.4): 0.55; (5)ACD/BCF (pH 5.5): 1.54; (6)ACD/BCF (pH 7.4): 1.54; (7)ACD/KOC (pH 5.5): 47.37; (8)ACD/KOC (pH 7.4): 47.37; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.449; (13)Molar Refractivity: 38.44 cm3; (14)Molar Volume: 143.3 cm3; (15)Polarizability: 15.24×10-24 cm3; (16)Surface Tension: 31.6 dyne/cm; (17)Enthalpy of Vaporization: 47.36 kJ/mol; (18)Vapour Pressure: 0.0465 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Exact Mass: 149.060742; (21)MonoIsotopic Mass: 149.060742; (22)Topological Polar Surface Area: 20.3; (23)Heavy Atom Count: 9; (24)Complexity: 91.1.
Preparation of N,N-Diethylchloroacetamide: It can be obtained by diethylamine and chloroacetyl chloride. This reaction needs reagents aq. NaOH, NH3 and solvent 1,2-dichloro-ethane at temperature of -15--10 °C. The reaction time is 45 min.
Uses of N,N-Diethylchloroacetamide: It is used as intermediate of pharmaceutical and as raw material of polyurethane additive. It is also used in organic synthesis. For example: it can react with phosphorous acid triethyl ester to get (diethylcarbamoyl-methyl)-phosphonic acid diethyl ester. This reaction must react at temperature of 180 °C for 8 hours. The yield is 84.2%.
When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of insufficient ventilation, wear suitable respiratory equipment. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
1. SMILES:ClCC(=O)N(CC)CC
2. InChI:InChI=1/C6H12ClNO/c1-3-8(4-2)6(9)5-7/h3-5H2,1-2H3
3. InChIKey:CQQUWTMMFMJEFE-UHFFFAOYAF
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LC50 | inhalation | 175mg/m3/4H (175mg/m3) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 35(6), Pg. 36, 1991. |
mouse | LC50 | inhalation | 270mg/m3/2H (270mg/m3) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 35(6), Pg. 36, 1991. |
mouse | LD50 | oral | 226mg/kg (226mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 35(6), Pg. 36, 1991. |
rat | LC50 | inhalation | 315mg/m3/4H (315mg/m3) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 35(6), Pg. 36, 1991. |
rat | LD50 | oral | 500mg/kg (500mg/kg) | Residue Reviews. Vol. 10, Pg. 97, 1965. | |
rat | LD50 | skin | 980mg/kg (980mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 33(2), Pg. 51, 1989. |