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Dimethylcarbamoyl chloride

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Name

Dimethylcarbamoyl chloride

EINECS 201-208-6
CAS No. 79-44-7 Density 1.146 g/cm3
PSA 20.31000 LogP 0.90680
Solubility decomposes in water Melting Point -33 °C
Formula C3H6ClNO Boiling Point 166.8 °C at 760 mmHg
Molecular Weight 107.54 Flash Point 68.3 °C
Transport Information UN 2262 8/PG 2 Appearance colorless to yellow liquid
Safety 53-45-9 Risk Codes 45-22-23-36/37/38
Molecular Structure Molecular Structure of 79-44-7 (Dimethylcarbamoyl chloride) Hazard Symbols ToxicT
Synonyms

Carbamicchloride, dimethyl- (9CI);Carbamoyl chloride, dimethyl- (6CI,7CI,8CI);(Dimethylamino)carbonyl chloride;(N,N-Dimethylamino)carbonyl chloride;1-Chloro-N,N-dimethylformamide;Dimethylcarbamic acid chloride;Dimethylcarbamoyl chloride;Dimethylcarbamyl chloride;Dimethylchloroformamide;N,N-Dimethylcarbamic acid chloride;N,N-Dimethylcarbamidoyl chloride;N,N-Dimethylcarbamoyl chloride;N,N-Dimethylcarbamyl chloride;N,N-Dimethylchloroformamide;NSC 122671;N,N-dimethyl carbamyl chloride;

Article Data 59

Dimethylcarbamoyl chloride Synthetic route

75-44-5

phosgene

124-40-3

dimethyl amine

79-44-7

N,N-Dimethylcarbamoyl chloride

Conditions
ConditionsYield
at 200℃; Temperature;96.2%
at 275℃;
With benzene at 0℃;
With toluene
In 1,4-dioxane at 0 - 20℃;
2757-23-5

chloro(chlorosulfanyl)methanone

124-40-3

dimethyl amine

79-44-7

N,N-Dimethylcarbamoyl chloride

Conditions
ConditionsYield
Stage #1: chloro(chlorosulfanyl)methanone; dimethyl amine In dichloromethane at 40℃; Inert atmosphere;
Stage #2: With chlorine In dichloromethane at 20℃;
88%
32315-10-9

bis(trichloromethyl) carbonate

124-40-3

dimethyl amine

79-44-7

N,N-Dimethylcarbamoyl chloride

Conditions
ConditionsYield
With sodium hydroxide for 0.0333333h; Neat (no solvent);88%
With sodium hydrogencarbonate In dichloromethane at -10℃;50.4%
With pyridine In dichloromethane at 0 - 5℃;
137-26-8

Thiram

79-44-7

N,N-Dimethylcarbamoyl chloride

Conditions
ConditionsYield
Stage #1: Thiram With chlorine In dichloromethane at 24 - 26℃; for 6.33333h; Cooling with ice;
Stage #2: With water; sodium hydrogencarbonate In dichloromethane Cooling with ice;
86.2%
137-26-8

Thiram

A

16420-13-6

N,N-Dimethylthiocarbamoyl chloride

B

79-44-7

N,N-Dimethylcarbamoyl chloride

Conditions
ConditionsYield
With sulfuryl dichloride In benzene at 50℃; for 6h;A 83.2%
B 3.1%
With sulfuryl dichloride In benzene at 60℃; for 4h;A 83.2%
B 4.8%
88470-22-8

N-Methoxy-N-chloro-N',N'-dimethylurea

A

7541-16-4

methyl N,N-dimethylcarbamate

B

79-44-7

N,N-Dimethylcarbamoyl chloride

Conditions
ConditionsYield
In tetrachloromethane at 20℃; for 600h;A 63.3%
B 70%
1585-74-6

dimethylchloroamine

201230-82-2

carbon monoxide

79-44-7

N,N-Dimethylcarbamoyl chloride

Conditions
ConditionsYield
With 5%-palladium/activated carbon at 55℃; under 750.075 Torr; for 2h; Reagent/catalyst; Temperature;56%
687-48-9

ethyl N,N-dimethylcarbamate

79-44-7

N,N-Dimethylcarbamoyl chloride

Conditions
ConditionsYield
With trichlorophosphate In acetonitrile for 3.5h; Heating;46.6%
227945-00-8

diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate sodium

A

diethyl 2-amino-6-{[(N,N-dimethylamino)-carbonyloxy-carbamoyl]-methyl}-azulene-1,3-dicarboxylate

