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Dimethylcarbamoyl chloride

Overview Production Physiochemical properties Applications Warning and Risk References
Dimethylcarbamoyl chloride
Dimethylcarbamoyl chloride structure
CAS No.
79-44-7
Chemical Name:
Dimethylcarbamoyl chloride
Synonyms
dmcc;DMCF;DMCL;tl389;TL 389;carbamyL;NCS-122671;Dimethylcarbamoyl;AKOS BBS-00004352;rcrawastenumberu097
CBNumber:
CB7672462
Molecular Formula:
C3H6ClNO
Formula Weight:
107.54
MOL File:
79-44-7.mol

Dimethylcarbamoyl chloride Properties

Melting point:
−33 °C(lit.)
Boiling point:
167-168 °C775 mm Hg(lit.)
Density 
1.168 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.453
Flash point:
155 °F
pka
-1.85±0.70(Predicted)
form 
Liquid
Specific Gravity
1.172
Water Solubility 
Decomposes
Sensitive 
Moisture Sensitive
BRN 
878197
CAS DataBase Reference
79-44-7(CAS DataBase Reference)
EWG's Food Scores
5
FDA UNII
5D54S95GT6
Proposition 65 List
Dimethylcarbamoyl Chloride
IARC
2A (Vol. 12, Sup 7, 71) 1999
NIST Chemistry Reference
Carbamic chloride, dimethyl-(79-44-7)
EPA Substance Registry System
Dimethylcarbamoyl chloride (79-44-7)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS06,GHS08
Signal word  Danger
Hazard statements  H227-H302-H315-H319-H331-H335-H350
Precautionary statements  P210e-P305+P351+P338-P405-P501a-P201-P261-P280-P304+P340+P312-P308+P313-P403+P233
Hazard Codes  T
Risk Statements  45-22-23-36/37/38
Safety Statements  53-45-99
RIDADR  UN 2262 8/PG 2
WGK Germany  3
RTECS  FD4200000
9
TSCA  Yes
HazardClass  8
PackingGroup  II
HS Code  29241990

Dimethylcarbamoyl chloride price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D152803 Dimethylcarbamyl chloride 98% 79-44-7 5g $29.9 2021-03-22 Buy
Sigma-Aldrich D152803 Dimethylcarbamyl chloride 98% 79-44-7 100g $35.7 2021-03-22 Buy
TCI Chemical D0695 Dimethylcarbamoyl Chloride >98.0%(GC)(T) 79-44-7 25g $24 2021-03-22 Buy
TCI Chemical D0695 Dimethylcarbamoyl Chloride >98.0%(GC)(T) 79-44-7 500g $102 2021-03-22 Buy
Alfa Aesar L03415 Dimethylcarbamyl chloride, 96% 79-44-7 25g $29.8 2021-03-22 Buy

Dimethylcarbamoyl chloride Chemical Properties,Uses,Production

Overview

Dimethylcarbamoyl chloride is a useful intermediate in the production of pharmaceuticals, pesticides, and dyes. However, due to its high toxicity that may induce both acute effects and be of cancer risk, it is strictly limited for application[1].

Production

Dimethylcarbamoyl chloride has been produced since 1961(IARC 1999)[2]. In 2009, it was produced commercially by one manufac¬turer in Europe and two manufacturers in India[3] and was available from 17 suppliers worldwide, including 8 U.S. suppliers[4]. No data on U.S. imports or exports of dimethyl¬ carbamoyl chloride were found. Under the U.S. Environmental Pro¬tection Agency’s Toxic Substances Control Act Inventory Update Rule, production plus imports of dimethylcarbamoyl chloride totaled be¬ tween 10,000 and 500,000 lb in 1990; no other inventory update re¬ports were filed[5].
Dimethylcarbamoyl chloride can be manufactured by the following several methods[6-8]:

Physiochemical properties

Dimethylcarbamoyl chloride appears as a clear liquid at room temperature with a pungent odor and a tear-penetrating effect, which decomposes rapidly in water[1-2].
Dimethylcarbamoyl chloride is similar with an acid chloride whose chlorine atom can be exchanged for other nucleophiles. Therefore, it is capable of reacting with alcohols, phenols and oximes to the corresponding N, N-dimethylcarbamates, with thiols to thiolourethanes, with amines and hydroxylamine to substituted ureas, and with imidazoles and triazoles to carbamoylazoles[9].

