Production Method 1

922-67-8

Reaction Conditions

1.1 Reagents: Trimethyl orthoformate Catalysts: Sulfuric acid Solvents: Dichloromethane ;  28 h, 40 °C

Reference

Environment-friendly preparation method of propiolic acid derivative

, China, , ,

Production Method 2

36993-85-8

97914-78-8

922-67-8

Reaction Conditions

Reference

Addition of 4-ethoxyimidazoles to dimethyl acetylenedicarboxylate and transformation of the adducts to pyrimidin-5-yl acetates

Furuya, Shuichi; Omura, Kiyoshi; Furukawa, Yoshiyasu, Chemical & Pharmaceutical Bulletin, 1988, 36(5), 1669-75

Production Method 3

922-67-8

Reaction Conditions

1.1 Reagents: Sulfuric acid ;  24 h, reflux

Reference

Approaches to the total synthesis of dl-vernolepin

Medwid, Effrey Brian, 1980, , ,

Production Method 4

922-67-8

Reaction Conditions

1.1 Reagents: Tetraethylammonium p-toluenesulfonate Solvents: Dimethylformamide

Reference

Esterification, etherification, and aldol condensation using cathodically generated organic olate anions

Fuchigami, Toshio; Awata, Takeshi; Nonaka, Tsutomu; Baizer, Manuel M., Bulletin of the Chemical Society of Japan, 1986, 59(9), 2873-9

Production Method 5

922-67-8

Reaction Conditions

1.1 Reagents: Sulfuric acid ;  48 h, 25 °C

Reference

Studies on the 1-aza-1'-oxa-[3,3]-sigmatropic rearrangement: synthesis of ortho-(β-oxoalkyl)anilides and regiospecifically substituted indoles

Burgoyne, William Franklin Jr., 1981, , ,

Production Method 6

61617-47-8

922-67-8

Reaction Conditions

Reference

Synthesis of linear alkynes by rearrangement

Krueger, A., Science of Synthesis, 2008, 43, 469-554

Production Method 7

922-67-8

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  0 °C; 1 - 12 h, 0 °C

Reference

Flash vacuum pyrolysis of 1-Aryl-1,2,3-triazole-4-carboxylate esters and -4-carboxamides

Habib, Osama M.; Mohamed, Asaad S.; Al-Awadi, Nouria A., Journal of Analytical and Applied Pyrolysis, 2023, 170,

Production Method 8

922-67-8

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ;  18 h, reflux

Reference

Metal-free synthesis of N-vinyl sulfoximines via DABCO-participated Michael addition of terminal carbonyl alkynes with N-chlorosulfoximines

Tang, Yisong; Tang, Yaonan; Rui, zhu; Zheng, Shaojun; Cheng, Xiaofang; et al, Tetrahedron, 2022, 129,

Production Method 9

922-67-8

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide Solvents: Dichloromethane ;  0 °C; 2 h, 0 °C; 0 °C → 23 °C; 23 °C
1.2 Solvents: Ethyl acetate ;  1 h, 0 °C

Reference

One-Pot Synthesis of Chromone Fused-Pyrrolo[2,1-a]isoquinolines and Indolizino[8,7-b]indoles: Iodine Promoted Oxidative [2+2+1] Annulation of O-acetylphenoxyacrylates with Tetrahydroisoquinolines and Noreleagnines

Shang, Zhi-Hao; Zhang, Xiang-Jin; Li, Yi-Ming; Wu, Rui-Xue; Zhang, Hui-Ru; et al, Journal of Organic Chemistry, 2021, 86(21), 15733-15742

Production Method 10

922-67-8

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  1 h, 0 °C; 5 h, rt

Reference

Asymmetric synthesis of dihydrocarbazoles through a Friedel-Crafts alkylation/annulation sequential reaction of indoles

Hu, Linfeng; Cao, Weidi; Wang, Kaixuan; Liu, Xiaohua; Feng, Xiaoming, Chemical Communications (Cambridge, 2021, 57(97), 13138-13141

Production Method 11

922-67-8

Reaction Conditions

1.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ;  30 min, 0 °C; rt

Reference

Palladium-Catalyzed Regio- and Stereoselective Coupling-Addition of Propiolates with Arylsulfonyl Hydrazides: A Pattern for Difunctionalization of Alkynes

Liu, Lixin; Sun, Kang; Su, Lebin; Dong, Jianyu; Cheng, Lei; et al, Organic Letters, 2018, 20(13), 4023-4027

Production Method 12

922-67-8

Reaction Conditions

1.1 Reagents: Sulfuric acid

Reference

Addition reactions of heterocyclic compounds. XL. Methyl propiolate with some quinolines, isoquinolines, and phenanthridines

Acheson, Richard M.; Verlander, M. S., Journal of the Chemical Society [Section] C: Organic, 1969, (17), 2311-15

