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Dimethyl carbate: Difference between revisions

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| ImageSize = 150px | ImageSize = 150px
| IUPACName = Dimethyl (1''R'',2''S'',3''R'',4''S'')-bicyclohept-5-ene-2,3-dicarboxylate | IUPACName = Dimethyl (1''R'',2''S'',3''R'',4''S'')-bicyclohept-5-ene-2,3-dicarboxylate
| OtherNames = Dimethyl ''cis''-5-norbornene-2,3-dicarboxylate ; Dimalone | OtherNames = Dimethyl ''cis''-5-norbornene-2,3-dicarboxylate; Dimalone
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 39589-98-5 | CASNo = 39589-98-5
| CASNo_Ref = {{cascite|correct|}} | CASNo_Ref = {{cascite|correct|}}
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BN2PH0TQOD | UNII = BN2PH0TQOD
| PubChem = | PubChem = 10921747
| ChemSpiderID = 10430159 | ChEBI = 136029
| ChemSpiderID = 10430159
⚫ | SMILES = O=C(OC)2(C(=O)OC)\1C2/C=C/1
| ATCCode_prefix = P03
⚫ | InChI = 1/C11H14O4/c1-14-10(12)8-6-3-4-7(5-6)9(8)11(13)15-2/h3-4,6-9H,5H2,1-2H3/t6-,7+,8-,9+
| ATCCode_suffix = BX05
⚫ | InChIKey = VGQLNJWOULYVFV-SPJNRGJMBT
⚫ | SMILES = O=C(OC)2(C(=O)OC)\1C2/C=C/1
| InChI = 1/C11H14O4/c1-14-10(12)8-6-3-4-7(5-6)9(8)11(13)15-2/h3-4,6-9H,5H2,1-2H3/t6-,7+,8-,9+ | StdInChI = 1S/C11H14O4/c1-14-10(12)8-6-3-4-7(5-6)9(8)11(13)15-2/h3-4,6-9H,5H2,1-2H3/t6-,7+,8-,9+
| InChIKey = VGQLNJWOULYVFV-SPJNRGJMBT | StdInChIKey = VGQLNJWOULYVFV-SPJNRGJMSA-N
⚫ | StdInChI = 1S/C11H14O4/c1-14-10(12)8-6-3-4-7(5-6)9(8)11(13)15-2/h3-4,6-9H,5H2,1-2H3/t6-,7+,8-,9+
⚫ | StdInChIKey = VGQLNJWOULYVFV-SPJNRGJMSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=11|H=14|O=4 | C=11 | H=14 | O=4
| Appearance = | Appearance =
| Density = 1.4852 g/cm<sup>3</sup><ref name=Merck>'']'', 11th Edition, '''3230'''</ref> | Density = 1.4852 g/cm<sup>3</sup><ref name=Merck>'']'', 11th Edition, '''3230'''</ref>
| MeltingPtC = 38 | MeltingPtC = 38
| Melting_ref = <ref name=Merck/> | MeltingPt_ref = <ref name=Merck/>
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section6={{Chembox Pharmacology
| MainHazards = | ATCCode_prefix = P03
| FlashPt = | ATCCode_suffix = BX05
}}
⚫ | AutoignitionPt =
|Section7={{Chembox Hazards
| MainHazards =
| FlashPt =
⚫ | AutoignitionPt =
}} }}
}} }}


'''Dimethyl carbate''' is an ].<ref>{{cite web | url = http://www.alanwood.net/pesticides/dimethyl%20carbate.html | title = Dimethyl carbate | publisher = AlanWood.net}}</ref> It can be prepared by the ] of ] and ].<ref>{{cite journal | title = Aluminum chloride catalyzed diene condensation. II. Stronger adherence to the Alder endo rule | author = Inukai, Takashi; Kojima, Takeshi | journal = Journal of Organic Chemistry | year = 1966 | volume = 31 | pages = 2032–2033 | issn = 0022-3263 | doi=10.1021/jo01344a543}}</ref> '''Dimethyl carbate''' is an ]. It can be prepared by the ] of ] and ].<ref>{{cite journal | title = Aluminum chloride catalyzed diene condensation. II. Stronger adherence to the Alder endo rule |author1=Inukai, Takashi |author2=Kojima, Takeshi | journal = Journal of Organic Chemistry | year = 1966 | volume = 31 | pages = 2032–2033 | issn = 0022-3263 | doi=10.1021/jo01344a543}}</ref>


==References== ==References==
{{Reflist}} {{Reflist}}

==External links==
* , PAN Pesticides Database


] ]

Latest revision as of 02:38, 14 February 2023

Not to be confused with Dimethyl carbonate.
Dimethyl carbate
Names
IUPAC name Dimethyl (1R,2S,3R,4S)-bicyclohept-5-ene-2,3-dicarboxylate
Other names Dimethyl cis-5-norbornene-2,3-dicarboxylate; Dimalone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H14O4/c1-14-10(12)8-6-3-4-7(5-6)9(8)11(13)15-2/h3-4,6-9H,5H2,1-2H3/t6-,7+,8-,9+Key: VGQLNJWOULYVFV-SPJNRGJMSA-N
  • InChI=1/C11H14O4/c1-14-10(12)8-6-3-4-7(5-6)9(8)11(13)15-2/h3-4,6-9H,5H2,1-2H3/t6-,7+,8-,9+Key: VGQLNJWOULYVFV-SPJNRGJMBT
SMILES
  • O=C(OC)2(C(=O)OC)\1C2/C=C/1
Properties
Chemical formula C11H14O4
Molar mass 210.229 g·mol
Density 1.4852 g/cm
Melting point 38 °C (100 °F; 311 K)
Pharmacology
ATC code P03BX05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Dimethyl carbate is an insect repellent. It can be prepared by the Diels–Alder reaction of dimethyl maleate and cyclopentadiene.

References

  1. ^ Merck Index, 11th Edition, 3230
  2. Inukai, Takashi; Kojima, Takeshi (1966). "Aluminum chloride catalyzed diene condensation. II. Stronger adherence to the Alder endo rule". Journal of Organic Chemistry. 31: 2032–2033. doi:10.1021/jo01344a543. ISSN 0022-3263.


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