Applications

Dimethylcarbamoyl chloride is used as an intermediate in the production of pharmaceuticals, pesticides, and dyes[10]. It is a reagent being capable of transferring a dimethylcarbamoyl group to alcoholic or phenolic hydroxyl groups forming dimethyl carbamates with pharmacological or pesticidal activities[11]. Dimethylcarbamoyl Chloride is also a reagent used in the induction of apoptosis in human lung adenocarcinoma by T-type calcium channel antagonist[12].
Dimethylcarbamoyl chloride is used as the starting material for the insecticide class of the dimethyl carbamates which act as inhibitors of acetylcholinesterase such as dimetilane and the related compounds isolane, pirimicarb and triazamate[13,14].
Dimethylcarbamoyl chloride can be used for the manufacturing of the quaternary ammonium compounds neostigmine, which finds pharmaceutical applications as acetylcholinesterase inhibitors[15].
Dimethylcarbamoyl chloride is also used in the synthesis of the benzodiazepine camazepam[16].

Warning and Risk

Dimethylcarbamoyl chloride can cause acute effect if not used properly. It is also a potential carcinogenic regent due to its high toxicity[17-20].
Acute effect
Workers exposing to dimethylcarbamoyl chloride can suffer from both eye irritation and liver disturbance. Acute inhalation exposure to dimethylcarbamoyl chloride has been found to result in damaged mucous membranes of the nose, throat, and lungs and cause difficulty in breathing in rats. Rats and rabbits experiments have also demonstrated that acute dermal exposure can cause skin irritation as well as conjunctivitis and keratitis in eyes. In addition, acute exposure of rats has also demonstrated dimethylcarbamoyl chloride to have high acute toxicity via inhalation and moderate acute toxicity via ingestion[17].
Cancer Risk
There are inadequate data on the carcinogenic effects of dimethylcarbamoyl chloride in humans[18, 21,22]. However, cancer risk of dimethylcarbamoyl chloride has been demonstrated in the rats and mice experiments. Inhalation exposure has been found to induce nasal tract carcinomas in rats and male hamsters. Skin tumors have also been observed among dermally exposed mice. Moreover, local sarcomas have been observed following subcutaneous injection in mice[21,22].

References

  1. https://ntp.niehs.nih.gov/ntp/roc/content/profiles/dimethylcarbamoylchloride.pdf
  2. http://www.allfordrugs.com/tag/dimethylcarbamoyl-chloride/
  3. SRI. 2009. Directory of Chemical Producers. Menlo Park, CA: SRI Consulting. Database edition. Last accessed: 4/22/09. 
  4. ChemSources. 2009. Chem Sources Chemical Search. Chemical Sources International. http://www. chemsources.com/chemonline.html and search on dimethylcarbamoyl chloride. Last accessed: 5/09. 
  5. EPA. 2004. Non-confidential IUR Production Volume Information. U.S. Environmental Protection Agency. http://www.epa.gov/oppt/iur/tools/data/2002-vol.html and search on CAS number. Last accessed: 4/21/05.
  6. G. Karimipour; S. Kowkabi; A. Naghiha[2015], "New aminoporphyrins bearing urea derivative substituents: synthesis, characterization, antibacterial and antifungal activity"[in German], Braz. Arch. Biol. Technol. 58[3], doi:10.1590/S1516-891320500024
  7. H. Babad; A.G. Zeiler[1973], "Chemistry of Phosgene"[in German], Chem. Rev. 73[1]: pp. 75–91, doi:10.1021/cr60281a005
  8. T. Saegusa; T. Tsuda; Y. Isegawa[1971], "Carbamoyl chloride formation from chloramine and carbon monoxide"[in German], J. Org. Chem. 36[6]: pp. 858–860, doi:10.1021/jo00805a033
  9. C.B. Kreutzberger, R.A. Olofson[2007-02-01]. "Dimethylcarbamoyl Chloride"[in German]. John Wiley&Sons, Ltd. Retrieved 2016-09-27.
  10. https://www.epa.gov/sites/production/files/2016-09/documents/dimethylcarbamoyl-chloride.pdf
  11. R.P. Pohanish[2011][in German], Sittig’s Handbook of Toxic and Hazardous Chemicals and Carcinogens, 6th Edition, Amsterdam: Elsevier, pp. 1045–1047, ISBN 978-1437778694
  12. https://www.trc-canada.com/product-detail/?D471295
  13. T. Grauer, H. Urwyler, "Production of 1-N, N-dimethylcarbamoyl-5-methyl-3-N, N-dimethyl-carbamoyl-oxy-pyrazole"
  14. J.A. Aeschlimann; M. Reinert[1931], "Pharmacological action of some analogues of physostigmine"[in German], J. Pharmacol. Exp. Ther. 43[3]: pp. 413–444
  15. J.A. Aeschlimann, "Disubstituted carbamic acid esters of phenols containing a basic constituent"
  16. "Verfahren zur Herstellung des 3-N, N-Dimethylcarbamoyl-oxy-1-methyl-5-phenyl-7-chlor-1,3-dihydro-2H-1,4-benzodiazepin-2-on"
  17. https://www.epa.gov/sites/production/files/2016-09/documents/dimethylcarbamoyl-chloride.pdf
  18. International Agency for Research on Cancer[IARC]. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man: Some Carbamates, Thiocarbamates and Carbazides. Volume 12. World Health Organization, Lyon. 1976. 
  19. U.S. Department of Health and Human Services. Hazardous Substances Data Bank[HSDB, online database]. National Toxicology Information Program, National Library of Medicine, Bethesda, MD. 1993. 
  20. U.S. Department of Health and Human Services. Registry of Toxic Effects of Chemical Substances[RTECS, online database]. National Toxicology Information Program, National Library of Medicine, Bethesda, MD. 1993. 
  21. International Agency for Research on Cancer[IARC]. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42. Supplement 7. World Health Organization, Lyon. 1987. 
  22. U.S. Department of Health and Human Services[DHHS]. The 8th Report on Carcinogens. 1998 Summary. Public Health Service, National Toxicology Program. Research Triangle Park, NC. 1998. 