B

79-44-7

N,N-Dimethylcarbamoyl chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamideA 17%
B n/a
75-44-5

phosgene

506-59-2

N,N-dimethylammonium chloride

79-44-7

N,N-Dimethylcarbamoyl chloride

Dimethylcarbamoyl chloride Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 199.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 12 , 1976,p. 77.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 12 , 1976,p. 77.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.

Dimethylcarbamoyl chloride Standards and Recommendations

ACGIH TLV: Suspected Human Carcinogen
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen
DOT Classification:  8; Label: Corrosive

Dimethylcarbamoyl chloride Specification

The IUPAC name of this chemical is N,N-dimethylcarbamoyl chloride. With the CAS registry number 79-44-7, it is also named as Chloroformic acid dimethylamide. The product's categories are Pharmaceutical Intermediates; Protection & Derivatization Reagents (for Synthesis); Synthetic Organic Chemistry. It is a colorless to yellow liquid with a pungent odor. And it is soluble in ether, carbon disulfide, benzene and other organic solvents. Additionally, Dimethylcarbamoyl chloride reacts with water or moisture in the air to form hydrochloric acid and dimethylcarbamic acid. Moreover, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.24; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.24; (4)ACD/LogD (pH 7.4): 0.24; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 32.23; (8)ACD/KOC (pH 7.4): 32.23; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0 ; (12)Index of Refraction: 1.436; (13)Molar Refractivity: 24.54 cm3; (14)Molar Volume: 93.8 cm3; (15)Polarizability: 9.73×10-24 cm3; (16)Surface Tension: 30.6 dyne/cm; (17)Enthalpy of Vaporization: 40.32 kJ/mol; (18)Vapour Pressure: 1.76 mmHg at 25°C; (19)Exact Mass: 107.013792; (20)MonoIsotopic Mass: 107.013792; (21)Topological Polar Surface Area: 20.3; (22)Heavy Atom Count: 6; (23)Complexity: 61.8.

Preparation of Dimethylcarbamoyl chloride: The formyl chlorination of dimethylamine and phosgene to get crude Dimethylchloroformamide. Then we can get the product by deacidification. Reaction equation: (CH3)2NH+COCl2→(CH3)2NCOCl + HCl

Uses of Dimethylcarbamoyl chloride: It is used in the production of medicine, pesticide, dyes, plastics, synthetic materials, and other fine organic chemical products, such as for the production of Neostigmine bromide and Neostigmine methyl sulfate. And it also can react with pyridin-3-ol to get dimethyl-carbamic acid-[3]pyridyl ester. This reaction needs reagent pyridine.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and irritating to eyes, respiratory system and skin. In addition, this chemical may cause cancer. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Avoid exposure - obtain special instructions before use. 

People can use the following data to convert to the molecule structure.
1. SMILES:ClC(=O)N(C)C
2. InChI:InChI=1/C3H6ClNO/c1-5(2)3(4)6/h1-2H3
3. InChIKey:YIIMEMSDCNDGTB-UHFFFAOYAG

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LCLo inhalation 1000mg/m3/10M (1000mg/m3)   National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. OCT1942,
mouse LD50 intraperitoneal 300mg/kg (300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Zentralblatt fuer Arbeitsmedizin und Arbeitsschutz. Vol. 24, Pg. 71, 1974.
 
rat LC50 inhalation 180ppm/6H (180ppm)   Journal of Environmental Pathology and Toxicology. Vol. 4(1), Pg. 107, 1980.
rat LD50 oral 1gm/kg (1000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Zentralblatt fuer Arbeitsmedizin und Arbeitsschutz. Vol. 24, Pg. 71, 1974.
 

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