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Chemistry
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dichloride
Glutaryl Chloride
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dichloride

[ CAS No. 2873-74-7 ] Glutaryl Chloride

Cat. No.: A496866
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Chemical Structure| 2873-74-7
Chemical Structure| 2873-74-7
 Structure of 2873-74-7 * Storage: Keep in dark place,Inert atmosphere,Room temperature
Purity Size Price USA Stock *0-1 Day Global Stock *5-7 Days Quantity
97% 5g $19.00 Inquiry Inquiry
97% 25g $45.00 Inquiry Inquiry
97% 100g $150.00 Inquiry Inquiry
97% 500g $524.00 Inquiry Inquiry

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* Storage: Keep in dark place,Inert atmosphere,Room temperature

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 2873-74-7 ]

COA NMR CNMR HPLC LC-MS

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Specification
Alternatived Products of [ 2873-74-7 ]
Product Citations

Product Details of [ 2873-74-7 ]

CAS No. :2873-74-7 MDL No. :MFCD00000755
Formula : C5H6Cl2O2 Boiling Point : -
Linear Structure Formula :ClCOCH2CH2CH2COCl InChI Key :YVOFTMXWTWHRBH-UHFFFAOYSA-N
M.W : 169.01 Pubchem ID :17887
Synonyms :
Chemical Name :Glutaroyl dichloride

Safety of [ 2873-74-7 ]

Signal Word:Danger Class:8(6.1)
Precautionary Statements:P264-P270-P280-P301+P310-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501 UN#:2922
Hazard Statements:H301-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2873-74-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2873-74-7 ]

[ 2873-74-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 2873-74-7 ]
  • [ 31358-13-1 ]
Reference： [1]Tetrahedron Letters,1970,p. 3431 - 3434
  • 2
  • [ 2873-74-7 ]
  • [ 64-17-5 ]
  • [ 870-78-0 ]
Reference： [1]Tetrahedron Asymmetry,1995,vol. 6,p. 2921 - 2924
  • 3
  • [ 67-56-1 ]
  • [ 2873-74-7 ]
  • [ 31358-13-1 ]
YieldReaction ConditionsOperation in experiment
95% Glutaryl chloride (20.00 g, 118.33 mmoles) was added with 13.33 ml (260.30 mmoles) of bromine at a temperature of 90C and the solution was irradiated with a 300 W lamp for 4 hours. The mixture was cooled to room temperature and 71.89 ml (1775 mmoles) of dry methanol was added with cooling (ice bath), then stirred for 12 hours. The solution was concentrated and the brown oily residue was added with 72 ml of water. The aqueous solution was repeatedly extracted with ethyl ether which, washed in succession with 5% NaHC03 and 2% NaHS03, dried (Na2S04) and concentrated to give 35.71 g of an orange oil. The crude oil was purified by distillation in a bulb tube at 140-145C/0.1 mmHg. Yield: 95% Rf: 0.56 (6:1 hexane-ethyl acetate) B. p.: 145C/0.1 mmHg (Lit. 2¹: 120C/0.01 mmHg) IR v (cm-1) : (Film) 1730 (C=OR). ¹H-NMR (CDC13): 2.49-3.00 (m, 2H, CH2), 3.82 (s, 6H, CH3x2), 4.36-4.50 (m, 2H, CHx2).
Reference： [1]Patent: WO2005/108402,2005,A1 .Location in patent: Page/Page column 10-13
  • 4
  • [ 2873-74-7 ]
  • [ 543-20-4 ]
  • [ 111-50-2 ]
  • [ 124-40-3 ]
  • [ 13424-80-1 ]
  • [ 3644-93-7 ]
  • [ 7334-51-2 ]
YieldReaction ConditionsOperation in experiment
71.87%Chromat.; 13.31%Chromat.; 13.49%Chromat. With triethylamine; In toluene; at -10 - 20℃; for 2h; Procedure B: Formation of Diamide (as a Mixture) by Reaction with a Dialkylamine Toluene and triethylamine are loaded and cooled to -10 C. The dialkylamine is then loaded in liquid form. The acid dichloride (as a mixture), diluted in toluene is then added slowly while maintaining the temperature below +10 C. The mixture is then stirred for two hours at room temperature. The salts formed during the reaction are then filtered off and washed with ethyl acetate. The thereby obtained filtrate is then evaporated on the rotary evaporator in order to obtain the reaction raw product. The final product is finally obtained after distillation under reduced pressure. Raw product=729 g (brown liquid) Final product=574 g (slightly yellow liquid) GC analysis (surface area)>98% (sum of the isomers) The obtained product is analyzed by gas chromatography. The analysis indicates (as a peak surface area): It is also noticed that it is free of crystals at these temperatures.
Reference： [1]Patent: US2012/29092,2012,A1 .Location in patent: Page/Page column 7
  • 5
  • [ 2873-74-7 ]
  • [ 870-78-0 ]
Reference： [1]Synthesis,2012,vol. 44,p. 2859 - 2862
  • 6
  • [ 2873-74-7 ]
  • [ 64-17-5 ]
  • [ 870-78-0 ]
  • [ 7209-00-9 ]
YieldReaction ConditionsOperation in experiment
6.34 g The previously prepared glutaryl dichloride (0.900 g, 5.32 mmol) was placed in a 3 neck flask fitted with a reflux condenser and a scrubber system consisting of 1 M NaOH (500 ml_) and 10% aq Na2S2C>3 (50 ml_) and warmed to 85 C. Neat bromine (0.7 ml) was added dropwise and then a 150 W sun lamp was placed in front of the reaction and continued to heat at 85 C for 4.5 hours. Once the bromination was complete, the reaction was placed under nitrogen and transferred via cannula to anhydrous ethanol at 0 C. Extra ethanol (3 x 5 mL) was used to wash the reaction vessel to ensure the dichloride was transferred quantitatively. The reaction was subsequently stirred at 0 C for 15 mins then allowed to stir at room temperature overnight. The next day, the reaction was cooled to 0 C then solid NaHCC was added slowly until C02 evolution ceased. The reaction was partitioned between water (20 mL) and ether (20 mL) then the aqueous phase was separated and washed with ether (2 x 20 mL). The combined organic phases were washed with 10% Na2S2C>3 solution followed by brine then dried (MgSCL) and concentrated in vacuo to afford a dark red oil. The crude product was purified via fractional distillation to afford a mixture of stereoisomers of the desired product with diethyl 2- bromopentanedioate as a minor product (6.34 g). 6H (400 MHz, CDCb) 4.51 (dd, J 8.0, 6.8, 2H, CH), 4.40 (t, J 8.0, 2H, CH), 4.28 (q, J 16.0, 8.0, 8H, CH2), 2.93-2.86 (dt, J 14.0, 8.0, 1 H, CH2), 2.68 (dd, J 7.8, 6.5, 2H, CH2), 2.65 (dt, J 14.0, 8.0, 1 H, CH2), 1.34 (t, J 8.0, 12H, CH3).
Reference： [1]Patent: WO2020/73097,2020,A1 .Location in patent: Paragraph 0156

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Technical Information

• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Heat of Combustion • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction
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