Chemical Properties

Clear colorless liquid

Uses

Dimethylcarbamoyl chloride has been used primarily as a chemical intermediate in the production of dyes, pharmaceuticals, pesticides, and rocket fuel (IARC 1999, HSDB 2009).

Uses

As a chemical intermediate in the manufacture of carbamate drugs and pesticides

General Description

A colorless to yellow liquid with a pungent odor. Burns to skin, eyes and mucous membranes. A lachrymator. Used to make dyes and pharmaceuticals.

Air & Water Reactions

Reacts with water or moisture in the air to form hydrochloric acid and dimethylcarbamic acid.

Reactivity Profile

Dimethylcarbamoyl chloride is water reactive. Incompatible with strong oxidizing agents, alcohols, bases (including amines). May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. Gives toxic fumes of NOx and HCl when burned [USCG, 1999].

Health Hazard

Material is extremely destructive to the mucous membranes, upper respiratory tract, eyes, and skin. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.

Fire Hazard

Special Hazards of Combustion Products: Toxic fumes of NO x and HCl

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by intraperitoneal route. Moderately toxic by inhalation and ingestion. Human mutation data reported. Can cause skin and paplllary tumors by skin contact, and squamous cell carcinoma by inhalation. Will react with water or steam to produce toxic and corrosive fumes. A powerful lachrymator. When heated to decomposition it emits very toxic fumes of Cland NOx. See also CHLORIDES.

Carcinogenicity

Dimethylcarbamoyl chloride is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Purification Methods

It must be distilled under high vacuum to avoid decomposition. [Beilstein 4 IV 224.]

Dimethylcarbamoyl chloride Preparation Products And Raw materials

Raw materials

Preparation Products


Dimethylcarbamoyl chloride Suppliers

Global( 209)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Career Henan Chemica Co
13203830695 0371-86658258
0371-86658258 Laboratory@coreychem.com CHINA 30281 58
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20012 60
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 20914 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3013 60
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Hubei xin bonus chemical co. LTD
86-13657291602
027-59338440 linda@hubeijusheng.com CHINA 23035 58
Shandong chuangyingchemical Co., Ltd.
18853181302
sale@chuangyingchem.com CHINA 5917 58
Changzhou Carman Chemical Co., Ltd.
15061933924
jane@carmanchem.com; catal@carmanchem.com CHINA 514 58

View Lastest Price from Dimethylcarbamoyl chloride manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2020-02-21 Dimethylcarbamoyl chloride
79-44-7
US $8.00 / KG 1g >98% HPLC kg--ton Career Henan Chemical Co
2019-08-30 Dimethylcarbamoyl chloride
79-44-7
US $1.00-1.00 / KG 1KG 98% 1kg;10kg;100kg career henan chemical co
2019-07-14 Dimethylcarbamoyl chloride
79-44-7
US $1.00 / KG 1KG 99% 25kg career henan chemical co

Dimethylcarbamoyl chloride Spectrum


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