Production Method 13

922-67-8

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol ,  Water

Reference

Some uses of organosilicon compounds in organic synthesis

Percival, Alan, 1977, , ,

Production Method 14

922-67-8

Reaction Conditions

1.1 Reagents: Methanol ,  Boron trifluoride etherate Solvents: Methanol

Reference

The stereochemistry of addition of trialkylammonium and pyridinium tetrafluoroborate salts to activated acetylenes. Preparation of novel dienophiles for Diels-Alder reactions

Jung, Michael E.; Buszek, Keith R., Journal of the American Chemical Society, 1988, 110(12), 3965-9

Production Method 15

922-67-8

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Methanol

Reference

Action of Grignard reagents on the esters of propiolic acid

Rhinesmith, Herbert S., Journal of Organic Chemistry, 1975, 40(12), 1773-6

Production Method 16

922-67-8

Reaction Conditions

Reference

Complete kinetic analysis of thermal stereomutations among the eight 2,3-dideuterio-2-(methoxymethyl)spiro[cyclopropane-1,1'-indenes]

Baldwin, John E.; Black, Kersey A., Journal of the American Chemical Society, 1984, 106(4), 1029-40

Production Method 17

16754-74-8

922-67-8

Reaction Conditions

Reference

Flash-vacuum pyrolysis of stabilized phosphorus ylides. Part 9. Preparation and pyrolysis of β,γ-dioxo ylides, β,β',γ,γ'-tetraoxo ylides and hexaoxo bis(ylides)

Aitken, R. Alan; Karodia, Nazira, Liebigs Annalen/Recueil, 1997, (4), 779-783

Production Method 18

922-67-8

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  1 h, reflux

Reference

Environmental impact analysis of surface printing and 3D inkjet printing applications using an imine based covalent organic framework: A life cycle assessment study

Espada, Juan J. ; Rodriguez, Rosalia; de la Pena, Alejandro; Ramos, Mar; Segura, Jose L. ; et al, Journal of Cleaner Production, 2023, 395,

Production Method 19

922-67-8

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: Toluene ;  12 h, reflux

Reference

Nature-inspired remodeling of (aza)indoles to meta-aminoaryl nicotinates for late-stage conjugation of vitamin B3 to (hetero)arylamines

Varun, Begur Vasanthkumar ; Vaithegi, Kannan ; Yi, Sihyeong ; Park, Seung Bum, Nature Communications, 2020, 11(1),

Production Method 20

922-67-8

Reaction Conditions

1.1 Reagents: p-Toluenesulfonic acid Solvents: Methanol

Reference

Pyridine-Based Organocatalysts for Regioselective syn-1,2-Silaboration of Terminal Alkynes and Allenes

Morimasa, Yohei; Kabasawa, Kosuke; Ohmura, Toshimichi ; Suginome, Michinori, Asian Journal of Organic Chemistry, 2019, 8(7), 1092-1096

methyl prop-2-ynoate Raw materials

• Methyl 2-oxo-3-(triphenyl-lambda~5~-phosphanylidene)propanoate
• 4(1H)-Pyrimidinone, 5-methyl-2-phenyl-
• Cyclopropaneacetic acid, α-diazo-2,3-dimethyl-, methyl ester, (1α,2α,3β)-
• 5-Pyrimidineacetic acid, 6-carboxy-1,4-dihydro-4-oxo-2-phenyl-

methyl prop-2-ynoate Preparation Products

• methyl prop-2-ynoate (922-67-8)

• 1. Exceptionally high temperature spin crossover in amide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complex revealed by variable temperature Raman spectroscopy and single crystal X-ray diffraction?
  Max Attwood,Hiroki Akutsu,Lee Martin,Toby J. Blundell,Pierre Le Maguere,Scott S. Turner Dalton Trans., 2021,50, 11843-11851
• 2. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 3. Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents
  Craig A. Kelly,David R. Rosseinsky Phys. Chem. Chem. Phys., 2001,3, 2086-2090
• 4. Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes?
  Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. Parkin J. Mater. Chem. A, 2020,8, 22075-22082
• 5. Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330
  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acid esters
• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acid derivatives Carboxylic acid esters
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 762-42-5(1,4-dimethyl but-2-ynedioate)
• 62500-21-4(Copper, (3-ethoxy-3-oxo-1-propynyl)-)
• 623-47-2(ethyl propiolate)
• 72036-29-4(Lithium,(3-methoxy-3-oxo-1-propynyl)- (9CI))
• 23326-27-4(Methyl 2-butynoate)
• 10227-18-6(Pentaacetyl-5-thioglucose)
• 31555-05-2(Methyl 4-hydroxybut-2-ynoate)
• 62796-54-7(2,4,6-Octatriynoic acid, methyl ester)
• 72036-30-7(Lithium, (3-ethoxy-3-oxo-1-propynyl)-)
• 88697-12-5(2,4-Hexadiynedioic acid, dimethyl ester)