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(Z)-3-Iodoacrylic acid is synthesized stereospecifically as the Z-isomer through the reaction of propiolic acid with methylmagnesium iodide in THF, followed by acetic acid workup, yielding the product in high purity and efficiency. (Z)-(3)-IODOACRYLIC ACID can also be obtained via hydroiodination of propiolic acid using aqueous hydroiodic acid, though under these conditions, it may isomerize to the E-form. The Z-isomer is a valuable intermediate in organic synthesis due to its defined stereochemistry.

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  • 6214-35-3 Structure
  • Basic information

    1. Product Name: (Z)-(3)-IODOACRYLIC ACID
    2. Synonyms: (Z)-(3)-IODOACRYLIC ACID;CIS-3-IODOACRYLIC ACID;cis-3-Iodoacrylic acid,98%;(2Z)-3-Iodo-2-propenoic acid;2-Propenoic acid, 3-iodo-, (2Z)-;(Z)-3-iodoprop-2-enoic acid
    3. CAS NO:6214-35-3
    4. Molecular Formula: C3H3IO2
    5. Molecular Weight: 197.96
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 6214-35-3.mol
  • Chemical Properties

    1. Melting Point: 65 °C
    2. Boiling Point: 248.3 °C at 760 mmHg
    3. Flash Point: 104 °C
    4. Appearance: White to yellow crystalline powder
    5. Density: 2.325 g/cm3
    6. Vapor Pressure: 0.00783mmHg at 25°C
    7. Refractive Index: 1.636
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. CAS DataBase Reference: (Z)-(3)-IODOACRYLIC ACID(CAS DataBase Reference)
    11. NIST Chemistry Reference: (Z)-(3)-IODOACRYLIC ACID(6214-35-3)
    12. EPA Substance Registry System: (Z)-(3)-IODOACRYLIC ACID(6214-35-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 6214-35-3(Hazardous Substances Data)

6214-35-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 6214-35-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,2,1 and 4 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 6214-35:
(6*6)+(5*2)+(4*1)+(3*4)+(2*3)+(1*5)=73
73 % 10 = 3
So 6214-35-3 is a valid CAS Registry Number.
InChI:InChI=1/C3H3IO2/c4-2-1-3(5)6/h1-2H,(H,5,6)/b2-1-

6214-35-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (Z)-3-iodoprop-2-enoic acid

1.2 Other means of identification

Product number -
Other names cis-3-iodopropenoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6214-35-3 SDS

6214-35-3Relevant articles and documents

Diastereoselective scalable synthesis of 2,6-trans-Piperidines using an aza-Michael reaction

Chowdhury, Somenath,Mao, Jianmin,Martynow, Jacek,Zhao, He,Duffy, Erin,Wu, Yusheng,Thakur, Vinay,Sirasani, Gopal,Tang, Yuanqing,Collin, Florine,Sinishtaj, Sandra,Bhattacharjee, Ashoke

, p. 371 - 374 (2019)

Highly efficient substrate and reagent controlled stereoselective synthesis of 2,6-trans-piperidine derivative (1) using an aza-Michael reaction is reported. This method was utilized to synthesize a variety of trans-piperidines on hundred-gram scales.

SIMPLE, STEREOSPECIFIC PREPARATION OF Z-3-IODOACRYLIC ACID FROM PROPIOLIC ACID AND METHYLMAGNESIUM IODIDE

Jung, Michael E.,Hagenah, Jeffrey A.,Long-Mei, Zeng

, p. 3973 - 3974 (1983)

Addition of propiolic acid to 2.2 equiv of methylmagnesium iodide in THF followed by workup with acetic acid produces only the Z-isomer of 3-iodoacrylic acid, 2, in high yield.

Revisiting the hydroiodination of propiolic acid

Zoller,Uguen

, p. 6719 - 6720 (1998)

Z-3-iodoacrylic acid Z-1, that formed by reacting propiolic acid 2 with 57% aqueous III at 80-85 °C, was efficiently converted into the isomeric acid E-1 by treatment in the same conditions.

Selective Ni-catalyzed cross-electrophile coupling of alkynes, fluoroalkyl halides, and vinyl halides

Chu, Lingling,Dai, Yubei,Wang, Fang,Zhu, Shengqing

supporting information, (2022/01/26)

We report a Ni-catalyzed three-component cross-electrophile coupling of alkynes with alkenyl halides and fluoroalkyl halides to generate fluoroalkyl-incorporated 1,3-dienes. This mild and operationally simple protocol is distinguished by its broad substra

PYRROLO[2,3-D]PYRIMIDIN-2-ONE ANTIMICROBIAL COMPOUNDS

-

Page/Page column 79, (2020/07/05)

The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. In some embodiments, the present disclosure provides pyrrolo[2,3-d]pyrimidin-2-ones useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans and animals.

AMINOMETHYLAMIDINE AND METHYLAMIDINE ANTIMICROBIAL COMPOUNDS

-

Page/Page column 173, (2019/12/28)

The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. In some embodiments, the present disclosure provides pyrrolo[2,3-d]pyrimidin-2-ones useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans and animals.

Studies toward the Total Synthesis of the Marine Macrolide Salarin C

Schrof, Raffael,Altmann, Karl-Heinz

supporting information, p. 7679 - 7683 (2018/12/11)

A convergent strategy for the synthesis of dideoxysalarin C (3) as a potential intermediate for the total synthesis of the marine macrolide salarin C (1) is described. The macrolactone core of 3 was assembled by Suzuki coupling between alkyl iodide 9 and

ANTIMICROBIALS AND METHODS OF MAKING AND USING SAME

-

Page/Page column 202, (2017/12/13)

The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. These compounds are useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans a

ANTIMICROBIALS AND METHODS OF MAKING AND USING SAME

-

Page/Page column 108, (2017/12/13)

The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. These compounds are useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans and animals. In some embodiments, the present disclosure provides a compound of Formula (I) or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer.

Pd/C-Cu mediated direct and one-pot synthesis of γ-ylidene butenolides

Rambabu,Bhavani,Nalivela, Kumara Swamy,Mukherjee, Soumita,Rao, M.V. Basaveswara,Pal, Manojit

, p. 2151 - 2155 (2013/04/24)

10% Pd/C in combination with CuI, PPh3, and Et3N has been identified as an effective catalyst system for the coupling of (Z)-3-iodoacrylic acid with terminal alkynes in 1,4-dioxane leading to the one-pot synthesis of γ-ylidene butenolides. The methodology showed remarkable regio- and stereoselectivity as only the five-membered lactone ring products were formed with an exocyclic double bond possessing Z-geometry.

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